Details
Stereochemistry | ACHIRAL |
Molecular Formula | 2C4H12NO7P2.Ca |
Molecular Weight | 536.254 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Ca++].NCCCC(O)(P(O)(O)=O)P(O)([O-])=O.NCCCC(O)(P(O)(O)=O)P(O)([O-])=O
InChI
InChIKey=VFAZUESUCBECNE-UHFFFAOYSA-L
InChI=1S/2C4H13NO7P2.Ca/c2*5-3-1-2-4(6,13(7,8)9)14(10,11)12;/h2*6H,1-3,5H2,(H2,7,8,9)(H2,10,11,12);/q;;+2/p-2
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 |
---|---|---|---|
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 |
---|---|---|---|---|
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 |
|||
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 |
---|---|---|---|---|
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 |
---|---|---|
Long-term therapy for postmenopausal osteoporosis: stronger bones but weaker arteries. | 1999 Jul 27 |
|
Bone loss. Therapeutic approaches for preventing bone loss in inflammatory arthritis. | 2001 |
|
A slow outward current and a hypoosmolality induced anion conductance in embryonic chicken osteoclasts. | 2001 |
|
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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Fractures after long-term alendronate therapy. | 2001 Apr |
|
Alendronate treatment for osteoporosis in patients infected with human immunodeficiency virus. | 2001 Aug 1 |
|
Prevention of bone loss in kidney graft recipients. | 2001 Feb-Mar |
|
Phosphate ions mediate chondrocyte apoptosis through a plasma membrane transporter mechanism. | 2001 Jan |
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Effects of oral alendronate in elderly patients with osteoporosis and mild primary hyperparathyroidism. | 2001 Jan |
|
Alendronate and naproxen are synergistic for development of gastric ulcers. | 2001 Jan 8 |
|
Male osteoporosis associated with longterm cyproterone treatment. | 2001 Jul |
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[Modern osteoporosis therapy. Only once weekly against osteoporosis]. | 2001 Jul 19 |
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[Bisphosphonates once weekly. Osteoporosis therapy becomes more effective]. | 2001 Jul 26 |
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Evidence-based medicine: putting theory into practice. | 2001 Mar |
|
Labelling of Re-ABP with 188Re for bone pain palliation. | 2001 Mar |
|
Osteoporosis: part II. Nonpharmacologic and pharmacologic treatment. | 2001 Mar 15 |
|
Once-a-week alendronate (Fosamax). | 2001 Mar 19 |
|
[Esophagitis associated with use of alendronate in 5 postmenopausic patients]. | 2001 May |
|
[Effects of aminobisphosphonates on the superior digestive tract mucosa]. | 2001 May |
|
[Alendronate-induced hepatocellular lesion]. | 2001 May |
|
Effects of suppressed bone turnover by bisphosphonates on microdamage accumulation and biomechanical properties in clinically relevant skeletal sites in beagles. | 2001 May |
|
Visualization of bisphosphonate-induced caspase-3 activity in apoptotic osteoclasts in vitro. | 2001 May |
|
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 |
|
Prevention of bone loss and fracture after lung transplantation: a pilot study. | 2001 Oct 15 |
|
Risedronate: a new oral bisphosphonate. | 2001 Sep |
|
Bisphosphonates for osteoporosis. | 2001 Sep |
|
Isoprenoid biosynthesis. Metabolite profiling of peppermint oil gland secretory cells and application to herbicide target analysis. | 2001 Sep |
|
Pharmacologic therapy for the treatment and prevention of 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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NON-SPECIFIC STOICHIOMETRY |
ACTIVE MOIETY
SUBSTANCE RECORD