Substance

ID:910

Names and Identifiers
Synonyms
Cerulenin
IUPAC Traditional name
@cerulenin
Brand Name
Helicocerin
IUPAC name
(2R,3S)-3-(nona-4,7-dienoyl)oxirane-2-carboxamide
Registration numbers
CAS Number
PubChem CID
PubChem SID
Properties
Physical Property
Solubility
Slightly soluble
Hydrophobicity(logP)
1.2
Molecule Details
Drug Groups
approved
Description
Cerulenin is an antifungal antibiotic that inhibits sterol and fatty acid biosynthesis. In fatty acid synthesis, reported to bind in equimolar ratio to b-keto-acyl-ACP synthase. In sterol synthesis, inhibits HMG-CoA synthetase activity. It is also shown to inhibit feeding and induce dramatic weight loss in mice. It is found naturally in the Cephalosporium caerulensfungus. [Wikipedia]
Indication
For use as a biochemical tool, Cerulenin is shown to cause dramatic weight loss in animals
Pharmacology
Cerulenin is an antifungal antibiotic isolated from Cephalosporium caerulens. It interrupts fungal growth by inhibiting the biosynthesis of sterols and fatty acids (inhibits bacterial fatty acid synthesis). It also inhibits HMG-CoA synthetase activity. Cerulenin produces metabolic effects similar to effects of leptin, but through mechanisms that are independent of, or down-stream from, both leptin and melanocortin receptors.
Toxicity
Oral, mouse LD50: 547 mg/kg. Symptoms of overexposure include moderate to severe erythema (redness) and moderate edema (raised skin), nausea, vomiting, and headache.
Affected Organisms
Humans and other mammals
Fungi
Bacteria
References
• Huang P, Zhu S, Lu S, Dai Z, Jin Y: [An experimental study on cerulenin induced apoptosis of human colonic cancer cells] Zhonghua Bing Li Xue Za Zhi. 2000 Apr;29(2):115-8. [Pubmed]
• Straub SG, Yajima H, Komatsu M, Aizawa T, Sharp GW: The effects of cerulenin, an inhibitor of protein acylation, on the two phases of glucose-stimulated insulin secretion. Diabetes. 2002 Feb;51 Suppl 1:S91-5. [Pubmed]
External Links
Molecular Spectra
No Data Available
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References
• Huang P, Zhu S, Lu S, Dai Z, Jin Y: [An experimental study on cerulenin induced apoptosis of human colonic cancer cells] Zhonghua Bing Li Xue Za Zhi. 2000 Apr;29(2):115-8. Pubmed
• Straub SG, Yajima H, Komatsu M, Aizawa T, Sharp GW: The effects of cerulenin, an inhibitor of protein acylation, on the two phases of glucose-stimulated insulin secretion. Diabetes. 2002 Feb;51 Suppl 1:S91-5. Pubmed