LEDOXANTRONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H27N5OS
Molecular Weight	397.537
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)CCN1N=C2C3=C1C=CC(NCCN)=C3SC4=C2C=CC(O)=C4

InChI

InChIKey=HPCHDLLMIWHKBW-UHFFFAOYSA-N

InChI=1S/C21H27N5OS/c1-3-25(4-2)11-12-26-17-8-7-16(23-10-9-22)21-19(17)20(24-26)15-6-5-14(27)13-18(15)28-21/h5-8,13,23,27H,3-4,9-12,22H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C21H27N5OS
Molecular Weight	397.537
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2447481 | https://www.ncbi.nlm.nih.gov/pubmed/9788570

LEDOXANTRONE, a benzothiopyranoindazole, is an intercalating agent. Its mechanism of action is probably due to DNA helicase blockade. It was under development for the treatment of prostate and ovarian cancers.

Originator

Approval Year

PubMed

Title	Date	PubMed
Phase II study of CI-958 in patients with hormone refractory prostate carcinoma.	2004-04	14739667
A phase II trial of CI-958 in recurrent platinum-sensitive ovarian carcinoma: a Gynecologic Oncology Group study.	2001-06	11371134
Antihelicase action of CI-958, a new drug for prostate cancer.	1998	9788570
Biochemical pharmacology and DNA-drug interactions by Cl-958, a new antitumor intercalator derived from a series of substituted 2H-[1]benzothiopyrano[4,3,2-cd]indazoles.	1988-01	2447481

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:27:17 GMT 2025` Edited by `admin` on `Mon Mar 31 19:27:17 GMT 2025`
Record UNII	8HBT2JRJ5T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CI-958

Preferred Name

English

LEDOXANTRONE

Official Name

English

Ledoxantrone [WHO-DD]

Common Name

English

ledoxantrone [INN]

Common Name

English

SEDOXANTRONE

Common Name

English

5-((2-AMINOETHYL)AMINO)-2-(2-(DIETHYLAMINO)ETHYL)-2H-(1)BENZOTHIOPYRANO(4,3,2-CD)INDAZOL-8-OL

Systematic Name

English

Code System Code Type Description

EVMPD

SUB08422MIG