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Record Information
Version3.6
Creation Date2006-05-17 15:35:22 UTC
Update Date2016-02-11 01:05:05 UTC
HMDB IDHMDB01915
Secondary Accession NumbersNone
Metabolite Identification
Common NameAlendronic acid
DescriptionAlendronate (Fosamax, Merck) is a bisphosphonate drug used for osteoporosis and several other bone diseases. It is marketed alone as well as in combination with vitamin D (2,800 U, under the name Fosavance).
Structure
Thumb
Synonyms
ValueSource
(4-amino-1-Hydroxybutylidene)bisphosphonic acidChEBI
Acide alendroniqueChEBI
acido AlendronicoChEBI
Acidum alendronicumChEBI
AlendronateChEBI
(4-amino-1-Hydroxybutylidene)bisphosphonateGenerator
Alendronate sodiumHMDB
Alendronate sodium hydrateHMDB
FosamaxHMDB
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
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 KeyInChIKey=OGSPWJRAVKPPFI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganophosphorus compounds
ClassOrganic phosphonic acids and derivatives
Sub ClassBisphosphonates
Direct ParentBisphosphonates
Alternative Parents
Substituents
  • Bisphosphonate
  • Organophosphonic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility16.9 mg/mLALOGPS
logP-1.3ALOGPS
logP-4.2ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)0.69ChemAxon
pKa (Strongest Basic)9.91ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area161.31 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity47.37 m3·mol-1ChemAxon
Polarizability19.4 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-2930000000-99692afb4ed253251947View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-0900000000-d2c07307d66e1c7d52e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0kdl-9500000000-c82a6e6e898154627c7dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Intestine
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Alendronate pathwaySMP00095Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-4 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022734
KNApSAcK IDNot Available
Chemspider ID2004
KEGG Compound IDC07752
BioCyc IDALENDRONATE
BiGG IDNot Available
Wikipedia LinkAlendronic acid
NuGOwiki LinkHMDB01915
Metagene LinkHMDB01915
METLIN ID818
PubChem Compound2088
PDB IDNot Available
ChEBI ID2567
References
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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [16095861 ]