U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C13H15BrN4O2
Molecular Weight 339.188
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BRODIMOPRIM

SMILES

COC1=CC(CC2=CN=C(N)N=C2N)=CC(OC)=C1Br

InChI

InChIKey=BFCRRLMMHNLSCP-UHFFFAOYSA-N
InChI=1S/C13H15BrN4O2/c1-19-9-4-7(5-10(20-2)11(9)14)3-8-6-17-13(16)18-12(8)15/h4-6H,3H2,1-2H3,(H4,15,16,17,18)

HIDE SMILES / InChI
Brodimoprim, is a new 2,4-diaminobenzylpyrimidine that , that selectively inhibits bacterial and resistance plasmid dihydrofolate reductases to a similar or greater extent than trimethoprim. Brodimoprim is two to three times more potent than trimethoprim and has more than 100-fold the affinity for dihydrofolate reductase with analogous enzymatic activity of eukaryotic cells. Brodimoprim’s in vitro activity is similar to that of trimethoprim. Brodimoprim is decidedly superior to trimethoprim in vivo in the mouse acute infection model, due to its much longer elimination half-life and better tissue diffusion. Acute and subacute toxicity tests in traditional laboratory animals show that there is little difference between brodimoprim and trimethoprim. Brodimoprim had no teratogenic or embryotoxic effects and mutagenic analysis was negative

Approval Year

PubMed

PubMed

TitleDatePubMed
Comparison of dosages, intervals, and drugs in the prevention of Pneumocystis carinii pneumonia.
1988 May
Antimicrobial activities of dihydrofolate reductase inhibitors, used singly or in combination with dapsone, against Mycobacterium ulcerans.
2001 Jan
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Relationships between structural and thermal properties of anhydrous and solvated crystalline forms of brodimoprim.
2007 May
Liquid chromatography/tandem mass spectrometry method for simultaneous evaluation of activities of five cytochrome P450s using a five-drug cocktail and application to cytochrome P450 phenotyping studies in rats.
2008 Aug 1
Establishment of a liquid chromatographic/mass spectrometry method for quantification of tetrandrine in rat plasma and its application to pharmacokinetic study.
2008 Nov 4
A compendium of antibiotic-induced transcription profiles reveals broad regulation of Pasteurella multocida virulence genes.
2008 Oct 15
The transcriptional response of Pasteurella multocida to three classes of antibiotics.
2009 Jul 14
Liquid chromatographic/mass spectrometry assay of bromotetrandrine in rat plasma and its application to pharmacokinetic study.
2009 Jun
Name Type Language
BRODIMOPRIM
INN   MART.   MI   WHO-DD  
INN  
Official Name English
BRODIMOPRIM [MI]
Common Name English
2,4-DIAMINO-5-(4-BROMO-3,5-DIMETHOXYBENZYL)PYRIMIDINE
Systematic Name English
Brodimoprim [WHO-DD]
Common Name English
brodimoprim [INN]
Common Name English
BRODIMOPRIM [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC J01EA02
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
WHO-VATC QJ01EA02
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
NCI_THESAURUS C2153
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
Code System Code Type Description
FDA UNII
V1YC7T6LLI
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
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DRUG BANK
DB13795
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
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SMS_ID
100000088666
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
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ChEMBL
CHEMBL31891
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
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RXCUI
19727
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
PRIMARY RxNorm
MESH
C037079
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
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NCI_THESAURUS
C73255
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
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EPA CompTox
DTXSID20205070
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
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WIKIPEDIA
BRODIMOPRIM
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
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MERCK INDEX
m2657
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
PRIMARY Merck Index
INN
4910
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
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ECHA (EC/EINECS)
260-238-8
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
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CAS
56518-41-3
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
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PUBCHEM
68760
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
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EVMPD
SUB05898MIG
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
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DRUG CENTRAL
398
Created by admin on Sat Dec 16 16:20:01 GMT 2023 , Edited by admin on Sat Dec 16 16:20:01 GMT 2023
PRIMARY