Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H12NO7P2.Na.3H2O |
Molecular Weight | 325.1237 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.[Na+].NCCCC(O)(P(O)(O)=O)P(O)([O-])=O
InChI
InChIKey=DCSBSVSZJRSITC-UHFFFAOYSA-M
InChI=1S/C4H13NO7P2.Na.3H2O/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);;3*1H2/q;+1;;;/p-1
Alendronic acid is a bisphosphonate drug used for osteoporosis, osteogenesis imperfecta, and several other bone diseases. It is marketed alone as well as in combination with vitamin D. Alendronate inhibits osteoclast-mediated bone-resorption. Like all bisphosphonates, it is chemically related to inorganic pyrophosphate, the endogenous regulator of bone turnover. But while pyrophosphate inhibits both osteoclastic bone resorption and the mineralization of the bone newly formed by osteoblasts, alendronate specifically inhibits bone resorption without any effect on mineralization at pharmacologically achievable doses. Its inhibition of bone-resorption is dose-dependent and approximately 1,000 times stronger than the equimolar effect of the first bisphosphonate drug, etidronate. Under therapy, normal bone tissue develops, and alendronate is deposited in the bone-matrix in a pharmacologically inactive form. For optimal action, enough calcium and vitamin D are needed in the body in order to promote normal bone development. Hypocalcemia should, therefore, be corrected before starting therapy. Treatment of post-menopausal women and people with osteogenesis imperfecta over the age of 22 with alendronic acid has demonstrated normalization of the rate of bone turnover, significant increase in BMD (bone mineral density) of the spine, hip, wrist and total body, and significant reductions in the risk of vertebral (spine) fractures, wrist fractures, hip fractures, and all non-vertebral fractures. In the Fracture Intervention Trial, the women with the highest risk of fracture (by virtue of pre-existing vertebral fractures) were treated with Fosamax 5 mg/day for two years followed by 10 mg/day for the third year. This resulted in approximately 50% reductions in fractures of the spine, hip, and wrist compared with the control group taking placebos. Both groups also took calcium and vitamin D.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1782 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18327899 |
260.0 nM [IC50] | ||
Target ID: CHEMBL4769 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18800762 |
436.52 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | FOSAMAX Approved UseINDICATIONS AND USAGE. FOSAMAX is a bisphosphonate indicated for: Treatment and prevention of osteoporosis in postmenopausal women (1.1, 1.2) Treatment to increase bone mass in men with osteoporosis (1.3) Treatment of glucocorticoid-induced osteoporosis (1.4) Treatment of Paget's disease of bone (1.5) Important limitations of use: The optimal duration of use has not been determined. The need for continued therapy should be re-evaluated on a periodic basis. (1.6) Launch Date1999 |
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Primary | FOSAMAX Approved UseINDICATIONS AND USAGE. FOSAMAX is a bisphosphonate indicated for: Treatment and prevention of osteoporosis in postmenopausal women (1.1, 1.2) Treatment to increase bone mass in men with osteoporosis (1.3) Treatment of glucocorticoid-induced osteoporosis (1.4) Treatment of Paget's disease of bone (1.5) Important limitations of use: The optimal duration of use has not been determined. The need for continued therapy should be re-evaluated on a periodic basis. (1.6) Launch Date1999 |
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Primary | FOSAMAX Approved UseINDICATIONS AND USAGE. FOSAMAX is a bisphosphonate indicated for: Treatment and prevention of osteoporosis in postmenopausal women (1.1, 1.2) Treatment to increase bone mass in men with osteoporosis (1.3) Treatment of glucocorticoid-induced osteoporosis (1.4) Treatment of Paget's disease of bone (1.5) Important limitations of use: The optimal duration of use has not been determined. The need for continued therapy should be re-evaluated on a periodic basis. (1.6) Launch Date1999 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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56.62 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28744102 |
70 mg single, oral dose: 70 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALENDRONATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
155.53 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28744102 |
70 mg single, oral dose: 70 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALENDRONATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.73 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28744102 |
70 mg single, oral dose: 70 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALENDRONATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
PubMed
Title | Date | PubMed |
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Consensus statement on the modern therapy of Paget's disease of bone from a Western Osteoporosis Alliance symposium. Biannual Foothills Meeting on Osteoporosis, Calgary, Alberta, Canada, September 9-10, 2000. | 2001 Apr |
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Analgesic effect of bisphosphonates in mice. | 2001 Apr |
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Treatment of osteoporosis with bisphosphonates. | 2001 Feb |
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Bisphosphonate therapy in fibrous dysplasia. | 2001 Jan |
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Visualization of bisphosphonate-induced caspase-3 activity in apoptotic osteoclasts in vitro. | 2001 May |
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Nitrogen-containing bisphosphonates induce apoptosis of Caco-2 cells in vitro by inhibiting the mevalonate pathway: a model of bisphosphonate-induced gastrointestinal toxicity. | 2001 Oct |
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Prevention of bone loss and fracture after lung transplantation: a pilot study. | 2001 Oct 15 |
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Bisphosphonates for osteoporosis. | 2001 Sep |
Patents
Sample Use Guides
Treatment of Osteoporosis in Postmenopausal Women: one 70 mg tablet once weekly
Prevention of Osteoporosis in Postmenopausal Women: one 35 mg tablet once weekly
Treatment to Increase Bone Mass in Men with Osteoporosis: one 70 mg tablet once weekly
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25339667
IGROV-1 ovarian carcinoma cells were stained with PKH26 (Sigma-Aldrich) according to the manufacturer’s instructions and then incubated with the indicated AA (Alendronic acid ) for 24 h. After washing, 1 3 106 target cells and 1 3 106 ex vivo expanded gd T cells were cocultured at 37°C/5% CO2 for 4 h and then stained with Annexin VFITC (BD Pharmingen)
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C67439
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EMA ASSESSMENT REPORTS |
VANTAVO (AUTHORIZED: OSTEOPOROSIS, POSTMENOPAUSAL)
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EMA ASSESSMENT REPORTS |
FOSAVANCE (AUTHORIZED: OSTEOPOROSIS, POSTMENOPAUSAL)
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NCI_THESAURUS |
C443
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EMA ASSESSMENT REPORTS |
ADROVANCE (AUTHORIZED: OSTEOPOROSIS, POSTMENOPAUSAL)
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SUB25411
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2UY4M2U3RA
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60736
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C973
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CHEMBL870
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BB-83
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100000089619
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Alendronate sodium
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DBSALT000315
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203152
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758931
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2566
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m1493
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1012780
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SUB25549
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ACTIVE MOIETY
SUBSTANCE RECORD