Acipimox

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Summary

Acipimox is a niacin derivative used in Fredrickson type IIb and type IV hyperlipoproteinemia.

Generic Name
Acipimox
DrugBank Accession Number
DB09055
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 154.125
Monoisotopic: 154.037842061
Chemical Formula
C6H6N2O3
Synonyms
  • Acipimox

Pharmacology

Indication

Used in the treatment of hyperlipidemias (abnormally elevated levels of any or all lipids and/or lipoproteins in the blood).

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

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.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Alendronic acidThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Alendronic acid is combined with Acipimox.
AmiodaroneThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Amiodarone is combined with Acipimox.
Amphotericin BThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Amphotericin B is combined with Acipimox.
AtorvastatinAcipimox may increase the myopathic rhabdomyolysis activities of Atorvastatin.
BaclofenThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Baclofen is combined with Acipimox.
BetamethasoneThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Betamethasone is combined with Acipimox.
BezafibrateThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Bezafibrate is combined with Acipimox.
BumetanideThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Bumetanide is combined with Acipimox.
CaptoprilThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Captopril is combined with Acipimox.
CarbimazoleThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Carbimazole is combined with Acipimox.
Interactions
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Food Interactions
Not Available

Products

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International/Other Brands
Acipicap (Zydus Cadila)

Categories

ATC Codes
C10AD06 — Acipimox
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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
Pyrazinium compounds / Vinylogous amides / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic zwitterions
show 2 more
Substituents
Aromatic heteromonocyclic compound / Azacycle / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic nitrogen compound / Organic oxide / Organic oxygen compound
show 7 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
K9AY9IR2SD
CAS number
51037-30-0
InChI Key
DJQOOSBJCLSSEY-UHFFFAOYSA-N
InChI
InChI=1S/C6H6N2O3/c1-4-2-7-5(6(9)10)3-8(4)11/h2-3H,1H3,(H,9,10)
IUPAC Name
5-carboxy-2-methylpyrazin-1-ium-1-olate
SMILES
CC1=[N+]([O-])C=C(N=C1)C(O)=O

References

General References
Not Available
KEGG Drug
D07190
PubChem Compound
5310993
PubChem Substance
347827819
ChemSpider
4470534
BindingDB
50208130
RxNav
16817
ChEBI
94688
ChEMBL
CHEMBL345714
ZINC
ZINC000001481960
Drugs.com
Drugs.com Drug Page
Wikipedia
Acipimox

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Active Not RecruitingTreatmentType 1 Diabetes Mellitus1
2CompletedTreatmentHypertriglyceridemias / Obesity, Abdominal / Resistance, Insulin1
2Enrolling by InvitationTreatmentBulimia Nervosa / Eating Disorders1
2TerminatedTreatmentAcute Heart Failure (AHF)1
2, 3CompletedBasic ScienceSyndrome, Metabolic1
2, 3CompletedBasic ScienceType 2 Diabetes Mellitus1
1CompletedTreatmentHealthy Volunteers1
1, 2CompletedTreatmentType 2 Diabetes Mellitus1
Not AvailableActive Not RecruitingTreatmentType 2 Diabetes Mellitus1
Not AvailableCompletedBasic ScienceBMI >30 kg/m2 / Diabetes1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CapsuleOral
CapsuleOral250 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility12.0 mg/mLALOGPS
logP-0.75ALOGPS
logP-2.5ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)-0.1ChemAxon
pKa (Strongest Basic)3.71ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.13 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.78 m3·mol-1ChemAxon
Polarizability13.83 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created on May 11, 2015 17:47 / Updated on May 27, 2021 02:57