NAV

Gemcabene

Identification

Generic Name
Gemcabene
DrugBank Accession Number
DB05123
Background

Gemcabene is a new drug that lowers low-density lipoprotein cholesterol (LDL-C), decreases triglycerides, and raises high-density lipoprotein cholesterol (HDL-C).

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 302.4064
Monoisotopic: 302.20932407
Chemical Formula
C16H30O5
Synonyms
  • Gemcabene
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Pharmacology

Indication

Investigated for use/treatment in atherosclerosis, cardiovascular disorders, and hyperlipidemia.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Medium-chain fatty acids
Alternative Parents
Methyl-branched fatty acids / Dicarboxylic acids and derivatives / Dialkyl ethers / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Branched fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dialkyl ether / Dicarboxylic acid or derivatives / Ether / Hydrocarbon derivative / Medium-chain fatty acid
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
B96UX1DDKS
CAS number
183293-82-5
InChI Key
SDMBRCRVFFHJKR-UHFFFAOYSA-N
InChI
InChI=1S/C16H30O5/c1-15(2,13(17)18)9-5-7-11-21-12-8-6-10-16(3,4)14(19)20/h5-12H2,1-4H3,(H,17,18)(H,19,20)
IUPAC Name
6-[(5-carboxy-5,5-dimethylpentyl)oxy]-2,2-dimethylhexanoic acid
SMILES
CC(C)(CCCCOCCCCC(C)(C)C(O)=O)C(O)=O

References

General References
  1. Mandema JW, Hermann D, Wang W, Sheiner T, Milad M, Bakker-Arkema R, Hartman D: Model-based development of gemcabene, a new lipid-altering agent. AAPS J. 2005 Oct 7;7(3):E513-22. [Article]
  2. Bays HE, McKenney JM, Dujovne CA, Schrott HG, Zema MJ, Nyberg J, MacDougall DE: Effectiveness and tolerability of a new lipid-altering agent, gemcabene, in patients with low levels of high-density lipoprotein cholesterol. Am J Cardiol. 2003 Sep 1;92(5):538-43. [Article]
PubChem Compound
157692
PubChem Substance
175426948
ChemSpider
138760
ChEMBL
CHEMBL2110686
ZINC
ZINC000001893031

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedBasic ScienceInsulin Sensitivity1
2CompletedTreatmentHigh Cholesterol4
2CompletedTreatmentHigh Cholesterol / Hypertriglyceridemias1
2CompletedTreatmentMixed Dyslipidaemia / Severe Hypertriglyceridemia (sHTG)1
2TerminatedTreatmentFatty Liver, Non-alcoholic Fatty Liver Disease, NAFLD1

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 Solubility0.0608 mg/mLALOGPS
logP3.16ALOGPS
logP4.11Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)4.38Chemaxon
pKa (Strongest Basic)-4.1Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area83.83 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity80.65 m3·mol-1Chemaxon
Polarizability35.21 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.646
Blood Brain Barrier+0.8956
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.6826
P-glycoprotein inhibitor INon-inhibitor0.8962
P-glycoprotein inhibitor IINon-inhibitor0.586
Renal organic cation transporterNon-inhibitor0.8887
CYP450 2C9 substrateNon-substrate0.8454
CYP450 2D6 substrateNon-substrate0.8917
CYP450 3A4 substrateSubstrate0.5213
CYP450 1A2 substrateNon-inhibitor0.8895
CYP450 2C9 inhibitorNon-inhibitor0.8733
CYP450 2D6 inhibitorNon-inhibitor0.9535
CYP450 2C19 inhibitorNon-inhibitor0.9241
CYP450 3A4 inhibitorNon-inhibitor0.908
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9776
Ames testNon AMES toxic0.8406
CarcinogenicityNon-carcinogens0.6998
BiodegradationNot ready biodegradable0.7872
Rat acute toxicity1.7859 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9692
hERG inhibition (predictor II)Non-inhibitor0.8241
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-2940000000-acea28a66ab4e0c27d88
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-100c-4693000000-0fe94b15ba8b2b4e7c5f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-aaca8a945e2b1acaf877
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-2629000000-ce6474a10a3c761e259b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-7910000000-8c5bcd95862562578d4d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9620000000-00bd350aead27ff3fe8c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052n-9400000000-af834af416320dd78db7
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-172.166
predicted
DeepCCS 1.0 (2019)
[M+H]+174.6916
predicted
DeepCCS 1.0 (2019)
[M+Na]+182.12996
predicted
DeepCCS 1.0 (2019)

Drug created at October 21, 2007 22:23 / Updated at February 21, 2021 18:51