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

Stem definition	Drug id	CAS RN
	38	77337-76-9

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
2	g	O

ADMET properties:

Property	Value	Reference
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:

Date	Agency	Company	Orphan
July 29, 2004	FDA	FOREST LABS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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:

Source	Code	Description
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|

Disease	Relation	SNOMED_ID
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 level	Dissociation constant	Type (acidic/basic)
pKa1	0.21	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
GABA-A receptor alpha-1/beta-3/gamma-2	Ion channel	P14867 P18507 P28472	GBRA1_HUMAN GBRG2_HUMAN GBRB3_HUMAN	POSITIVE MODULATOR				WOMBAT-PK	CHEMBL
Glutamate [NMDA] receptor	Ion channel	O15399 O60391 Q05586 Q12879 Q13224 Q14957 Q8TCU5	NMDE4_HUMAN NMD3B_HUMAN NMDZ1_HUMAN NMDE1_HUMAN NMDE2_HUMAN NMDE3_HUMAN NMD3A_HUMAN	ANTAGONIST				CHEMBL	CHEMBL

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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