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
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)
| 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 |
DescriptionCurator's Comment: Drug developer of this compound, Gemphire Therapeutics Inc.: http://www.gemphire.com/
Curator's Comment: Drug developer of this compound, Gemphire Therapeutics Inc.: http://www.gemphire.com/
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
| Title | Date | PubMed |
|---|---|---|
| Renal organic anion transporter-mediated drug-drug interaction between gemcabene and quinapril. | 2009-07 |
|
| Model-based drug development. | 2007-07 |
|
| Model-based development of gemcabene, a new lipid-altering agent. | 2005-10-07 |
|
| Udp-glucuronosyltransferase 2b7 is the major enzyme responsible for gemcabene glucuronidation in human liver microsomes. | 2005-09 |
|
| Effectiveness and tolerability of a new lipid-altering agent, gemcabene, in patients with low levels of high-density lipoprotein cholesterol. | 2003-09-01 |
| Substance Class |
Chemical
Created
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| Record UNII |
B96UX1DDKS
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Validated (UNII)
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FDA ORPHAN DRUG |
419313
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NCI_THESAURUS |
C98150
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DB05123
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183293-82-5
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CHEMBL2110686
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C72794
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SALT/SOLVATE -> PARENT |
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