Acipimox

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

Identification

Name
Acipimox
Accession Number
DB09055
Type
Small Molecule
Groups
Approved, Investigational
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.

Structure
Thumb
Synonyms
Not Available
International/Other Brands
Acipicap (Zydus Cadila)
Categories
UNII
K9AY9IR2SD
CAS number
51037-30-0
Weight
Average: 154.125
Monoisotopic: 154.037842061
Chemical Formula
C6H6N2O3
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

Pharmacology

Indication

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

Structured Indications
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
Aluminium clofibrateAcipimox may increase the myopathic rhabdomyolysis activities of Aluminium clofibrate.Experimental
AtorvastatinAcipimox may increase the myopathic rhabdomyolysis activities of Atorvastatin.Approved
BezafibrateAcipimox may increase the myopathic rhabdomyolysis activities of Bezafibrate.Approved
CerivastatinAcipimox may increase the myopathic rhabdomyolysis activities of Cerivastatin.Withdrawn
CiprofibrateAcipimox may increase the myopathic rhabdomyolysis activities of Ciprofibrate.Approved, Investigational
ClofibrateAcipimox may increase the myopathic rhabdomyolysis activities of Clofibrate.Approved, Investigational
ClofibrideAcipimox may increase the myopathic rhabdomyolysis activities of Clofibride.Experimental
EtofibrateAcipimox may increase the myopathic rhabdomyolysis activities of Etofibrate.Approved
FenofibrateAcipimox may increase the myopathic rhabdomyolysis activities of Fenofibrate.Approved
Fenofibric acidAcipimox may increase the myopathic rhabdomyolysis activities of Fenofibric acid.Approved
FluvastatinAcipimox may increase the myopathic rhabdomyolysis activities of Fluvastatin.Approved
GemfibrozilAcipimox may increase the myopathic rhabdomyolysis activities of Gemfibrozil.Approved
LovastatinAcipimox may increase the myopathic rhabdomyolysis activities of Lovastatin.Approved, Investigational
MevastatinAcipimox may increase the myopathic rhabdomyolysis activities of Mevastatin.Experimental
PitavastatinAcipimox may increase the myopathic rhabdomyolysis activities of Pitavastatin.Approved
PravastatinAcipimox may increase the myopathic rhabdomyolysis activities of Pravastatin.Approved
RonifibrateAcipimox may increase the myopathic rhabdomyolysis activities of Ronifibrate.Experimental
RosuvastatinAcipimox may increase the myopathic rhabdomyolysis activities of Rosuvastatin.Approved
SimfibrateAcipimox may increase the myopathic rhabdomyolysis activities of Simfibrate.Experimental
SimvastatinAcipimox may increase the myopathic rhabdomyolysis activities of Simvastatin.Approved
UbidecarenoneAcipimox may increase the myopathic rhabdomyolysis activities of Ubidecarenone.Approved, Experimental
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D07190
PubChem Compound
5310993
PubChem Substance
347827819
ChemSpider
4470534
BindingDB
50208130
ChEBI
94688
ChEMBL
CHEMBL345714
Drugs.com
Drugs.com Drug Page
Wikipedia
Acipimox
ATC Codes
C10AD06 — Acipimox

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers1
1, 2CompletedTreatmentType 2 Diabetes Mellitus1
2CompletedTreatmentHypertriglyceridemias / Insulin Resistance / Obesity, Abdominal1
2Enrolling by InvitationTreatmentBulimia Nervosa (BN) / Eating Disorder1
2TerminatedTreatmentAcute Heart Failure (AHF)1
2, 3Active Not RecruitingBasic ScienceMetabolic Syndromes1
2, 3CompletedBasic ScienceType 2 Diabetes Mellitus1
3Active Not RecruitingTreatmentDiabetes, Diabetes Mellitus Type 11
Not AvailableCompletedBasic ScienceBMI >30 kg/m2 / Diabetes1
Not AvailableCompletedBasic ScienceCongestive Cardiomyopathy / Type 2 Diabetes Mellitus1
Not AvailableCompletedBasic ScienceHypopituitarism / Insulin Resistance / Metabolism1
Not AvailableCompletedPreventionCardiovascular Disease (CVD) / Heart Diseases / Human Immunodeficiency Virus (HIV) Infections / Hyperlipidemias / Hypertriglyceridemias / Insulin Resistance1
Not AvailableCompletedTreatmentHeart Failure, Unspecified1
Not AvailableNot Yet RecruitingBasic ScienceAssessing Muscle Amino Acid Balance1
Not AvailableNot Yet RecruitingBasic ScienceType 2 Diabetes Mellitus1
Not AvailableRecruitingBasic ScienceBrain Diseases / Endocrine System Diseases / Glucose Metabolism Disorders / Hypopituitarism / Insulin Resistance / Metabolic Diseases / Pituitary Diseases1
Not AvailableRecruitingTreatmentType 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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

Taxonomy

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
Pyrazine carboxylic acid / Pyrazinium / Heteroaromatic compound / Vinylogous amide / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives / Azacycle / Organic nitrogen compound / Organic zwitterion
show 7 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on May 11, 2015 11:47 / Updated on November 09, 2017 04:44