CHEBI:131724 - iclaprim

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ChEBI Name iclaprim
ChEBI ID CHEBI:131724
Definition A racemate consisting of equimolar amounts of (R)- and (S)-iclaprim. Both enantiomers exhibit similar, potent bactericidal activity against major Gram-positive pathogens, notably methicillin-sensitive and -resistant Staphylococcus aureus (MSSA and MRSA, respectively).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kevin
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Formula C19H22N4O3
Net Charge 0
Average Mass 354.404
Monoisotopic Mass 354.16919
Roles Classification
Biological Role(s): EC 1.5.1.3 (dihydrofolate reductase) inhibitor
An EC 1.5.1.* (oxidoreductase acting on donor CH-NH group, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of dihydrofolate reductase (EC 1.5.1.3).
antibacterial drug
A drug used to treat or prevent bacterial infections.
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
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ChEBI Ontology
Outgoing iclaprim (CHEBI:131724) has part (R)-iclaprim (CHEBI:131752)
iclaprim (CHEBI:131724) has part (S)-iclaprim (CHEBI:131753)
iclaprim (CHEBI:131724) has role antibacterial drug (CHEBI:36047)
iclaprim (CHEBI:131724) has role EC 1.5.1.3 (dihydrofolate reductase) inhibitor (CHEBI:50683)
iclaprim (CHEBI:131724) is a racemate (CHEBI:60911)
IUPAC Name
rac-5-[(2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl)methyl]pyrimidine-2,4-diamine
Synonyms Sources
5-((2RS)-2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-ylmethyl)pyrimidine-2,4-diamine ChemIDplus
AR 100 ChemIDplus
AR-100 ChemIDplus
Manual Xrefs Databases
D08337 KEGG DRUG
Iclaprim Wikipedia
View more database links
Registry Numbers Types Sources
192314-93-5 CAS Registry Number ChemIDplus
192314-93-5 CAS Registry Number KEGG DRUG
9951587 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17623694 PubMed citation Europe PMC
17714029 PubMed citation Europe PMC
18246524 PubMed citation Europe PMC
19257839 PubMed citation Europe PMC
19622858 PubMed citation Europe PMC
Last Modified
22 February 2017