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

Identification
NameAcipimox
Accession NumberDB09055
TypeSmall Molecule
GroupsApproved
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
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
ProductsNot Available
International Brands
NameCompany
AcipicapZydus Cadila
Brand mixturesNot Available
Categories
UNIIK9AY9IR2SD
CAS number51037-30-0
WeightAverage: 154.125
Monoisotopic: 154.037842061
Chemical FormulaC6H6N2O3
InChI KeyDJQOOSBJCLSSEY-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
PharmacodynamicsNot 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.

Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
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
ClofibrateAcipimox may increase the myopathic rhabdomyolysis activities of Clofibrate.Approved
EtofibrateAcipimox may increase the myopathic rhabdomyolysis activities of Etofibrate.Approved
FenofibrateAcipimox may increase the myopathic rhabdomyolysis activities of Fenofibrate.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
RosuvastatinAcipimox may increase the myopathic rhabdomyolysis activities of Rosuvastatin.Approved
SimvastatinAcipimox may increase the myopathic rhabdomyolysis activities of Simvastatin.Approved
UbidecarenoneAcipimox may increase the myopathic rhabdomyolysis activities of Coenzyme Q10.Experimental
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesC10AD06 — Acipimox
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers1
1, 2CompletedTreatmentType 2 Diabetes Mellitus1
2CompletedTreatmentHypertriglyceridemias / Insulin Resistance / Obesity, Abdominal1
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 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
Not AvailableUnknown StatusBasic ScienceHypopituitarism / Insulin Resistance / Metabolism1
Properties
StateSolid
Experimental PropertiesNot 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 featuresNot Available
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrazines
Direct ParentPyrazine carboxylic acids
Alternative ParentsPyrazinium compounds / Vinylogous amides / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic zwitterions
SubstituentsPyrazine carboxylic acid / Pyrazinium / Heteroaromatic compound / Vinylogous amide / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives / Azacycle / Organic nitrogen compound / Organic zwitterion
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Drug created on May 11, 2015 11:47 / Updated on September 14, 2017 13:27