Alendronic acid (CED0002504)

Record Information

Version

1.0

Creation Date

2009-07-15 20:43:20 UTC

Update Date

2026-05-14 16:44:34 UTC

SynCED ID

CED0002504

Secondary Accession Numbers

CHEM002111
T3D2666

Identification

Common Name

Alendronic acid

Class

Small Molecule

Description

Alendronic acid belongs to the bisphosphonates, a subclass of organic phosphonic acids and derivatives within the organic compounds. It is an exogenous solid with the formula C4H13NO7P2 and an average molecular weight of 249.10 g/mol. This compound is used as a drug (PMC8713161) and a bone density conservation agent (PMC8713161). It acts as an inhibitor of EC 2.5.1.1 (dimethylallyltranstransferase) (PMC8713161). Its protein targets include farnesyl pyrophosphate synthase (FDPS), tyrosine-protein phosphatase non-receptor type 4 (PTPN4), receptor-type tyrosine-protein phosphatase S (PTPRS), receptor-type tyrosine-protein phosphatase epsilon (PTPRE), V-type proton ATPase catalytic subunit A (ATP6V1A), and geranylgeranyl pyrophosphate synthase (GGPS1). The action of alendronic acid on bone tissue is based partly on its affinity for hydroxyapatite, which is part of the mineral matrix of bone. It also targets farnesyl pyrophosphate (FPP) synthase, acting as an analogue of isoprenoid diphosphate lipids to inhibit this enzyme in the mevalonate pathway. Alendronic acid is found in healthcare, pharmaceuticals, and veterinary products as a drug for the treatment of bone diseases, and it has been detected in the prostate and intestine. The recorded exposure route is oral. It is used for the treatment of osteoporosis (PMC10516574, PMC10547673, PMC10889292, PMC11012270, PMC11036926, PMC12025247, PMC12896522, PMC2686344, PMC2971711), multiple myeloma (PMC4293349, PMC4684366, PMC6924235), hypercalcemia (PMC6924235), glucocorticoid-induced osteoporosis (PMC5114204), breast cancer (PMC7829671), and prostate cancer (PMC7829671). It has therapeutic effects on prostate cancer (PMC3932719), ovarian cancer (PMC1828067, PMC7192836), osteoporosis (PMC10425235), pain (PMC4257480), heart failure (PMC6452576), and breast cancer (PMC6607035). Associated health effects include an increase in arthritis (PMC10560398), hypophosphatemia (PMC2686344), nausea (PMC9738991), fever (PMC2971711), and a decrease in lung cancer (PMC7793382).

Contaminant Type

Amine
Antihypocalcemic Agent
Antiresorptive
Bisphosphonate
Bone Density Conservation Agent
Drug
Food Toxin
Human Neurotoxin
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(4-Amino-1-hydroxybutylidene)bisphosphonic acid	ChEBI
Acide alendronique	ChEBI
Acido alendronico	ChEBI
Acidum alendronicum	ChEBI
Alendronate	ChEBI
(4-Amino-1-hydroxybutylidene)bisphosphonate	Generator
4-Amino-1-hydroxybutylidene 1,1-biphosphonate	MeSH
Alendronate monosodium salt, trihydrate	MeSH
Alendronate sodium	MeSH
Aminohydroxybutane bisphosphonate	MeSH
Fosamax	MeSH
Alendronate sodium hydrate	HMDB
Sodium, alendronate	MeSH, HMDB
4 amino 1 Hydroxybutylidene 1,1 biphosphonate	MeSH, HMDB
Bisphosphonate, aminohydroxybutane	MeSH, HMDB

Chemical Formula

C₄H₁₃NO₇P₂

Average Molecular Mass

249.096 g/mol

Monoisotopic Mass

249.017 g/mol

CAS Registry Number

66376-36-1

IUPAC Name

(4-amino-1-hydroxy-1-phosphonobutyl)phosphonic acid

Traditional Name

alendronate

SMILES

NCCCC(O)(P(O)(O)=O)P(O)(O)=O

InChI Identifier

InChI=1S/C4H13NO7P2/c5-3-1-2-4(6,13(7,8)9)14(10,11)12/h6H,1-3,5H2,(H2,7,8,9)(H2,10,11,12)

InChI Key

OGSPWJRAVKPPFI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bisphosphonates. These are organic compounds containing two phosphonate groups linked together through a carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphonic acids and derivatives

Sub Class

Bisphosphonates

Direct Parent

Bisphosphonates

Alternative Parents

Substituents

Bisphosphonate
Organophosphonic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organophosphorus compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary amino compound (CHEBI:2567 )
1,1-bis(phosphonic acid) (CHEBI:2567 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Intestine
Prostate

Applications

bone density conservation agent

Biological Roles

Chemical Roles

EC 2.5.1.1 (dimethylallyltranstransferase) inhibitor ?

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	234 dec°C
Boiling Point	Not Available
Solubility	1mg/L

Predicted Properties

Property	Value	Source
Water Solubility	16.9 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-4.2	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	0.69	ChemAxon
pKa (Strongest Basic)	9.91	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	161.31 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	47.37 m³·mol⁻¹	ChemAxon
Polarizability	19.4 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-001i-9010000000-6b540b3cfe12455ee047	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-001i-9020000000-f4a0f6418448b2108371	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-2930000000-99692afb4ed253251947	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0900000000-d2c07307d66e1c7d52e8	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0kdl-9500000000-c82a6e6e898154627c7d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ue9-0590000000-ed1b4585584330309b42	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uyi-4900000000-42101c55bda7e112b2af	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-9330000000-8ac66f69531027a0950f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kb-2590000000-2c9bde6c398541c5cb71	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-017i-6950000000-d1f8822b01485883083d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-003r-9000000000-7b5e5c1f9b218640040b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0090000000-0b08500c08babf97a735	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-005a-9050000000-04116055e92ba5f8a66f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03gi-9000000000-8274f2b488ab919859ff	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0090000000-eb3a6c3bae79932540c8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0190000000-7b88a34c07f93b4e4779	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9100000000-12b406fbd4d8f99b2d4d	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
2132.0 Log mg/kg [1200:3800]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

The action of Alendronate on bone tissue is based partly on its affinity for hydroxyapatite, which is part of the mineral matrix of bone. Alendronate also targets farnesyl pyrophosphate (FPP) synthase. Nitrogen-containing bisphosphonates (such as pamidronate, alendronate, risedronate, ibandronate and zoledronate) appear to act as analogues of isoprenoid diphosphate lipids, thereby inhibiting FPP synthase, an enzyme in the mevalonate pathway. Inhibition of this enzyme in osteoclasts prevents the biosynthesis of isoprenoid lipids (FPP and GGPP) that are essential for the post-translational farnesylation and geranylgeranylation of small GTPase signalling proteins. This activity inhibits osteoclast activity and reduces bone resorption and turnover. In postmenopausal women, it reduces the elevated rate of bone turnover, leading to, on average, a net gain in bone mass.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Alendronate can damage the esophagus both by toxicity from the medication itself and by nonspecific irritation secondary to contact between the pill and the esophageal mucosa, similar to other cases of "pill esophagitis."

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Reference
arthritis?A disorder characterized by inflammation involving a joint. (NCI CTCAE)	associated_with	increase	PMC10560398
lung cancer?A respiratory system cancer that is located in the lung. (DO)	associated_with	decrease	PMC7793382
breast cancer?A breast cancer that has material basis in abnormally proliferating cells derives from epithelial cells. (DO)	has_therapeutic_effect_on	Not Available	PMC6607035
breast cancer?A breast cancer that has material basis in abnormally proliferating cells derives from epithelial cells. (DO)	is_treatment_for	Not Available	PMC7829671
osteoporosis?A disorder characterized by reduced bone mass, with a decrease in cortical thickness and in the number and size of the trabeculae of cancellous bone (but normal chemical composition), resulting in increased fracture incidence. (NCI CTCAE)	is_treatment_for	Not Available	PMC10516574 , PMC10547673 , PMC10889292 , PMC11012270 , PMC11036926 , PMC12025247 , PMC12896522 , PMC2686344 , PMC2686344 , PMC2971711
osteoporosis?A disorder characterized by reduced bone mass, with a decrease in cortical thickness and in the number and size of the trabeculae of cancellous bone (but normal chemical composition), resulting in increased fracture incidence. (NCI CTCAE)	has_therapeutic_effect_on	Not Available	PMC10425235
multiple myeloma?A myeloid neoplasm that is located in the plasma cells in bone marrow. (DO)	is_treatment_for	Not Available	PMC4293349 , PMC4684366 , PMC6924235
fever?A disorder characterized by an abnormally high body temperature.	associated_with	Not Available	PMC2971711
pain?A disorder characterized by the sensation of marked discomfort, distress or agony. (NCI CTCAE)	has_therapeutic_effect_on	Not Available	PMC4257480 , PMC4257480 , PMC4257480 , PMC4257480
Prostate cancer?A male reproductive organ cancer that is located in the prostate. (DO)	has_therapeutic_effect_on	Not Available	PMC3932719
Prostate cancer?A male reproductive organ cancer that is located in the prostate. (DO)	is_treatment_for	Not Available	PMC7829671
hypercalcemia?A disorder characterized by laboratory test results that indicate an elevation in the concentration of calcium (corrected for albumin) in blood. (NCI CTCAE)	is_treatment_for	Not Available	PMC6924235
nausea?A disorder characterized by a queasy sensation and/or the urge to vomit. (NCI CTCAE)	associated_with	Not Available	PMC9738991
heart failure?A disorder characterized by the inability of the heart to pump blood at an adequate volume to meet tissue metabolic requirements, or, the ability to do so only at an elevation in the filling pressure. (NCI CTCAE)	has_therapeutic_effect_on	Not Available	PMC6452576
ovarian cancer?A female reproductive organ cancer that is located in the ovary. (DO)	has_therapeutic_effect_on	Not Available	PMC1828067 , PMC7192836
glucocorticoid-induced osteoporosis?	is_treatment_for	Not Available	PMC5114204
hypophosphatemia?A disorder characterized by laboratory test results that indicate a low concentration of phosphates in the blood. (NCI CTCAE)	associated_with	Not Available	PMC2686344
hyperparathyroidism?A disorder characterized by an increase in production of parathyroid hormone by the parathyroid glands. This results in hypercalcemia (abnormally high levels of calcium in the blood). (NCI CTCAE)	associated_with	increase	PMC2686344
osteonecrosis?A disorder characterized by necrotic changes in the bone tissue due to interruption of blood supply. Most often affecting the epiphysis of the long bones, the necrotic changes result in the collapse and the destruction of the bone structure. (NCI CTCAE)	associated_with	Not Available	PMC3656696 , PMC4015053
esophagitis?	associated_with	Not Available	PMC7793382
Osteogenesis Imperfecta?Osteogenesis imperfecta (OI), also known as brittle bone disease, is a group of genetic disorders that mainly affect the bones. It results in bones that break easily. The severity may be mild to severe. Other symptoms may include a blue tinge to the whites of the eye, short height, loose joints, hearing loss, breathing problems and problems with the teeth. Complications may include cervical artery dissection and aortic dissection. There are at least nine different types of OI. Type I is the most common. Symptoms vary from person to person. Osteogenesis imperfecta is a genetic disorder commonly caused by mutations in the COL1A1 and COL1A2 genes which are responsible for the production of collagen type 1. Approximately 90% of people with OI are heterozygous for mutations in both the COL1A1 and COL1A2 genes. In the United States, the incidence of osteogenesis imperfecta is estimated to be one per 20,000 live births. An estimated 20,000 to 50,000 people are affected by OI in the United States. The most common types are I - IV. (Wikipedia)	has_therapeutic_effect_on	Not Available	PMC12545228
Osteogenesis Imperfecta?Osteogenesis imperfecta (OI), also known as brittle bone disease, is a group of genetic disorders that mainly affect the bones. It results in bones that break easily. The severity may be mild to severe. Other symptoms may include a blue tinge to the whites of the eye, short height, loose joints, hearing loss, breathing problems and problems with the teeth. Complications may include cervical artery dissection and aortic dissection. There are at least nine different types of OI. Type I is the most common. Symptoms vary from person to person. Osteogenesis imperfecta is a genetic disorder commonly caused by mutations in the COL1A1 and COL1A2 genes which are responsible for the production of collagen type 1. Approximately 90% of people with OI are heterozygous for mutations in both the COL1A1 and COL1A2 genes. In the United States, the incidence of osteogenesis imperfecta is estimated to be one per 20,000 live births. An estimated 20,000 to 50,000 people are affected by OI in the United States. The most common types are I - IV. (Wikipedia)	is_treatment_for	Not Available	PMC8435630

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000367	Drugs for treatment of bone diseases?Drugs for the treatment of bone diseases, such as bisphosphonates and calcitonin, are synthetic chemicals designed to prevent bone loss and promote bone health.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000505	Amplifiers?Amplifiers, commonly used in various electronic devices to enhance signal strength, can be a source of synthetic chemical contamination due to the materials and processes involved in their production and disposal.	Electrical & Electronic Equipment	Not Available
CEDs000506	Antennas?Antennas, commonly used in communication technologies, can be a source of synthetic chemical contamination through the materials and coatings used in their construction.	Electrical & Electronic Equipment	Not Available
CEDs000511	Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.	Electrical & Electronic Equipment	Not Available
CEDs000517	Electric Switches?Electric switches, integral components in numerous devices, can be a source of synthetic chemical contamination due to the materials and manufacturing processes involved in their production.	Electrical & Electronic Equipment	Not Available
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	Not Available
CEDs000519	Electrodes?Electrodes, used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials from which they are constructed and the processes involved in their manufacturing.	Electrical & Electronic Equipment	Not Available
CEDs000521	Fixed Capacitors And Their Manufacture?Fixed capacitors are passive electronic components used to store and release electrical energy, playing a critical role in various circuits.	Electrical & Electronic Equipment	Not Available
CEDs000524	Hybrid Capacitors?Hybrid capacitors are energy storage devices that combine the properties of electrolytic and supercapacitors, utilizing a combination of electrochemical principles to achieve higher energy density and power density.	Electrical & Electronic Equipment	Not Available
CEDs000530	Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.	Electrical & Electronic Equipment	Not Available
CEDs000537	Television Systems?Television systems can be a source of synthetic chemical contamination due to the various materials and components used in their manufacture and operation.	Electrical & Electronic Equipment	Not Available
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	Not Available
CEDs000551	Processing Fish?Processing fish can lead to synthetic chemical contamination through various stages of production and preservation.	Food, food processing & cookware	Not Available
CEDs000555	Bleaching Agents?Bleaching agents are chemical substances used to whiten or lighten materials, often employed in various cleaning products for their stain removal and disinfecting properties.	Household cleaning & consumer products	Not Available
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	Not Available
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	Not Available
CEDs000560	Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.	Household cleaning & consumer products	Not Available
CEDs000561	Perfumes Within Detergents And Soaps?Perfumes within detergents and soaps are synthetic fragrance compounds added to enhance the sensory experience of cleaning products.	Household cleaning & consumer products	Not Available
CEDs000563	Soap Detergents?Soap detergents are synthetic surfactants designed to enhance the cleaning efficacy of water by reducing surface tension, allowing for better interaction with dirt and grease.	Household cleaning & consumer products	Not Available
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	Not Available
CEDs000578	Making Cigars?The process of making cigars involves several steps, including the cultivation of tobacco, fermentation, and the application of various additives to enhance flavor and preservation.	Industrial manufacturing & chemical processing	Not Available
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	Not Available
CEDs000583	Anchoring Equipment?Anchoring equipment, commonly used in marine applications, can be a source of synthetic chemical contamination due to the materials and coatings utilized in their manufacturing.	Marine, shipping & aquaculture	Not Available
CEDs000584	Buoys?Buoys, often used for navigation and marine monitoring, can be sources of synthetic chemical contamination due to the materials and coatings employed in their construction.	Marine, shipping & aquaculture	Not Available
CEDs000592	Marine Propulsion Or Steering?Marine propulsion and steering systems often rely on various synthetic chemicals, including lubricants, fuels, and hydraulic fluids.	Marine, shipping & aquaculture	Not Available
CEDs000595	Ships?Ships, as vehicles for international trade and transportation, can be significant sources of synthetic chemical contamination in marine environments.	Marine, shipping & aquaculture	Not Available
CEDs000600	Herbicides And Algicides?Herbicides and algicides are synthetic chemicals primarily used to control unwanted plants and algae in various environments.	Agriculture & land management	Not Available
CEDs000605	Pest Repellants?Pest repellents, often formulated from synthetic chemicals, are widely used to protect crops from insect infestations and other pests.	Agriculture & land management	Not Available
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	Not Available
CEDs000614	Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.	Personal care & cosmetics	Not Available
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	Not Available
CEDs000635	Buttons?Buttons, often made from synthetic materials such as polyester, nylon, or polycarbonate, can be a source of synthetic chemical contamination during their production, use, and disposal.	Textiles, leather & furnishings	Not Available
CEDs000642	Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.	Textiles, leather & furnishings	Not Available
CEDs000650	Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.	Textiles, leather & furnishings	Not Available
CEDs000679	Phosphatic Fertilisers?Phosphatic fertilizers are synthetic chemical products primarily composed of phosphorus, which is essential for plant growth.	Agriculture & land management	Not Available
CEDs000684	Cements?Cements are a composite material primarily used as a binding agent in construction applications, formed by the calcination of limestone and clay minerals at high temperatures.	Building & Construction	Not Available
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	Not Available
CEDs000688	Glass Coatings?Glass coatings are synthetic chemical formulations applied to glass surfaces to enhance properties such as durability, UV resistance, and aesthetic appeal.	Building & Construction	Not Available
CEDs000693	Silica Glass?Silica glass, primarily composed of silicon dioxide (SiO2), is widely used in various applications, including windows, glass facades, and insulation materials.	Building & Construction	Not Available
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	Not Available
CEDs000697	Submarines?Submarines, while essential for military and research purposes, can be a source of synthetic chemical contamination due to their use of various industrial chemicals.	Marine, shipping & aquaculture	Not Available
CEDs000727	Printing Machines Or Presses?Printing machines or presses commonly utilize synthetic chemicals such as inks, solvents, and cleaning agents.	Paper, pulp & fiber products	Not Available
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	Not Available
CEDs000738	Cooling Circuit Water?Cooling circuit water is utilized in various industrial processes to absorb and dissipate heat generated during operations.	Industrial manufacturing & chemical processing	Not Available
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	Not Available
CEDs000740	Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.	Paper, pulp & fiber products	Not Available
CEDs000741	Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.	Paper, pulp & fiber products	Not Available
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	Not Available

Pathways

3 pathwaysPathway Source: PathBank

Alendronate Action Pathway

Alendronic acid Drug Metabolism

Alendronic acid Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Isopentenyl-diphosphate Delta-isomerase 1	O35760	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.731 Applicability Domain 0.731 Statistical Significance 1.00e-05 Supporting Reference Compounds 1 E-value 0.0778492
Click to view 3D structure	Farnesyl pyrophosphate synthase	P05369	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.731 Applicability Domain 0.731 Statistical Significance 1.00e-05 Supporting Reference Compounds 1 E-value 0.0778492
Click to view 3D structure	Farnesyl pyrophosphate synthase	P14324	Humans	Predicted (SEA)	Prediction Confidence Score 0.591 Applicability Domain 0.731 Statistical Significance 3.00e-05 Supporting Reference Compounds 22 E-value 0.233548
Click to view 3D structure	Farnesyl pyrophosphate synthase	Q0GKD7	Leishmania donovani	Predicted (SEA)	Prediction Confidence Score 0.517 Applicability Domain 0.556 Statistical Significance 4.00e-05 Supporting Reference Compounds 14 E-value 0.311397
Click to view 3D structure	Geranylgeranyl pyrophosphate synthase	O95749	Humans	Predicted (SEA)	Prediction Confidence Score 0.511 Applicability Domain 0.556 Statistical Significance 5.00e-05 Supporting Reference Compounds 15 E-value 0.389246
Click to view 3D structure	Farnesyl pyrophosphate synthase	Q4QBL1	Leishmania major	Predicted (SEA)	Prediction Confidence Score 0.308 Applicability Domain 0.556 Statistical Significance 4.00e-05 Supporting Reference Compounds 5 E-value 0.311397
Click to view 3D structure	Sodium- and chloride-dependent GABA transporter 2	P31646	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.296 Applicability Domain 0.296 Low confidence Statistical Significance 2.20e-04 Supporting Reference Compounds 1 E-value 1.71268
Click to view 3D structure	Type IV secretion-like conjugative transfer relaxase protein TraI	B1LRJ1	Escherichia coli (strain SMS-3-5 / SECEC)	Predicted (SEA)	Prediction Confidence Score 0.28 Applicability Domain 0.28 Low confidence Statistical Significance 1.00e-05 Supporting Reference Compounds 1 E-value 0.0778492
Click to view 3D structure	Farnesyl diphosphate synthase	Q8WS26	Trypanosoma cruzi	Predicted (SEA)	Prediction Confidence Score 0.27 Applicability Domain 0.556 Statistical Significance 2.10e-04 Supporting Reference Compounds 5 E-value 1.63483
Click to view 3D structure	Geranylgeranyl pyrophosphate synthase BTS1	Q12051	Saccharomyces cerevisiae S288c	Predicted (SEA)	Prediction Confidence Score 0.262 Applicability Domain 0.297 Low confidence Statistical Significance 1.00e-04 Supporting Reference Compounds 4 E-value 0.778492
Click to view 3D structure	Hexokinase	Q8ST54	Trypanosoma cruzi	Predicted (SEA)	Prediction Confidence Score 0.257 Applicability Domain 0.556 Statistical Significance 3.70e-04 Supporting Reference Compounds 7 E-value 2.88042
Click to view 3D structure	Farnesyl diphosphate synthase	P22939	Escherichia coli (strain K12)	Predicted (SEA)	Prediction Confidence Score 0.254 Applicability Domain 0.333 Statistical Significance 7.00e-05 Supporting Reference Compounds 4 E-value 0.544945
Click to view 3D structure	Farnesyl diphosphate synthase	Q197X6	Toxoplasma gondii	Predicted (SEA)	Prediction Confidence Score 0.248 Applicability Domain 0.343 Statistical Significance 3.50e-04 Supporting Reference Compounds 4 E-value 2.72472
Click to view 3D structure	Phosphoglycerate kinase	P00560	Saccharomyces cerevisiae S288c	Predicted (SEA)	Prediction Confidence Score 0.235 Applicability Domain 0.235 Low confidence Statistical Significance 1.10e-04 Supporting Reference Compounds 1 E-value 0.856341
Click to view 3D structure	Carbonic anhydrase 14	Q9ULX7	Humans	Predicted (SEA)	Prediction Confidence Score 0.233 Applicability Domain 0.297 Low confidence Statistical Significance 0.113 Supporting Reference Compounds 172 E-value 879.696
Click to view 3D structure	Acetylpolyamine amidohydrolase	Q48935	Mycoplana ramosa	Predicted (SEA)	Prediction Confidence Score 0.231 Applicability Domain 0.231 Low confidence Statistical Significance 5.10e-04 Supporting Reference Compounds 1 E-value 3.97031
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	Prediction Confidence Score 0.23 Applicability Domain 0.297 Low confidence Statistical Significance 0.2394 Supporting Reference Compounds 372 E-value 1863.94
Click to view 3D structure	Butyrophilin subfamily 3 member A1	O00481	Humans	Predicted (SEA)	Prediction Confidence Score 0.223 Applicability Domain 0.297 Low confidence Statistical Significance 1.00e-04 Supporting Reference Compounds 3 E-value 0.778492
Click to view 3D structure	Spermine synthase	Q3SZA5	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.222 Applicability Domain 0.222 Low confidence Statistical Significance 7.00e-05 Supporting Reference Compounds 1 E-value 0.544945
Click to view 3D structure	Mitochondrial 2-oxodicarboxylate carrier	Q8BZ09	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.222 Applicability Domain 0.222 Low confidence Statistical Significance 7.00e-05 Supporting Reference Compounds 1 E-value 0.544945
Click to view 3D structure	Ditrans,polycis-undecaprenyl-diphosphate synthase ((2E,6E)-farnesyl-diphosphate specific)	P60472	Escherichia coli (strain K12)	Predicted (SEA)	Prediction Confidence Score 0.216 Applicability Domain 0.216 Low confidence Statistical Significance 0.0034 Supporting Reference Compounds 1 E-value 26.7023
Click to view 3D structure	Carbonic anhydrase 4	P22748	Humans	Predicted (SEA)	Prediction Confidence Score 0.213 Applicability Domain 0.273 Low confidence Statistical Significance 0.2207 Supporting Reference Compounds 193 E-value 1717.9
Click to view 3D structure	Deoxyhypusine synthase	Q9GSW0	Plasmodium falciparum	Predicted (SEA)	Prediction Confidence Score 0.212 Applicability Domain 0.212 Low confidence Statistical Significance 0.0023 Supporting Reference Compounds 1 E-value 18.2946
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	Prediction Confidence Score 0.21 Applicability Domain 0.297 Low confidence Statistical Significance 0.3796 Supporting Reference Compounds 332 E-value 2955.16
Click to view 3D structure	Putative agmatine deiminase	Q8DW17	Streptococcus mutans serotype c (strain ATCC 700610 / UA159)	Predicted (SEA)	Prediction Confidence Score 0.206 Applicability Domain 0.206 Low confidence Statistical Significance 7.40e-04 Supporting Reference Compounds 1 E-value 5.76084
Click to view 3D structure	Farnesyl pyrophosphate synthase	P14324	Humans	Known	The action of Alendronate on bone tissue is based partly on its affinity for hydroxyapatite, which is part of the mineral matrix of bone. Alendronate also targets farnesyl pyrophosphate (FPP) synthase. Nitrogen-containing bisphosphonates (such as pamidronate, alendronate, risedronate, ibandronate and zoledronate) appear to act as analogues of isoprenoid diphosphate lipids, thereby inhibiting FPP synthase, an enzyme in the mevalonate pathway. Inhibition of this enzyme in osteoclasts prevents the biosynthesis of isoprenoid lipids (FPP and GGPP) that are essential for the post-translational farnesylation and geranylgeranylation of small GTPase signalling proteins. This activity inhibits osteoclast activity and reduces bone resorption and turnover. In postmenopausal women, it reduces the elevated rate of bone turnover, leading to, on average, a net gain in bone mass.
Click to view 3D structure	Receptor-type tyrosine-protein phosphatase S	Q13332	Humans	Known	Not Available
Click to view 3D structure	Geranylgeranyl pyrophosphate synthase	O95749	Humans	Known	Not Available
Click to view 3D structure	Receptor-type tyrosine-protein phosphatase epsilon	P23469	Humans	Known	Not Available
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 4	P29074	Humans	Known	The action of Alendronate on bone tissue is based partly on its affinity for hydroxyapatite, which is part of the mineral matrix of bone. Alendronate also targets farnesyl pyrophosphate (FPP) synthase. Nitrogen-containing bisphosphonates (such as pamidronate, alendronate, risedronate, ibandronate and zoledronate) appear to act as analogues of isoprenoid diphosphate lipids, thereby inhibiting FPP synthase, an enzyme in the mevalonate pathway. Inhibition of this enzyme in osteoclasts prevents the biosynthesis of isoprenoid lipids (FPP and GGPP) that are essential for the post-translational farnesylation and geranylgeranylation of small GTPase signalling proteins. This activity inhibits osteoclast activity and reduces bone resorption and turnover. In postmenopausal women, it reduces the elevated rate of bone turnover, leading to, on average, a net gain in bone mass.
Click to view 3D structure	V-type proton ATPase catalytic subunit A	P38606	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00630

HMDB ID

HMDB0001915

FooDB ID

FDB022734

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

ALENDRONATE

METLIN ID

818

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Masahiko Dohi, Yuji Makino, Takao Hujii, “Sodium alendronate preparation for local administration.” U.S. Patent US5958908, issued September, 1997.

MSDS

Link

General References

Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [PubMed: 18048412]
Russell RG, Watts NB, Ebetino FH, Rogers MJ: Mechanisms of action of bisphosphonates: similarities and differences and their potential influence on clinical efficacy. Osteoporos Int. 2008 Jun;19(6):733-59. doi: 10.1007/s00198-007-0540-8. [PubMed: 18214569]
Virtanen SS, Vaananen HK, Harkonen PL, Lakkakorpi PT: Alendronate inhibits invasion of PC-3 prostate cancer cells by affecting the mevalonate pathway. Cancer Res. 2002 May 1;62(9):2708-14. [PubMed: 11980672]
Ezra A, Hoffman A, Breuer E, Alferiev IS, Monkkonen J, El Hanany-Rozen N, Weiss G, Stepensky D, Gati I, Cohen H, Tormalehto S, Amidon GL, Golomb G: A peptide prodrug approach for improving bisphosphonate oral absorption. J Med Chem. 2000 Oct 5;43(20):3641-52. [PubMed: 11020278]
Cremers SC, van Hogezand R, Banffer D, den Hartigh J, Vermeij P, Papapoulos SE, Hamdy NA: Absorption of the oral bisphosphonate alendronate in osteoporotic patients with Crohn's disease. Osteoporos Int. 2005 Dec;16(12):1727-30. Epub 2005 Jun 15. [PubMed: 15959617]
Sarno M, Sarno L, Baylink D, Drinkwater B, Farley S, Kleerekoper M, Lang R, Lappe J, Licata A, McClung M, Miller P, Nattrass S, Recker R, Schwartz EN, Tucci JR, Wolf S, Powell H, Tjersland G, Warnick GR: Excretion of sweat and urine pyridinoline crosslinks in healthy controls and subjects with established metabolic bone disease. Clin Chem Lab Med. 2001 Mar;39(3):223-8. [PubMed: 11350019]
Rossini M, Gatti D, Isaia G, Sartori L, Braga V, Adami S: Effects of oral alendronate in elderly patients with osteoporosis and mild primary hyperparathyroidism. J Bone Miner Res. 2001 Jan;16(1):113-9. [PubMed: 11149474]
Makowski GS, Ramsby ML: Autoactivation profiles of calcium-dependent matrix metalloproteinase-2 and -9 in inflammatory synovial fluid: effect of pyrophosphate and bisphosphonates. Clin Chim Acta. 2005 Aug;358(1-2):182-91. [PubMed: 15921672]
Yalcin F, Gurgan S, Gurgan T: The effect of menopause, hormone replacement therapy (HRT), alendronate (ALN), and calcium supplements on saliva. J Contemp Dent Pract. 2005 May 15;6(2):10-7. [PubMed: 15915200]
Rudge S, Hailwood S, Horne A, Lucas J, Wu F, Cundy T: Effects of once-weekly oral alendronate on bone in children on glucocorticoid treatment. Rheumatology (Oxford). 2005 Jun;44(6):813-8. Epub 2005 Feb 3. [PubMed: 15695300]
Ravn P, Thompson DE, Ross PD, Christiansen C: Biochemical markers for prediction of 4-year response in bone mass during bisphosphonate treatment for prevention of postmenopausal osteoporosis. Bone. 2003 Jul;33(1):150-8. [PubMed: 12919710]
Chesnut CH 3rd, Harris ST: Short-term effect of alendronate on bone mass and bone remodeling in postmenopausal women. Osteoporos Int. 1993;3 Suppl 3:S17-9. [PubMed: 8298198]
Yun MH, Kwon KI: High-performance liquid chromatography method for determining alendronate sodium in human plasma by detecting fluorescence: application to a pharmacokinetic study in humans. J Pharm Biomed Anal. 2006 Jan 23;40(1):168-72. Epub 2005 Aug 10. [PubMed: 16095861]
Drugs.com - http://www.drugs.com/cons/Alendronate.html

Alendronic acid (CED0002504)

Structure for CHEM002111: Alendronic acid

Structure