SICCANIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H30O3
Molecular Weight	342.4718
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC2=C([C@@H]3OC[C@@]45CCCC(C)(C)[C@@H]4CC[C@](C)(O2)[C@H]35)C(O)=C1

InChI

InChIKey=UGGAILYEBCSZIV-ITJSPEIASA-N

InChI=1S/C22H30O3/c1-13-10-14(23)17-15(11-13)25-21(4)9-6-16-20(2,3)7-5-8-22(16)12-24-18(17)19(21)22/h10-11,16,18-19,23H,5-9,12H2,1-4H3/t16-,18-,19-,21-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H30O3
Molecular Weight	342.4718
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/19505951
Curator's Comment: description was created based on several sources, including http://www.bioaustralis.com/pdfs/Siccanin.pdf http://www.ncbi.nlm.nih.gov/pubmed/4250609

Siccanin is an unusual, fused, phenolic pentacycle first isolated from Helminthosporium siccans and reported in 1962 as a potent antifungal agent. Siccanin inhibits succinate dehydrogenase in the terminal electron transport system. More recent studies note the proximity of the siccanin binding site to the quinone-binding site of the enzyme. Species-selective inhibition by siccanin is unique among succinate dehydrogenase inhibitors and offers a lead for new chemotherapeutics.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
succinate dehydrogenase from P. aeruginosa, P. putida 1 Target ID: succinate dehydrogenase from P. aeruginosa, P. putida Sources: http://www.ncbi.nlm.nih.gov/pubmed/19505951	Inhibitor 8504		0.9 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Superficial dermatophyte infections 1 Sources: http://www.ncbi.nlm.nih.gov/pubmed/488524	Curative		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Siccanin rediscovered as a species-selective succinate dehydrogenase inhibitor.	2009-09	19505951
Siccanin: a new antifungal antibiotic with antidermatophytic properties. In vitro studies.	1985-12	3830412
The therapeutic action of Siccanin in superficial dermatophyte infections.	1979	488524

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The in vitro antifungal properties of the antibiotic siccanin were determined by the minimal inhibitory concentrations (MIC) values against 51 fungal strains (yeasts and filamentous fungi). The comparison was made with econazole, clotrimazole, 5-fluorocytosine and griseofulvin. The results show the useful antidermatophytic activity of siccanin

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:29:08 GMT 2025` Edited by `admin` on `Wed Apr 02 08:29:08 GMT 2025`
Record UNII	L702S858Z6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SICCANIN

Official Name

English

NSC-135048

Preferred Name

English

SICCANIN [MI]

Common Name

English

siccanin [INN]

Common Name

English

SICCANIN [JAN]

Common Name

English

Siccanin [WHO-DD]

Common Name

English

SICCANIN [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C514