08D

Sulfamethoxazole

Created:2011-10-13
Last modified:  2020-05-26

Help

Find related ligands:

Chemical Details

Formal Charge0
Atom Count28
Chiral Atom Count0
Bond Count29
Aromatic Bond Count11
2D diagram of 08D
Toggle HydrogenToggle Labels

Chemical Component Summary

NameSulfamethoxazole
Synonyms4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide; SMX; SMZ
Systematic Name (OpenEye OEToolkits)4-azanyl-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
FormulaC10 H11 N3 O3 S
Molecular Weight253.278
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs12.01O=S(=O)(Nc1noc(c1)C)c2ccc(N)cc2
SMILESCACTVS3.370Cc1onc(N[S](=O)(=O)c2ccc(N)cc2)c1
SMILESOpenEye OEToolkits1.7.6Cc1cc(no1)NS(=O)(=O)c2ccc(cc2)N
Canonical SMILESCACTVS3.370 Cc1onc(N[S](=O)(=O)c2ccc(N)cc2)c1
Canonical SMILESOpenEye OEToolkits1.7.6 Cc1cc(no1)NS(=O)(=O)c2ccc(cc2)N
InChIInChI1.03 InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
InChIKeyInChI1.03 JLKIGFTWXXRPMT-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank IDDB01015 
NameSulfamethoxazole
Groups approved
DescriptionSulfamethoxazole is a bacteriostatic sulfonamide antibiotic that interferes with folic acid synthesis in susceptible bacteria.[L11830] It is generally given in combination with [trimethoprim], which inhibits a sequential step in bacterial folic acid synthesis - these agents work synergistically to block two consecutive steps in the biosynthesis of nucleic acids and proteins which are necessary for bacterial growth and division, and using them in conjunction helps to slow the development of bacterial resistance.[L11830] In this combination, sulfamethoxazole is useful for the treatment of a variety of bacterial infections, including those of the urinary, respiratory, and gastrointestinal tracts.
Synonyms
  • Sulfamethoxazole
  • Sulphamethoxazole
  • 4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide
  • 3-Sulfanilamido-5-methylisoxazole
  • 3-(p-Aminophenylsulfonamido)-5-methylisoxazole
Brand Names
  • Teva-trimel
  • Sulfamethox-TMP DS
  • Septra DS Tablets
  • Sulfamethoxazole and Trimethoprim DS
  • Trisulfa S Suspension
IndicationSulfamethoxazole is indicated in combination with trimethoprim, in various formulations, for the following infections caused by bacteria with documented susceptibility: urinary tract infections, acute otitis media in pediatric patients (when clinically indicated), acute exacerbations of chronic bronchitis in adults, enteritis caused by susceptible _Shigella_, prophylaxis and treatment of _Pneumocystis jiroveci_ pneumonia, and travelers' diarrhea caused by enterotoxigenic _E. coli_.[L11830,L11863] In Canada, additional indications include the adjunctive treatment of cholera, treatment of bacillary dysentery, nocardiosis, and second-line treatment of brucellosis in combination with [gentamicin] or [rifampicin].[L11851]
Categories
  • Agents causing hyperkalemia
  • Agents Causing Muscle Toxicity
  • Amines
  • Aniline Compounds
  • Anti-Bacterial Agents
ATC-Code
  • J04AM08
  • J01EE01
  • G01AE10
  • J01EC01
CAS number723-46-6

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
NameTarget SequencePharmacological ActionActions
Dihydropteroate synthaseMKLFAQGTSLDLSHPHVMGILNVTPDSFSDGGTHNSLIDAVKHANLMINA...unknownantagonist
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate,inhibitor
Arylamine N-acetyltransferase 1MDIEAYLERIGYKKSRNKLDLETLTDILQHQIRAVPFENLNIHCGDAMDL...unknownsubstrate
Arylamine N-acetyltransferase 2MDIEAYFERIGYKNSRNKLDLETLTDILEHQIRAVPFENLNMHCGQAMEL...unknownsubstrate
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 5329
ChEMBL CHEMBL443
ChEBI CHEBI:9332
CCDC/CSD SLFNMB02, SLFNMB09, SLFNMB01, GUSHAD01, SLFNMB06, SLFNMB08, SLFNMB04, SLFNMB07, SLFNMB03, QIBCIQ, QIBCEM, SLFNMB05, QIBCOW, SLFNMB12, SLFNMB11, SLFNMB13, SLFNMB15, SLFNMB17, SLFNMB18, SLFNMB14, SLFNMB16, SLFNMB19, SLFNMB20, SLFNMB21, GUSHAD06, GUSHAD18, GUSHAD22, GUSHAD15, GUSHAD09, GUSHAD03, GUSHAD20, GUSHAD04, GUSHAD10, GUSHAD16, GUSHAD17, GUSHAD19, GUSHAD13, GUSHAD11, GUSHAD08, GUSHAD14, GUSHAD21, SLFNMB10, GUSHAD12, GUSHAD02, GUSHAD05, GUSHAD07
COD 4100620, 4100621, 4508170, 1551659