Brodimoprim - Wikipedia

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Brodimoprim
Clinical data

ATC code	J01EA02 (WHO)
Identifiers
IUPAC name 5-[(4-Bromo-3,5-dimethoxyphenyl)methyl]pyrimidine-2,4-diamine
CAS Number	56518-41-3^Y
PubChem CID	68760
ChemSpider	62004^Y
UNII	V1YC7T6LLI
KEGG	D07238^Y
ChEBI	CHEBI:131726
ChEMBL	ChEMBL31891^Y
CompTox Dashboard (EPA)	DTXSID20205070
ECHA InfoCard	100.054.745
Chemical and physical data
Formula	C₁₃H₁₅BrN₄O₂
Molar mass	339.193 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	225 to 228 °C (437 to 442 °F)
SMILES Brc1c(OC)cc(cc1OC)Cc2cnc(nc2N)N
InChI 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)^Y Key:BFCRRLMMHNLSCP-UHFFFAOYSA-N^Y
(verify)

Brodimoprim is a structural derivative of trimethoprim. In brodimoprim, the 4-methoxy group of trimethoprim is replaced with a bromine atom.

As trimethoprim, brodimoprim is a selective inhibitor of bacterial dihydrofolate reductase.^[1]

References

^ Thomson CJ (December 1993). "Trimethoprim and brodimoprim resistance of gram-positive and gram-negative bacteria". Journal of Chemotherapy. 5 (6): 458–64. PMID 8195838.

Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)

Short-acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine (Sulfasalazine) Sulfafurazole (Acetyl sulfisoxazole) Sulfanilamide Prontosil Sulfathiazole (Phthalylsulfathiazole, Succinylsulfathiazole) Sulfathiourea
Intermediate-acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole
Long-acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone
Other/ungrouped	Mafenide Sulfacetamide Sulfaclozine Sulfadicramide Sulfaguanidine Sulfametrole Sulfanitran

Combinations

Other DHPS inhibitors

Quinolones
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)

2nd generation	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡/Levonadifloxacin/Alalevonadifloxacin Norfloxacin^‡ Pefloxacin^‡ Rufloxacin^‡
3rd generation	Levofloxacin^# Balofloxacin^‡ Grepafloxacin^‡ Pazufloxacin^‡ Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin^‡
4th generation	Besifloxacin Delafloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin^# Clinafloxacin^† Garenoxacin^‡ Prulifloxacin^‡ Sitafloxacin^‡ Trovafloxacin^‡/Alatrofloxacin^‡
Veterinary	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin^‡

Newer non-fluorinated

Related (DG)

Nitroimidazole derivatives	Secnidazole

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin^# Rifabutin^# Rifapentine^# Rifaximin Rifalazil^§
Lipiarmycins	Fidaxomicin

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