ContaminantDB: Acipimox

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 05:34:03 UTC

Update Date

2016-11-09 01:15:52 UTC

Accession Number

CHEM018826

Identification

Common Name

Acipimox

Class

Small Molecule

Description

Acipimox is a niacin derivative used as a hypolipidemic agent. It is used in low doses and may have less marked adverse effects, although it is unclear whether the recommended dose is as effective as are standard doses of nicotinic acid. Acipimox inhibits the production of triglycerides by the liver and the secretion of VLDL, which leads indirectly to a modest reduction in LDL and increase in HDL. Long-term administration is associated with reduced mortality, but unwanted effects limit its clinical use. Adverse effects include flushing (associated with Prostaglandin D2), palpitations, and GI disturbances. Flushing can be reduced by taking aspirin 20-30 min before taking Acipimox. High doses can cause disorders of liver function, impair glucose tolerance and precipitate gout.

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Olbetam	MeSH
5-Methylpyrazine-2-carboxylic acid 4-oxide	MeSH
Nedios	MeSH
Olbemox	MeSH
5-Methylpyrazinecarboxylic acid 4-oxide	MeSH
6-Methyl-1-oxo-1λ⁵-pyrazine-3-carboxylate	Generator

Chemical Formula

C₆H₆N₂O₃

Average Molecular Mass

154.125 g/mol

Monoisotopic Mass

154.038 g/mol

CAS Registry Number

51037-30-0

IUPAC Name

5-carboxy-2-methylpyrazin-1-ium-1-olate

Traditional Name

acipimox

SMILES

CC1=[N+]([O-])C=C(N=C1)C(O)=O

InChI Identifier

InChI=1S/C6H6N2O3/c1-4-2-7-5(6(9)10)3-8(4)11/h2-3H,1H3,(H,9,10)

InChI Key

DJQOOSBJCLSSEY-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyrazine carboxylic acids. These are heterocyclic compounds containing a pyrazine ring substituted by one or more carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Pyrazine carboxylic acids

Alternative Parents

Substituents

Pyrazine carboxylic acid
Pyrazinium
Heteroaromatic compound
Vinylogous amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organic nitrogen compound
Organic zwitterion
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	12 g/L	ALOGPS
logP	-0.75	ALOGPS
logP	-2.5	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	-0.1	ChemAxon
pKa (Strongest Basic)	3.71	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.78 m³·mol⁻¹	ChemAxon
Polarizability	13.83 Å³	ChemAxon
Number of Rings	1	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	splash10-0udi-8900000000-6b400135a0c1c53a5c1c	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 (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-79e2bf2c3f4d319b7a0c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4j-1900000000-bac15ed7c3c400abb27e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052e-9100000000-d4da13ec7ca4d527893f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-47393df4caddbc4ad8d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1900000000-50e3d954395de1c5541f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fk9-9100000000-2f3bdd52eb5d17aa9545	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	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	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	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H 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

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB09055

HMDB ID

HMDB0247941

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Acipimox

Chemspider ID

4470534

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Acipimox (CHEM018826)

Structure for CHEM018826: Acipimox