08D

Sulfamethoxazole

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

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Chemical Details
Formal Charge	0
Atom Count	28
Chiral Atom Count	0
Bond Count	29
Aromatic Bond Count	11

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Chemical Component Summary
Name	Sulfamethoxazole
Synonyms	4-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
Formula	C₁₀ H₁₁ N₃ O₃ S
Molecular Weight	253.278
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=S(=O)(Nc1noc(c1)C)c2ccc(N)cc2
SMILES	CACTVS	3.370	Cc1onc(N[S](=O)(=O)c2ccc(N)cc2)c1
SMILES	OpenEye OEToolkits	1.7.6	Cc1cc(no1)NS(=O)(=O)c2ccc(cc2)N
Canonical SMILES	CACTVS	3.370	Cc1onc(N[S](=O)(=O)c2ccc(N)cc2)c1
Canonical SMILES	OpenEye OEToolkits	1.7.6	Cc1cc(no1)NS(=O)(=O)c2ccc(cc2)N
InChI	InChI	1.03	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)
InChIKey	InChI	1.03	JLKIGFTWXXRPMT-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB01015 ?
Name	Sulfamethoxazole
Groups	approved
Description	Sulfamethoxazole 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	3-(p-Aminophenylsulfonamido)-5-methylisoxazole 3-Sulfanilamido-5-methylisoxazole 4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide Sulfamethoxazole SMX Sulfametoxazol Sulphamethoxazole
Brand Names	Nu-cotrimox Sus 40/8mg/ml Bactrim Roche Inj Septra Pediatric Suspension Septra Grape Protrin Tab Protrin Df Tab Septra DS Tablets Nu-cotrimox-DS Tab 800/160mg Bactrim DS Roche Tab Trisulfa S Suspension Roubac Tab 80/400 Teva-trimel Bactrim Bactrim DS Sulfamethoxazole and Trimethoprim Double Strength Sulfamethoxazole and Trimethoprim for Injection, USP Sulfatrim Sulfamethox-TMP DS Bactrim Roche Tab Apo-sulfatrim Oral Suspension Sulfameth/Trimeth-DS SULFAMETHOXAZOLE AND TRIMETHOPRIM double strength Sulfamethoxazole and Trimethoprim Injection, BP Sulfamethoxazole Tab 500mg Trisulfa DS Tab Sulfamethoxazole and Trimethoprim (Double Strength) Sulfamethoxazole Roubac Tab 160/800 Sulfatrim DS Sulfatrim Pediatric Teva-trimel DS Riva-sep DS Nu-cotrimox Tab 400/80mg SULFAMETHOXAZOLE and TRIMETHOPRIM SulfatrimTM Pediatric Suspension Bactrim Roche Suspension Paediatric Sulfamethoxazole and Trimethoprim DS Septra DS Sulfamethoxazole and Trimethoprim sulfamethoxazole-trimethoprim (SMZ) Apo Sulfamethoxazole Tab 500mg Sulfamethoxazole and Trimethoprim Tablets Trisulfa Tab Septra Septra Injection
Indication	Sulfamethoxazole 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 Anti-Infective Agents Antibacterials for Systemic Use Antibiotics for Pneumocystis Pneumonia Antiinfectives for Systemic Use Antimycobacterials Benzene Derivatives Benzenesulfonamides Blood Glucose Lowering Agents BSEP/ABCB11 Inhibitors BSEP/ABCB11 Substrates Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (strength unknown) Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Drugs causing inadvertant photosensitivity Drugs for Treatment of Tuberculosis Drugs that are Mainly Renally Excreted Genito Urinary System and Sex Hormones Gynecological Antiinfectives and Antiseptics Hypoglycemia-Associated Agents Intermediate-Acting Antibacterial Sulfonamides Methemoglobinemia Associated Agents Photosensitizing Agents Potential QTc-Prolonging Agents QTc Prolonging Agents Sulfanilamides Sulfonamide Antibacterial Sulfonamides Sulfonamides and trimethoprim Sulfones Sulfur Compounds
ATC-Code	J04AM08 J01EE01 G01AE10 J01EC01
CAS number	723-46-6

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Dihydropteroate synthase	MKLFAQGTSLDLSHPHVMGILNVTPDSFSDGGTHNSLIDAVKHANLMINA...	unknown	antagonist
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate,inhibitor
Arylamine N-acetyltransferase 1	MDIEAYLERIGYKKSRNKLDLETLTDILQHQIRAVPFENLNIHCGDAMDL...	unknown	substrate
Arylamine N-acetyltransferase 2	MDIEAYFERIGYKNSRNKLDLETLTDILEHQIRAVPFENLNMHCGQAMEL...	unknown	substrate
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	substrate
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	inhibitor
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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 Name	Reference
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