Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H13NO7P2 |
Molecular Weight | 249.096 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCCC(O)(P(O)(O)=O)P(O)(O)=O
InChI
InChIKey=OGSPWJRAVKPPFI-UHFFFAOYSA-N
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)
Molecular Formula | C4H13NO7P2 |
Molecular Weight | 249.096 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|---|---|
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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The effect of alendronate on fracture-related healthcare utilization and costs: the fracture intervention trial. | 2001 |
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Alendronate influences bending force of femoral diaphysis after orchidectomy in rats. | 2001 |
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Initiation of osteoporosis treatment after bone mineral density testing. | 2001 |
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Bone loss. Therapeutic approaches for preventing bone loss in inflammatory arthritis. | 2001 |
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Alendronate: an update of its use in osteoporosis. | 2001 |
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Comparison of bone and total alkaline phosphatase and bone mineral density in postmenopausal osteoporotic women treated with alendronate. | 2001 |
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A slow outward current and a hypoosmolality induced anion conductance in embryonic chicken osteoclasts. | 2001 |
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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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A controlled study of the effects of alendronate in a growing mouse model of osteogenesis imperfecta. | 2001 Aug |
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Guidelines for treatment of osteoporosis in men. | 2001 Aug |
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Effect of alendronate on bone mineral density in male idiopathic osteoporosis. | 2001 Aug |
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Alendronate treatment for osteoporosis in patients infected with human immunodeficiency virus. | 2001 Aug 1 |
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Alendronate in rheumatoid arthritis patients treated with methotrexate and glucocorticoids. | 2001 Feb |
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[Can use of antibiotics in acute bronchitis be reduced?]. | 2001 Feb 10 |
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Fosamax for HIV-related bone problems? | 2001 Jul |
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Emerging therapies in osteoporosis. | 2001 Jul |
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Role of bisphosphonates and calcitonin in the prevention and treatment of osteoporosis. | 2001 Jul |
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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 |
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[Bisphosphonate treatment prevents hip fractures in 70-79 year old women with osteoporotic vertebral fractures]. | 2001 Jul 14 |
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[Osteoporosis and multiple pregnancy--a case report with positive outcome]. | 2001 Jul 15 |
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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 |
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[Modern osteoporosis therapy. Only once weekly against osteoporosis]. | 2001 Jul 19 |
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New possibilities for diagnosis and treatment of osteoporosis. | 2001 Jul-Aug |
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American Association of Clinical Endocrinologists 2001 Medical Guidelines for Clinical Practice for the Prevention and Management of Postmenopausal Osteoporosis. | 2001 Jul-Aug |
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Medication update. | 2001 Jun |
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Prevalence and determinants of osteoporosis drug prescription among patients with high exposure to glucocorticoid drugs. | 2001 Jun |
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Re: Lanza et al.--Endoscopic comparison of alendronate and risedronate. | 2001 Jun |
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Osteoporosis. | 2001 Jun |
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Osteoporosis in men. | 2001 Jun 15 |
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Estimating probability of non-response to treatment using mixture distributions. | 2001 Jun 30 |
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Excretion of sweat and urine pyridinoline crosslinks in healthy controls and subjects with established metabolic bone disease. | 2001 Mar |
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Prevention of corticosteroid induced osteoporosis in inpatients recently discharged from a tertiary teaching hospital. | 2001 Mar |
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Managing menopause after breast cancer: balancing risks and benefits. | 2001 Mar |
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Osteoporosis. Efficacy and safety of a bisphosphonate dosed once weekly. | 2001 Mar |
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Once-a-week alendronate (Fosamax). | 2001 Mar 19 |
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[Alendronate-induced hepatocellular lesion]. | 2001 May |
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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 |
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Bones and Crohn's: should we treat Crohn's disease patients with alendronate? | 2001 May |
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Bisphosphonates alendronate and ibandronate inhibit artery calcification at doses comparable to those that inhibit bone resorption. | 2001 May |
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Effects of suppressed bone turnover by bisphosphonates on microdamage accumulation and biomechanical properties in clinically relevant skeletal sites in beagles. | 2001 May |
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Visualization of bisphosphonate-induced caspase-3 activity in apoptotic osteoclasts in vitro. | 2001 May |
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Absolute vs. relative numbers in evaluating drug therapy. | 2001 May 15 |
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[Treatment of osteoporosis. Compliance is significantly enhanced]. | 2001 May 31 |
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[Radiopharmacokinetic and gammagraphic studies for calculating personalized dosimetry]. | 2001 May-Jun |
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Prevention of bone loss and fracture after lung transplantation: a pilot study. | 2001 Oct 15 |
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Comparison of calcitonin, alendronate and fluorophosphate effects on ovariectomized rat bone. | 2001 Sep |
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Bisphosphonate therapy for Paget's disease in a patient with hypoparathyroidism: profound hypocalcemia, rapid response, and prolonged remission. | 2001 Sep |
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Regression to the mean: what does it mean? Using bone density results to monitor treatment of osteoporosis. | 2001 Spring |
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What is the impact of osteoporosis education and bone mineral density testing for postmenopausal women in a managed care setting? | 2001 Summer |
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)
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:43:35 GMT 2023
by
admin
on
Fri Dec 15 15:43:35 GMT 2023
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Record UNII |
X1J18R4W8P
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
166603
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WHO-ATC |
M05BB05
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NDF-RT |
N0000175579
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LIVERTOX |
22
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WHO-VATC |
QM05BB05
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WHO-VATC |
QM05BB06
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NDF-RT |
N0000007707
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WHO-ATC |
M05BB06
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NCI_THESAURUS |
C443
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WHO-ATC |
M05BB03
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NCI_THESAURUS |
C67439
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WHO-VATC |
QM05BB03
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WHO-ATC |
M05BA04
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WHO-VATC |
QM05BA04
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FDA ORPHAN DRUG |
844921
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X1J18R4W8P
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DB00630
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X1J18R4W8P
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DTXSID5022568
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C61625
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3141
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Alendronate
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6462
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m1493
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PRIMARY | Merck Index | ||
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D019386
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7990
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236083
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CHEMBL870
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ALENDRONIC ACID
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100000085258
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46041
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2088
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2567
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66376-36-1
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SUB05307MIG
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SOLVATE->ANHYDROUS | |||
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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PROTEIN BINDING | PHARMACOKINETIC |
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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Route of Elimination | PHARMACOKINETIC |
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