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%
Elimination half-life	3–8 hours
Identifiers
IUPAC name 4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzene-1-sulfonamide
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 InfoCard	100.005.129
Chemical and physical data
Formula	C₉H₁₀N₄O₂S₂
Molar mass	270.33 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	208 °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	Chlortetracycline Demeclocycline Oxytetracycline Tetracycline
Others	Amphenicol: Chloramphenicol Aminoglycosides: Amikacin Gentamicin Neomycin Quinolones: Nadifloxacin Streptogramin: Virginiamycin Rifamycin: Rifaximin other: Bacitracin Fusidic acid Mupirocin Tyrothricin

Chemotherapeutics

Sulfonamides	Mafenide Silver sulfadiazine Sulfamerazine Sulfamethizole Sulfanilamide Sulfathiazole
Antivirals	Aciclovir Berdazimer sodium Docosanol Edoxudine Ibacitabine Idoxuridine Imiquimod Inosine Lysine Lysozyme Penciclovir Podophyllotoxin Resiquimod Tromantadine
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 (Sulfamethazine, Sulfadimerazine, Sulfadimezine) 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)

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	Secnidazole

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	Sulfacetamide Sulfadicramide Sulfafenazol Sulfafurazole Sulfamethizole
Antivirals	Aciclovir Famciclovir Fomivirsen Ganciclovir Idoxuridine Interferon Trifluridine Vidarabine
Fluoroquinolones	Besifloxacin Ciprofloxacin Gatifloxacin Levofloxacin (+dexamethasone) Lomefloxacin Moxifloxacin Norfloxacin Ofloxacin Tosufloxacin
Other	Bibrocathol Chlorhexidine Dibrompropamidine Hexamidine Nitrofural Picloxydine Polihexanide Povidone-iodine Propamidine Resorcinol Sodium borate Sodium propionate

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