Gemcabene

Identification

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Name
Gemcabene
Accession Number
DB05123
Type
Small Molecule
Groups
Investigational
Description

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

Structure
Thumb
Synonyms
Not Available
Categories
UNII
B96UX1DDKS
CAS number
183293-82-5
Weight
Average: 302.4064
Monoisotopic: 302.20932407
Chemical Formula
C16H30O5
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

Pharmacology

Indication

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

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

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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. [PubMed:16353929]
  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. [PubMed:12943873]
External Links
PubChem Compound
157692
PubChem Substance
175426948
ChemSpider
138760
ChEMBL
CHEMBL2110686

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceHigh Cholesterol3
1, 2Active Not RecruitingTreatmentFatty Liver / Hypertriglyceridemias / Lipodystrophy, Familial Partial / NASH - Nonalcoholic Steatohepatitis1
2Active Not RecruitingTreatmentNon-Alcoholic Fatty Liver Disease (NAFLD)1
2Active Not RecruitingTreatmentMixed hypercholesterolemia / Severe Hypertriglyceridemia1
2CompletedBasic ScienceInsulin Sensitivity1
2CompletedTreatmentHigh Cholesterol4
2CompletedTreatmentHigh Cholesterol / Hypertriglyceridemias1

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-MSNot Available
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 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
Medium-chain fatty acid / Methyl-branched fatty acid / Branched fatty acid / Dicarboxylic acid or derivatives / Ether / Dialkyl ether / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available

Drug created on October 21, 2007 16:23 / Updated on August 02, 2019 07:43