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
KEGG	D08337 Y
ChEMBL	ChEMBL134561 N
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C19H22N4O3
Molar mass	354.403 g/mol
3D model (JSmol)	Interactive image
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?)  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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 Streptococcus pneumoniae 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.

Iclaprim was granted fast track status by the FDA, but approval of the drug was eventually declined in 2009 and no further development has taken place since then.

Further reading

• Schneider P, Hawser S, Islam K (December 2003). "Iclaprim, a novel diaminopyrimidine with potent activity on trimethoprim sensitive and resistant bacteria" (PDF). Bioorg Med Chem Lett. 13 (23): 4217–21. doi:10.1016/j.bmcl.2003.07.023. PMID 14623005.CS1 maint: Multiple names: authors list (link)