ChemFOnt: Showing chemical card for Acamprosate (CFc000009138)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:11 UTC

Chemfont ID

CFc000009138

Molecule Identification

Common Name

Acamprosate

Definition

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.

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 Weight

181.21

Monoisotopic Molecular Weight

181.040878535

IUPAC Name

3-acetamidopropane-1-sulfonic acid

Traditional Name

acamprosate

CAS Registry Number

77337-76-9

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 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014797)

Source

Exogenous

Exogenous (HMDB: HMDB0014797)

Process

Not Available

Role

Industrial application

Neurotransmitter agent (HMDB: HMDB0014797)

Physical Properties

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0014797

DrugBank ID

DB00659

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

64300

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Acamprosate

METLIN ID

Not Available

PubChem Compound

71158

PDB ID

Not Available

ChEBI ID

51041

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Acamprosate (CFc000009138)

MOL for CFc000009138 (Acamprosate)

3D MOL for CFc000009138 (Acamprosate)

3D SDF for CFc000009138 (Acamprosate)

3D-SDF for CFc000009138 (Acamprosate)

PDB for CFc000009138 (Acamprosate)

3D PDB for CFc000009138 (Acamprosate)

SMILES for CFc000009138 (Acamprosate)

INCHI for CFc000009138 (Acamprosate)

Structure for CFc000009138 (Acamprosate)

3D Structure for CFc000009138 (Acamprosate)