Iclaprim

Iclaprim
Clinical data

Routes of administration	Oral, intravenous
ATC code	J01EA03 (WHO)
Legal status
Legal status	Investigational
Pharmacokinetic data
Bioavailability	Good (oral)
Identifiers
IUPAC name (RS)-5-[(2- cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl)methyl]pyrimidine-2,4-diamine
CAS Number	192314-93-5^Y
PubChem (CID)	213043
ChemSpider	184736^N
UNII	42445HUU0O^N
KEGG	D08337^Y
ChEBI	CHEBI:131724^N
ChEMBL	CHEMBL134561^N
ECHA InfoCard	100.130.860
Chemical and physical data
Formula	C₁₉H₂₂N₄O₃
Molar mass	354.403 g/mol
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
SMILES COC1=C(C2=C(C=CC(O2)C3CC3)C(=C1)CC4=CN=C(N=C4N)N)OC
InChI InChI=1S/C19H22N4O3/c1-24-15-8-11(7-12-9-22-19(21)23-18(12)20)13-5-6-14(10-3-4-10)26-16(13)17(15)25-2/h5-6,8-10,14H,3-4,7H2,1-2H3,(H4,20,21,22,23)^N Key:HWJPWWYTGBZDEG-UHFFFAOYSA-N^N
^NY (what is this?)

Iclaprim (INN), codenamed AR-100 and RO-48-2622, is a diaminopyrimidine dihydrofolate reductase (DHFR)-inhibiting extended-spectrum antibiotic active against gram positive organisms being developed for the treatment of complicated skin and soft tissue infections caused by antibiotic-resistant bacteria. It is structurally related to trimethoprim. In Phase III clinical trials, intravenously-administered iclaprim was found to be as effective as and better tolerated than linezolid in people with skin and soft tissue infections, many caused by methicillin-resistant Staphylococcus aureus (MRSA).In vitro, iclaprim is highly active against MRSA, vancomycin-resistant Staphylococcus aureus (VRSA), strains of resistant to several common antibiotics, and some Gram-negative bacteria.

A new drug application for iclaprim was filed with the U.S. Food and Drug Administration in March 2008, and a marketing authorisation application (MAA) was accepted by the European Medicines Agency on August 21, 2008. Phase II clinical trials are being conducted to assess whether iclaprim can be taken by mouth as well as intravenously and whether it is effective for the treatment of hospital-acquired pneumonia.