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192314-93-5,MFCD09837803
Catalog No.:AA002FRJ

192314-93-5 | Iclaprim

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50mg
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA002FRJ
Chemical Name:
Iclaprim
CAS Number:
192314-93-5
Molecular Formula:
C19H22N4O3
Molecular Weight:
354.4030
MDL Number:
MFCD09837803
SMILES:
COc1cc(Cc2cnc(nc2N)N)c2c(c1OC)OC(C=C2)C1CC1
Properties
Computed Properties
 
Complexity:
515  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
5  
Undefined Atom Stereocenter Count:
1  
XLogP3:
2.5  

Literature

Title: Meta-analysis of randomized controlled trials of vancomycin for the treatment of patients with gram-positive infections: focus on the study design.

Journal: Mayo Clinic proceedings 20120401

Title: Toward new therapeutics for skin and soft tissue infections: propargyl-linked antifolates are potent inhibitors of MRSA and Streptococcus pyogenes.

Journal: PloS one 20120101

Title: Structure-based design of new DHFR-based antibacterial agents: 7-aryl-2,4-diaminoquinazolines.

Journal: Bioorganic & medicinal chemistry letters 20110915

Title: Cumulative clinical experience from over a decade of use of levofloxacin in community-acquired pneumonia: critical appraisal and role in therapy.

Journal: Drug, healthcare and patient safety 20110101

Title: Antimicrobial treatment of nosocomial meticillin-resistant Staphylococcus aureus (MRSA) pneumonia: current and future options.

Journal: International journal of antimicrobial agents 20101101

Title: Mechanisms of resistance to antimicrobial drugs in pathogenic Gram-positive cocci.

Journal: Mini reviews in medicinal chemistry 20100901

Title: Enantioselective synthesis of iclaprim enantiomers--a versatile approach to 2-substituted chiral chromenes.

Journal: The Journal of organic chemistry 20100604

Title: [Update on antimicrobial chemotherapy].

Journal: Medecine et maladies infectieuses 20100301

Title: Future treatment options for Gram-positive infections--looking ahead.

Journal: Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases 20091201

Title: New antimicrobial agents for methicillin-resistant Staphylococcus aureus.

Journal: Critical care and resuscitation : journal of the Australasian Academy of Critical Care Medicine 20091201

Title: New treatments for methicillin-resistant Staphylococcus aureus.

Journal: Current opinion in critical care 20091001

Title: [New antibiotics: small or big advances?].

Journal: Der Internist 20091001

Title: Treatments for skin and soft-tissue and surgical site infections due to MDR Gram-positive bacteria.

Journal: The Journal of infection 20090901

Title: 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.

Journal: Acta crystallographica. Section D, Biological crystallography 20090801

Title: Antimicrobial development in the era of emerging resistance.

Journal: Mini reviews in medicinal chemistry 20090701

Title: Iclaprim, a novel diaminopyrimidine for the treatment of resistant gram-positive infections.

Journal: The Annals of pharmacotherapy 20090601

Title: Increased hydrophobic interactions of iclaprim with Staphylococcus aureus dihydrofolate reductase are responsible for the increase in affinity and antibacterial activity.

Journal: The Journal of antimicrobial chemotherapy 20090401

Title: New antimicrobial molecules and new antibiotic strategies.

Journal: Seminars in respiratory and critical care medicine 20090401

Title: In vitro activity of iclaprim and comparison agents tested against Neisseria gonorrhoeae including medium growth supplement effects.

Journal: Diagnostic microbiology and infectious disease 20090301

Title: Iclaprim: a novel dihydrofolate reductase inhibitor for skin and soft tissue infections.

Journal: Future microbiology 20090301

Title: Activity of iclaprim against clinical isolates of Streptococcus pyogenes and Streptococcus agalactiae.

Journal: The Journal of antimicrobial chemotherapy 20090201

Title: New antibiotics for healthcare-associated pneumonia.

Journal: Seminars in respiratory and critical care medicine 20090201

Title: Regulatory watch: Non-inferiority-trial discussions impact new drug applications.

Journal: Nature reviews. Drug discovery 20090101

Title: Bench-to-bedside review: Understanding the impact of resistance and virulence factors on methicillin-resistant Staphylococcus aureus infections in the intensive care unit.

Journal: Critical care (London, England) 20090101

Title: New antibiotics for antibiotic-resistant bacteria.

Journal: F1000 biology reports 20090101

Title: The determinants of the antibiotic resistance process.

Journal: Infection and drug resistance 20090101

Title: Evidence based approach to the treatment of community-associated methicillin-resistant Staphylococcus aureus.

Journal: Infection and drug resistance 20090101

Title: What's new and not so new on the antimicrobial horizon?

Journal: Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases 20081201

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20081001

Title: Investigational antimicrobial drugs for bloodstream infections.

Journal: Current opinion in investigational drugs (London, England : 2000) 20080801

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20080601

Title: Iclaprim, a diaminopyrimidine dihydrofolate reductase inhibitor for the potential treatment of antibiotic-resistant staphylococcal infections.

Journal: Current opinion in investigational drugs (London, England : 2000) 20080201

Title: Pharmacologic options for CNS infections caused by resistant Gram-positive organisms.

Journal: Expert review of anti-infective therapy 20080201

Title: A review of telavancin in the treatment of complicated skin and skin structure infections (cSSSI).

Journal: Therapeutics and clinical risk management 20080201

Title: Registered and investigational drugs for the treatment of methicillin-resistant Staphylococcus aureus infection.

Journal: Recent patents on anti-infective drug discovery 20080101

Title: [New antimicrobials against Gram-positive organisms].

Journal: Nefrologia : publicacion oficial de la Sociedad Espanola Nefrologia 20080101

Title: Current and novel antibiotics against resistant Gram-positive bacteria.

Journal: Infection and drug resistance 20080101

Title: Effect of human plasma on the antimicrobial activity of iclaprim in vitro.

Journal: The Journal of antimicrobial chemotherapy 20071201

Title: In vitro activity of the novel diaminopyrimidine, iclaprim, in combination with folate inhibitors and other antimicrobials with different mechanisms of action.

Journal: The Journal of antimicrobial chemotherapy 20071201

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20071201

Title: Activity of iclaprim against Legionella pneumophila.

Journal: The Journal of antimicrobial chemotherapy 20071001

Title: Alternatives to vancomycin for the treatment of methicillin-resistant Staphylococcus aureus infections.

Journal: Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20070915

Title: Concentrations in plasma, epithelial lining fluid, alveolar macrophages and bronchial mucosa after a single intravenous dose of 1.6 mg/kg of iclaprim (AR-100) in healthy men.

Journal: The Journal of antimicrobial chemotherapy 20070901

Title: Iclaprim.

Journal: Expert opinion on investigational drugs 20070901

Title: Investigational treatments for postoperative surgical site infections.

Journal: Expert opinion on investigational drugs 20070201

Title: Infections associated with orthopedic implants.

Journal: Current opinion in infectious diseases 20060801

Title: Antibacterial drug discovery and development--SRI's 11th Annual Summit. Antibacterial trends and current research.

Journal: IDrugs : the investigational drugs journal 20060601

Title: Dihydrofolate reductase inhibitors as antibacterial agents.

Journal: Biochemical pharmacology 20060330

Title: Recently approved and investigational antibiotics for treatment of severe infections caused by Gram-positive bacteria.

Journal: Current opinion in microbiology 20051001

Title: Iclaprim, a novel diaminopyrimidine with potent activity on trimethoprim sensitive and resistant bacteria.

Journal: Bioorganic & medicinal chemistry letters 20031201

Title: Schneider P, et al. Iclaprim, a novel diaminopyrimidine with potent activity on trimethoprim sensitive and resistant bacteria. Bioorg Med Chem Lett. 2003 Dec 1;13(23):4217-21.

Title: Kohlhoff SA, et al. Iclaprim. Expert Opin Investig Drugs. 2007 Sep;16(9):1441-8.

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