ContaminantDB: Acamprosate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (14)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:22 UTC

Update Date

2026-05-14 16:45:19 UTC

Accession Number

CHEM002242

Identification

Common Name

Acamprosate

Class

Small Molecule

Description

Acamprosate, also known by the brand name Campral™, is a drug used for treating alcohol dependence. Acamprosate is thought to stabilize the chemical balance in the brain that would otherwise be disrupted by alcoholism, possibly by blocking glutaminergic N-methyl-D-aspartate receptors, while gamma-aminobutyric acid type A receptors are activated. Reports indicate that acamprosate only works with a combination of attending support groups and abstinence from alcohol. Certain serious side effects include allergic reactions, irregular heartbeats, and low or high blood pressure, while less serious side effects include headaches, insomnia, and impotence. Acamprosate should not be taken by people with kidney problems or allergies to the drug.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Alcohol Deterrent
Amide
Amine
Drug
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Acetamido-1-propanesulfonic acid	ChEBI
Acamprosato	ChEBI
Acamprosatum	ChEBI
N-Acetylhomotaurine	ChEBI
Aotal	Kegg
3-Acetamido-1-propanesulfonate	Generator
3-Acetamido-1-propanesulphonate	Generator
3-Acetamido-1-propanesulphonic acid	Generator
Acamprosic acid	Generator
3-(Acetylamino)propanesulphonic acid	HMDB
Campral	HMDB
Campral ec	HMDB
N-Acetylhomotaurine, monopotassium salt	HMDB
N-Acetylhomotaurine, zinc (2:1) salt	HMDB
Regtect	HMDB
Acamprosate calcium	HMDB
N-Acetylhomotaurine, calcium (2:1) salt	HMDB
N-Acetylhomotaurine, magnesium (2:1) salt	HMDB
N-Acetylhomotaurine, monolithium salt	HMDB
N-Acetylhomotaurine, monosodium salt	HMDB
Zulex	HMDB
Calcium acetyl homotaurinate	HMDB
Calcium acetylhomotaurine	HMDB
Sodium acetylhomotaurine	HMDB
AOTA	HMDB
Acamprostate	HMDB
Calcium acetylhomotaurinate	HMDB
Acetyl homotaurinate, calcium	HMDB
Acetylhomotaurinate, calcium	HMDB
N Acetylhomotaurine, monolithium salt	HMDB
Acetylhomotaurine, calcium	HMDB
Acetylhomotaurine, sodium	HMDB
N Acetylhomotaurine, monosodium salt	HMDB
N Acetylhomotaurine	HMDB
N Acetylhomotaurine, monopotassium salt	HMDB

Chemical Formula

C₅H₁₁NO₄S

Average Molecular Mass

181.210 g/mol

Monoisotopic Mass

181.041 g/mol

CAS Registry Number

77337-76-9

IUPAC Name

3-acetamidopropane-1-sulfonic acid

Traditional Name

acamprosate

SMILES

CC(=O)NCCCS(O)(=O)=O

InChI Identifier

InChI=1S/C5H11NO4S/c1-5(7)6-3-2-4-11(8,9)10/h2-4H2,1H3,(H,6,7)(H,8,9,10)

InChI Key

AFCGFAGUEYAMAO-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfonic acids and derivatives

Sub Class

Organosulfonic acids and derivatives

Direct Parent

Organosulfonic acids

Alternative Parents

Substituents

Organosulfonic acid
Sulfonyl
Alkanesulfonic acid
Carboximidic acid
Carboximidic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organosulfonic acid (CHEBI:51041 )
acetamides (CHEBI:51041 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

neurotransmitter agent

Biological Roles

neurotransmitter agent

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	1.88e+01 g/L

Predicted Properties

Property	Value	Source
Water Solubility	18.8 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-2.8	ChemAxon
logS	-0.98	ALOGPS
pKa (Strongest Acidic)	-1.1	ChemAxon
pKa (Strongest Basic)	-0.47	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.47 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	38.91 m³·mol⁻¹	ChemAxon
Polarizability	17.17 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-007o-9100000000-8420bb56903c56b30a73	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-1900000000-095fc64fb4490a8d6b4d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-c177d5ee7162b0b8756d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-40eaa1bb480a68330940	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-1900000000-35bfe6cae36755d1cf1c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0059-9500000000-d366cda3213379d7501b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-9000000000-4374601f59e1dc8df0eb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-9000000000-011f30e0257faffd4553	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-c179316d784a91f87c59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-8cf123c7cf7dddcf6838	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-1900000000-84a7d1cc6ca5022d4da7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0059-9500000000-4503d9afc6bab741521b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-9000000000-8c2ba21c044eeada7839	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-9000000000-dd14c920c5211780d172	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-1900000000-dac38f625c8648b643c4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-0900000000-3684e08456a971400c3d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-0900000000-6137fe4463b3675f55eb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-58f776a52000101b8fb7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0006-0900000000-d8de420d40b45a34ea95	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001l-0900000000-1bb28abe8034966ad829	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-0900000000-343cd651472c88796a61	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05g0-5900000000-0c71e48c69c18769563d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9300000000-181e815cd85a7505ce4a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-4900000000-1f6b18b2f30371ea12ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9500000000-50bd4d569514037edb1b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-ec0629ff72c5e58a0413	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

The absolute bioavailability of acamprosate after oral administration is about 11%. The food effect on absorption is not clinically significant and no adjustment of dose is necessary.

Mechanism of Toxicity

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. It seems to inhibit NMDA receptors while activating GABA receptors.

Metabolism

Acamprosate does not undergo metabolism. Route of Elimination: Following oral administration of CAMPRAL™, the major route of excretion is via the kidneys as acamprosate. Half Life: 20 - 33 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the maintenance of abstinence from alcohol in patients with alcohol dependence who are abstinent at treatment initiation

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

In all reported cases of acute overdosage with acamprosate (total reported doses of up to 56 grams of acamprosate calcium), the only symptom that could be reasonably associated with acamprosate was diarrhea.

Treatment

Treatment consists of discontinuation of Acamprosate together with appropriate symptomatic therapy. The judicious use of a cardioselective beta-receptor blocker may beconsidered, bearing in mind that such medication can produce bronchospasm. (8)

Concentrations

Not Available

External Links

DrugBank ID

DB00659

HMDB ID

HMDB0014797

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID