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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

Molecular Formula C4H13NO7P2
Molecular Weight 249.096
Charge 0
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

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
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 15:43:35 GMT 2023
Edited
by admin
on Fri Dec 15 15:43:35 GMT 2023
Record UNII
X1J18R4W8P
Record Status Validated (UNII)
Record Version
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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 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
WHO-ATC M05BB05
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
NDF-RT N0000175579
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
LIVERTOX 22
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
WHO-VATC QM05BB05
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
WHO-VATC QM05BB06
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
NDF-RT N0000007707
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
WHO-ATC M05BB06
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
NCI_THESAURUS C443
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
WHO-ATC M05BB03
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
NCI_THESAURUS C67439
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
WHO-VATC QM05BB03
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
WHO-ATC M05BA04
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
WHO-VATC QM05BA04
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
FDA ORPHAN DRUG 844921
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
Code System Code Type Description
DAILYMED
X1J18R4W8P
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
DRUG BANK
DB00630
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
FDA UNII
X1J18R4W8P
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
DRUG CENTRAL
112
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID5022568
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
NCI_THESAURUS
C61625
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
IUPHAR
3141
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
LACTMED
Alendronate
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
INN
6462
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
MERCK INDEX
m1493
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY Merck Index
MESH
D019386
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
HSDB
7990
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
RXCUI
236083
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
ChEMBL
CHEMBL870
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
WIKIPEDIA
ALENDRONIC ACID
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
SMS_ID
100000085258
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
RXCUI
46041
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
ALTERNATIVE
PUBCHEM
2088
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
CHEBI
2567
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
CAS
66376-36-1
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
EVMPD
SUB05307MIG
Created by admin on Fri Dec 15 15:43:35 GMT 2023 , Edited by admin on Fri Dec 15 15:43:35 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
ORAL BIOAVAILABILITY PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
PROTEIN BINDING PHARMACOKINETIC
ORAL BIOAVAILABILITY PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Route of Elimination PHARMACOKINETIC