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Details

Stereochemistry ACHIRAL
Molecular Formula C4H12NO7P2.Na.3H2O
Molecular Weight 325.1237
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALENDRONATE SODIUM

SMILES

O.O.O.[Na+].NCCCC(O)(P(O)(O)=O)P(O)([O-])=O

InChI

InChIKey=DCSBSVSZJRSITC-UHFFFAOYSA-M
InChI=1S/C4H13NO7P2.Na.3H2O/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);;3*1H2/q;+1;;;/p-1

HIDE SMILES / InChI

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 ( + / - )

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 Na
Molecular Weight 22.9898
Charge 1
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.

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
Apoptosis of osteoclast-like cells induced by alendronate is related to Fas gene expression.
2000 Aug
Cost effectiveness of nasal calcitonin in postmenopausal women: use of Cochrane Collaboration methods for meta-analysis within economic evaluation.
2001
Bone loss. Therapeutic approaches for preventing bone loss in inflammatory arthritis.
2001
Alendronate: an update of its use in osteoporosis.
2001
Inhibition of leukotriene function can modulate particulate-induced changes in bone cell differentiation and activity.
2001
Analgesic effect of bisphosphonates in mice.
2001 Apr
[Research and advertisement. Differences in the effectiveness of alendronate according to risk groups].
2001 Apr 30
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
Alendronate in rheumatoid arthritis patients treated with methotrexate and glucocorticoids.
2001 Feb
[Can use of antibiotics in acute bronchitis be reduced?].
2001 Feb 10
[Diagnosis of primary Sjogren's syndrome].
2001 Feb 20
Prevention of bone loss in kidney graft recipients.
2001 Feb-Mar
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
American Association of Clinical Endocrinologists 2001 Medical Guidelines for Clinical Practice for the Prevention and Management of Postmenopausal Osteoporosis.
2001 Jul-Aug
Medication update.
2001 Jun
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
Osteoporosis: part II. Nonpharmacologic and pharmacologic treatment.
2001 Mar 15
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
Effects of suppressed bone turnover by bisphosphonates on microdamage accumulation and biomechanical properties in clinically relevant skeletal sites in beagles.
2001 May
Visualization of bisphosphonate-induced caspase-3 activity in apoptotic osteoclasts in vitro.
2001 May
Absolute vs. relative numbers in evaluating drug therapy.
2001 May 15
[Radiopharmacokinetic and gammagraphic studies for calculating personalized dosimetry].
2001 May-Jun
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
Bisphosphonates for osteoporosis.
2001 Sep
Isoprenoid biosynthesis. Metabolite profiling of peppermint oil gland secretory cells and application to herbicide target analysis.
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
Regression to the mean: what does it mean? Using bone density results to monitor treatment of osteoporosis.
2001 Spring
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 Fri Dec 15 15:52:06 UTC 2023
Edited
by admin
on Fri Dec 15 15:52:06 UTC 2023
Record UNII
2UY4M2U3RA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALENDRONATE SODIUM
ORANGE BOOK   USAN   USP   USP-RS   WHO-DD  
USAN  
Official Name English
ALENDRONATE SODIUM TRIHYDRATE [EMA EPAR]
Common Name English
G-704650
Code English
SODIUM HYDROGEN (4-AMINO-1-HYDROXY-1-PHOSPHONOBUTYL)PHOSPHONATE TRIHYDRATE
Systematic Name English
ADROVANCE
Brand Name English
Alendronate sodium [WHO-DD]
Common Name English
ALENDRONATE SODIUM [USP MONOGRAPH]
Common Name English
ALENDRONATE SODIUM [USAN]
Common Name English
ALENDRONIC ACID MONOSODIUM SALT TRIHYDRATE [MI]
Common Name English
NSC-722597
Code English
ALENDRONIC ACID (AS ALENDRONATE SODIUM)
Common Name English
ALENDRONATE SODIUM [USP-RS]
Common Name English
ALENDRONATE SODIUM [ORANGE BOOK]
Common Name English
FOSAMAX
Brand Name English
MK-217
Code English
ALENDRONIC ACID MONOSODIUM SALT TRIHYDRATE
MI  
Common Name English
ALENDRONATE SODIUM COMPONENT OF FOSAMAX PLUS D
Common Name English
FOSAVANCE
Brand Name English
FOSAMAX PLUS D COMPONENT ALENDRONATE SODIUM
Common Name English
NSC-758931
Code English
SODIUM ALENDRONATE
EP  
Common Name English
ALENDRONATE SODIUM HYDRATE [JAN]
Common Name English
G-704,650
Code English
SODIUM ALENDRONATE TRIHYDRATE
Common Name English
ALENDRONATE (AS SODIUM)
Common Name English
SODIUM ALENDRONATE TRIHYDRATE [EP MONOGRAPH]
Common Name English
VANTAVO
Brand Name English
PHOSPHONIC ACID, (4-AMINO-1-HYDROXYBUTYLIDENE)BIS-, MONOSODIUM SALT, TRIHYDRATE
Common Name English
ALENDRONATE SODIUM HYDRATE
JAN  
Common Name English
ALENDRONATE SODIUM TRIHYDRATE
EMA EPAR  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67439
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
EMA ASSESSMENT REPORTS VANTAVO (AUTHORIZED: OSTEOPOROSIS, POSTMENOPAUSAL)
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
EMA ASSESSMENT REPORTS FOSAVANCE (AUTHORIZED: OSTEOPOROSIS, POSTMENOPAUSAL)
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
NCI_THESAURUS C443
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
EMA ASSESSMENT REPORTS ADROVANCE (AUTHORIZED: OSTEOPOROSIS, POSTMENOPAUSAL)
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
Code System Code Type Description
EVMPD
SUB25411
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
PRIMARY
DAILYMED
2UY4M2U3RA
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
PRIMARY
PUBCHEM
60736
Created by admin on Fri Dec 15 15:52:07 UTC 2023 , Edited by admin on Fri Dec 15 15:52:07 UTC 2023
PRIMARY
NCI_THESAURUS
C973
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
PRIMARY
FDA UNII
2UY4M2U3RA
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
PRIMARY
ChEMBL
CHEMBL870
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
PRIMARY
USAN
BB-83
Created by admin on Fri Dec 15 15:52:07 UTC 2023 , Edited by admin on Fri Dec 15 15:52:07 UTC 2023
PRIMARY
SMS_ID
100000089619
Created by admin on Fri Dec 15 15:52:07 UTC 2023 , Edited by admin on Fri Dec 15 15:52:07 UTC 2023
PRIMARY
WIKIPEDIA
Alendronate sodium
Created by admin on Fri Dec 15 15:52:07 UTC 2023 , Edited by admin on Fri Dec 15 15:52:07 UTC 2023
PRIMARY
DRUG BANK
DBSALT000315
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
PRIMARY
RXCUI
203152
Created by admin on Fri Dec 15 15:52:07 UTC 2023 , Edited by admin on Fri Dec 15 15:52:07 UTC 2023
PRIMARY RxNorm
NSC
758931
Created by admin on Fri Dec 15 15:52:07 UTC 2023 , Edited by admin on Fri Dec 15 15:52:07 UTC 2023
PRIMARY
CHEBI
2566
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
PRIMARY
EVMPD
SUB12769MIG
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
PRIMARY
NSC
722597
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
PRIMARY
CAS
121268-17-5
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
PRIMARY
MERCK INDEX
m1493
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID7047801
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
PRIMARY
RS_ITEM_NUM
1012780
Created by admin on Fri Dec 15 15:52:07 UTC 2023 , Edited by admin on Fri Dec 15 15:52:07 UTC 2023
PRIMARY
EVMPD
SUB25549
Created by admin on Fri Dec 15 15:52:06 UTC 2023 , Edited by admin on Fri Dec 15 15:52:06 UTC 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY