EPIROPRIM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H23N5O2
Molecular Weight	353.4182
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC1=CC(CC2=C(N)N=C(N)N=C2)=CC(OCC)=C1N3C=CC=C3

InChI

InChIKey=NMARPFMJVCXSAV-UHFFFAOYSA-N

InChI=1S/C19H23N5O2/c1-3-25-15-10-13(9-14-12-22-19(21)23-18(14)20)11-16(26-4-2)17(15)24-7-5-6-8-24/h5-8,10-12H,3-4,9H2,1-2H3,(H4,20,21,22,23)

HIDE SMILES / InChI

Molecular Formula	C19H23N5O2
Molecular Weight	353.4182
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://adisinsight.springer.com/drugs/800002670 | https://www.ncbi.nlm.nih.gov/pubmed/8726004 | https://www.ncbi.nlm.nih.gov/pubmed/10493608 | https://www.ncbi.nlm.nih.gov/pubmed/7986011

Epiroprim (Ro 11-8958) is a dihydrofolate reductase inhibitor. Epiroprim displayed activity against a broad range of bacteria including mycobacteria, staphylococci, enterococci, pneumococci, and streptococci as well as against Toxoplasma gondii. Epiroprim development has been discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Synergistic combinations of Ro 11-8958 and other dihydrofolate reductase inhibitors with sulfamethoxazole and dapsone for therapy of experimental pneumocystosis.	1993 Jul	8363372
Activity of epiroprim (Ro 11-8958), a dihydrofolate reductase inhibitor, alone and in combination with dapsone against Toxoplasma gondii.	1994 Aug	7986011
A pilot study on the efficacy of epiroprim against developmental stages of Toxoplasma gondii and Pneumocystis carinii in animal models.	1995	7624286
New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.	1995 Nov 24	7490723
Efficacy of epiroprim (Ro11-8958), a new dihydrofolate reductase inhibitor, in the treatment of acute Toxoplasma infection in mice.	1996 Mar	8600759
Combination of PS-15, epiroprim, or pyrimethamine with dapsone in prophylaxis of Toxoplasma gondii and Pneumocystis carinii dual infection in a rat model.	1996 Sep	8878582
Synthesis and biological evaluation of nonclassical 2,4-diamino-5-methylpyrido[2,3-d]pyrimidines with novel side chain substituents as potential inhibitors of dihydrofolate reductases.	1997 Feb 14	9046338
Selective Pneumocystis carinii dihydrofolate reductase inhibitors: design, synthesis, and biological evaluation of new 2,4-diamino-5-substituted-furo[2,3-d]pyrimidines.	1998 Apr 9	9548816
Antimicrobial activities of dihydrofolate reductase inhibitors, used singly or in combination with dapsone, against Mycobacterium ulcerans.	2001 Jan	11152437
Synthesis of 2,4-diamino-6-(thioarylmethyl)pyrido[2,3-d]pyrimidines as dihydrofolate reductase inhibitors.	2001 Nov	11597474

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:43:14 GMT 2023` Edited by `admin` on `Fri Dec 15 15:43:14 GMT 2023`
Record UNII	9G69D95443
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPIROPRIM

Official Name

English

2,4-DIAMINO-5-(3,5-DIETHOXY-4-PYRROL-1-YLBENZYL)PYRIMIDINE

Systematic Name

English

RO 11-8958

Code

English

epiroprim [INN]

Common Name

English

TCMDC-137295

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C2153