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]
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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)

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
UNII: 42445HUU0O
DrugBank ID: DB06358
TTD ID: D04LBC
INTEDE ID: DR1897

Repurposed Drugs (RPD)

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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]

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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.