alendronate   

GtoPdb Ligand ID: 3141

Synonyms: ABDP | BPH 1 | Fosamax® | MK-217
alendronate is an approved drug (FDA (1995), EMA (2005))
Compound class: Synthetic organic
Comment: Alendronate is a bisphosphonate drug.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 6
Rotatable bonds 5
Topological polar surface area 180.93
Molecular weight 249.02
XLogP -4.3
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES NCCCC(P(=O)(O)O)(P(=O)(O)O)O
Isomeric SMILES NCCCC(P(=O)(O)O)(P(=O)(O)O)O
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)
InChI Key OGSPWJRAVKPPFI-UHFFFAOYSA-N
References
1. Bergstrom JD, Bostedor RG, Masarachia PJ, Reszka AA, Rodan G. (2000)
Alendronate is a specific, nanomolar inhibitor of farnesyl diphosphate synthase.
Arch. Biochem. Biophys., 373 (1): 231-41. [PMID:10620343]
2. Dunford JE, Thompson K, Coxon FP, Luckman SP, Hahn FM, Poulter CD, Ebetino FH, Rogers MJ. (2001)
Structure-activity relationships for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates.
J. Pharmacol. Exp. Ther., 296 (2): 235-42. [PMID:11160603]