Sulfamethizole

Sulfamethizole
Clinical data

AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a682231
ATC code	B05CA04 (WHO) D06BA04 (WHO) J01EB02 (WHO) S01AB01 (WHO) QJ01EQ02 (WHO)
Pharmacokinetic data
Protein binding	98–99%
Biological half-life	3–8 hours
Identifiers
IUPAC name 4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)- benzenesulfonamide
CAS Number	144-82-1^Y
PubChem CID	5328
DrugBank	DB00576^Y
ChemSpider	5137^Y
UNII	25W8454H16
KEGG	D00870^Y
ChEBI	CHEBI:9331^Y
ChEMBL	CHEMBL1191^Y
ECHA InfoCard	100.005.129
Chemical and physical data
Formula	C₉H₁₀N₄O₂S₂
Molar mass	270.333 g/mol
3D model (JSmol)	Interactive image
SMILES O=S(=O)(Nc1nnc(s1)C)c2ccc(N)cc2
InChI InChI=1S/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13)^Y Key:VACCAVUAMIDAGB-UHFFFAOYSA-N^Y
(verify)

Sulfamethizole is a sulfonamide antibiotic.

References

Ratanajamit C, Skriver M, Nørgaard M, Jepsen P, Schønheyder H, Sørensen H (2003). "Adverse pregnancy outcome in users of sulfamethizole during pregnancy: a population-based observational study.". J Antimicrob Chemother. 52 (5): 837–41. PMID 14519675. doi:10.1093/jac/dkg438.
Kerrn M, Frimodt-Møller N, Espersen F (2003). "Effects of Sulfamethizole and Amdinocillin against Escherichia coli Strains (with Various Susceptibilities) in an Ascending Urinary Tract Infection Mouse Model". Antimicrob Agents Chemother. 47 (3): 1002–9. PMC 149286 . PMID 12604534. doi:10.1128/AAC.47.3.1002-1009.2003.
Watanabe H, Hastings J (1990). "Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine". Biochim Biophys Acta. 1017 (3): 229–34. PMID 2372557. doi:10.1016/0005-2728(90)90189-B.

Tetracycline and derivatives	Demeclocycline Chlortetracycline Oxytetracycline Tetracycline
Others	Amphenicol: Chloramphenicol Aminoglycosides: Neomycin Gentamicin Amikacin Quinolone: Nadifloxacin Streptogramin: Virginiamycin Rifamycin: Rifaximin other: Fusidic acid Bacitracin Tyrothricin Mupirocin

Sulfonamides	Silver sulfadiazine Sulfathiazole Mafenide Sulfamethizole Sulfanilamide Sulfamerazine
Antivirals	Aciclovir Penciclovir Idoxuridine Edoxudine Imiquimod Resiquimod Podophyllotoxin Docosanol Tromantadine Inosine Lysozyme Ibacitabine Lysine
Other	Ingenol mebutate Metronidazole

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

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 Sulfanitran

Combinations

Other DHPS inhibitors

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

Related (DG)

Nitro- imidazole derivatives	Metronidazole^# Tinidazole Ornidazole
Nitrofuran derivatives	Nitrofurantoin^# Furazolidone^‡ Nifurtoinol

RNA synthesis

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

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