1.0 2009-07-15 20:43:20 UTC 2026-05-14 16:44:34 UTC T3D2666 Alendronic acid SmallMolecule 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). Drug Food Toxin Synthetic Toxin Organic Compound Amine Drug Food Toxin Antihypocalcemic Agent Bisphosphonate Bone Density Conservation Agent Antiresorptive Metabolite Synthetic Compound Human Neurotoxin (4-Amino-1-hydroxybutylidene)bisphosphonic acid Acide Alendronique Acido Alendronico Acidum Alendronicum Alendronate Alendronate Sodium Alendronate sodium hydrate Alenotop Alned Arendal Beenos Berlex Binosto Denfos Densidron Dronat Durost Fixopan Forosa Fosagen Fosalen Fosamax Fosmin Fostolin Fosval Huesobone Lendrate Oseolen Ostemax C4H13NO7P2 249.096 249.016724799 (4-amino-1-hydroxy-1-phosphonobutyl)phosphonic acid alendronate 66376-36-1 NCCCC(O)(P(O)(O)=O)P(O)(O)=O 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) OGSPWJRAVKPPFI-UHFFFAOYSA-N Organic compounds Organic acids and derivatives Organic phosphonic acids and derivatives Bisphosphonates Bisphosphonates Hydrocarbon derivatives Monoalkylamines Organic oxides Organic phosphonic acids Organooxygen compounds Organophosphorus compounds Organopnictogen compounds Aliphatic acyclic compound Amine Bisphosphonate Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organophosphonic acid Organophosphorus compound Organopnictogen compound Primary aliphatic amine Primary amine Aliphatic acyclic compounds 1,1-bis(phosphonic acid) primary amino compound Detected and Not Quantified Exogenous Cytoplasm Membrane Intestine Prostate Alendronate Action Pathway SMP0000095 Alendronic acid Drug Metabolism SMP0130694 Alendronic acid Drug Metabolism Action Pathway SMP0143076 Solid White powder. melting_point 234 dec°C solubility 1mg/L logp -4.3 logp -1.34 ALOGPS logs -1.17 ALOGPS solubility 1.69e+01 g/l ALOGPS logp -4.2 ChemAxon pka_strongest_acidic 0.69 ChemAxon pka_strongest_basic 9.91 ChemAxon iupac (4-amino-1-hydroxy-1-phosphonobutyl)phosphonic acid ChemAxon average_mass 249.096 ChemAxon mono_mass 249.016724799 ChemAxon smiles NCCCC(O)(P(O)(O)=O)P(O)(O)=O ChemAxon formula C4H13NO7P2 ChemAxon inchi 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) ChemAxon inchikey OGSPWJRAVKPPFI-UHFFFAOYSA-N ChemAxon polar_surface_area 161.31 ChemAxon refractivity 47.37 ChemAxon polarizability 19.4 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Relative to an intravenous (IV) reference dose, the mean oral bioavailability of alendronate in women was 0.7% for doses ranging from 5 to 40 mg when administered after an overnight fast and two hours before a standardized breakfast. Oral bioavailability of the 10 mg tablet in men (0.59%) was similar to that in women (0.78%) when administered after an overnight fast and 2 hours before breakfast. 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. There is no evidence that alendronate is metabolized in humans or animals. Route of Elimination: Following a single IV dose of [14C]alendronate, approximately 50% of the radioactivity was excreted in the urine within 72 hours and little or no radioactivity was recovered in the feces. Half Life: >10 years No indication of carcinogenicity to humans (not listed by IARC). For the treatment and prevention of osteoporosis in women and Paget's disease of bone in both men and women. #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3bf3124248> 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." DB00630 HMDB01915 2088 CHEMBL870 2004 C07752 125700 145000 2567 ALENDRONATE Alendronic acid Alendronate 18048412 18214569 11980672 11020278 15959617 11350019 11149474 15921672 15915200 15695300 12919710 8298198 16095861 Drugs.com: http://www.drugs.com/cons/Alendronate.html BE0000776 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. Inhibitory 0.0442 uM BindingDB 25313 Inhibitory 0.3931 uM BindingDB 25313 IC50 0.05 uM BindingDB 25313 IC50 0.26 uM BindingDB 25313 IC50 0.95 uM BindingDB 25313 IC50 0.955 uM BindingDB 25313 IC50 2.249 uM BindingDB 25313 BE0003567 BE0003570 IC50 436.52 uM BindingDB 25313 IC50 440 uM BindingDB 25313 BE0004801 BE0003568 BE0000980 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. BE0003569