Iclaprim

Drugbox
IUPAC_name = 5- [(2-cyclopropyl-7,8-dimethoxy-2"H"-chromen-5- yl)methyl] pyrimidine-2,4-diamine

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CAS_number = 192314-93​-5
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ATC_suffix =
PubChem = 213043
DrugBank =
C=19 |H=22 |N=4 |O=3
molecular_weight = 354.403 g/mol
smiles = COC1=C(C2=C(C=CC(O2)C3CC3)C(=C1)CC4=CN=C(N=C4N)N)OC
bioavailability = Good (oral)
protein_bound =
metabolism =
elimination_half-life =
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legal_status = Investigational
routes_of_administration = Intravenous (oral under investigation)

Iclaprim (INN), codenamed AR-100 and RO-48-2622, is a dihydrofolate reductase inhibitor 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).cite press release |url=http://www.reuters.com/article/pressRelease/idUS92327+19-Mar-2008+PRN20080319 |title=Arpida Submits New Drug Application for Intravenous Iclaprim for Treatment of Skin Infections |date=March 19, 2008 |publisher=Reuters |accessdate=2008-08-24] cite press release |url=http://www.breitbart.com/article.php?id=prnw.20080821.UKTH008&show_article=1 |title=Arpida's iclaprim MAA Accepted for Review by EMEA |date=August 21, 2008 |publisher=PR Newswire |accessdate=2008-08-24] "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.cite journal |author=Kohlhoff SA, Sharma R |title=Iclaprim |journal=Expert Opin Investig Drugs |volume=16 |issue=9 |pages=1441–8 |year=2007 |month=September |pmid=17714029 |doi=10.1517/13543784.16.9.1441 |url=]

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. [cite journal |author=Peppard WJ, Schuenke CD |title=Iclaprim, a diaminopyrimidine dihydrofolate reductase inhibitor for the potential treatment of antibiotic-resistant staphylococcal infections |journal=Curr Opin Investig Drugs |volume=9 |issue=2 |pages=210–25 |year=2008 |month=February |pmid=18246524 |doi= |url=]

References

Further reading

*cite journal |author=Schneider P, Hawser S, Islam K |title=Iclaprim, a novel diaminopyrimidine with potent activity on trimethoprim sensitive and resistant bacteria |journal=Bioorg Med Chem Lett |volume=13 |issue=23 |pages=4217–21 |year=2003 |month=December |pmid=14623005 |doi= |url=http://www.tufts.edu/med/biochemistry/DrugDesign/docs/Readings/antibacterials/sdarticle.pdf