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Details

Stereochemistry ACHIRAL
Molecular Formula C16H28O5.Ca
Molecular Weight 340.469
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GEMCABENE CALCIUM

SMILES

[Ca++].CC(C)(CCCCOCCCCC(C)(C)C([O-])=O)C([O-])=O

InChI

InChIKey=ZJKZKKPIKDNHDM-UHFFFAOYSA-L
InChI=1S/C16H30O5.Ca/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);/q;+2/p-2

HIDE SMILES / InChI

Molecular Formula Ca
Molecular Weight 40.078
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C16H28O5
Molecular Weight 300.3905
Charge -2
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
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 15:30:34 GMT 2023
Edited
by admin
on Fri Dec 15 15:30:34 GMT 2023
Record UNII
Z9AM8GST2F
Record Status Validated (UNII)
Record Version
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Name Type Language
GEMCABENE CALCIUM
USAN  
USAN  
Official Name English
HEXANOIC ACID, 6,6'-OXYBIS(2,2-DIMETHYL-, CALCIUM SALT (1:1)
Common Name English
PD-072953-0038
Code English
GEMCABENE CALCIUM [USAN]
Common Name English
CI-1027
Code English
CALCIUM 6,6'-OXYBIS(2,2-DIMETHYLHEXANOATE)
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C98150
Created by admin on Fri Dec 15 15:30:34 GMT 2023 , Edited by admin on Fri Dec 15 15:30:34 GMT 2023
Code System Code Type Description
CAS
209789-08-2
Created by admin on Fri Dec 15 15:30:34 GMT 2023 , Edited by admin on Fri Dec 15 15:30:34 GMT 2023
PRIMARY
EPA CompTox
DTXSID00175181
Created by admin on Fri Dec 15 15:30:34 GMT 2023 , Edited by admin on Fri Dec 15 15:30:34 GMT 2023
PRIMARY
PUBCHEM
157691
Created by admin on Fri Dec 15 15:30:34 GMT 2023 , Edited by admin on Fri Dec 15 15:30:34 GMT 2023
PRIMARY
SMS_ID
300000042560
Created by admin on Fri Dec 15 15:30:34 GMT 2023 , Edited by admin on Fri Dec 15 15:30:34 GMT 2023
PRIMARY
USAN
NN-10
Created by admin on Fri Dec 15 15:30:34 GMT 2023 , Edited by admin on Fri Dec 15 15:30:34 GMT 2023
PRIMARY
NCI_THESAURUS
C75255
Created by admin on Fri Dec 15 15:30:34 GMT 2023 , Edited by admin on Fri Dec 15 15:30:34 GMT 2023
PRIMARY
ChEMBL
CHEMBL2110686
Created by admin on Fri Dec 15 15:30:34 GMT 2023 , Edited by admin on Fri Dec 15 15:30:34 GMT 2023
PRIMARY
FDA UNII
Z9AM8GST2F
Created by admin on Fri Dec 15 15:30:34 GMT 2023 , Edited by admin on Fri Dec 15 15:30:34 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY