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Record Information
StatusExpected but not Quantified
Creation Date2006-05-17 15:35:22 UTC
Update Date2020-02-26 21:23:36 UTC
Secondary Accession Numbers
  • HMDB01915
Metabolite Identification
Common NameAlendronic acid
DescriptionAlendronic acid, also known as alendronate or acido alendronico, belongs to the class of organic compounds known as bisphosphonates. These are organic compounds containing two phosphonate groups linked together through a carbon atoms. Endocytic vesicles are acidified, releasing alendronic acid to the cytosol of osteoclasts where they induce apoptosis. It is marketed alone as well as in combination with vitamin D (2,800 U, under the name Fosavance). Alendronic acid is a very strong basic compound (based on its pKa). In humans, alendronic acid is involved in alendronate action pathway. In postmenopausal women, it reduces the elevated rate of bone turnover, leading to, on average, a net gain in bone mass. Alendronic acid is a potentially toxic compound.
(4-Amino-1-hydroxybutylidene)bisphosphonic acidChEBI
Acide alendroniqueChEBI
Acido alendronicoChEBI
Acidum alendronicumChEBI
Alendronate sodiumHMDB
Alendronate sodium hydrateHMDB
Sodium, alendronateHMDB
4-Amino-1-hydroxybutylidene 1,1-biphosphonateHMDB
Aminohydroxybutane bisphosphonateHMDB
4 Amino 1 hydroxybutylidene 1,1 biphosphonateHMDB
Alendronate monosodium salt, trihydrateHMDB
Bisphosphonate, aminohydroxybutaneHMDB
Chemical FormulaC4H13NO7P2
Average Molecular Weight249.096
Monoisotopic Molecular Weight249.016724799
IUPAC Name(4-amino-1-hydroxy-1-phosphonobutyl)phosphonic acid
Traditional Namealendronate
CAS Registry Number66376-36-1
InChI Identifier
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphonic acids and derivatives
Sub ClassBisphosphonates
Direct ParentBisphosphonates
Alternative Parents
  • 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 FrameworkAliphatic acyclic compounds
External Descriptors

Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility16.9 g/LALOGPS
pKa (Strongest Acidic)0.69ChemAxon
pKa (Strongest Basic)9.91ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area161.31 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity47.37 m³·mol⁻¹ChemAxon
Polarizability19.4 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9010000000-6b540b3cfe12455ee047Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-9020000000-f4a0f6418448b2108371Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-2930000000-99692afb4ed253251947Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-0900000000-d2c07307d66e1c7d52e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0kdl-9500000000-c82a6e6e898154627c7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0590000000-ed1b4585584330309b42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uyi-4900000000-42101c55bda7e112b2afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9330000000-8ac66f69531027a0950fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-2590000000-2c9bde6c398541c5cb71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-017i-6950000000-d1f8822b01485883083dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9000000000-7b5e5c1f9b218640040bSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Intestine
  • Prostate
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00630
Phenol Explorer Compound IDNot Available
FooDB IDFDB022734
KNApSAcK IDNot Available
Chemspider ID2004
KEGG Compound IDC07752
BiGG IDNot Available
Wikipedia LinkAlendronic_acid
PubChem Compound2088
PDB IDNot Available
ChEBI ID2567
Food Biomarker OntologyNot Available
VMH IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]