Iclaprim

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Iclaprim
Accession Number
DB06358
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
AR-100 / AR-100.001 / RO 48-2622 / RO-48-2622
Product Ingredients
IngredientUNIICASInChI Key
Iclaprim Mesylate7U972CJ5AT474793-41-4BQCQVDMEHSONNK-UHFFFAOYSA-N
Categories
UNII
42445HUU0O
CAS number
192314-93-5
Weight
Average: 354.41
Monoisotopic: 354.169190584
Chemical Formula
C19H22N4O3
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

Pharmacology

Indication

Investigated for use/treatment in bacterial infection, skin infections/disorders, obesity, liver disease, kidney disease, and pneumonia.

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.

TargetActionsOrganism
UDihydrofolate reductaseNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(6R)-Folinic acidThe therapeutic efficacy of Iclaprim can be decreased when used in combination with (6R)-Folinic acid.
(6S)-5,6,7,8-tetrahydrofolateThe therapeutic efficacy of Iclaprim can be decreased when used in combination with (6S)-5,6,7,8-tetrahydrofolate.
Folic AcidThe therapeutic efficacy of Iclaprim can be decreased when used in combination with Folic Acid.
LeucovorinThe therapeutic efficacy of Iclaprim can be decreased when used in combination with Leucovorin.
LevoleucovorinThe therapeutic efficacy of Iclaprim can be decreased when used in combination with Levoleucovorin.
Tetrahydrofolic acidThe therapeutic efficacy of Iclaprim can be decreased when used in combination with Tetrahydrofolic acid.
Triglu-5-Formyl-TetrahydrofolateThe therapeutic efficacy of Iclaprim can be decreased when used in combination with Triglu-5-Formyl-Tetrahydrofolate.
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:14623005]
External Links
ChemSpider
184736
BindingDB
18070
ChEBI
131751
ChEMBL
CHEMBL134561
Wikipedia
Iclaprim
ATC Codes
J01EA03 — Iclaprim

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2TerminatedTreatmentHealth-Care-Associated Pneumonia / Pneumonia, Hospital-Acquired / Ventilator-Associated Pneumonia (VAP)1
3CompletedTreatmentSkin Diseases, Bacterial1
3CompletedTreatmentSkin Structures and Soft Tissue Infections2

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
PropertyValueSource
Water Solubility0.142 mg/mLALOGPS
logP2.35ALOGPS
logP2.49ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)17.32ChemAxon
pKa (Strongest Basic)7.15ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.51 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity101.99 m3·mol-1ChemAxon
Polarizability37.53 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Human
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 on March 19, 2008 10:27 / Updated on November 02, 2018 09:01