GIRACODAZOLE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H11ClN4O
Molecular Weight	190.631
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC[C@H](Cl)[C@@H](O)C1=CN=C(N)N1

InChI

InChIKey=YILCGOCHVFQMTC-WVZVXSGGSA-N

InChI=1S/C6H11ClN4O/c7-3(1-8)5(12)4-2-10-6(9)11-4/h2-3,5,12H,1,8H2,(H3,9,10,11)/t3-,5+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C6H11ClN4O
Molecular Weight	190.631
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1783523 | https://www.ncbi.nlm.nih.gov/pubmed/1575768 | https://www.ncbi.nlm.nih.gov/pubmed/17321546 | https://www.ncbi.nlm.nih.gov/pubmed/7805184

Giracodazole (also Girodazole or RP 49532A) is a marine compound has been isolated from the sponge Pseudaxinyssa cantharella. It has shown broad antitumor activity in experimental models and has been studied as a potential antitumor compound that inhibits protein synthesis in cell cultures and in cell free systems. Dose-limiting toxic effects that were observed were delayed hypotension and severe asthenia. Independent of dose level, transient nausea and vomiting were reported during infusion. As a result of this toxicity profile, no phase II clinical trial was conducted for Giracodazole.

Approval Year

PubMed

Title	Date	PubMed
The structures of antibiotics bound to the E site region of the 50 S ribosomal subunit of Haloarcula marismortui: 13-deoxytedanolide and girodazole.	2007-04-13	17321546
Phase I study of RP 49532A, a new protein-synthesis inhibitor, in patients with advanced refractory solid tumors.	1995	7805184
Mode of action of the antitumor compound girodazole (RP 49532A, NSC 627434).	1992-04-15	1575768

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:18:53 GMT 2025` Edited by `admin` on `Mon Mar 31 18:18:53 GMT 2025`
Record UNII	RU19QYB9WZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GIRACODAZOLE

Official Name

English

(.ALPHA.S)-2-AMINO-.ALPHA.-((1S)-2-AMINO-1-CHLOROETHYL)IMIDAZOLE-4-METHANOL

Preferred Name

English

giracodazole [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C274