For research use only. Not for therapeutic Use.
Iclaprim（Cat No.:R012908）is a diaminopyrimidine antibiotic with potent activity against Gram-positive bacteria, including multi-drug-resistant strains such as methicillin-resistant Staphylococcus aureus (MRSA). It works by inhibiting the bacterial enzyme dihydrofolate reductase, which is essential for DNA synthesis and cell replication. Developed for treating acute bacterial skin and skin structure infections (ABSSSI) and hospital-acquired pneumonia, Iclaprim is known for its targeted mechanism, which reduces the risk of cross-resistance with other antibiotic classes. Its efficacy and safety profile make it a promising option in the fight against resistant bacterial infections.
| Catalog Number | R012908 |
| CAS Number | 192314-93-5 |
| Synonyms | 5-[(2-Cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-yl)methyl]-2,4-pyrimidine-?diamine; AR 100;? |
| Molecular Formula | C₁₉H₂₂N₄O₃ |
| Purity | ≥95% |
| Target | Bacterial |
| Storage | -20°C |
| IUPAC Name | 5-[(2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl)methyl]pyrimidine-2,4-diamine |
| 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) |
| InChIKey | HWJPWWYTGBZDEG-UHFFFAOYSA-N |
| SMILES | COC1=C(C2=C(C=CC(O2)C3CC3)C(=C1)CC4=CN=C(N=C4N)N)OC |
| Reference | </br>1:Enantioselective synthesis of iclaprim enantiomers–a versatile approach to 2-substituted chiral chromenes. Tahtaoui C, Demailly A, Guidemann C, Joyeux C, Schneider P.J Org Chem. 2010 Jun 4;75(11):3781-5. doi: 10.1021/jo100566c. PMID: 20446707 </br>2:In vitro bactericidal activity of iclaprim in human plasma. Laue H, Valensise T, Seguin A, Lociuro S, Islam K, Hawser S.Antimicrob Agents Chemother. 2009 Oct;53(10):4542-4. doi: 10.1128/AAC.00766-09. Epub 2009 Aug 3. PMID: 19651909 Free PMC Article</br>3:Inhibitory properties and X-ray crystallographic study of the binding of AR-101, AR-102 and iclaprim in ternary complexes with NADPH and dihydrofolate reductase from Staphylococcus aureus. Oefner C, Parisi S, Schulz H, Lociuro S, Dale GE.Acta Crystallogr D Biol Crystallogr. 2009 Aug;65(Pt 8):751-7. doi: 10.1107/S0907444909013936. Epub 2009 Jul 10. PMID: 19622858 </br>4:Efficacy of iclaprim against wild-type and thymidine kinase-deficient methicillin-resistant Staphylococcus aureus isolates in an in vitro fibrin clot model. Entenza JM, Haldimann A, Giddey M, Lociuro S, Hawser S, Moreillon P.Antimicrob Agents Chemother. 2009 Sep;53(9):3635-41. doi: 10.1128/AAC.00325-09. Epub 2009 Jun 29. PMID: 19564362 Free PMC Article</br>5:Iclaprim, a novel diaminopyrimidine for the treatment of resistant gram-positive infections. Sincak CA, Schmidt JM.Ann Pharmacother. 2009 Jun;43(6):1107-14. doi: 10.1345/aph.1L167. Epub 2009 May 12. Review. PMID: 19435963 </br>6:Multicenter, randomized study of the efficacy and safety of intravenous iclaprim in complicated skin and skin structure infections. Krievins D, Brandt R, Hawser S, Hadvary P, Islam K.Antimicrob Agents Chemother. 2009 Jul;53(7):2834-40. doi: 10.1128/AAC.01383-08. Epub 2009 May 4. PMID: 19414572 Free PMC Article</br>7:Potency and bactericidal activity of iclaprim against recent clinical gram-positive isolates. Sader HS, Fritsche TR, Jones RN.Antimicrob Agents Chemother. 2009 May;53(5):2171-5. doi: 10.1128/AAC.00129-09. Epub 2009 Mar 16. PMID: 19289528 Free PMC Article</br>8:Iclaprim: a novel dihydrofolate reductase inhibitor for skin and soft tissue infections. Morgan A, Cofer C, Stevens DL.Future Microbiol. 2009 Mar;4(2):131-44. doi: 10.2217/17460913.4.2.131. Review. PMID: 19257839 </br>9:In vitro activity of iclaprim and comparison agents tested against Neisseria gonorrhoeae including medium growth supplement effects. Jones RN, Biedenbach DJ, Sader HS.Diagn Microbiol Infect Dis. 2009 Mar;63(3):339-41. doi: 10.1016/j.diagmicrobio.2008.04.002. PMID: 19216944 </br>10:Increased hydrophobic interactions of iclaprim with Staphylococcus aureus dihydrofolate reductase are responsible for the increase in affinity and antibacterial activity. Oefner C, Bandera M, Haldimann A, Laue H, Schulz H, Mukhija S, Parisi S, Weiss L, Lociuro S, Dale GE.J Antimicrob Chemother. 2009 Apr;63(4):687-98. doi: 10.1093/jac/dkp024. Epub 2009 Feb 11. PMID: 19211577 |
