Heparin (CED0000506)

Record Information

Version

1.0

Creation Date

2009-07-05 03:16:06 UTC

Update Date

2026-08-29 05:25:43 UTC

SynCED ID

CED0000506

Secondary Accession Numbers

CHEM002092
T3D2566

Identification

Common Name

Heparin

Class

Small Molecule

Description

Heparin belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds. With an average molecular weight of 1,040 g/mol, Heparin is a heavy molecule. This endogenous compound has the chemical formula C26H41NO34S4 and exists as a solid at room temperature. It is detected in various tissues, including the liver, lung, mast cells, adipose tissue, adrenal cortex, adrenal gland, bladder, epidermis, fibroblasts, intestine, kidney, muscle, nerve cells, neuron, pancreas, placenta, platelet, prostate, skeletal muscle, spleen, stratum corneum, testes, and thyroid gland. Heparin functions biologically as a cofactor (PMC10901620, PMC3923226) and an anticoagulant (PMC10609962, PMC11417148). Its mechanism of action is antithrombin-dependent, acting mainly by accelerating the neutralization of certain activated coagulation factors by antithrombin. It interacts with antithrombin III, prothrombin, and factor X, and its antithrombotic effect correlates to the inhibition of factor Xa. Recorded protein targets include antithrombin-III (SERPINC1), prothrombin (F2), coagulation factor X (F10), P-selectin (SELP), platelet factor 4 (PF4), fibroblast growth factor receptor 2 (FGFR2), fibroblast growth factor 19 (FGF19), and fibroblast growth factor 2 (FGF2). Industrially, it is used as a softener and conditioner. In pharmaceutical and veterinary contexts, heparin is used as an antithrombotic agent, vasoprotective, or ophthalmological, with exposure routes including intraluminal, intraperitoneal, intravenous, irrigation, and subcutaneous administration. It is used to treat thrombosis (PMC11314107, PMC1492602, PMC3952273, PMC4165720, PMC9313999) and COVID-19 (PMC8000639), and it has therapeutic effects on stroke (PMC13479649) and inflammation (PMC10891305). Associated health effects include bleeding (PMC4165720, PMC9487313), thrombocytopenia (PMC1492602, PMC3952273), thrombosis (PMC3952273), osteoporosis (PMC10891305), and acute myeloid leukemia (PMC7500703).

Contaminant Type

Animal Toxin
Anticoagulant
Drug
Ester
Fibrinolytic Agent
Food Toxin
Heparin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
alpha-Heparin	HMDB
Clivarine	HMDB
Heparin sodium	HMDB
Arteven	HMDB
Bemiparin	HMDB
Certoparin	HMDB
Clexane	HMDB
Dalteparin	HMDB
Enoxaparin	HMDB
Eparina	HMDB
Fraxiparin	HMDB
Heparin sulfate	HMDB
Heparin sulphate	HMDB
Heparinate	HMDB
Heparinic acid	HMDB
Heparinsodiumsalt	HMDB
Thromboliquine	HMDB

Chemical Formula

C₂₆H₄₁NO₃₄S₄

Average Molecular Mass

1039.850 g/mol

Monoisotopic Mass

1039.039 g/mol

CAS Registry Number

9005-49-6

IUPAC Name

Not Available

Traditional Name

Not Available

SMILES

CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@@H]2[C@@H](O)O[C@H](O[C@H]3[C@H](O)[C@@H](OS(O)(=O)=O)C(O)O[C@H]3C(O)=O)[C@H](OS(O)(=O)=O)[C@H]2CS(O)(=O)=O)O[C@@H]1C(O)=O

InChI Identifier

InChI=1S/C26H41NO34S4/c1-4(28)27-7-9(30)8(29)6(2-52-63(43,44)45)53-24(7)56-15-10(31)11(32)25(58-19(15)21(36)37)55-13-5(3-62(40,41)42)14(60-64(46,47)48)26(59-22(13)38)57-16-12(33)17(61-65(49,50)51)23(39)54-18(16)20(34)35/h5-19,22-26,29-33,38-39H,2-3H2,1H3,(H,27,28)(H,34,35)(H,36,37)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)/t5-,6+,7+,8+,9+,10+,11+,12-,13-,14+,15-,16-,17+,18+,19-,22-,23?,24+,25+,26-/m0/s1

InChI Key

ZFGMDIBRIDKWMY-PASTXAENSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as disaccharide sulfates. These are disaccharides carrying one or more sulfate group on a sugar unit.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Disaccharide sulfates

Alternative Parents

Substituents

Disaccharide sulfate
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Hydroxy acid
Sulfuric acid monoamide
Oxane
Pyran
Sulfuric acid monoester
Sulfate-ester
Sulfuric acid ester
Alkyl sulfate
Organic sulfuric acid or derivatives
Hemiacetal
Secondary alcohol
Carboxylic acid
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Acetal
Organopnictogen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Bladder
Epidermis
Fibroblasts
Intestine
Kidney
Liver
Lung
Mast Cell
Muscle
Nerve Cells
Neuron
Pancreas
Placenta
Platelet
Prostate
Skeletal Muscle
Spleen
Stratum Corneum
Testes
Thyroid Gland

Applications

anticoagulant

Biological Roles

cofactor (PMC10901620 , PMC3923226.2 )?A chemical that is required by an enzyme for its intended chemical activity
anticoagulant (PMC10609962 )?

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Soluble

Predicted Properties

Property	Value	Source
Water Solubility	6.57 g/L	ALOGPS
logP	-2.4	ALOGPS
logS	-2	ALOGPS
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-024i-9080060104-dc860b4a7ce58fd52110	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-1390361204-e7c2baa60fadc54b4c3b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-3690210001-0728ab2405590f54c338	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00su-9440030785-2eb4eb48190a77309146	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-6091020418-6cfda3db3a285e8c209a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00fr-3092050311-5d7837df267ca3df6ece	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Heparin-induced thrombocytopenia (HIT) is caused by the formation of abnormal antibodies that activate platelets. Heparin occurs naturally in the human body, but the development of HIT antibodies suggests heparin sulfate may act as a hapten, and thus be targeted by the immune system. In HIT, the immune system forms antibodies against heparin when it is bound to a protein called platelet factor 4 (PF4). These antibodies are usually of the IgG class and their development usually takes about five days. However, those who have been exposed to heparin in the last few months may still have circulating IgG, as IgG-type antibodies generally continue to be produced even when their precipitant has been removed. This is similar to immunity against certain microorganisms, with the difference that the HIT antibody does not persist more than three months. HIT antibodies have been found in individuals with thrombocytopenia and thrombosis who had no prior exposure to heparin sulfate, but the majority are found in people who are receiving heparin. The IgG antibodies form a complex with heparin and PF4 in the bloodstream. The tail of the antibody then binds to the FcγIIa receptor, a protein on the surface of the platelet. This results in platelet activation and the formation of platelet microparticles, which initiate the formation of blood clots; the platelet count falls as a result, leading to thrombocytopenia. (Wikipedia) The cause of the serum aminotransferase elevations during heparin therapy is not known, but it is likely due to a direct hepatotoxic effect on the liver (28). Heparin-induced hyperkalemia is the result of heparin-induced aldosterone suppression (Wikipedia). The most important, but probably not the only mechanism of aldosterone inhibition appears to involve reduction in both the number and affinity of the angiotensin-II receptors in the zona glomerulosa (25). Alopecia connected to chronic heparin use may be due to the antimitotic effect of heparin on the epithelial cells (26). Heparin causes bone loss by decreasing bone formation. The few studies of the mechanism of bone loss have revealed decreased bone formation, increasing bone resorption, or both (29).

Carcinogenicity (IARC Classification)

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

Minimum Risk Level

Not Available

Symptoms

Heparin sodium - Mouse, median lethal dose greater than 5000 mg/kg. Another side effect is heparin induced thrombocytopenia (HIT syndrome). HIT is caused by an immunological reaction that makes platelets form clots within the blood vessels, thereby using up coagulation factors

Treatment

Protamine sulfate (1 mg per 100 units of heparin that had been given over the past four hours) has been given to counteract the anticoagulant effect of heparin. (Wikipedia)

Health Effects

Health Effect	Relationship	Direction	Reference
inflammation?	has_therapeutic_effect_on	Not Available	PMC10891305
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)	associated_with	Not Available	PMC10891305
stroke?	has_therapeutic_effect_on	Not Available	PMC13479649
thrombocytopenia?	associated_with	Not Available	PMC1492602 , PMC3952273
bleeding?A losing of blood as a result of injury oir illness.	associated_with	Not Available	PMC4165720 , PMC4165720 , PMC9487313
COVID-19?	is_treatment_for	Not Available	PMC8000639
thrombosis?A formation of a blood clot inside a blood vessel, obstructing the flow of blood through the circulatory system.	is_treatment_for	Not Available	PMC11314107 , PMC1492602 , PMC3952273 , PMC4165720 , PMC9313999
thrombosis?A formation of a blood clot inside a blood vessel, obstructing the flow of blood through the circulatory system.	associated_with	Not Available	PMC3952273
acute myeloid leukemia?Acute myeloid leukemia (AML) is a cancer of the myeloid line of blood cells, characterized by the rapid growth of abnormal cells that build up in the bone marrow and blood and interfere with normal blood cell production. Symptoms may include feeling tired, shortness of breath, easy bruising and bleeding, and increased risk of infection. Occasionally, spread may occur to the brain, skin, or gums. As an acute leukemia, AML progresses rapidly and is typically fatal within weeks or months if left untreated. Risk factors include smoking, previous chemotherapy or radiation therapy, myelodysplastic syndrome, and exposure to the chemical benzene. AML affected about one million people and resulted in 147,000 deaths globally. It most commonly occurs in older adults. Males are affected more often than females.	associated_with	Not Available	PMC7500703
osteosarcoma?	is_treatment_for	Not Available	PMC12205921
coronary thrombosis?	is_treatment_for	Not Available	PMC8543113

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000233	Brushes?Brushes used in personal care and cosmetics can be a source of synthetic chemical contamination due to the materials and coatings used in their manufacturing.	Personal care & cosmetics	Not Available
CEDs000273	Antithrombotic agents?Antithrombotic agents are synthetic chemicals designed to prevent blood clot formation, commonly used in the treatment and management of cardiovascular diseases.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000292	Vasoprotectives?Vasoprotectives are synthetic compounds designed to enhance vascular health and improve blood circulation.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000405	Ophthalmologicals?Ophthalmologicals are a category of synthetic chemicals used primarily for the treatment of eye disorders, including medications such as anti-inflammatories, antibiotics, and lubricants.	Healthcare, pharmaceuticals & veterinary products	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
CEDs000527	Magnets?Magnets, commonly used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials used in their production.	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
CEDs000549	Preparation Of Wine Or Sparkling Wine?The preparation of wine or sparkling wine involves various stages, including fermentation, aging, and bottling, which can introduce potential sources of synthetic chemical contamination.	Food, food processing & cookware	Not Available
CEDs000552	Processing Meats?Processing meats can lead to synthetic chemical contamination primarily through the use of additives and preservatives.	Food, food processing & cookware	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
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
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
CEDs000607	Rodenticides(1)?Rodenticides are synthetic chemicals specifically formulated to control rodent populations, serving as a crucial tool in managing pests that can damage crops and spread diseases.	Agriculture & land management	Not Available
CEDs000608	Rodenticides?Rodenticides are chemical substances specifically designed to control rodent populations by causing death through various mechanisms, including anticoagulation or neurotoxicity.	Agriculture & land management	Not Available
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	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
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	Not Available
CEDs000617	Lip Care Products?Lip care products, including lipsticks, balms, and glosses, often contain a variety of synthetic chemicals such as parabens, phthalates, and synthetic fragrances.	Personal care & cosmetics	Not Available
CEDs000618	Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.	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
CEDs000678	Nitrogenous Fertilisers?Nitrogenous fertilizers are synthetic chemical compounds primarily used to enhance plant growth by supplying essential nitrogen, a crucial nutrient for photosynthesis and protein synthesis.	Agriculture & land management	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
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
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
CEDs000743	Sludge Treatment?Sludge treatment involves the processing of waste materials generated from wastewater treatment plants, which often contain a variety of organic and inorganic substances.	Wastewater, sanitation & biosolids	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

5 pathwaysPathway Source: PathBank

Heparin.

Fc Epsilon Receptor I Signaling in Mast Cells

Heparin Action Pathway

Heparin

Heparin Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	CD44 antigen	P16070	Humans	Predicted (SEA)	Prediction Confidence Score 0.548 Applicability Domain 0.548 Statistical Significance 1.00e-05 Supporting Reference Compounds 1 E-value 0.0778492
Click to view 3D structure	CD44 antigen	P15379	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.548 Applicability Domain 0.548 Statistical Significance 1.00e-05 Supporting Reference Compounds 1 E-value 0.0778492
Click to view 3D structure	Neurotrophic factor BDNF precursor form	P23560	Humans	Predicted (SEA)	Prediction Confidence Score 0.522 Applicability Domain 0.522 Statistical Significance 1.00e-05 Supporting Reference Compounds 2 E-value 0.0778492
Click to view 3D structure	Pleiotrophin	P21246	Humans	Predicted (SEA)	Prediction Confidence Score 0.522 Applicability Domain 0.522 Statistical Significance 1.00e-05 Supporting Reference Compounds 1 E-value 0.0778492
Click to view 3D structure	Bone morphogenetic protein 6	P22004	Humans	Predicted (SEA)	Prediction Confidence Score 0.404 Applicability Domain 0.404 Statistical Significance 5.00e-05 Supporting Reference Compounds 1 E-value 0.389246
Click to view 3D structure	Platelet factor 4	P02776	Humans	Predicted (SEA)	Prediction Confidence Score 0.404 Applicability Domain 0.404 Statistical Significance 5.00e-05 Supporting Reference Compounds 1 E-value 0.389246
Click to view 3D structure	Interferon gamma	P01579	Humans	Predicted (SEA)	Prediction Confidence Score 0.339 Applicability Domain 0.404 Statistical Significance 7.00e-05 Supporting Reference Compounds 2 E-value 0.544945
Click to view 3D structure	Midkine	P21741	Humans	Predicted (SEA)	Prediction Confidence Score 0.331 Applicability Domain 0.522 Statistical Significance 2.00e-05 Supporting Reference Compounds 3 E-value 0.155698
Click to view 3D structure	N-acetyllactosaminide alpha-1,3-galactosyltransferase	P50127	Sus scrofa	Predicted (SEA)	Prediction Confidence Score 0.301 Applicability Domain 0.301 Statistical Significance 3.10e-04 Supporting Reference Compounds 1 E-value 2.41333
Click to view 3D structure	Endopolygalactyuronase	P79074	Chondrostereum purpureum	Predicted (SEA)	Prediction Confidence Score 0.289 Applicability Domain 0.289 Low confidence Statistical Significance 3.00e-05 Supporting Reference Compounds 1 E-value 0.233548
Click to view 3D structure	Trehalose-phosphatase	A8NS89	Brugia malayi	Predicted (SEA)	Prediction Confidence Score 0.284 Applicability Domain 0.284 Low confidence Statistical Significance 8.20e-04 Supporting Reference Compounds 1 E-value 6.38364
Click to view 3D structure	Killer cell lectin-like receptor subfamily B member 1A	P27471	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.263 Applicability Domain 0.349 Statistical Significance 2.30e-04 Supporting Reference Compounds 2 E-value 1.79053
Click to view 3D structure	Antithrombin-III	P01008	Humans	Predicted (SEA)	Prediction Confidence Score 0.257 Applicability Domain 0.43 Statistical Significance 8.00e-05 Supporting Reference Compounds 3 E-value 0.622794
Click to view 3D structure	Alpha-amylase	Q7M328	Sus scrofa domesticus	Predicted (SEA)	Prediction Confidence Score 0.247 Applicability Domain 0.247 Low confidence Statistical Significance 2.30e-04 Supporting Reference Compounds 1 E-value 1.79053
Click to view 3D structure	Heparanase	Q9Y251	Humans	Predicted (SEA)	Prediction Confidence Score 0.238 Applicability Domain 0.355 Statistical Significance 3.30e-04 Supporting Reference Compounds 11 E-value 2.56902
Click to view 3D structure	E-selectin	P98105	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.237 Applicability Domain 0.237 Low confidence Statistical Significance 2.90e-04 Supporting Reference Compounds 1 E-value 2.25763
Click to view 3D structure	Fibroblast growth factor 1	P05230	Humans	Predicted (SEA)	Prediction Confidence Score 0.235 Applicability Domain 0.356 Statistical Significance 2.00e-04 Supporting Reference Compounds 6 E-value 1.55698
Click to view 3D structure	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	P54751	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.233 Applicability Domain 0.233 Low confidence Statistical Significance 6.90e-04 Supporting Reference Compounds 1 E-value 5.3716
Click to view 3D structure	Endo-beta-N-acetylglucosaminidase	Q9ZB22	Arthrobacter protophormiae	Predicted (SEA)	Prediction Confidence Score 0.227 Applicability Domain 0.227 Low confidence Statistical Significance 8.60e-04 Supporting Reference Compounds 1 E-value 6.69503
Click to view 3D structure	Fibronectin	P02751	Humans	Predicted (SEA)	Prediction Confidence Score 0.226 Applicability Domain 0.226 Low confidence Statistical Significance 2.20e-04 Supporting Reference Compounds 1 E-value 1.71268
Click to view 3D structure	N-acetylglucosamine-6-phosphate deacetylase	Q9Y303	Humans	Predicted (SEA)	Prediction Confidence Score 0.22 Applicability Domain 0.22 Low confidence Statistical Significance 0.001 Supporting Reference Compounds 1 E-value 7.94062
Click to view 3D structure	Sialic acid-binding Ig-like lectin 7	Q9Y286	Humans	Predicted (SEA)	Prediction Confidence Score 0.218 Applicability Domain 0.218 Low confidence Statistical Significance 2.50e-04 Supporting Reference Compounds 1 E-value 1.94623
Click to view 3D structure	Fibroblast growth factor 2	P09038	Humans	Predicted (SEA)	Prediction Confidence Score 0.217 Applicability Domain 0.275 Low confidence Statistical Significance 3.80e-04 Supporting Reference Compounds 9 E-value 2.95827
Click to view 3D structure	Beta-1,4-galactosyltransferase 1	P08037	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.21 Applicability Domain 0.276 Low confidence Statistical Significance 0.0036 Supporting Reference Compounds 2 E-value 28.1036
Click to view 3D structure	Gap junction alpha-1 protein	P17302	Humans	Predicted (SEA)	Prediction Confidence Score 0.208 Applicability Domain 0.208 Low confidence Statistical Significance 9.80e-04 Supporting Reference Compounds 1 E-value 7.62922
Click to view 3D structure	Prothrombin	P00734	Humans	Known	The mechanism of action of heparin is antithrombin-dependent. It acts mainly by accelerating the rate of the neutralization of certain activated coagulation factors by antithrombin, but other mechanisms may also be involved. The antithrombotic effect of heparin is well correlated to the inhibition of factor Xa. Heparin interacts with antithrombin III, prothrombin and factor X.
Click to view 3D structure	Antithrombin-III	P01008	Humans	Known	The mechanism of action of heparin is antithrombin-dependent. It acts mainly by accelerating the rate of the neutralization of certain activated coagulation factors by antithrombin, but other mechanisms may also be involved. The antithrombotic effect of heparin is well correlated to the inhibition of factor Xa. Heparin interacts with antithrombin III, prothrombin and factor X.
Click to view 3D structure	Coagulation factor X	P00742	Humans	Known	The mechanism of action of heparin is antithrombin-dependent. It acts mainly by accelerating the rate of the neutralization of certain activated coagulation factors by antithrombin, but other mechanisms may also be involved. The antithrombotic effect of heparin is well correlated to the inhibition of factor Xa. Heparin interacts with antithrombin III, prothrombin and factor X.
Click to view 3D structure	Heparanase	Q9Y251	Humans	Known	The mechanism of action of heparin is antithrombin-dependent. It acts mainly by accelerating the rate of the neutralization of certain activated coagulation factors by antithrombin, but other mechanisms may also be involved. The antithrombotic effect of heparin is well correlated to the inhibition of factor Xa. Heparin interacts with antithrombin III, prothrombin and factor X.
Click to view 3D structure	P-selectin	P16109	Humans	Known	The mechanism of action of heparin is antithrombin-dependent. It acts mainly by accelerating the rate of the neutralization of certain activated coagulation factors by antithrombin, but other mechanisms may also be involved. The antithrombotic effect of heparin is well correlated to the inhibition of factor Xa. Heparin interacts with antithrombin III, prothrombin and factor X.
Click to view 3D structure	Coagulation factor IX	P00740	Humans	Known	The mechanism of action of heparin is antithrombin-dependent. It acts mainly by accelerating the rate of the neutralization of certain activated coagulation factors by antithrombin, but other mechanisms may also be involved. The antithrombotic effect of heparin is well correlated to the inhibition of factor Xa. Heparin interacts with antithrombin III, prothrombin and factor X.
Click to view 3D structure	Fibroblast growth factor 19	O95750	Humans	Known	Not Available
Click to view 3D structure	Fibroblast growth factor 2	P09038	Humans	Known	Not Available
Click to view 3D structure	Fibroblast growth factor 4	P08620	Humans	Known	Not Available
Click to view 3D structure	Fibroblast growth factor receptor 1	P11362	Humans	Known	Not Available
Click to view 3D structure	Fibroblast growth factor receptor 2	P21802	Humans	Known	Not Available
Click to view 3D structure	Fibroblast growth factor receptor 4	P22455	Humans	Known	Not Available
Click to view 3D structure	Platelet factor 4	P02776	Humans	Known	Not Available
Click to view 3D structure	Vascular endothelial growth factor A, long form	P15692	Humans	Known	Not Available
Click to view 3D structure	Thrombin	Q28731	Oryctolagus cuniculus	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0001394

FooDB ID

FDB022599

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

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PDB ID

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Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

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ECMDB ID

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References

Synthesis Reference

Fernando Fussi, Gianfranco Fedeli, “Oligo-heteropolysaccharides having a heparin-like activity method for their preparation and pharmaceutical compositions based thereon.” U.S. Patent US4757057, issued June, 1952.

MSDS

Link

General References

Linhardt RJ, Gunay NS: Production and chemical processing of low molecular weight heparins. Semin Thromb Hemost. 1999;25 Suppl 3:5-16. [PubMed: 10549711]
Ferro DR, Provasoli A, Ragazzi M, Casu B, Torri G, Bossennec V, Perly B, Sinay P, Petitou M, Choay J: Conformer populations of L-iduronic acid residues in glycosaminoglycan sequences. Carbohydr Res. 1990 Jan 15;195(2):157-67. [PubMed: 2331699]
Mulloy B, Forster MJ, Jones C, Davies DB: N.m.r. and molecular-modelling studies of the solution conformation of heparin. Biochem J. 1993 Aug 1;293 ( Pt 3):849-58. [PubMed: 8352752]
Hirsh J, Raschke R: Heparin and low-molecular-weight heparin: the Seventh ACCP Conference on Antithrombotic and Thrombolytic Therapy. Chest. 2004 Sep;126(3 Suppl):188S-203S. [PubMed: 15383472]
Petitou M, Herault JP, Bernat A, Driguez PA, Duchaussoy P, Lormeau JC, Herbert JM: Synthesis of thrombin-inhibiting heparin mimetics without side effects. Nature. 1999 Apr 1;398(6726):417-22. [PubMed: 10201371]
Spruill WJ, Wade WE, Huckaby WG, Leslie RB: Achievement of anticoagulation by using a weight-based heparin dosing protocol for obese and nonobese patients. Am J Health Syst Pharm. 2001 Nov 15;58(22):2143-6. [PubMed: 11760916]
McDonald MM, Jacobson LJ, Hay WW Jr, Hathaway WE: Heparin clearance in the newborn. Pediatr Res. 1981 Jul;15(7):1015-8. [PubMed: 7254945]
Betz G, Nowbakht P, Imboden R, Imanidis G: Heparin penetration into and permeation through human skin from aqueous and liposomal formulations in vitro. Int J Pharm. 2001 Oct 9;228(1-2):147-59. [PubMed: 11576777]
Sun Y, Chai TC: Effects of dimethyl sulphoxide and heparin on stretch-activated ATP release by bladder urothelial cells from patients with interstitial cystitis. BJU Int. 2002 Sep;90(4):381-5. [PubMed: 12175393]
Kandrotas RJ: Heparin pharmacokinetics and pharmacodynamics. Clin Pharmacokinet. 1992 May;22(5):359-74. [PubMed: 1505142]
Delhumeau A, Moreau X, Chapotte C, Houi N, Bigorgne JC: Heparin-associated thrombocytopenia syndrome: an underestimated etiology of adrenal hemorrhage. Intensive Care Med. 1993;19(8):475-7. [PubMed: 8294632]
Lortat-Jacob H, Brisson C, Guerret S, Morel G: Non-receptor-mediated tissue localization of human interferon-gamma: role of heparan sulfate/heparin-like molecules. Cytokine. 1996 Jul;8(7):557-66. [PubMed: 8891437]
Harig F, Meier C, Hakami L, Strasser R, Bretzger J, Munch F, Vestweber-Wilmes E, Singer H, Weyand M, Cesnjevar R: Does the additional use of heparin-coated extracorporeal circuits (ECC) optimize the effect of modified ultrafiltration (MUF) in pediatric perfusion? Thorac Cardiovasc Surg. 2006 Apr;54(3):168-72. [PubMed: 16639677]
Tonda R, Galan AM, Pino M, Hernandez MR, Ayats C, Pomar JL, Ordinas A, Escolar G: In vitro evaluation of platelet reactivity toward annuloplasty devices treated with heparin coating: studies under flow conditions. J Biomed Mater Res A. 2005 Oct 1;75(1):192-8. [PubMed: 16044416]
Haram K, Bjorge L, Sandset PM: Successful preconceptional prophylactic treatment with combined acetyl salicylic acid and low-molecular heparin (Fragmin) in a case of antiphospholipid-antibody syndrome with prior life-threatening hemolysis, elevated liver enzymes and low-platelet syndrome: a case report. Acta Obstet Gynecol Scand. 2005 Dec;84(12):1213-4. [PubMed: 16305714]
Harding SA, Din JN, Sarma J, Josephs DH, Fox KA, Newby DE: Promotion of proinflammatory interactions between platelets and monocytes by unfractionated heparin. Heart. 2006 Nov;92(11):1635-8. Epub 2006 May 18. [PubMed: 16709700]
Christensen K, Larsson R, Emanuelsson H, Elgue G, Larsson A: Effects on blood compatibility in vitro by combining a direct P2Y12 receptor inhibitor and heparin coating of stents. Platelets. 2006 Aug;17(5):318-27. [PubMed: 16928604]
Applebaum DM, Goldberg AP, Pykalisto OJ, Brunzell JD, Hazzard WR: Effect of estrogen on post-heparin lipolytic activity. Selective decline in hepatic triglyceride lipase. J Clin Invest. 1977 Apr;59(4):601-8. [PubMed: 845252]
Yeh RW, Everett BM, Foo SY, Dorer DJ, Laposata M, Van Cott EM, Jang IK: Predictors for the development of elevated anti-heparin/platelet factor 4 antibody titers in patients undergoing cardiac catheterization. Am J Cardiol. 2006 Aug 1;98(3):419-21. Epub 2006 Jun 12. [PubMed: 16860036]
Harel A, Fainaru M, Rubinstein M, Tal N, Schwartz M: Fish apolipoprotein-A-I has heparin binding activity: implication for nerve regeneration. J Neurochem. 1990 Oct;55(4):1237-43. [PubMed: 2118944]
Bengtsson E, Aspberg A, Heinegard D, Sommarin Y, Spillmann D: The amino-terminal part of PRELP binds to heparin and heparan sulfate. J Biol Chem. 2000 Dec 29;275(52):40695-702. [PubMed: 11007795]
Brunnee T, Reddigari SR, Shibayama Y, Kaplan AP, Silverberg M: Mast cell derived heparin activates the contact system: a link to kinin generation in allergic reactions. Clin Exp Allergy. 1997 Jun;27(6):653-63. [PubMed: 9208186]
Weaver JC, Vanbever R, Vaughan TE, Prausnitz MR: Heparin alters transdermal transport associated with electroporation. Biochem Biophys Res Commun. 1997 May 29;234(3):637-40. [PubMed: 9175766]
Williams MS, Ng'alla LS: Heparin therapy leads to platelet activation and prolongation of PFA-100 closure time. J Cardiovasc Pharmacol Ther. 2005 Dec;10(4):273-80. [PubMed: 16382263]
Oster JR, Singer I, Fishman LM: Heparin-induced aldosterone suppression and hyperkalemia. Am J Med. 1995 Jun;98(6):575-86. [PubMed: 7778574]
Sarris E, Tsele E, Bagiatoudi G, Salpigidis K, Stavrianaki D, Kaklamanis L, Siakotos M: Diffuse alopecia in a hemodialysis patient caused by a low-molecular-weight heparin, tinzaparin. Am J Kidney Dis. 2003 May;41(5):E15. [PubMed: 12778433]
Drugs.com - http://www.drugs.com/cons/Heparin.html
LiverTox - Heparin - http://livertox.nih.gov/Heparin.htm
UpToDate - Drugs that affect bone metabolism - http://www.uptodate.com/contents/drugs-that-affect-bone-metabolism
American Academy of Pediatrics Committee on Fetus and Newborn and Committee on Drugs. Benzyl alcohol: toxic agent in neonatal units. Pediatrics. 1983; 72:356-8. [PubMed] [IDIS 175725]
Anon. Benzyl alcohol may be toxic to newborns. FDA Drug Bull. 1982; 12:10-1. [PubMed]
Anon. Neonatal deaths associated with use of benzyl alcohol—United States. MMWR Morb Mortal Wkly Rep. 1982; 31:290-1. [PubMed] [IDIS 150868]
Abbott Laboratories. Heparin lock flush solution, USP 100 USP units/mL prescribing information. North Chicago, IL; 1998 Jul.

Heparin (CED0000506)

Structure for CHEM002092: Heparin

Structure