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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
Structure of ICLAPRIM, (S)-

SMILES

COC1=CC(CC2=C(N)N=C(N)N=C2)=C3C=C[C@@H](OC3=C1OC)C4CC4

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

HIDE SMILES / InChI

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..

Approval Year

PubMed

PubMed

TitleDatePubMed
Recently approved and investigational antibiotics for treatment of severe infections caused by Gram-positive bacteria.
2005 Oct
Dihydrofolate reductase inhibitors as antibacterial agents.
2006 Mar 30
Gateways to clinical trials.
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
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
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
Evidence based approach to the treatment of community-associated methicillin-resistant Staphylococcus aureus.
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
Activity of iclaprim against clinical isolates of Streptococcus pyogenes and Streptococcus agalactiae.
2009 Feb
Iclaprim: a novel dihydrofolate reductase inhibitor for skin and soft tissue infections.
2009 Mar
[Update on antimicrobial chemotherapy].
2010 Mar
Mechanisms of resistance to antimicrobial drugs in pathogenic Gram-positive cocci.
2010 Sep
Patents

Patents

Sample Use Guides

AR-102 0.003-0.03% Ophthalmic Solution
Route of Administration: Topical
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:11:27 GMT 2023
Edited
by admin
on Sat Dec 16 11:11:27 GMT 2023
Record UNII
7P9VLC9Y9D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ICLAPRIM, (S)-
Common Name English
2,4-PYRIMIDINEDIAMINE, 5-(((2S)-2-CYCLOPROPYL-7,8-DIMETHOXY-2H-1-BENZOPYRAN-5-YL)METHYL)-
Systematic Name English
Code System Code Type Description
PUBCHEM
44141864
Created by admin on Sat Dec 16 11:11:27 GMT 2023 , Edited by admin on Sat Dec 16 11:11:27 GMT 2023
PRIMARY
CAS
1208116-66-8
Created by admin on Sat Dec 16 11:11:27 GMT 2023 , Edited by admin on Sat Dec 16 11:11:27 GMT 2023
PRIMARY
FDA UNII
7P9VLC9Y9D
Created by admin on Sat Dec 16 11:11:27 GMT 2023 , Edited by admin on Sat Dec 16 11:11:27 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> ENANTIOMER
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