Details
| Stereochemistry | MIXED |
| Molecular Formula | C14H22O4 |
| Molecular Weight | 254.3221 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCC1OC(=O)C(=C)C1C(O)=O
InChI
InChIKey=VCWLZDVWHQVAJU-UHFFFAOYSA-N
InChI=1S/C14H22O4/c1-3-4-5-6-7-8-9-11-12(13(15)16)10(2)14(17)18-11/h11-12H,2-9H2,1H3,(H,15,16)
| Molecular Formula | C14H22O4 |
| Molecular Weight | 254.3221 |
| Charge | 0 |
| Count |
|
| Stereochemistry | MIXED |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Tetrahydro-4-Methylene-2-octyl-5-oxo-3-furancarboxylic acid or C75 is an inhibitor of fatty acid synthase. Additionally, C75 increased fatty acid oxidation and ATP levels by increasing carnitine palmitoyltransferase I (CPT I) activity. Unlike the activation produced by C75, the CoA derivative is a potent competitive inhibitor that binds tightly but reversibly to CPT I. C75 exerts antitumor and anti-obese potential. C75 has two enantiomers: (-)-C75 inhibits FAS activity in vitro and has a cytotoxic effect on tumor cell lines, without affecting food consumption, (+)-C75 inhibits CPT1 and its administration produces anorexia, suggesting that central inhibition of CPT1 is essential for the anorectic effect of C75.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pharmacological inhibitors of mammalian fatty acid synthase suppress DNA replication and induce apoptosis in tumor cell lines. | 1998 Oct 15 |
|
| Synthesis and antitumor activity of an inhibitor of fatty acid synthase. | 2000 Mar 28 |
|
| Chronic C75 treatment of diet-induced obese mice increases fat oxidation and reduces food intake to reduce adipose mass. | 2004 Jul |
|
| C75, a fatty acid synthase inhibitor, reduces food intake via hypothalamic AMP-activated protein kinase. | 2004 May 7 |
|
| Characterization of the inactivation of rat fatty acid synthase by C75: inhibition of partial reactions and protection by substrates. | 2005 Jun 15 |
|
| Effect of centrally administered C75, a fatty acid synthase inhibitor, on ghrelin secretion and its downstream effects. | 2005 Mar 15 |
|
| Disconnection between the early onset anorectic effects by C75 and hypothalamic fatty acid synthase inhibition in rodents. | 2005 Mar 21 |
|
| Novel effect of C75 on carnitine palmitoyltransferase I activity and palmitate oxidation. | 2006 Apr 11 |
|
| The effects of C75, an inhibitor of fatty acid synthase, on sleep and metabolism in mice. | 2012 |
|
| Differential pharmacologic properties of the two C75 enantiomers: (+)-C75 is a strong anorectic drug; (-)-C75 has antitumor activity. | 2013 May |
|
| Fatty acid synthase inhibitor C75 ameliorates experimental colitis. | 2014 Jan 17 |
|
| Differential in radiosensitizing potency of enantiomers of the fatty acid synthase inhibitor C75. | 2017 Jan |
Sample Use Guides
Mice: C75 (5 mg/kg body weight) or dimethyl sulfoxide (DMSO) (vehicle) was administered intraperitoneally.
Rats: intravenous infusion of C75 (1 mg/kg body weight) or vehicle (DMSO).
Route of Administration:
Other
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:31:24 GMT 2023
by
admin
on
Sat Dec 16 10:31:24 GMT 2023
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| Record UNII |
8E9A8CTX2H
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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218137-86-1
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8E9A8CTX2H
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4248455
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DTXSID401189534
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admin on Sat Dec 16 10:31:24 GMT 2023 , Edited by admin on Sat Dec 16 10:31:24 GMT 2023
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