acamprosate 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
38 77337-76-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • acamprosaic acid
  • acamprosate
  • campral
  • zulex
  • acamprosate calcium
  • calcium acetylhomotaurinate
  • N-acetylhomotaurine
  • calcium acetylhomotaurine
The mechanism of action of acamprosate in maintenance of alcohol abstinence is not completely understood. Chronic alcohol exposure is hypothesized to alter the normal balance between neuronal excitation and inhibition. In vitro and in vivo studies in animals have provided evidence to suggest acamprosate may interact with glutamate and GABA neurotransmitter systems centrally, and has led to the hypothesis that acamprosate restores this balance.
  • Molecular weight: 181.21
  • Formula: C5H11NO4S
  • CLOGP: -2.46
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 2
  • TPSA: 83.47
  • ALOGS: -0.98
  • ROTB: 4
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 71.27 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 11 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.30 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 3.75 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 1 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 3.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
July 29, 2004 FDA FOREST LABS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Ventricular fibrillation 95.88 49.06 23 693 11844 63476462
Electrocardiogram QT prolonged 77.66 49.06 28 688 59502 63428804
Torsade de pointes 73.32 49.06 19 697 13332 63474974

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Anticoagulation drug level above therapeutic 77.86 35.89 16 743 2100 34954072
Hepatitis acute 62.15 35.89 17 742 7584 34948588
Wrong dose 43.43 35.89 8 751 591 34955581
Intentional overdose 39.12 35.89 19 740 43655 34912517

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Anticoagulation drug level above therapeutic 66.73 34.09 15 1420 3605 79739348
Ventricular fibrillation 58.93 34.09 22 1413 31904 79711049
Overdose 58.43 34.09 38 1397 184168 79558785
Torsade de pointes 57.50 34.09 19 1416 19293 79723660
Intentional overdose 54.86 34.09 30 1405 105930 79637023
Electrocardiogram QT prolonged 50.71 34.09 27 1408 90359 79652594
Hepatitis acute 49.11 34.09 16 1419 15526 79727427
Alcoholism 45.22 34.09 11 1424 3712 79739241
Coma 42.62 34.09 25 1410 100624 79642329
Intentional self-injury 41.00 34.09 17 1418 32402 79710551
Wrong dose 36.61 34.09 8 1427 1686 79741267
Injection site reaction 35.37 34.09 18 1417 54767 79688186

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N07BB03 NERVOUS SYSTEM
OTHER NERVOUS SYSTEM DRUGS
DRUGS USED IN ADDICTIVE DISORDERS
Drugs used in alcohol dependence
MeSH PA D000427 Alcohol Deterrents
MeSH PA D002491 Central Nervous System Agents
CHEBI has role CHEBI:35703 Xenobiotic
CHEBI has role CHEBI:35942 neurotransmitter agents
CHEBI has role CHEBI:78298 environmental contaminants

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Alcoholism indication 7200002
Suicidal thoughts contraindication 6471006
Acute nephropathy contraindication 58574008
Impaired renal function disorder contraindication 197663003




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 0.21 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
GABA-A receptor alpha-1/beta-3/gamma-2 Ion channel POSITIVE MODULATOR WOMBAT-PK CHEMBL
Glutamate [NMDA] receptor Ion channel ANTAGONIST CHEMBL CHEMBL

External reference:

IDSource
4021476 VUID
N0000148859 NUI
D02780 KEGG_DRUG
77337-73-6 SECONDARY_CAS_RN
152761 RXNORM
C0284941 UMLSCUI
CHEBI:51041 CHEBI
CHEMBL1201293 ChEMBL_ID
CHEMBL2068724 ChEMBL_ID
D000077443 MESH_DESCRIPTOR_UI
DB00659 DRUGBANK_ID
7106 IUPHAR_LIGAND_ID
6473 INN_ID
N4K14YGM3J UNII
71158 PUBCHEM_CID
391698009 SNOMEDCT_US
391699001 SNOMEDCT_US
420804003 SNOMEDCT_US
4021476 VANDF
17781 MMSL
205049 MMSL
50782 MMSL
50783 MMSL
59283 MMSL
d04986 MMSL
005217 NDDF
006125 NDDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Acamprosate Calcium HUMAN PRESCRIPTION DRUG LABEL 1 0093-5352 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 26 sections
Acamprosate Calcium HUMAN PRESCRIPTION DRUG LABEL 1 0378-6333 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 28 sections
Acamprosate Calcium HUMAN PRESCRIPTION DRUG LABEL 1 0378-6333 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 28 sections
Acamprosate Calcium HUMAN PRESCRIPTION DRUG LABEL 1 0904-7213 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 26 sections
Acamprosate Calcium HUMAN PRESCRIPTION DRUG LABEL 1 10135-636 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 28 sections
Acamprosate Calcium HUMAN PRESCRIPTION DRUG LABEL 1 42291-104 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 26 sections
Acamprosate Calcium HUMAN PRESCRIPTION DRUG LABEL 1 60687-121 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 26 sections
Acamprosate Calcium HUMAN PRESCRIPTION DRUG LABEL 1 60687-121 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 26 sections
Campral HUMAN PRESCRIPTION DRUG LABEL 1 68151-4760 TABLET, DELAYED RELEASE 333 mg ORAL NDA 29 sections
acamprosate calcium HUMAN PRESCRIPTION DRUG LABEL 1 68382-569 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 25 sections
Acamprosate Calcium HUMAN PRESCRIPTION DRUG LABEL 1 68462-435 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 26 sections
Acamprosate Calcium HUMAN PRESCRIPTION DRUG LABEL 1 68462-435 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 26 sections
acamprosate calcium HUMAN PRESCRIPTION DRUG LABEL 1 70771-1057 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 25 sections