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 Date9.3381119E11 |
|||
| 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 Date9.3381119E11 |
|||
| 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 Date9.3381119E11 |
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 |
|---|---|---|
| The effect of alendronate on fracture-related healthcare utilization and costs: the fracture intervention trial. | 2001 |
|
| Cost effectiveness of nasal calcitonin in postmenopausal women: use of Cochrane Collaboration methods for meta-analysis within economic evaluation. | 2001 |
|
| Alendronate influences bending force of femoral diaphysis after orchidectomy in rats. | 2001 |
|
| Initiation of osteoporosis treatment after bone mineral density testing. | 2001 |
|
| Bone loss. Therapeutic approaches for preventing bone loss in inflammatory arthritis. | 2001 |
|
| Alendronate: an update of its use in osteoporosis. | 2001 |
|
| Comparison of bone and total alkaline phosphatase and bone mineral density in postmenopausal osteoporotic women treated with alendronate. | 2001 |
|
| Inhibition of leukotriene function can modulate particulate-induced changes in bone cell differentiation and activity. | 2001 |
|
| A slow outward current and a hypoosmolality induced anion conductance in embryonic chicken osteoclasts. | 2001 |
|
| A controlled study of the effects of alendronate in a growing mouse model of osteogenesis imperfecta. | 2001 Aug |
|
| Guidelines for treatment of osteoporosis in men. | 2001 Aug |
|
| Alendronate increases degree and uniformity of mineralization in cancellous bone and decreases the porosity in cortical bone of osteoporotic women. | 2001 Aug |
|
| Effect of alendronate on bone mineral density in male idiopathic osteoporosis. | 2001 Aug |
|
| Effect of 17beta-estradiol or alendronate on the bone densitometry, bone histomorphometry and bone metabolism of ovariectomized rats. | 2001 Aug |
|
| Alendronate treatment for osteoporosis in patients infected with human immunodeficiency virus. | 2001 Aug 1 |
|
| Fosamax for HIV-related bone problems? | 2001 Jul |
|
| Emerging therapies in osteoporosis. | 2001 Jul |
|
| Role of bisphosphonates and calcitonin in the prevention and treatment of osteoporosis. | 2001 Jul |
|
| Male osteoporosis associated with longterm cyproterone treatment. | 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 |
|
| The use of scintigraphy to demonstrate the rapid esophageal transit of the oval film-coated placebo risedronate tablet compared to a round uncoated placebo tablet when administered with minimal volumes of water. | 2001 Jul 17 |
|
| [Modern osteoporosis therapy. Only once weekly against osteoporosis]. | 2001 Jul 19 |
|
| [Bisphosphonates once weekly. Osteoporosis therapy becomes more effective]. | 2001 Jul 26 |
|
| New possibilities for diagnosis and treatment of osteoporosis. | 2001 Jul-Aug |
|
| American Association of Clinical Endocrinologists 2001 Medical Guidelines for Clinical Practice for the Prevention and Management of Postmenopausal Osteoporosis. | 2001 Jul-Aug |
|
| Effect of topical alendronate on root resorption of dried replanted dog teeth. | 2001 Jun |
|
| Medication update. | 2001 Jun |
|
| Prevalence and determinants of osteoporosis drug prescription among patients with high exposure to glucocorticoid drugs. | 2001 Jun |
|
| Re: Lanza et al.--Endoscopic comparison of alendronate and risedronate. | 2001 Jun |
|
| Osteoporosis. | 2001 Jun |
|
| Osteoporosis in men. | 2001 Jun 15 |
|
| [Esophagitis associated with use of alendronate in 5 postmenopausic patients]. | 2001 May |
|
| [Effects of aminobisphosphonates on the superior digestive tract mucosa]. | 2001 May |
|
| Why do older women discontinue hormone replacement therapy? | 2001 May |
|
| [Alendronate-induced hepatocellular lesion]. | 2001 May |
|
| 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 |
|
| [Treatment of osteoporosis. Compliance is significantly enhanced]. | 2001 May 31 |
|
| [Radiopharmacokinetic and gammagraphic studies for calculating personalized dosimetry]. | 2001 May-Jun |
|
| 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 |
|
| Comparison of calcitonin, alendronate and fluorophosphate effects on ovariectomized rat bone. | 2001 Sep |
|
| The molecular mechanism of action of the antiresorptive and antiinflammatory drug clodronate: evidence for the formation in vivo of a metabolite that inhibits bone resorption and causes osteoclast and macrophage apoptosis. | 2001 Sep |
|
| Risedronate: a new oral bisphosphonate. | 2001 Sep |
|
| Update on alendronate for osteoporosis: once-weekly dosing. | 2001 Sep |
|
| Isoprenoid biosynthesis. Metabolite profiling of peppermint oil gland secretory cells and application to herbicide target analysis. | 2001 Sep |
|
| Bisphosphonate therapy for Paget's disease in a patient with hypoparathyroidism: profound hypocalcemia, rapid response, and prolonged remission. | 2001 Sep |
|
| Alendronate does not interfere with 99mTc-methylene diphosphonate bone scanning. | 2001 Sep |
|
| Pharmacologic therapy for the treatment and prevention of osteoporosis. | 2001 Sep |
|
| Vgamma2Vdelta2 T-cell receptor-mediated recognition of aminobisphosphonates. | 2001 Sep 1 |
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 |
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| Record Version |
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23700496
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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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