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

Similar Structures

Weight: Average: 154.125
Monoisotopic: 154.037842061
Chemical Formula: C₆H₆N₂O₃

Synonyms

Acipimox

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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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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Fredrickson classification type iv hyperlipidemia		••••••••••••			•••••••
Treatment of	Fredrickson type iib hyperlipidemia		••••••••••••			•••••••

Contraindications & Blackbox Warnings

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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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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
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Alendronic 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.

Food Interactions

Not Available

Products

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International/Other Brands: Acipicap (Zydus Cadila)

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
RxNav: 16817
ChEBI: 94688
ChEMBL: CHEMBL345714
ZINC: ZINC000001481960
Drugs.com: Drugs.com Drug Page
Wikipedia: Acipimox

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

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

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 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	132.7825551	predicted	DarkChem Lite v0.1.0
[M-H]-	107.37802	predicted	DeepCCS 1.0 (2019)
[M+H]+	135.7369551	predicted	DarkChem Lite v0.1.0
[M+H]+	110.69462	predicted	DeepCCS 1.0 (2019)
[M+Na]+	133.2142551	predicted	DarkChem Lite v0.1.0
[M+Na]+	119.820435	predicted	DeepCCS 1.0 (2019)

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

Acipimox

Identification

Structure for Acipimox (DB09055)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)