Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C28H42O8S |
| Molecular Weight | 538.693 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OCC(CO)(CO)COC(=O)CCCCCC[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)C2=CC3=CC=CC=C3S2
InChI
InChIKey=UCGXLCPNFJKWEF-ZSXJVMONSA-N
InChI=1S/C28H42O8S/c29-15-28(16-30,17-31)18-36-27(35)10-4-2-1-3-8-20-21(24(34)14-23(20)33)11-12-22(32)26-13-19-7-5-6-9-25(19)37-26/h5-7,9,13,20-24,29-34H,1-4,8,10-12,14-18H2/t20-,21-,22-,23+,24-/m1/s1
| Molecular Formula | C28H42O8S |
| Molecular Weight | 538.693 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| 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 |
|---|---|---|
| Iclaprim, a novel diaminopyrimidine with potent activity on trimethoprim sensitive and resistant bacteria. | 2003 Dec 1 |
|
| Recently approved and investigational antibiotics for treatment of severe infections caused by Gram-positive bacteria. | 2005 Oct |
|
| Infections associated with orthopedic implants. | 2006 Aug |
|
| Antibacterial drug discovery and development--SRI's 11th Annual Summit. Antibacterial trends and current research. | 2006 Jun |
|
| Dihydrofolate reductase inhibitors as antibacterial agents. | 2006 Mar 30 |
|
| Gateways to clinical trials. | 2007 Dec |
|
| In vitro activity of the novel diaminopyrimidine, iclaprim, in combination with folate inhibitors and other antimicrobials with different mechanisms of action. | 2007 Dec |
|
| Effect of human plasma on the antimicrobial activity of iclaprim in vitro. | 2007 Dec |
|
| Investigational treatments for postoperative surgical site infections. | 2007 Feb |
|
| Activity of iclaprim against Legionella pneumophila. | 2007 Oct |
|
| Iclaprim. | 2007 Sep |
|
| 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 Sep |
|
| Alternatives to vancomycin for the treatment of methicillin-resistant Staphylococcus aureus infections. | 2007 Sep 15 |
|
| [New antimicrobials against Gram-positive organisms]. | 2008 |
|
| Investigational antimicrobial drugs for bloodstream infections. | 2008 Aug |
|
| What's new and not so new on the antimicrobial horizon? | 2008 Dec |
|
| A review of telavancin in the treatment of complicated skin and skin structure infections (cSSSI). | 2008 Feb |
|
| Pharmacologic options for CNS infections caused by resistant Gram-positive organisms. | 2008 Feb |
|
| Iclaprim, a diaminopyrimidine dihydrofolate reductase inhibitor for the potential treatment of antibiotic-resistant staphylococcal infections. | 2008 Feb |
|
| Registered and investigational drugs for the treatment of methicillin-resistant Staphylococcus aureus infection. | 2008 Jan |
|
| Gateways to clinical trials. | 2008 Jun |
|
| Gateways to clinical trials. | 2008 Oct |
|
| 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 |
|
| New antimicrobial molecules and new antibiotic strategies. | 2009 Apr |
|
| Increased hydrophobic interactions of iclaprim with Staphylococcus aureus dihydrofolate reductase are responsible for the increase in affinity and antibacterial activity. | 2009 Apr |
|
| 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 Aug |
|
| New antimicrobial agents for methicillin-resistant Staphylococcus aureus. | 2009 Dec |
|
| Future treatment options for Gram-positive infections--looking ahead. | 2009 Dec |
|
| New antibiotics for healthcare-associated pneumonia. | 2009 Feb |
|
| Activity of iclaprim against clinical isolates of Streptococcus pyogenes and Streptococcus agalactiae. | 2009 Feb |
|
| Regulatory watch: Non-inferiority-trial discussions impact new drug applications. | 2009 Jan |
|
| Antimicrobial development in the era of emerging resistance. | 2009 Jul |
|
| Iclaprim, a novel diaminopyrimidine for the treatment of resistant gram-positive infections. | 2009 Jun |
|
| Iclaprim: a novel dihydrofolate reductase inhibitor for skin and soft tissue infections. | 2009 Mar |
|
| In vitro activity of iclaprim and comparison agents tested against Neisseria gonorrhoeae including medium growth supplement effects. | 2009 Mar |
|
| New antibiotics for antibiotic-resistant bacteria. | 2009 May 28 |
|
| [New antibiotics: small or big advances?]. | 2009 Oct |
|
| New treatments for methicillin-resistant Staphylococcus aureus. | 2009 Oct |
|
| Treatments for skin and soft-tissue and surgical site infections due to MDR Gram-positive bacteria. | 2009 Sep |
|
| Enantioselective synthesis of iclaprim enantiomers--a versatile approach to 2-substituted chiral chromenes. | 2010 Jun 4 |
|
| [Update on antimicrobial chemotherapy]. | 2010 Mar |
|
| Mechanisms of resistance to antimicrobial drugs in pathogenic Gram-positive cocci. | 2010 Sep |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 21:48:43 GMT 2023
by
admin
on
Fri Dec 15 21:48:43 GMT 2023
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| Record UNII |
54923Z352W
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| Record Status |
Validated (UNII)
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| Record Version |
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