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Details

Stereochemistry ACHIRAL
Molecular Formula C4H13NO7P2
Molecular Weight 249.0962
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALENDRONIC ACID

SMILES

C(CC(O)(P(=O)(O)O)P(=O)(O)O)CN

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
Long-term therapy for postmenopausal osteoporosis: stronger bones but weaker arteries.
1999 Jul 27
Ocular inflammation associated with alendronate therapy.
1999 Jun
[Pain relief with alendronate therapy in a breast cancer patient with bone metastasis].
2000 Apr
Apoptosis of osteoclast-like cells induced by alendronate is related to Fas gene expression.
2000 Aug
Alendronate is a specific, nanomolar inhibitor of farnesyl diphosphate synthase.
2000 Jan 1
A peptide prodrug approach for improving bisphosphonate oral absorption.
2000 Oct 5
Initiation of osteoporosis treatment after bone mineral density testing.
2001
Alendronate: an update of its use in osteoporosis.
2001
A slow outward current and a hypoosmolality induced anion conductance in embryonic chicken osteoclasts.
2001
Hyposecretion of the adrenal androgen dehydroepiandrosterone sulfate and its relation to clinical variables in inflammatory arthritis.
2001
Fractures after long-term alendronate therapy.
2001 Apr
Risk of ulcer soars with combination of arthritis drugs.
2001 Apr
Analgesic effect of bisphosphonates in mice.
2001 Apr
Effect of alendronate on bone mineral density in male idiopathic osteoporosis.
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
Alendronate in rheumatoid arthritis patients treated with methotrexate and glucocorticoids.
2001 Feb
Osteoporosis therapies for rheumatoid arthritis patients: minimizing gastrointestinal side effects.
2001 Feb
[Diagnosis of primary Sjogren's syndrome].
2001 Feb 20
Prevention of bone loss in kidney graft recipients.
2001 Feb-Mar
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 treatment prevents hip fractures in 70-79 year old women with osteoporotic vertebral fractures].
2001 Jul 14
New possibilities for diagnosis and treatment of osteoporosis.
2001 Jul-Aug
Prevalence and determinants of osteoporosis drug prescription among patients with high exposure to glucocorticoid drugs.
2001 Jun
Osteoporosis.
2001 Jun
Osteoporosis in men.
2001 Jun 15
Estimating probability of non-response to treatment using mixture distributions.
2001 Jun 30
Excretion of sweat and urine pyridinoline crosslinks in healthy controls and subjects with established metabolic bone disease.
2001 Mar
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
Managing menopause after breast cancer: balancing risks and benefits.
2001 Mar
Osteoporosis. Efficacy and safety of a bisphosphonate dosed once weekly.
2001 Mar
Effect of alendronate and MK-677 (a growth hormone secretagogue), individually and in combination, on markers of bone turnover and bone mineral density in postmenopausal osteoporotic women.
2001 Mar
Labelling of Re-ABP with 188Re for bone pain palliation.
2001 Mar
Once-a-week alendronate (Fosamax).
2001 Mar 19
[Esophagitis associated with use of alendronate in 5 postmenopausic patients].
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
Effects of suppressed bone turnover by bisphosphonates on microdamage accumulation and biomechanical properties in clinically relevant skeletal sites in beagles.
2001 May
Absolute vs. relative numbers in evaluating drug therapy.
2001 May 15
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
Bisphosphonate therapy for Paget's disease in a patient with hypoparathyroidism: profound hypocalcemia, rapid response, and prolonged remission.
2001 Sep
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)
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
ALENDRONIC ACID [WHO-DD]
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
Classification Tree Code System Code
FDA ORPHAN DRUG 166603
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
WHO-ATC M05BB05
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
NDF-RT N0000175579
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
LIVERTOX 22
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
WHO-VATC QM05BB05
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
WHO-VATC QM05BB06
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
NDF-RT N0000007707
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
WHO-ATC M05BB06
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
NCI_THESAURUS C443
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
WHO-ATC M05BB03
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
NCI_THESAURUS C67439
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
WHO-VATC QM05BB03
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
WHO-ATC M05BA04
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
WHO-VATC QM05BA04
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
Code System Code Type Description
DRUG BANK
DB00630
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY
FDA UNII
X1J18R4W8P
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY
DRUG CENTRAL
112
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY
EPA CompTox
66376-36-1
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY
NCI_THESAURUS
C61625
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY
IUPHAR
3141
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY
LACTMED
Alendronate
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY
INN
6462
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY
MERCK INDEX
M1493
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY Merck Index
MESH
D019386
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY
HSDB
7990
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY
RXCUI
236083
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY
ChEMBL
CHEMBL870
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY
WIKIPEDIA
ALENDRONIC ACID
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY
RXCUI
46041
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
ALTERNATIVE
PUBCHEM
2088
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY
CAS
66376-36-1
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY
EVMPD
SUB05307MIG
Created by admin on Sat Jun 26 06:43:48 UTC 2021 , Edited by admin on Sat Jun 26 06:43:48 UTC 2021
PRIMARY