Iclaprim
Identification
- Generic Name
- Iclaprim
- DrugBank Accession Number
- DB06358
- Background
Not Available
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 354.41
Monoisotopic: 354.169190584 - Chemical Formula
- C19H22N4O3
- Synonyms
- Iclaprim
- External IDs
- AR-100
- AR-100.001
- RO 48-2622
- RO-48-2622
Pharmacology
- Indication
Investigated for use/treatment in bacterial infection, skin infections/disorders, obesity, liver disease, kidney disease, and pneumonia.
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- Pharmacodynamics
Not Available
- Mechanism of action
Iclaprim is a novel diaminopyrimidine, and an inhibitor of dihydrofolate reductase, which has shown potent, extended-spectrum in vitro activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus, vancomycin-intermediate and vancomycin-resistant S. aureus and macrolide-, quinolone- and trimethoprim-resistant strains. In addition, iclaprim has demonstrated activity against Streptococcus pneumoniae including penicillin-, erythromycin-, levofloxacin- and trimethoprim/sulfamethoxazole-resistant strains.
Target Actions Organism UDihydrofolate reductase Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetazolamide The therapeutic efficacy of Iclaprim can be increased when used in combination with Acetazolamide. Folic acid The therapeutic efficacy of Iclaprim can be decreased when used in combination with Folic acid. Leucovorin The therapeutic efficacy of Iclaprim can be decreased when used in combination with Leucovorin. Levoleucovorin The therapeutic efficacy of Iclaprim can be decreased when used in combination with Levoleucovorin. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Iclaprim Mesylate 7U972CJ5AT 474793-41-4 BQCQVDMEHSONNK-UHFFFAOYSA-N
Categories
- ATC Codes
- J01EA03 — Iclaprim
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 42445HUU0O
- CAS number
- 192314-93-5
- InChI Key
- HWJPWWYTGBZDEG-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 5-[(2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl)methyl]pyrimidine-2,4-diamine
- SMILES
- COC1=CC(CC2=CN=C(N)N=C2N)=C2C=CC(OC2=C1OC)C1CC1
References
- General References
- Schneider P, Hawser S, Islam K: Iclaprim, a novel diaminopyrimidine with potent activity on trimethoprim sensitive and resistant bacteria. Bioorg Med Chem Lett. 2003 Dec 1;13(23):4217-21. [Article]
- External Links
- ChemSpider
- 184736
- BindingDB
- 18070
- ChEBI
- 131751
- ChEMBL
- CHEMBL134561
- Wikipedia
- Iclaprim
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Bacterial skin infections 1 3 Completed Treatment Complicated Skin and Skin Structure Infection 1 3 Completed Treatment Skin and skin structure infections 2 2 Terminated Treatment Healthcare-associated Pneumonia (HCAP) / Hospital-Acquired Pneumonia / Ventilator Associated Bacterial Pneumonia (VABP) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.142 mg/mL ALOGPS logP 2.35 ALOGPS logP 2.49 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 17.32 Chemaxon pKa (Strongest Basic) 7.15 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 105.51 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 101.99 m3·mol-1 Chemaxon Polarizability 37.53 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0009000000-84bd9a5653cca48073ec Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0009000000-3dc59f30dc86ad78addb Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0009000000-b9538285b676e7a5f8ca Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0049000000-e7582a888fb23070072e Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-08fr-1179000000-0b7a4266291bd39274ba Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-002b-0091000000-5af35df9f6fa3f23af43 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Nadph binding
- Specific Function
- Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA pre...
- Gene Name
- DHFR
- Uniprot ID
- P00374
- Uniprot Name
- Dihydrofolate reductase
- Molecular Weight
- 21452.61 Da
Drug created at March 19, 2008 16:27 / Updated at February 21, 2021 18:52