Details of the Drug

General Information of Drug (ID: DM7YNV9)

Drug Name
Iclaprim
Synonyms
192314-93-5; AR-100; 5-[(2-cyclopropyl-7,8-dimethoxy-2h-chromen-5-yl)methyl]pyrimidine-2,4-diamine; RO-48-2622; Mersarex; 5-((2-Cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl)methyl)pyrimidine-2,4-diamine; Iclaprim [USAN:INN]; Iclaprim (USAN/INN); 2,4-Pyrimidinediamine, 5-((2-cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-yl)methyl)-; 2,4-Pyrimidinediamine, 5-[(2-cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-yl)methyl]-; AR 100; AC1Q4WM5; SCHEMBL379386; CHEMBL134561; AC1L4U54; SCHEMBL12899446; CTK4E0971; BDBM18070; Iclaprim [INN]; AR-102; AR-100001; 5-((2RS)-2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-ylmethyl)pyrimidine-2,4-diamine
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Phase 3 [1]
Pneumonia CA40 Phase 2 [2]
Acute bacterial skin infection 1C41 Application submitted [3]
ATC Code
J01EA03: Iclaprim
J01EA: Trimethoprim and derivatives
J01E: SULFONAMIDES AND TRIMETHOPRIM
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 354.4
Logarithm of the Partition Coefficient (xlogp) 2.5
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 7
Chemical Identifiers
Formula
C19H22N4O3
IUPAC Name
5-[(2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl)methyl]pyrimidine-2,4-diamine
Canonical SMILES
COC1=C(C2=C(C=CC(O2)C3CC3)C(=C1)CC4=CN=C(N=C4N)N)OC
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)
InChIKey
HWJPWWYTGBZDEG-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
213043
ChEBI ID
CHEMBL134561
CAS Number
192314-93-5
UNII
42445HUU0O
DrugBank ID
DB06358
TTD ID
D04LBC
INTEDE ID
DR1897
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Dihydrofolate reductase (Bact DHFR) TTV8DM2 DYR_ECOLI Modulator [4]
Dihydrofolate reductase (DHFR) TTYZVDJ DYR_HUMAN Inhibitor [3]
Prostaglandin receptor (PTGR) TT9B4N3 NOUNIPROTAC Modulator [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [6]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [6]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 How many modes of action should an antibiotic have Curr Opin Pharmacol. 2008 Oct;8(5):564-73.
2 ClinicalTrials.gov (NCT00523250) Ocular Hypotensive Efficacy of AR-102. U.S. National Institutes of Health.
3 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
4 Iclaprim: a novel dihydrofolate reductase inhibitor for skin and soft tissue infections.Future Microbiol.2009 Mar;4(2):131-44.
5 Novel ocular antihypertensive compounds in clinical trials. Clin Ophthalmol. 2011; 5: 667-677.
6 An updated review of iclaprim: a potent and rapidly bactericidal antibiotic for the treatment of skin and skin structure infections and nosocomial pneumonia caused by gram-positive including multidrug-resistant bacteria. Open Forum Infect Dis. 2018 Jan 6;5(2):ofy003.