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]
------------------------------------------------------------------------------------

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:131751
CAS Number: 192314-93-5
DrugBank ID: DB06358
TTD ID: D04LBC
INTEDE ID: DR1897

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)

MIA Detail

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.