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Details

Stereochemistry ACHIRAL
Molecular Formula C16H30O5
Molecular Weight 302.4064
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GEMCABENE

SMILES

CC(C)(CCCCOCCCCC(C)(C)C(O)=O)C(O)=O

InChI

InChIKey=SDMBRCRVFFHJKR-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C16H30O5
Molecular Weight 302.4064
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Gemcabene calcium (PD 72953), the monocalcium salt of a dialkyl ether dicarboxylic acid, is a lipid-regulating compound that was first described in 1998. It down-regulates apolipoprotein C-III expression, enhancing the clearance of very low density lipoprotein (LDL), and reduces plasma triglycerides. It also raises high-density lipoprotein cholesterol (HDL). Unlike fibrates (blood trygliceride level lowering drugs), its mechanism of action is not linked to agonist or antagonist activity on PPAR-α receptors. There is limited information on the exact mechanism of action, but an anti-inflammatory profile was found, associated with a lowered expression of the high-sensitivity C-reactive protein gene regulating mechanisms. Gemcabene (administered as 6, 6’-oxybis [2, 2-dimethyl-4-hexanoic acid] monocalcium salt) has been investigated for treatment in a wide range of hyperlipidaemias, as well as atherosclerosis, and cardiovascular disorders. Gemcabene is generally well tolerated. One phase 2 study testing the preliminary efficacy and safety of gemcabene in children with established nonalcoholic fatty liver disease has been stopped early due to increasing weight and a rise in liver fat content in patients. Clinical trials are still ongoing.

Approval Year

PubMed

PubMed

TitleDatePubMed
Effectiveness and tolerability of a new lipid-altering agent, gemcabene, in patients with low levels of high-density lipoprotein cholesterol.
2003 Sep 1
Model-based development of gemcabene, a new lipid-altering agent.
2005 Oct 7
Udp-glucuronosyltransferase 2b7 is the major enzyme responsible for gemcabene glucuronidation in human liver microsomes.
2005 Sep
Model-based drug development.
2007 Jul
Renal organic anion transporter-mediated drug-drug interaction between gemcabene and quinapril.
2009 Jul
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:43:59 GMT 2023
Edited
by admin
on Fri Dec 15 15:43:59 GMT 2023
Record UNII
B96UX1DDKS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GEMCABENE
INN  
INN  
Official Name English
HEXANOIC ACID, 6,6'-OXYBIS 2,2-DIMETHYL-
Common Name English
PD-0072953
Code English
gemcabene [INN]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 419313
Created by admin on Fri Dec 15 15:43:59 GMT 2023 , Edited by admin on Fri Dec 15 15:43:59 GMT 2023
NCI_THESAURUS C98150
Created by admin on Fri Dec 15 15:43:59 GMT 2023 , Edited by admin on Fri Dec 15 15:43:59 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID60171407
Created by admin on Fri Dec 15 15:43:59 GMT 2023 , Edited by admin on Fri Dec 15 15:43:59 GMT 2023
PRIMARY
DRUG BANK
DB05123
Created by admin on Fri Dec 15 15:43:59 GMT 2023 , Edited by admin on Fri Dec 15 15:43:59 GMT 2023
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FDA UNII
B96UX1DDKS
Created by admin on Fri Dec 15 15:43:59 GMT 2023 , Edited by admin on Fri Dec 15 15:43:59 GMT 2023
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CAS
183293-82-5
Created by admin on Fri Dec 15 15:43:59 GMT 2023 , Edited by admin on Fri Dec 15 15:43:59 GMT 2023
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ChEMBL
CHEMBL2110686
Created by admin on Fri Dec 15 15:43:59 GMT 2023 , Edited by admin on Fri Dec 15 15:43:59 GMT 2023
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PUBCHEM
157692
Created by admin on Fri Dec 15 15:43:59 GMT 2023 , Edited by admin on Fri Dec 15 15:43:59 GMT 2023
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INN
8229
Created by admin on Fri Dec 15 15:43:59 GMT 2023 , Edited by admin on Fri Dec 15 15:43:59 GMT 2023
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SMS_ID
300000034205
Created by admin on Fri Dec 15 15:43:59 GMT 2023 , Edited by admin on Fri Dec 15 15:43:59 GMT 2023
PRIMARY
NCI_THESAURUS
C72794
Created by admin on Fri Dec 15 15:43:59 GMT 2023 , Edited by admin on Fri Dec 15 15:43:59 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY