ICRF-193 (CHEBI:93771)

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ChEBI Name	ICRF-193

ChEBI ID	CHEBI:93771

Definition	An N-alkylpiperazine that is butane which is substituted by a 3,5-dioxopiperazin-1-yl group at positions 2 and 3. The meso isomer.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C12H18N4O4

Net Charge

Average Mass

282.296

Monoisotopic Mass

282.13281

InChI

InChI=1S/C12H18N4O4/c1-7(15-3-9(17)13-10(18)4-15)8(2)16-5-11(19)14-12(20)6-16/h7-8H,3-6H2,1-2H3,(H,13,17,18)(H,14,19,20)/t7-,8+

InChIKey

OBYGAPWKTPDTAS-OCAPTIKFSA-N

SMILES

C[C@H]([C@H](C)N1CC(=O)NC(=O)C1)N2CC(=O)NC(=O)C2

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands. apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	ICRF-193 (CHEBI:93771) has role antineoplastic agent (CHEBI:35610) ICRF-193 (CHEBI:93771) has role apoptosis inducer (CHEBI:68495) ICRF-193 (CHEBI:93771) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750) ICRF-193 (CHEBI:93771) is a N-alkylpiperazine (CHEBI:46845)

IUPAC Name

4,4'-(2R,3S)-butane-2,3-diyldipiperazine-2,6-dione

Synonyms	Sources
ICRF 193	ChemIDplus
ICRF-193	LINCS
meso-2,3-bis(2,6-dioxopiperazin-4-yl)butane	ChEBI
meso-4,4'-(1,2-dimethylethylene)di-2,6-piperazinedione	ChEBI
meso-4,4'-(3,2-butanediyl)-bis(2,6-piperazinedione)	ChEBI

Registry Number	Type	Source
21416-88-6	CAS Registry Number	ChemIDplus

Last Modified

29 January 2019

General Comment
2019-01-29	Relevant Articles: Tanabe, K., Ikegami, Y., Ishida, R. and Andoh, T. (1991) Inhibition of topoisomerase II by antitumor agents bis(2,6-dioxopiperazine) derivatives. Cancer Research, 51(18), 4903-4908