Sulfametoxydiazine

Sulfametoxydiazine
Systematic (IUPAC) name

4-amino-N-(5-methoxy-2-pyrimidinyl)benzenesulfonamide
Identifiers
CAS Number	651-06-9^N
ATC code	J01ED04 (WHO)
PubChem	CID 5326
ChemSpider	5135^Y
UNII	3L179F09D6^Y
KEGG	D02517^Y
ChEBI	CHEBI:53727^Y
ChEMBL	CHEMBL1200359^N
NIAID ChemDB	008164
Chemical data
Formula	C₁₁H₁₂N₄O₃S
Molar mass	280.303 g/mol
SMILES O=S(=O)(Nc1ncc(OC)cn1)c2ccc(N)cc2
InChI InChI=1S/C11H12N4O3S/c1-18-9-6-13-11(14-7-9)15-19(16,17)10-4-2-8(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)^Y Key:GPTONYMQFTZPKC-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Sulfametoxydiazine (INN) or sulfamethoxydiazine (USAN: sulfameter) is a long-acting sulfonamide antibacterial. It is used as a leprostatic agent and in the treatment of urinary tract infections.

Antibacterials: nucleic acid inhibitors (J01E, J01M)

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

DHFR inhibitor

2,4-Diaminopyrimidine
- Trimethoprim^#
- Brodimoprim
- Tetroxoprim
- Iclaprim^†

Sulfonamides
(DHPS inhibitor)

Short- acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine Sulfafurazole Sulfanilamide Prontosil Sulfathiazole Sulfathiourea

Intermediate- acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole

Long- acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone

Other/ungrouped	Sulfacetamide Sulfadicramide Sulfametrole

Combinations

Trimethoprim/sulfamethoxazole^#

Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication)

1st g.

Fluoro-
quinolones

2nd g.	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡ Norfloxacin^‡ Pefloxacin^‡ Rufloxacin^‡

3rd g.	Levofloxacin Balofloxacin^‡ Grepafloxacin^‡ Pazufloxacin^‡ Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin^‡

4th g.	Besifloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin Clinafloxacin^† Garenoxacin^‡ Prulifloxacin^‡ Sitafloxacin^‡ Trovafloxacin^‡/Alatrofloxacin^‡

Vet.	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin

Newer non-fluorinated

Nemonoxacin

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitro- imidazole derivatives	Metronidazole^# Tinidazole Ornidazole

Nitrofuran derivatives	Nitrofurantoin^# Furazolidone^‡ Nifurtoinol

RNA synthesis

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

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Antimycobacterials, including tuberculosis treatment and leprostatic agents (J04)

Nucleic acid inhibitor

Rifamycins/ RNA polymerase inhibitor	Rifampicin^# Rifabutin Rifapentine Rifalazil^§

Antifolates/DSI	Dapsone^# Acedapsone Aldesulfone sodium

ASA	4-Aminosalicylic acid^# (Calcium aminosalicylate Sodium aminosalicylate)

Protein synthesis inhibitor

Aminoglycosides	Amikacin^# Capreomycin^# Kanamycin^# Streptomycin^#

Oxazolidone	Linezolid

Cell envelope antibiotic

Peptidoglycan layer	Alanine analogue: Cycloserine^#

Arabinogalactan layer	Ethylenediamine/arabinosyltransferase inhibitor: Ethambutol^# SQ109^†

Mycolic acid layer	Hydrazides/mycolic acid synth. inhibition: Isoniazid^# Thiocarbamides: Ethionamide^# Prothionamide Thiocarlide

Other/unknown

Combinations

Rifampicin/isoniazid/pyrazinamide

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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