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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
Structure of C-75

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)

HIDE SMILES / InChI

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

PubMed

TitleDatePubMed
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
Differential pharmacologic properties of the two C75 enantiomers: (+)-C75 is a strong anorectic drug; (-)-C75 has antitumor activity.
2013 May
Differential in radiosensitizing potency of enantiomers of the fatty acid synthase inhibitor C75.
2017 Jan
Patents

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
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 Sat Dec 16 10:31:24 GMT 2023
Edited
by admin
on Sat Dec 16 10:31:24 GMT 2023
Record UNII
8E9A8CTX2H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
C-75
Common Name English
3-FURANCARBOXYLIC ACID, TETRAHYDRO-4-METHYLENE-2-OCTYL-5-OXO-
Systematic Name English
Code System Code Type Description
CAS
218137-86-1
Created by admin on Sat Dec 16 10:31:24 GMT 2023 , Edited by admin on Sat Dec 16 10:31:24 GMT 2023
PRIMARY
FDA UNII
8E9A8CTX2H
Created by admin on Sat Dec 16 10:31:24 GMT 2023 , Edited by admin on Sat Dec 16 10:31:24 GMT 2023
PRIMARY
PUBCHEM
4248455
Created by admin on Sat Dec 16 10:31:24 GMT 2023 , Edited by admin on Sat Dec 16 10:31:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID401189534
Created by admin on Sat Dec 16 10:31:24 GMT 2023 , Edited by admin on Sat Dec 16 10:31:24 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY