U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ALENDRONIC ACID

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)

HIDE SMILES / InChI
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

9.3381119E11
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

9.3381119E11
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

9.3381119E11
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
Ocular inflammation associated with alendronate therapy.
1999 Jun
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
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
Short-term effects of three continuous hormone replacement therapy regimens on platelet tritiated imipramine binding and mood scores: a prospective randomized trial.
2001 Apr
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
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
Osteoporosis therapies for rheumatoid arthritis patients: minimizing gastrointestinal side effects.
2001 Feb
[Diagnosis of primary Sjogren's syndrome].
2001 Feb 20
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
Phosphate ions mediate chondrocyte apoptosis through a plasma membrane transporter mechanism.
2001 Jan
Bisphosphonate therapy in fibrous dysplasia.
2001 Jan
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
Prevalence and determinants of osteoporosis drug prescription among patients with high exposure to glucocorticoid drugs.
2001 Jun
Evidence-based medicine: putting theory into practice.
2001 Mar
Managing menopause after breast cancer: balancing risks and benefits.
2001 Mar
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
[Treatment of osteoporosis. Compliance is significantly enhanced].
2001 May 31
[Radiopharmacokinetic and gammagraphic studies for calculating personalized dosimetry].
2001 May-Jun
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

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)
Name Type Language
ALENDRONIC ACID
EMA EPAR   INN   MI   WHO-DD  
INN  
Official Name English
ALENDRONIC ACID [EMA EPAR]
Common Name English
P,P'-(4-AMINO-1-HYDROXYBUTYLIDENE)BISPHOSPHONIC ACID
Systematic Name English
.ALPHA.-HYDROXY-.DELTA.-AMINOBUTYLIDENEDIPHOSPHONIC ACID
Systematic Name English
ABDP
Common Name English
ALENDRONATE [VANDF]
Common Name English
(4-AMINO-1-HYDROXYBUTYLIDENE)DIPHOSPHONIC ACID
Systematic Name English
PHOSPHONIC ACID, (4-AMINO-1-HYDROXYBUTYLIDENE)BIS-
Common Name English
alendronic acid [INN]
Common Name English
PHOSPHONIC ACID, P,P'-(4-AMINO-1-HYDROXYBUTYLIDENE)BIS-
Common Name English
4-AMINO-1-HYDROXYBUTANE-1,1-DIPHOSPHONIC ACID
Systematic Name English
ALENDRONATE [MART.]
Common Name English
(4-AMINO-1-HYDROXYBUTANE-1,1-DIYL)BIS(PHOSPHONIC ACID)
Systematic Name English
ALENDRONIC ACID [MI]
Common Name English
ALENDRONATE
MART.   VANDF  
Common Name English
Alendronic acid [WHO-DD]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 166603
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
WHO-ATC M05BB05
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
NDF-RT N0000175579
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
LIVERTOX 22
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
WHO-VATC QM05BB05
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
WHO-VATC QM05BB06
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
NDF-RT N0000007707
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
WHO-ATC M05BB06
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
NCI_THESAURUS C443
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
WHO-ATC M05BB03
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
NCI_THESAURUS C67439
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
WHO-VATC QM05BB03
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
WHO-ATC M05BA04
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
WHO-VATC QM05BA04
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
FDA ORPHAN DRUG 844921
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
Code System Code Type Description
DAILYMED
X1J18R4W8P
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
DRUG BANK
DB00630
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
FDA UNII
X1J18R4W8P
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
DRUG CENTRAL
112
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
EPA CompTox
DTXSID5022568
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
NCI_THESAURUS
C61625
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
IUPHAR
3141
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
LACTMED
Alendronate
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
INN
6462
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
MERCK INDEX
M1493
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY Merck Index
MESH
D019386
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
HSDB
7990
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
RXCUI
236083
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
ChEMBL
CHEMBL870
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
WIKIPEDIA
ALENDRONIC ACID
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
SMS_ID
100000085258
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
RXCUI
46041
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
ALTERNATIVE
PUBCHEM
2088
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
CHEBI
2567
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
CAS
66376-36-1
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY
EVMPD
SUB05307MIG
Created by admin on Wed Jul 05 23:12:25 UTC 2023 , Edited by admin on Wed Jul 05 23:12:25 UTC 2023
PRIMARY