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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10716717
Curator's Comment: 2000
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10716717 |
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Target ID: CHEMBL1293194 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Pharmacological inhibitors of mammalian fatty acid synthase suppress DNA replication and induce apoptosis in tumor cell lines. | 1998 Oct 15 |
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Synthesis and antitumor activity of an inhibitor of fatty acid synthase. | 2000 Mar 28 |
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Differential pharmacologic properties of the two C75 enantiomers: (+)-C75 is a strong anorectic drug; (-)-C75 has antitumor activity. | 2013 May |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18355682
Human prostate tumor-cultured cell lines (PC-3, 22Rv1, LNCaP and LAPC-4), were treated with a fatty acid synthase (FAS) inhibitor (C75, 100 microM) under anoxia
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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8E9A8CTX2H
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4248455
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DTXSID401189534
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