Sulfametrole

Chemical compound

J01EE03 (WHO) (with trimethoprim)

Legal statusLegal status

In general: ℞ (Prescription only)

Identifiers

IUPAC name

4-amino-N-(4-methoxy-1,2,5-thiadiazol-3-yl)benzenesulfonamide

CAS Number

32909-92-5

PubChem CID

64939

ChemSpider

58466

UNII

F5AK41IPQG

KEGG

D08541^Y

ChEBI

CHEBI:88258^Y

ECHA InfoCard100.046.611

Chemical and physical dataFormulaC₉H₁₀N₄O₃S₂Molar mass286.32 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

COc1c(nsn1)NS(=O)(=O)c2ccc(cc2)N

InChI

InChI=1S/C9H10N4O3S2/c1-16-9-8(11-17-12-9)13-18(14,15)7-4-2-6(10)3-5-7/h2-5H,10H2,1H3,(H,11,13)
Key:IZOYMGQQVNAMHS-UHFFFAOYSA-N

(verify)

Sulfametrole (INN) is a sulfonamide antibacterial.

It can be given with trimethoprim.^[1]

References

^ Plummer FA, Nsanze H, D'Costa LJ, et al. (July 1983). "Single-dose therapy of chancroid with trimethoprim-sulfametrole". N. Engl. J. Med. 309 (2): 67–71. doi:10.1056/NEJM198307143090202. PMID 6343878.

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^‡ 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