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Iclaprim

CAS No.:
192314-93-5
Catalog Number:
AG002FUB
Molecular Formula:
C19H22N4O3
Molecular Weight:
354.4030
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
98%
1 week
United States
$307
- +
5mg
98%
1 week
United States
$807
- +
10mg
98%
1 week
United States
$1307
- +
50mg
98%
1 week
United States
$4140
- +
100mg
98%
1 week
United States
$6640
- +
Product Description
Catalog Number:
AG002FUB
Chemical Name:
Iclaprim
CAS Number:
192314-93-5
Molecular Formula:
C19H22N4O3
Molecular Weight:
354.4030
MDL Number:
MFCD09837803
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)
InChI Key:
HWJPWWYTGBZDEG-UHFFFAOYSA-N
SMILES:
COc1cc(Cc2cnc(nc2N)N)c2c(c1OC)OC(C=C2)C1CC1
Properties
Complexity:
515  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
354.169g/mol
Formal Charge:
0
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
354.41g/mol
Monoisotopic Mass:
354.169g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
106A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
2.5  
Literature
Title Journal
Meta-analysis of randomized controlled trials of vancomycin for the treatment of patients with gram-positive infections: focus on the study design. Mayo Clinic proceedings 20120401
Toward new therapeutics for skin and soft tissue infections: propargyl-linked antifolates are potent inhibitors of MRSA and Streptococcus pyogenes. PloS one 20120101
Structure-based design of new DHFR-based antibacterial agents: 7-aryl-2,4-diaminoquinazolines. Bioorganic & medicinal chemistry letters 20110915
Cumulative clinical experience from over a decade of use of levofloxacin in community-acquired pneumonia: critical appraisal and role in therapy. Drug, healthcare and patient safety 20110101
Antimicrobial treatment of nosocomial meticillin-resistant Staphylococcus aureus (MRSA) pneumonia: current and future options. International journal of antimicrobial agents 20101101
Mechanisms of resistance to antimicrobial drugs in pathogenic Gram-positive cocci. Mini reviews in medicinal chemistry 20100901
Enantioselective synthesis of iclaprim enantiomers--a versatile approach to 2-substituted chiral chromenes. The Journal of organic chemistry 20100604
[Update on antimicrobial chemotherapy]. Medecine et maladies infectieuses 20100301
Future treatment options for Gram-positive infections--looking ahead. Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases 20091201
New antimicrobial agents for methicillin-resistant Staphylococcus aureus. Critical care and resuscitation : journal of the Australasian Academy of Critical Care Medicine 20091201
New treatments for methicillin-resistant Staphylococcus aureus. Current opinion in critical care 20091001
[New antibiotics: small or big advances?]. Der Internist 20091001
Treatments for skin and soft-tissue and surgical site infections due to MDR Gram-positive bacteria. The Journal of infection 20090901
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. Acta crystallographica. Section D, Biological crystallography 20090801
Antimicrobial development in the era of emerging resistance. Mini reviews in medicinal chemistry 20090701
Iclaprim, a novel diaminopyrimidine for the treatment of resistant gram-positive infections. The Annals of pharmacotherapy 20090601
Increased hydrophobic interactions of iclaprim with Staphylococcus aureus dihydrofolate reductase are responsible for the increase in affinity and antibacterial activity. The Journal of antimicrobial chemotherapy 20090401
New antimicrobial molecules and new antibiotic strategies. Seminars in respiratory and critical care medicine 20090401
In vitro activity of iclaprim and comparison agents tested against Neisseria gonorrhoeae including medium growth supplement effects. Diagnostic microbiology and infectious disease 20090301
Iclaprim: a novel dihydrofolate reductase inhibitor for skin and soft tissue infections. Future microbiology 20090301
Activity of iclaprim against clinical isolates of Streptococcus pyogenes and Streptococcus agalactiae. The Journal of antimicrobial chemotherapy 20090201
New antibiotics for healthcare-associated pneumonia. Seminars in respiratory and critical care medicine 20090201
Regulatory watch: Non-inferiority-trial discussions impact new drug applications. Nature reviews. Drug discovery 20090101
Bench-to-bedside review: Understanding the impact of resistance and virulence factors on methicillin-resistant Staphylococcus aureus infections in the intensive care unit. Critical care (London, England) 20090101
New antibiotics for antibiotic-resistant bacteria. F1000 biology reports 20090101
The determinants of the antibiotic resistance process. Infection and drug resistance 20090101
Evidence based approach to the treatment of community-associated methicillin-resistant Staphylococcus aureus. Infection and drug resistance 20090101
What's new and not so new on the antimicrobial horizon? Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases 20081201
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20081001
Investigational antimicrobial drugs for bloodstream infections. Current opinion in investigational drugs (London, England : 2000) 20080801
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20080601
Iclaprim, a diaminopyrimidine dihydrofolate reductase inhibitor for the potential treatment of antibiotic-resistant staphylococcal infections. Current opinion in investigational drugs (London, England : 2000) 20080201
Pharmacologic options for CNS infections caused by resistant Gram-positive organisms. Expert review of anti-infective therapy 20080201
A review of telavancin in the treatment of complicated skin and skin structure infections (cSSSI). Therapeutics and clinical risk management 20080201
Registered and investigational drugs for the treatment of methicillin-resistant Staphylococcus aureus infection. Recent patents on anti-infective drug discovery 20080101
[New antimicrobials against Gram-positive organisms]. Nefrologia : publicacion oficial de la Sociedad Espanola Nefrologia 20080101
Current and novel antibiotics against resistant Gram-positive bacteria. Infection and drug resistance 20080101
Effect of human plasma on the antimicrobial activity of iclaprim in vitro. The Journal of antimicrobial chemotherapy 20071201
In vitro activity of the novel diaminopyrimidine, iclaprim, in combination with folate inhibitors and other antimicrobials with different mechanisms of action. The Journal of antimicrobial chemotherapy 20071201
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20071201
Activity of iclaprim against Legionella pneumophila. The Journal of antimicrobial chemotherapy 20071001
Alternatives to vancomycin for the treatment of methicillin-resistant Staphylococcus aureus infections. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20070915
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. The Journal of antimicrobial chemotherapy 20070901
Iclaprim. Expert opinion on investigational drugs 20070901
Investigational treatments for postoperative surgical site infections. Expert opinion on investigational drugs 20070201
Infections associated with orthopedic implants. Current opinion in infectious diseases 20060801
Antibacterial drug discovery and development--SRI's 11th Annual Summit. Antibacterial trends and current research. IDrugs : the investigational drugs journal 20060601
Dihydrofolate reductase inhibitors as antibacterial agents. Biochemical pharmacology 20060330
Recently approved and investigational antibiotics for treatment of severe infections caused by Gram-positive bacteria. Current opinion in microbiology 20051001
Iclaprim, a novel diaminopyrimidine with potent activity on trimethoprim sensitive and resistant bacteria. Bioorganic & medicinal chemistry letters 20031201
Properties