Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H22N4O3 |
| Molecular Weight | 354.403 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(OC)C2=C(C=C[C@@H](O2)C3CC3)C(CC4=C(N)N=C(N)N=C4)=C1
InChI
InChIKey=HWJPWWYTGBZDEG-CQSZACIVSA-N
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)/t14-/m1/s1
| Molecular Formula | C19H22N4O3 |
| Molecular Weight | 354.403 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Aerie Pharmaceuticals, Inc. (Bridgewater, NJ), was developing a novel prostaglandin analog, AR-102, that had 150-fold greater selectivity and 30-fold greater potency at the FP receptor than latanoprost. In preclinical studies, the drug has shown greater IOP-lowering efficacy and alonger duration of action than latanoprost and betterocular tolerability than travoprost. AR-102 was in early-stage clinical development for glaucoma, which was discontinued later..
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Antimicrobial treatment of nosocomial meticillin-resistant Staphylococcus aureus (MRSA) pneumonia: current and future options. | 2010-11 |
|
| Mechanisms of resistance to antimicrobial drugs in pathogenic Gram-positive cocci. | 2010-09 |
|
| Enantioselective synthesis of iclaprim enantiomers--a versatile approach to 2-substituted chiral chromenes. | 2010-06-04 |
|
| [Update on antimicrobial chemotherapy]. | 2010-03 |
|
| New antimicrobial agents for methicillin-resistant Staphylococcus aureus. | 2009-12 |
|
| Future treatment options for Gram-positive infections--looking ahead. | 2009-12 |
|
| [New antibiotics: small or big advances?]. | 2009-10 |
|
| New treatments for methicillin-resistant Staphylococcus aureus. | 2009-10 |
|
| Treatments for skin and soft-tissue and surgical site infections due to MDR Gram-positive bacteria. | 2009-09 |
|
| 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. | 2009-08 |
|
| Antimicrobial development in the era of emerging resistance. | 2009-07 |
|
| Iclaprim, a novel diaminopyrimidine for the treatment of resistant gram-positive infections. | 2009-06 |
|
| New antibiotics for antibiotic-resistant bacteria. | 2009-05-28 |
|
| New antimicrobial molecules and new antibiotic strategies. | 2009-04 |
|
| Increased hydrophobic interactions of iclaprim with Staphylococcus aureus dihydrofolate reductase are responsible for the increase in affinity and antibacterial activity. | 2009-04 |
|
| Iclaprim: a novel dihydrofolate reductase inhibitor for skin and soft tissue infections. | 2009-03 |
|
| In vitro activity of iclaprim and comparison agents tested against Neisseria gonorrhoeae including medium growth supplement effects. | 2009-03 |
|
| New antibiotics for healthcare-associated pneumonia. | 2009-02 |
|
| Activity of iclaprim against clinical isolates of Streptococcus pyogenes and Streptococcus agalactiae. | 2009-02 |
|
| Regulatory watch: Non-inferiority-trial discussions impact new drug applications. | 2009-01 |
|
| Evidence based approach to the treatment of community-associated methicillin-resistant Staphylococcus aureus. | 2009 |
|
| The determinants of the antibiotic resistance process. | 2009 |
|
| Bench-to-bedside review: Understanding the impact of resistance and virulence factors on methicillin-resistant Staphylococcus aureus infections in the intensive care unit. | 2009 |
|
| What's new and not so new on the antimicrobial horizon? | 2008-12 |
|
| Gateways to clinical trials. | 2008-10 |
|
| Investigational antimicrobial drugs for bloodstream infections. | 2008-08 |
|
| Gateways to clinical trials. | 2008-06 |
|
| A review of telavancin in the treatment of complicated skin and skin structure infections (cSSSI). | 2008-02 |
|
| Pharmacologic options for CNS infections caused by resistant Gram-positive organisms. | 2008-02 |
|
| Iclaprim, a diaminopyrimidine dihydrofolate reductase inhibitor for the potential treatment of antibiotic-resistant staphylococcal infections. | 2008-02 |
|
| Registered and investigational drugs for the treatment of methicillin-resistant Staphylococcus aureus infection. | 2008-01 |
|
| Current and novel antibiotics against resistant Gram-positive bacteria. | 2008 |
|
| [New antimicrobials against Gram-positive organisms]. | 2008 |
|
| Gateways to clinical trials. | 2007-12 |
|
| In vitro activity of the novel diaminopyrimidine, iclaprim, in combination with folate inhibitors and other antimicrobials with different mechanisms of action. | 2007-12 |
|
| Effect of human plasma on the antimicrobial activity of iclaprim in vitro. | 2007-12 |
|
| Activity of iclaprim against Legionella pneumophila. | 2007-10 |
|
| Alternatives to vancomycin for the treatment of methicillin-resistant Staphylococcus aureus infections. | 2007-09-15 |
|
| Iclaprim. | 2007-09 |
|
| 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. | 2007-09 |
|
| Investigational treatments for postoperative surgical site infections. | 2007-02 |
|
| Infections associated with orthopedic implants. | 2006-08 |
|
| Antibacterial drug discovery and development--SRI's 11th Annual Summit. Antibacterial trends and current research. | 2006-06 |
|
| Dihydrofolate reductase inhibitors as antibacterial agents. | 2006-03-30 |
|
| Recently approved and investigational antibiotics for treatment of severe infections caused by Gram-positive bacteria. | 2005-10 |
|
| Iclaprim, a novel diaminopyrimidine with potent activity on trimethoprim sensitive and resistant bacteria. | 2003-12-01 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 23:41:12 GMT 2025
by
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on
Mon Mar 31 23:41:12 GMT 2025
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| Record UNII |
7P9VLC9Y9D
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| Record Status |
Validated (UNII)
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| Record Version |
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1208116-66-8
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| Related Record | Type | Details | ||
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ENANTIOMER -> ENANTIOMER |
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RACEMATE -> ENANTIOMER |
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