acamprosate 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AURKA,AXL,BRAF,BTK,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GSK3B,ITK,JAK1,JAK2,JAK3,MAP2K6,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPKAPK2,MTOR,NTRK2,PDK1,PDK2,PDK4,PIK3CB,PIK3CD,PIK3CG,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ZAP70 49
kinase-selectivity-class ACVR2B,AXL,BRAF,CAMK2D,CDK1,CDK16,CDK3,CDK4,CDK6,CDK7,CDK9,CLK4,DDR1,DYRK1A,DYRK2,EPHB4,ERBB2,FLT3,GRK2,GSK3B,IRAK1,IRAK3,JAK2,MAP2K6,MAP3K21,MAPK14,MAPK7,SIK2,STK16,STK33,SYK,TEK,TYRO3,ZAP70 34
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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
Electrocardiogram QT prolonged 132.59 45.44 43 900 72413 90555091
Ventricular fibrillation 130.36 45.44 30 913 14014 90613490
Torsade de pointes 82.08 45.44 21 922 15161 90612343
Hyperhidrosis 66.51 45.44 31 912 136274 90491230
Intentional self-injury 47.79 45.44 16 927 29318 90598186
Alcoholism 46.64 45.44 9 934 1791 90625713

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 71.82 34.89 16 1085 2574 42617660
Hepatitis acute 56.37 34.89 17 1084 8958 42611276
Delirium 52.41 34.89 26 1075 52493 42567741
Overdose 42.68 34.89 29 1072 105235 42514999
Coma 40.44 34.89 22 1079 53532 42566702
Intentional overdose 38.47 34.89 21 1080 51435 42568799
Wrong dose 37.30 34.89 8 1093 1076 42619158

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
Electrocardiogram QT prolonged 113.44 36.04 50 1983 108910 110478356
Ventricular fibrillation 81.26 36.04 30 2003 41283 110545983
Overdose 72.60 36.04 48 1985 233746 110353520
Anticoagulation drug level above therapeutic 62.72 36.04 15 2018 4615 110582651
Coma 62.02 36.04 34 1999 117835 110469431
Torsade de pointes 61.90 36.04 21 2012 22579 110564687
Alcoholism 60.67 36.04 14 2019 3693 110583573
Intentional overdose 53.07 36.04 32 2001 132469 110454797
Hepatitis acute 45.80 36.04 16 2017 18750 110568516
Hyperhidrosis 45.24 36.04 33 2000 187265 110400001
Intentional self-injury 38.27 36.04 17 2016 37412 110549854
Delirium 37.69 36.04 26 2007 134999 110452267

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
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:35474 anxiolytic drug
CHEBI has role CHEBI:35476 antipsychotic agent
CHEBI has role CHEBI:35703 xenobiotic
CHEBI has role CHEBI:35942 neurotransmitter agent
CHEBI has role CHEBI:78298 environmental contaminant

Related Drugs by ATC class:

N07BB Drugs used in alcohol dependence 4 drugs
calcium carbimidedisulfiramnalmefenenaltrexone

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
17781 MMSL
205049 MMSL
50782 MMSL
59283 MMSL
d04986 MMSL
4021476 VANDF
005217 NDDF
006125 NDDF
391698009 SNOMEDCT_US
391699001 SNOMEDCT_US
420804003 SNOMEDCT_US
N4K14YGM3J INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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 0615-8560 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 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 69452-353 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 26 sections
acamprosate calcium HUMAN PRESCRIPTION DRUG LABEL 1 70518-4616 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 25 sections
acamprosate calcium HUMAN PRESCRIPTION DRUG LABEL 1 70771-1057 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 25 sections