Iclaprim
-
Iclaprim
structure -
-
CAS No:
192314-93-5
-
Formula:
C19H22N4O3
-
Chemical Name:
Iclaprim
-
Synonyms:
2,4-Pyrimidinediamine,5-[(2-cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-yl)methyl]-;5-[(2-Cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-yl)methyl]-2,4-pyrimidinediamine;Iclaprim;5-[(2-Cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl)methyl]pyrimidine-2,4-diamine;AR 100
-
CAS No:
Description
Iclaprim is a new selective bacterial Dihydrofolate inhibitor, which can inhibit the growth of S. aureus (MRSA) with an MIC90 of 0.06 mg/mL.
5-[(2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl)methyl]pyrimidine-2,4-diamine is an aminopyrimidine that is 5-methylpyrimidine-2,4-diamine in which one of the hydrogens of the methyl group has been replaced by a 2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl group. It is an aminopyrimidine, a member of chromenes and a member of cyclopropanes.
Characteristics
106
2.20
1.332±0.06 g/cm3(Predicted)
616.7±65.0 °C(Predicted)
326.8±34.3 °C
1.666
3.84E-15mmHg at 25°C
Safety Information
|Warning|H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]|P201, P202, P281, P308+P313, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Drug Information
Investigated for use/treatment in bacterial infection, skin infections/disorders, obesity, liver disease, kidney disease, and pneumonia.
Inhibitors of the enzyme, dihydrofolate reductase (TETRAHYDROFOLATE DEHYDROGENASE), which converts dihydrofolate (FH2) to tetrahydrofolate (FH4). They are frequently used in cancer chemotherapy. (From AMA, Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Folic Acid Antagonists.)
Iclaprim is a novel diaminopyrimidine, and an inhibitor of dihydrofolate reductase, which has shown potent, extended-spectrum in vitro activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus, vancomycin-intermediate and vancomycin-resistant S. aureus and macrolide-, quinolone- and trimethoprim-resistant strains. In addition, iclaprim has demonstrated activity against Streptococcus pneumoniae including penicillin-, erythromycin-, levofloxacin- and trimethoprim/sulfamethoxazole-resistant strains.
AR 100
Iclaprim Use and Manufacturing
Iclaprim is a novel antibacterial agent that is currently in development for the treatment of complicated skin and skin structure infections (cSSSI).
Computed Properties
Molecular Weight:354.4
XLogP3:2.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:5
Exact Mass:354.16919058
Monoisotopic Mass:354.16919058
Topological Polar Surface Area:106
Heavy Atom Count:26
Complexity:515
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes