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

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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Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
UDihydrofolate reductaseNot AvailableHumans
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
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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.
DrugInteraction
AcetazolamideThe therapeutic efficacy of Iclaprim can be increased when used in combination with Acetazolamide.
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.
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Iclaprim Mesylate7U972CJ5AT474793-41-4BQCQVDMEHSONNK-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
  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. [Article]
ChemSpider
184736
BindingDB
18070
ChEBI
131751
ChEMBL
CHEMBL134561
Wikipedia
Iclaprim

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentBacterial skin infections1
3CompletedTreatmentComplicated Skin and Skin Structure Infection1
3CompletedTreatmentSkin and skin structure infections2
2TerminatedTreatmentHealthcare-associated Pneumonia (HCAP) / Nosocomial 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
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

Targets

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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