CHEBI:71417 - procarbazine

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ChEBI Name procarbazine
ChEBI ID CHEBI:71417
Definition A benzamide obtained by formal condensation of the carboxy group of 4-[(2-methylhydrazino)methyl]benzoic acid with the amino group of isopropylamine. An antineoplastic chemotherapy drug used for treatment of Hodgkin's lymphoma. Metabolism yields azo-procarbazine and hydrogen peroxide, which results in the breaking of DNA strands.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:8432
Supplier Information ChemicalBook:CB6208758, ChemicalBook:CB9208759, eMolecules:495925
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Methionine (symbol Met or M) () is an essential amino acid in humans. As the precursor of other non-essential amino acids such as cysteine and taurine, versatile compounds such as SAM-e, and the important antioxidant glutathione, methionine plays a critical role in the metabolism and health of many species, including humans. Methionine is also involved in angiogenesis and various processes related to DNA transcription, epigenetic expression, and gene regulation. Methionine was first isolated in 1921 by John Howard Mueller. It is encoded by the codon AUG. It was named by Satoru Odake in 1925, as an abbreviation of its structural description 2-amino-4-(methylthio)butanoic acid.
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Formula C12H19N3O
Net Charge 0
Average Mass 221.29880
Monoisotopic Mass 221.15281
InChI InChI=1S/C12H19N3O/c1-9(2)15-12(16)11-6-4-10(5-7-11)8-14-13-3/h4-7,9,13-14H,8H2,1-3H3,(H,15,16)
InChIKey CPTBDICYNRMXFX-UHFFFAOYSA-N
SMILES CNNCc1ccc(cc1)C(=O)NC(C)C
Roles Classification
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing procarbazine (CHEBI:71417) has role antineoplastic agent (CHEBI:35610)
procarbazine (CHEBI:71417) is a benzamides (CHEBI:22702)
procarbazine (CHEBI:71417) is a hydrazines (CHEBI:24631)
procarbazine (CHEBI:71417) is conjugate base of procarbazine(1+) (CHEBI:71431)
Incoming procarbazine(1+) (CHEBI:71431) is conjugate acid of procarbazine (CHEBI:71417)
IUPAC Name
N-(1-methylethyl)-4-[(2-methylhydrazino)methyl]benzamide
INNs Sources
procarbazina DrugBank
procarbazine WHO MedNet
procarbazine KEGG DRUG
procarbazinum DrugBank
Synonyms Sources
1-Methyl-2-(p-(isopropylcarbamoyl)benzyl)hydrazine ChemIDplus
2-(p-Isopropylcarbamoylbenzyl)-1-methylhydrazine ChemIDplus
4-((2-Methylhydrazino)methyl)-N-isopropylbenzamide ChemIDplus
N-(1-Methylethyl)-4-((2-methylhydrazino)methyl)benzamide ChemIDplus
N-4-Isopropylcarbamoylbenzyl-N'-methylhydrazine ChemIDplus
N-isopropyl-4-[(2-methylhydrazino)methyl]benzamide IUPAC
N-Isopropyl-α-(2-methylhydrazino)-p-toluamide NIST Chemistry WebBook
N-Isopropyl-p-(2-methylhydrazinomethyl)-benzamide ChemIDplus
p-(2-Methylhydrazinomethyl)-N-isopropylbenzamide NIST Chemistry WebBook
Procarbazin DrugBank
Manual Xrefs Databases
2272 DrugCentral
BE618638 Patent
C07402 KEGG COMPOUND
D08423 KEGG DRUG
DB01168 DrugBank
HMDB0015299 HMDB
LSM-2272 LINCS
Procarbazine Wikipedia
US2007122414 Patent
US2008107661 Patent
US3520926 Patent
US3830840 Patent
View more database links
Registry Numbers Types Sources
671-16-9 CAS Registry Number KEGG COMPOUND
671-16-9 CAS Registry Number ChemIDplus
671-16-9 CAS Registry Number NIST Chemistry WebBook
958270 Reaxys Registry Number Reaxys
Citations Types Sources
21420247 PubMed citation Europe PMC
21703849 PubMed citation Europe PMC
21740300 PubMed citation Europe PMC
21870118 PubMed citation Europe PMC
22423248 PubMed citation Europe PMC
22708037 PubMed citation Europe PMC
22744756 PubMed citation Europe PMC
22851558 PubMed citation Europe PMC
22913972 PubMed citation Europe PMC
23071237 PubMed citation Europe PMC
Last Modified
22 February 2017