Sulfamethizole

Sulfamethizole
Systematic (IUPAC) name

4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)- benzenesulfonamide
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a682231
Pharmacokinetic data
Protein binding	98–99%
Biological half-life	3–8 hours
Identifiers
CAS Number	144-82-1^Y
ATC code	B05CA04 (WHO) D06BA04 J01EB02 S01AB01 QJ01EQ02
PubChem	CID 5328
DrugBank	DB00576^Y
ChemSpider	5137^Y
UNII	25W8454H16^Y
KEGG	D00870^Y
ChEBI	CHEBI:9331^Y
ChEMBL	CHEMBL1191^Y
Chemical data
Formula	C₉H₁₀N₄O₂S₂
Molar mass	270.333 g/mol
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. doi:10.1093/jac/dkg438. PMID 14519675.
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. doi:10.1128/AAC.47.3.1002-1009.2003. PMC 149286. PMID 12604534.
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. doi:10.1016/0005-2728(90)90189-B. PMID 2372557.

Antibiotics and chemotherapeutics for dermatological use (D06)

Antibiotics

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

Chemotherapeutics

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

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

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