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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
Structure of ALENDRONATE SODIUM MONOHYDRATE

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

HIDE SMILES / InChI

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.

Originator

Sources: Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, Issue 2, Pages 433-7, Journal, 1978

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
260.0 nM [IC50]
436.52 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FOSAMAX

Approved Use

INDICATIONS 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 Date

1999
Primary
FOSAMAX

Approved Use

INDICATIONS 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 Date

1999
Primary
FOSAMAX

Approved Use

INDICATIONS 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 Date

1999
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
56.62 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
155.53 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.73 h
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

PubMed

TitleDatePubMed
Apoptosis of osteoclast-like cells induced by alendronate is related to Fas gene expression.
2000 Aug
The effect of alendronate on fracture-related healthcare utilization and costs: the fracture intervention trial.
2001
Initiation of osteoporosis treatment after bone mineral density testing.
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
Risk of ulcer soars with combination of arthritis drugs.
2001 Apr
Analgesic effect of bisphosphonates in mice.
2001 Apr
[Research and advertisement. Differences in the effectiveness of alendronate according to risk groups].
2001 Apr 30
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
Alendronate treatment for osteoporosis in patients infected with human immunodeficiency virus.
2001 Aug 1
Clinical and radiological improvement of periodontal disease in patients with type 2 diabetes mellitus treated with alendronate: a randomized, placebo-controlled trial.
2001 Feb
Treatment of osteoporosis with bisphosphonates.
2001 Feb
Two-year effects of alendronate on bone mineral density and vertebral fracture in patients receiving glucocorticoids: a randomized, double-blind, placebo-controlled extension trial.
2001 Jan
Once-a-week alendronate for postmenopausal osteoporosis is as effective as once-daily dosing.
2001 Jan
Emerging therapies in osteoporosis.
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
[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
Effect of topical alendronate on root resorption of dried replanted dog teeth.
2001 Jun
Re: Lanza et al.--Endoscopic comparison of alendronate and risedronate.
2001 Jun
Osteoporosis.
2001 Jun
Osteoporosis in men.
2001 Jun 15
Estimating probability of non-response to treatment using mixture distributions.
2001 Jun 30
Prevention of corticosteroid induced osteoporosis in inpatients recently discharged from a tertiary teaching hospital.
2001 Mar
Evidence-based medicine: putting theory into practice.
2001 Mar
Osteoporosis: part II. Nonpharmacologic and pharmacologic treatment.
2001 Mar 15
[Esophagitis associated with use of alendronate in 5 postmenopausic patients].
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
Bones and Crohn's: should we treat Crohn's disease patients with alendronate?
2001 May
Visualization of bisphosphonate-induced caspase-3 activity in apoptotic osteoclasts in vitro.
2001 May
New insight into calcinosis of juvenile dermatomyositis: a study of composition and treatment.
2001 May
[Treatment of osteoporosis. Compliance is significantly enhanced].
2001 May 31
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
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
Bisphosphonates for osteoporosis.
2001 Sep
Update on alendronate for osteoporosis: once-weekly dosing.
2001 Sep
Alendronate does not interfere with 99mTc-methylene diphosphonate bone scanning.
2001 Sep
Vgamma2Vdelta2 T-cell receptor-mediated recognition of aminobisphosphonates.
2001 Sep 1
Regression to the mean: what does it mean? Using bone density results to monitor treatment of osteoporosis.
2001 Spring
What is the impact of osteoporosis education and bone mineral density testing for postmenopausal women in a managed care setting?
2001 Summer
Patents

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
by admin
on Sat Dec 16 15:42:54 GMT 2023
Edited
by admin
on Sat Dec 16 15:42:54 GMT 2023
Record UNII
R8NDF40ZAR
Record Status Validated (UNII)
Record Version
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Name Type Language
ALENDRONATE SODIUM MONOHYDRATE
Common Name English
PHOSPHONIC ACID, (4-AMINO-1-HYDROXYBUTYLIDENE)BIS-, MONOSODIUM SALT, MONOHYDRATE
Systematic Name English
ALENDRONATE MONOSODIUM MONOHYDRATE
Common Name English
PHOSPHONIC ACID, P,P'-(4-AMINO-1-HYDROXYBUTYLIDENE)BIS-, SODIUM SALT, HYDRATE (1:1)
Systematic Name English
MONOSODIUM ALENDRONATE MONOHYDRATE
Common Name English
Code System Code Type Description
PUBCHEM
23700496
Created by admin on Sat Dec 16 15:42:55 GMT 2023 , Edited by admin on Sat Dec 16 15:42:55 GMT 2023
PRIMARY
SMS_ID
100000089599
Created by admin on Sat Dec 16 15:42:55 GMT 2023 , Edited by admin on Sat Dec 16 15:42:55 GMT 2023
PRIMARY
CAS
260055-05-8
Created by admin on Sat Dec 16 15:42:55 GMT 2023 , Edited by admin on Sat Dec 16 15:42:55 GMT 2023
PRIMARY
FDA UNII
R8NDF40ZAR
Created by admin on Sat Dec 16 15:42:55 GMT 2023 , Edited by admin on Sat Dec 16 15:42:55 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
Related Record Type Details
ACTIVE MOIETY