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
Structure for Acipimox (DB09055)
- 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).
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAlendronic acid The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Alendronic acid is combined with Acipimox. Amiodarone The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Amiodarone is combined with Acipimox. Amphotericin B The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Amphotericin B is combined with Acipimox. Atorvastatin Acipimox may increase the myopathic rhabdomyolysis activities of Atorvastatin. Baclofen The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Baclofen is combined with Acipimox. Betamethasone The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Betamethasone is combined with Acipimox. Bezafibrate The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Bezafibrate is combined with Acipimox. Bumetanide The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Bumetanide is combined with Acipimox. Captopril The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Captopril is combined with Acipimox. Carbimazole The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Carbimazole is combined with Acipimox. 
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- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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
- External Links
- KEGG Drug
- D07190
- PubChem Compound
- 5310993
- PubChem Substance
- 347827819
- ChemSpider
- 4470534
- BindingDB
- 50208130
- 16817
- ChEBI
- 94688
- ChEMBL
- CHEMBL345714
- ZINC
- ZINC000001481960
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Acipimox
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Type 1 Diabetes Mellitus 1 2 Completed Treatment Hypertriglyceridemias / Obesity, Abdominal / Resistance, Insulin 1 2 Enrolling by Invitation Treatment Bulimia Nervosa / Eating Disorders 1 2 Terminated Treatment Acute Heart Failure (AHF) 1 2, 3 Completed Basic Science Syndrome, Metabolic 1 2, 3 Completed Basic Science Type 2 Diabetes Mellitus 1 1 Completed Treatment Healthy Subjects (HS) 1 1, 2 Completed Treatment Type 2 Diabetes Mellitus 1 Not Available Completed Basic Science Brain Disorders / Endocrine System Diseases / Hypopituitarism / Metabolic Diseases / Metabolism Disorder, Glucose / Pituitary Diseases / Resistance, Insulin 1 Not Available Completed Basic Science Diabetes / Obesity 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral Capsule Oral 250 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 12.0 mg/mL 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 - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created at May 11, 2015 17:47 / Updated at May 27, 2021 02:57