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
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 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
Bones and Crohn's: should we treat Crohn's disease patients with alendronate?
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
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
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

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 Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
WHO-ATC M05BB05
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
NDF-RT N0000175579
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
LIVERTOX 22
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
WHO-VATC QM05BB05
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
WHO-VATC QM05BB06
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
NDF-RT N0000007707
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
WHO-ATC M05BB06
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
NCI_THESAURUS C443
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
WHO-ATC M05BB03
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
NCI_THESAURUS C67439
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
WHO-VATC QM05BB03
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
WHO-ATC M05BA04
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
WHO-VATC QM05BA04
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
Code System Code Type Description
DAILYMED
X1J18R4W8P
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
DRUG BANK
DB00630
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
FDA UNII
X1J18R4W8P
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
DRUG CENTRAL
112
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
EPA CompTox
DTXSID5022568
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
NCI_THESAURUS
C61625
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
IUPHAR
3141
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
LACTMED
Alendronate
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
INN
6462
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
MERCK INDEX
M1493
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY Merck Index
MESH
D019386
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
HSDB
7990
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
RXCUI
236083
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
ChEMBL
CHEMBL870
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
WIKIPEDIA
ALENDRONIC ACID
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
RXCUI
46041
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
ALTERNATIVE
PUBCHEM
2088
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
CHEBI
2567
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
CAS
66376-36-1
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY
EVMPD
SUB05307MIG
Created by admin on Fri Dec 16 17:59:21 UTC 2022 , Edited by admin on Fri Dec 16 17:59:21 UTC 2022
PRIMARY