Sulfamethizole

Chemical compound

B05CA04 (WHO) D06BA04 (WHO) J01EB02 (WHO) S01AB01 (WHO) QJ01EQ02 (WHO)

Pharmacokinetic dataProtein binding98–99%Elimination half-life3–8 hoursIdentifiers

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

CompTox Dashboard (EPA)

DTXSID5023615

ECHA InfoCard100.005.129

Chemical and physical dataFormulaC₉H₁₀N₄O₂S₂Molar mass270.33 g·mol⁻¹3D model (JSmol)

Interactive image

Melting point208 °C (406 °F)

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.^[1]

References

^ Ayankojo AG, Tretjakov A, Reut J, Boroznjak R, Öpik A, Rappich J, et al. (January 2016). "Molecularly Imprinted Polymer Integrated with a Surface Acoustic Wave Technique for Detection of Sulfamethizole". Analytical Chemistry. 88 (2): 1476–1484. doi:10.1021/acs.analchem.5b04735. PMID 26704414.

Ratanajamit C, Skriver MV, Nørgaard M, Jepsen P, Schønheyder HC, Sørensen HT (November 2003). "Adverse pregnancy outcome in users of sulfamethizole during pregnancy: a population-based observational study". The Journal of Antimicrobial Chemotherapy. 52 (5): 837–841. doi:10.1093/jac/dkg438. PMID 14519675.
Kerrn MB, Frimodt-Møller N, Espersen F (March 2003). "Effects of sulfamethizole and amdinocillin against Escherichia coli strains (with various susceptibilities) in an ascending urinary tract infection mouse model". Antimicrobial Agents and Chemotherapy. 47 (3): 1002–1009. doi:10.1128/AAC.47.3.1002-1009.2003. PMC 149286. PMID 12604534.
Watanabe H, Hastings JW (June 1990). "Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine". Biochimica et Biophysica Acta (BBA) - Bioenergetics. 1017 (3): 229–234. 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 Quinolones: 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 Tirbanibulin

Antibacterials that inhibit nucleic acid (J01E, J01M)

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

DHFR inhibitor

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

Sulfonamides
(DHPS inhibitor)

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

Trimethoprim/sulfamethoxazole^#
Ormetoprim/sulfadimethoxine
Pyrimethamine/dapsone
Pyrimethamine/sulfadoxine

Other DHPS inhibitors

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

1st generation

Fluoroquinolones

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)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitroimidazole derivatives	Metronidazole^# Ornidazole Secnidazole Tinidazole
Nitrofuran derivatives	Furazolidone^‡ Nifuroxazide Nifurtoinol Nifurzide Nitrofurantoin^# Nitrofurazone

RNA synthesis

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

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

v t e Ophthalmologicals: anti-infectives (S01A)
Antibiotics	amphenicols (Chloramphenicol Azidamfenicol) tetracyclines (Tetracycline Chlortetracycline Oxytetracycline) aminoglycosides (Dihydrostreptomycin Neomycin Framycetin Kanamycin Amikacin Tobramycin Gentamicin Netilmicin Micronomicin) macrolides (Erythromycin Natamycin) beta-lactams (Ampicillin Benzylpenicillin) polypeptides (Polymyxin B Tyrothricin) Rifamycin Fusidic acid
Sulfonamides	Sulfamethizole Sulfafurazole Sulfadicramide Sulfacetamide Sulfafenazol
Antivirals	Idoxuridine Trifluridine Aciclovir Interferon Vidarabine Famciclovir Fomivirsen Ganciclovir
Other	Nitrofural Bibrocathol Resorcinol Sodium borate Hexamidine Chlorhexidine Sodium propionate Ofloxacin Norfloxacin Ciprofloxacin Dibrompropamidine Propamidine Picloxydine Lomefloxacin Povidone-iodine Levofloxacin (+dexamethasone) Gatifloxacin