Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C4H12NO7P2.Na.H2O |
| Molecular Weight | 289.0932 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.[Na+].NCCCC(O)(P(O)(O)=O)P(O)([O-])=O
InChI
InChIKey=DUYCFMAOEDAKDN-UHFFFAOYSA-M
InChI=1S/C4H13NO7P2.Na.H2O/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);;1H2/q;+1;/p-1
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C4H12NO7P2 |
| Molecular Weight | 248.0881 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
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 |
260.0 nM [IC50] | ||
Target ID: CHEMBL4769 |
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 |
|||
| 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 |
|
| Ocular inflammation associated with alendronate therapy. | 1999 Jun |
|
| [Pain relief with alendronate therapy in a breast cancer patient with bone metastasis]. | 2000 Apr |
|
| Alendronate is a specific, nanomolar inhibitor of farnesyl diphosphate synthase. | 2000 Jan 1 |
|
| The effect of alendronate on fracture-related healthcare utilization and costs: the fracture intervention trial. | 2001 |
|
| Alendronate influences bending force of femoral diaphysis after orchidectomy in rats. | 2001 |
|
| Bone loss. Therapeutic approaches for preventing bone loss in inflammatory arthritis. | 2001 |
|
| Comparison of bone and total alkaline phosphatase and bone mineral density in postmenopausal osteoporotic women treated with alendronate. | 2001 |
|
| A slow outward current and a hypoosmolality induced anion conductance in embryonic chicken osteoclasts. | 2001 |
|
| Phenotypic characteristics of human monocytes undergoing transendothelial migration. | 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 |
|
| Analgesic effect of bisphosphonates in mice. | 2001 Apr |
|
| A controlled study of the effects of alendronate in a growing mouse model of osteogenesis imperfecta. | 2001 Aug |
|
| Effect of alendronate on bone mineral density in male idiopathic osteoporosis. | 2001 Aug |
|
| Alendronate in rheumatoid arthritis patients treated with methotrexate and glucocorticoids. | 2001 Feb |
|
| Osteoporosis therapies for rheumatoid arthritis patients: minimizing gastrointestinal side effects. | 2001 Feb |
|
| Structure-activity relationships for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates. | 2001 Feb |
|
| [Can use of antibiotics in acute bronchitis be reduced?]. | 2001 Feb 10 |
|
| Phosphate ions mediate chondrocyte apoptosis through a plasma membrane transporter mechanism. | 2001 Jan |
|
| Bisphosphonate therapy in fibrous dysplasia. | 2001 Jan |
|
| Effects of oral alendronate in elderly patients with osteoporosis and mild primary hyperparathyroidism. | 2001 Jan |
|
| Fosamax for HIV-related bone problems? | 2001 Jul |
|
| Role of bisphosphonates and calcitonin in the prevention and treatment of osteoporosis. | 2001 Jul |
|
| Additional beneficial effects of alendronate in growth hormone (GH)-deficient adults with osteoporosis receiving long-term recombinant human GH replacement therapy: a randomized controlled trial. | 2001 Jul |
|
| [Bisphosphonate treatment prevents hip fractures in 70-79 year old women with osteoporotic vertebral fractures]. | 2001 Jul 14 |
|
| [Osteoporosis and multiple pregnancy--a case report with positive outcome]. | 2001 Jul 15 |
|
| [Modern osteoporosis therapy. Only once weekly against osteoporosis]. | 2001 Jul 19 |
|
| American Association of Clinical Endocrinologists 2001 Medical Guidelines for Clinical Practice for the Prevention and Management of Postmenopausal Osteoporosis. | 2001 Jul-Aug |
|
| Medication update. | 2001 Jun |
|
| Osteoporosis. | 2001 Jun |
|
| Osteoporosis in men. | 2001 Jun 15 |
|
| Estimating probability of non-response to treatment using mixture distributions. | 2001 Jun 30 |
|
| Excretion of sweat and urine pyridinoline crosslinks in healthy controls and subjects with established metabolic bone disease. | 2001 Mar |
|
| Prevention of corticosteroid induced osteoporosis in inpatients recently discharged from a tertiary teaching hospital. | 2001 Mar |
|
| Managing menopause after breast cancer: balancing risks and benefits. | 2001 Mar |
|
| Osteoporosis. Efficacy and safety of a bisphosphonate dosed once weekly. | 2001 Mar |
|
| Effect of alendronate and MK-677 (a growth hormone secretagogue), individually and in combination, on markers of bone turnover and bone mineral density in postmenopausal osteoporotic women. | 2001 Mar |
|
| Labelling of Re-ABP with 188Re for bone pain palliation. | 2001 Mar |
|
| By the way, doctor. I recently heard that I can take Fosamax once a week for osteoporosis, rather than every day. Is it really effective when taken this way? Is there a downside? | 2001 May |
|
| Bones and Crohn's: should we treat Crohn's disease patients with alendronate? | 2001 May |
|
| Bisphosphonates alendronate and ibandronate inhibit artery calcification at doses comparable to those that inhibit bone resorption. | 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 |
|
| Absolute vs. relative numbers in evaluating drug therapy. | 2001 May 15 |
|
| [Treatment of osteoporosis. Compliance is significantly enhanced]. | 2001 May 31 |
|
| [Radiopharmacokinetic and gammagraphic studies for calculating personalized dosimetry]. | 2001 May-Jun |
|
| Prevention of bone loss and fracture after lung transplantation: a pilot study. | 2001 Oct 15 |
|
| Comparison of calcitonin, alendronate and fluorophosphate effects on ovariectomized rat bone. | 2001 Sep |
|
| Bisphosphonate therapy for Paget's disease in a patient with hypoparathyroidism: profound hypocalcemia, rapid response, and prolonged remission. | 2001 Sep |
|
| Regression to the mean: what does it mean? Using bone density results to monitor treatment of osteoporosis. | 2001 Spring |
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
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)
| Substance Class |
Chemical
Created
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admin
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Edited
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| Record UNII |
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| Record Status |
Validated (UNII)
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| Record Version |
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100000089599
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260055-05-8
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PARENT -> SALT/SOLVATE |
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ANHYDROUS->SOLVATE |
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ACTIVE MOIETY |
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