Sulfamethoxazole

Identification

Summary

Sulfamethoxazole is an oral sulfonamide antibiotic, given in combination with trimethoprim, used to treat a variety of infections of the urinary tract, respiratory system, and gastrointestinal tract.

Brand Names

Bactrim, Septra, Sulfatrim

Generic Name

Sulfamethoxazole

DrugBank Accession Number

DB01015

Background

Sulfamethoxazole is a bacteriostatic sulfonamide antibiotic that interferes with folic acid synthesis in susceptible bacteria.⁹ 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.⁹ In this combination, sulfamethoxazole is useful for the treatment of a variety of bacterial infections, including those of the urinary, respiratory, and gastrointestinal tracts.

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 253.278
Monoisotopic: 253.052111923
Chemical Formula: C₁₀H₁₁N₃O₃S

Synonyms

3-(p-Aminophenylsulfonamido)-5-methylisoxazole
3-Sulfanilamido-5-methylisoxazole
4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide
SMX
Sulfamethoxazole
Sulfametoxazol
Sulphamethoxazole

External IDs

NSC-147832
RO 4-2130
STX-608

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Pharmacology

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.^9,11

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.¹⁰

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group
Used in combination to treat	Acute exacerbation of chronic bronchitis (aecb) caused by susceptible bacteria	Combination Product in combination with: Trimethoprim (DB00440)	••••••••••••	•••••
Used in combination to treat	Acute otitis media caused by susceptible bacteria	Combination Product in combination with: Trimethoprim (DB00440)	••••••••••••	•••••••••
Used in combination to treat	Brucellosis	Regimen in combination with: Trimethoprim (DB00440), Rifampicin (DB01045)	••••••••••••
Used in combination to treat	Brucellosis	Regimen in combination with: Gentamicin (DB00798), Trimethoprim (DB00440)	••••••••••••
Used in combination to treat	Dysentery, bacillary	Combination Product in combination with: Trimethoprim (DB00440)	••••••••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Sulfamethoxazole is a bacteriostatic sulfonamide antibiotic that inhibits a critical step in bacterial folate synthesis. It is generally given in combination with trimethoprim, a dihydrofolate reductase inhibitor, which inhibits the reduction of dihydrofolic acid to tetrahydrofolic acid.⁹ Studies have shown that bacterial resistance develops more slowly with the combination of the two drugs than with either trimethoprim or sulfamethoxazole alone, as together they inhibit sequential steps in the bacterial folate synthesis pathway.⁹

Sulfonamides, including sulfamethoxazole, have been implicated in hypersensitivity reactions - these agents should be discontinued at the first sign of a developing rash, as this may signal the start of a more severe reaction such as Stevens-Johnson syndrome or toxic epidermal necrolysis. Sulfamethoxazole treatment may contribute to folate deficiency and should therefore be used with caution in patients at a higher risk of developing a deficiency. Hemolysis has been observed in patients with glucose-6-phosphate dehydrogenase deficiency who are using sulfamethoxazole/trimethoprim.⁹

Mechanism of action

Sulfamethoxazole is a sulfonamide that inhibits bacterial dihydrofolic acid synthesis due to its structural similarity to an endogenous substrate, para-aminobenzoic acid (PABA).^1,2 Most bacteria meet their need for folic acid by synthesizing it from PABA, as opposed to Animalia that require exogenous folic acid sources.¹⁰ Sulfamethoxazole competitively inhibits dihydropteroate synthase, the enzyme responsible for bacterial conversion of PABA to dihydrofolic acid.³ Inhibition of this pathway prevents the synthesis of tetrahydrofolate and, ultimately, the synthesis of bacterial purines and DNA, resulting in a bacteriostatic effect.⁴

Target	Actions	Organism
ADihydropteroate synthase	antagonist	Escherichia coli (strain K12)

Absorption

Sulfamethoxazole is rapidly absorbed following oral administration and has a bioavailability of 85-90%.⁵ The T_max is approximately 1-4 hours following oral administration, and the C_max at steady-state is 57.4 - 68.0 μg/mL.⁹

Volume of distribution

The volume of distribution sulfamethoxazole following a single oral dose was found to be 13 L.⁵ Sulfamethoxazole distributes into sputum, vaginal fluid, middle ear fluid, breast milk, and the placenta.⁹

Protein binding

Sulfamethoxazole is approximately 70% bound to plasma proteins,⁹ primarily to albumin.¹⁰

Metabolism

Sulfamethoxazole metabolism is mediated primarily by arylamine N-acetyltransferase (NAT) enzymes, which are responsible for acetylation of sulfamethoxazole at its N4 position.^7,9 Sulfamethoxazole may also undergo oxidation at its C5 and N4 atoms, the latter of which is catalyzed by CYP2C9.⁹ Glucuronidation of the N4 atom, likely mediated by unspecified UGT enzymes, is an additional minor route of metabolism.⁷ None of the identified metabolites of sulfamethoxazole appear to carry antimicrobial activity.⁹

The hydroxylamine metabolite of sulfamethoxazole, generated via oxidation by CYP2C9, may be further converted to a more reactive nitroso- metabolite.⁷

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Sulfamethoxazole

Route of elimination

Elimination occurs primarily via glomerular filtration and tubular secretion in the kidneys, with urine concentrations generally considerably higher than plasma concentrations.⁹ Approximately 84.5% of a single oral dose of sulfamethoxazole is recovered in the urine within 72 hours, of which ~30% is free sulfamethoxazole and the remainder is the N4-acetylated metabolite.⁹

Half-life

The average serum half-life of sulfamethoxazole is 10 hours and may be increased in patients with severely impaired renal function.⁹

Clearance

The oral and renal clearance of sulfamethoxazole have been estimated as 1.2 ± 0.2 and 0.22 ± 0.05 L/h, respectively.⁸

Adverse Effects

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Toxicity

The oral LD₅₀ of sulfamethoxazole in mice and rats is 2300 mg/kg and 6200 mg/kg, respectively.¹²

Signs or symptoms of sulfonamide overdose include anorexia, colic, nausea, vomiting, dizziness, headache, drowsiness, and unconsciousness. Less common symptoms may include pyrexia, hematuria, and crystalluria. Later manifestations of overdose may include blood dyscrasias and jaundice.⁹ Treatment should be symptomatic and supportive, and may include gastric lavage or forced emesis if applicable. Monitor patient lab work for evidence of blood dyscrasias or electrolyte imbalances.⁹

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Interacting Gene/Enzyme	Allele name	Genotype(s)	Defining Change(s)	Type(s)	Description	Details
Glucose-6-phosphate 1-dehydrogenase	Villeurbanne	Not Available	1000_1002delACC	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Torun	Not Available	1006A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Sunderland	Not Available	105_107delCAT	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Iwatsuki	Not Available	1081G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Serres	Not Available	1082C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Tondela	Not Available	1084_1101delCTGAACGAGCGCAAGGCC	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Loma Linda	Not Available	1089C->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Aachen	Not Available	1089C->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Tenri	Not Available	1096A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Montpellier	Not Available	1132G>A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Calvo Mackenna	Not Available	1138A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Riley	Not Available	1139T->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Olomouc	Not Available	1141T->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Tomah	Not Available	1153T->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Lynwood	Not Available	1154G->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Madrid	Not Available	1155C->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Iowa, Walter Reed, Springfield	Not Available	1156A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Beverly Hills, Genova, Iwate, Niigata, Yamaguchi	Not Available	1160G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Hartford	Not Available	1162A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Praha	Not Available	1166A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Krakow	Not Available	1175T>C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Wisconsin	Not Available	1177C->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Nashville, Anaheim, Portici	Not Available	1178G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Alhambra	Not Available	1180G->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Bari	Not Available	1187C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Puerto Limon	Not Available	1192G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Covao do Lobo	Not Available	1205C>A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Clinic	Not Available	1215G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Utrecht	Not Available	1225C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Suwalki	Not Available	1226C->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Riverside	Not Available	1228G->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Japan, Shinagawa	Not Available	1229G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Kawasaki	Not Available	1229G->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Munich	Not Available	1231A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Georgia	Not Available	1284C->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Sumare	Not Available	1292T->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Telti/Kobe	Not Available	1318C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Santiago de Cuba, Morioka	Not Available	1339G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Harima	Not Available	1358T->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Figuera da Foz	Not Available	1366G->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Amiens	Not Available	1367A>T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Bangkok Noi	Not Available	1376G->T, 1502T->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Fukaya	Not Available	1462G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Campinas	Not Available	1463G->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Buenos Aires	Not Available	1465C>T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Arakawa	Not Available	1466C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Brighton	Not Available	1488_1490delGAA	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Kozukata	Not Available	159G->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Amsterdam	Not Available	180_182delTCT	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	No name	Not Available	202G->A, 376A->G, 1264C>G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Swansea	Not Available	224T->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Urayasu	Not Available	281_283delAGA	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Vancouver	Not Available	317C->G544C->T592C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Mt Sinai	Not Available	376A->G, 1159C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Plymouth	Not Available	488G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Volendam	Not Available	514C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Shinshu	Not Available	527A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Chikugo	Not Available	535A->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Tsukui	Not Available	561_563delCTC	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Pedoplis-Ckaro	Not Available	573C>G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Santiago	Not Available	593G->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Minnesota, Marion, Gastonia, LeJeune	Not Available	637G->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Cincinnati	Not Available	637G->T, 1037A->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Harilaou	Not Available	648T->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	North Dallas	Not Available	683_685delACA	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Asahikawa	Not Available	695G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Durham	Not Available	713A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Stonybrook	Not Available	724_729delGGCACT	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Wayne	Not Available	769C->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Aveiro	Not Available	806G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Cleveland Corum	Not Available	820G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Lille	Not Available	821A>T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Bangkok	Not Available	825G>C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Sugao	Not Available	826C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	La Jolla	Not Available	832T->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Wexham	Not Available	833C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Piotrkow	Not Available	851T>C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	West Virginia	Not Available	910G->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Omiya	Not Available	921G->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Nara	Not Available	953_976delCCACCAAAGGGTACCTGGAC GACC	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Manhattan	Not Available	962G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Rehevot	Not Available	964T->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Honiara	Not Available	99A->G / 1360C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Tokyo, Fukushima	Not Available	1246G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Chatham	Not Available	1003G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Fushan	Not Available	1004C->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Partenope	Not Available	1052G->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Ierapetra	Not Available	1057C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Anadia	Not Available	1193A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Abeno	Not Available	1220A->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Surabaya	Not Available	1291G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Pawnee	Not Available	1316G->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	S. Antioco	Not Available	1342A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Cassano	Not Available	1347G->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Hermoupolis	Not Available	1347G->C / 1360C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Union,Maewo, Chinese-2, Kalo	Not Available	1360C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Andalus	Not Available	1361G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Cosenza	Not Available	1376G->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Canton, Taiwan- Hakka, Gifu-like, Agrigento-like	Not Available	1376G->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Flores	Not Available	1387C->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Kaiping, Anant, Dhon, Sapporo-like, Wosera	Not Available	1388G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Kamogawa	Not Available	169C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Costanzo	Not Available	179T>C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Amazonia	Not Available	185C->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Songklanagarind	Not Available	196T->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Hechi	Not Available	202G->A / 871G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Namouru	Not Available	208T->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Bao Loc	Not Available	352T>C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Crispim	Not Available	375G->T, 379G->T383T->C384C>T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Acrokorinthos	Not Available	376A->G / 463C->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Santa Maria	Not Available	376A->G / 542A->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Ananindeua	Not Available	376A->G / 871G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Vanua Lava	Not Available	383T->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Valladolid	Not Available	406C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Belem	Not Available	409C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Liuzhou	Not Available	442G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Shenzen	Not Available	473G>A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Taipei ‚ÄúChinese- 3‚Äù	Not Available	493A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Toledo	Not Available	496C>T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Naone	Not Available	497G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Nankang	Not Available	517T->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Miaoli	Not Available	519C->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Mediterranean, Dallas, Panama‚ Sassari, Cagliari, Birmingham	Not Available	563C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Coimbra Shunde	Not Available	592C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Nilgiri	Not Available	593G>A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Radlowo	Not Available	679C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Roubaix	Not Available	811G>C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Haikou	Not Available	835A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Chinese-1	Not Available	835A->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Mizushima	Not Available	848A>G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Osaka	Not Available	853C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Viangchan, Jammu	Not Available	871G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Seoul	Not Available	916G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Ludhiana	Not Available	929G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Farroupilha	Not Available	977C->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Chinese-5	Not Available	1024C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Rignano	Not Available	130G>A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Orissa	Not Available	131C->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	G6PDNice	Not Available	1380G>C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Kamiube, Keelung	Not Available	1387C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Neapolis	Not Available	1400C->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Aures	Not Available	143T->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Split	Not Available	1442C->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Kambos	Not Available	148C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Palestrina	Not Available	170G>A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Metaponto	Not Available	172G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Musashino	Not Available	185C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Asahi	Not Available	202G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	A- (202), Ferrara I	Not Available	202G->A / 376A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Murcia Oristano	Not Available	209A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Ube Konan	Not Available	241C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Lagosanto	Not Available	242G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Guangzhou	Not Available	274C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Hammersmith	Not Available	323T->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Sinnai	Not Available	34G->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	A- (680)	Not Available	376A->G / 680G->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	A- (968), Betica,Selma, Guantanamo	Not Available	376A->G / 968T->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Salerno Pyrgos	Not Available	383T>G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Quing Yan	Not Available	392G->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Lages	Not Available	40G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Ilesha	Not Available	466G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Mahidol	Not Available	487G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Malaga	Not Available	542A->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Sibari	Not Available	634A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Mexico City	Not Available	680G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Nanning	Not Available	703C->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Seattle, Lodi, Modena, Ferrara II, Athens-like	Not Available	844G->C	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Bajo Maumere	Not Available	844G->T	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Montalbano	Not Available	854G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Kalyan-Kerala, Jamnaga, Rohini	Not Available	949G->A	ADR Inferred	Increased risk of dose-related hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Gaohe	Not Available	95A->G	ADR Inferred	Increased risk of dose-related hemolysis.	Details

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
Integrate drug-drug interactions in your software
Abacavir	Sulfamethoxazole may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abatacept	The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Abatacept.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Sulfamethoxazole.
Abrocitinib	The metabolism of Abrocitinib can be decreased when combined with Sulfamethoxazole.
Acalabrutinib	The serum concentration of Acalabrutinib can be increased when it is combined with Sulfamethoxazole.

Food Interactions

No interactions found.

Products

Drug product information from 10+ global regions

Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.

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Product Images

International/Other Brands

Gantanol / Sinomin / Urobak

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Sulfamethoxazole Tab 500mg	Tablet	500 mg / tab	Oral	Pro Doc Limitee	1978-12-31	1999-08-12

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Apo Sulfamethoxazole Tab 500mg	Tablet	500 mg	Oral	Apotex Corporation	1978-12-31	2018-09-14
Sulfamethoxazole and Trimethoprim	Tablet	800 mg/1	Oral	Remedy Repack	2012-07-16	2012-11-09

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Apo-sulfatrim Oral Suspension	Sulfamethoxazole (40 mg / mL) + Trimethoprim (8 mg / mL)	Suspension	Oral	Apotex Corporation	1989-12-31	Not applicable
APO-SULFATRIM PEDIATRIC TABLET	Sulfamethoxazole (100 mg) + Trimethoprim (20 mg)	Tablet	Oral	PHARMAFORTE SINGAPORE PTE LTD	1988-04-28	Not applicable
APO-SULFATRIM TABLET	Sulfamethoxazole (400 mg) + Trimethoprim (80 mg)	Tablet	Oral	PHARMAFORTE SINGAPORE PTE LTD	1988-04-27	Not applicable
B.S. SUSPENSION	Sulfamethoxazole (200 mg/5ml) + Trimethoprim (40 mg/5ml)	Suspension	Oral	APEX PHARMA MARKETING PTE. LTD.	1988-04-28	Not applicable
B.S. TABLET	Sulfamethoxazole (400 mg) + Trimethoprim (80 mg)	Tablet	Oral	APEX PHARMA MARKETING PTE. LTD.	1988-10-05	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
TRIMOKS FORT TABLET, 20 ADET	Sulfamethoxazole (800 mg) + Trimethoprim (160 mg)	Tablet	Oral	ATABAY KİMYA SAN. VE TİC. A.Ş.	2013-01-29	Not applicable
TRIMOKS PED. 100 ML SUSPANSIYON	Sulfamethoxazole (400 mg) + Trimethoprim (80 mg)	Suspension	Oral	ATABAY KİMYA SAN. VE TİC. A.Ş.	2013-01-29	Not applicable
TRIMOKS TABLET, 30 ADET	Sulfamethoxazole (400 mg) + Trimethoprim (80 mg)	Tablet	Oral	ATABAY KİMYA SAN. VE TİC. A.Ş.	2013-01-29	Not applicable

Chemical Identifiers

UNII: JE42381TNV
CAS number: 723-46-6
InChI Key: JLKIGFTWXXRPMT-UHFFFAOYSA-N
InChI: 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)
IUPAC Name: 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide
SMILES: CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1

References

Synthesis Reference

Yasushi Takagishi, Kiichiro Ohsuga, Sadao Ohama, "Suppository containing sulfamethoxazole/trimethoprim complex and process for preparing the same." U.S. Patent US4461765, issued December, 1975.

US4461765

General References

Kazanjian P, Locke AB, Hossler PA, Lane BR, Bartlett MS, Smith JW, Cannon M, Meshnick SR: Pneumocystis carinii mutations associated with sulfa and sulfone prophylaxis failures in AIDS patients. AIDS. 1998 May 28;12(8):873-8. doi: 10.1097/00002030-199808000-00009. [Article]
Khalil I, Ronn AM, Alifrangis M, Gabar HA, Satti GM, Bygbjerg IC: Dihydrofolate reductase and dihydropteroate synthase genotypes associated with in vitro resistance of Plasmodium falciparum to pyrimethamine, trimethoprim, sulfadoxine, and sulfamethoxazole. Am J Trop Med Hyg. 2003 May;68(5):586-9. doi: 10.4269/ajtmh.2003.68.586. [Article]
Yun MK, Wu Y, Li Z, Zhao Y, Waddell MB, Ferreira AM, Lee RE, Bashford D, White SW: Catalysis and sulfa drug resistance in dihydropteroate synthase. Science. 2012 Mar 2;335(6072):1110-4. doi: 10.1126/science.1214641. [Article]
Kemnic TR, Coleman M: Trimethoprim Sulfamethoxazole . [Article]
Novelli A, Rosi E: Pharmacological properties of oral antibiotics for the treatment of uncomplicated urinary tract infections. J Chemother. 2017 Dec;29(sup1):10-18. doi: 10.1080/1120009X.2017.1380357. [Article]
Bushby SR: Synergy of trimethoprim-sulfamethoxazole. Can Med Assoc J. 1975 Jun 14;112(13 Spec No):63-6. [Article]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
van der Ven AJ, Mantel MA, Vree TB, Koopmans PP, van der Meer JW: Formation and elimination of sulphamethoxazole hydroxylamine after oral administration of sulphamethoxazole. Br J Clin Pharmacol. 1994 Aug;38(2):147-50. doi: 10.1111/j.1365-2125.1994.tb04339.x. [Article]
FDA Approved Drug Products: Bactrim (sulfamethoxazole/trimethoprim) oral tablets [Link]
Health Canada Product Monograph: Septra (sulfamethoxazole/trimethoprim) for intravenous injection [Link]
FDA Approved Drug Products: Sulfamethoxazole/Trimethoprim oral suspension [Link]
CaymanChem: Sulfamethoxazole MSDS [Link]

External Links

Human Metabolome Database: HMDB0015150
KEGG Drug: D00447
KEGG Compound: C07315
PubChem Compound: 5329
PubChem Substance: 46508111
ChemSpider: 5138
BindingDB: 50029770
RxNav: 10180
ChEBI: 9332
ChEMBL: CHEMBL443
ZINC: ZINC000000089763
Therapeutic Targets Database: DNC001393
PharmGKB: PA451544
PDBe Ligand: 08D
RxList: RxList Drug Page
Wikipedia: Sulfamethoxazole

PDB Entries

3tzf / 6y08 / 6ysx / 8ak6 / 8opu

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Educational/Counseling/Training	Diarrhea / Human Immunodeficiency Virus (HIV) Infections / Malaria / Opportunistic Infections / Pneumonia	1
4	Completed	Prevention	Acquired Immune Deficiency Syndrome (AIDS) / Anemia / Human Immunodeficiency Virus (HIV) Infections / Neutropenia / Newborn Infants	1
4	Completed	Prevention	Allograft Rejection / Asymptomatic Bacteriuria / Hospitalizations / Microbiologic Resistance / Urinary Tract Infection	1
4	Completed	Prevention	Antibiotic Side Effect / Human Immunodeficiency Virus Type 1 (HIV-1) Infection / Opportunistic Infections / Pneumocystis Jirovecii Pneumonia / Preventive Therapy	1
4	Completed	Prevention	Asymptomatic Bacteriuria / Urinary Tract Infection	1

Pharmacoeconomics

Manufacturers

Hoffmann la roche inc
Ascot hosp pharmaceuticals inc div travenol laboratories inc
Barr laboratories inc
Heather drug co inc
Sandoz inc
Watson laboratories inc
Shionogi usa inc

Packagers

Medisca Inc.

Dosage Forms

Form	Route	Strength
Tablet	Oral	500 mg
Tablet	Oral	100 mg
Tablet	Oral	400 mg
Tablet	Oral	400 MG
Tablet	Oral	800 MG
Tablet, soluble	Oral	800 MG
Injection, solution	Intravenous
Injection, solution, concentrate	Intramuscular; Intravenous
Liquid	Intravenous
Suspension
Suspension	Oral	200 mg/5ml
Tablet, film coated	Oral
Tablet	Oral	800 mg
Capsule, coated	Oral
Tablet, soluble	Oral
Powder	Not applicable	1 g/1g
Injection	Intravenous
Injection, solution, concentrate	Intravenous
Suspension	Oral
Tablet	Oral
Tablet	Oral	800 mg/1
Tablet	Oral	500 mg / tab
Suspension	Parenteral
Solution	Parenteral
Tablet	Oral	400.00 mg
Solution
Syrup	Oral
Solution	Intravenous
Solution	Intramuscular
Powder, for suspension	Oral
Capsule
Tablet, coated	Oral
Tablet, sugar coated	Oral

Prices

Unit description	Cost	Unit
Sulfamethoxazole-TMP DS 800-160 mg tablet	0.94USD	tablet
Sulfamethoxazole powder	0.41USD	g

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	167 °C	PhysProp
water solubility	610 mg/L (at 37 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	0.89	HANSCH,C ET AL. (1995)
logS	-2.62	ADME Research, USCD

Predicted Properties

Property	Value	Source
Water Solubility	0.459 mg/mL	ALOGPS
logP	0.79	ALOGPS
logP	0.79	Chemaxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	6.16	Chemaxon
pKa (Strongest Basic)	1.97	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	98.22 Å²	Chemaxon
Rotatable Bond Count	2	Chemaxon
Refractivity	64.5 m³·mol^-1	Chemaxon
Polarizability	24.99 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9382
Caco-2 permeable	-	0.5346
P-glycoprotein substrate	Non-substrate	0.8884
P-glycoprotein inhibitor I	Non-inhibitor	0.9362
P-glycoprotein inhibitor II	Non-inhibitor	0.8754
Renal organic cation transporter	Non-inhibitor	0.9195
CYP450 2C9 substrate	Non-substrate	0.7652
CYP450 2D6 substrate	Non-substrate	0.9115
CYP450 3A4 substrate	Non-substrate	0.7632
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9025
CYP450 3A4 inhibitor	Non-inhibitor	0.9744
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7151
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Non-carcinogens	0.8193
Biodegradation	Not ready biodegradable	0.9882
Rat acute toxicity	1.6422 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9143
hERG inhibition (predictor II)	Non-inhibitor	0.8956

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (9.61 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0005-9120000000-73aebd463dbf4176fb01
GC-MS Spectrum - EI-B	GC-MS	splash10-05mo-8900000000-8a6ba1e89f89f5cb1e3c
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-0zfr-2960000000-9e8c6c452dea7906eac4
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-0a4i-4901000000-b25f2b64f82210ccef6f
LC-MS/MS Spectrum - LC-ESI-QTOF , negative	LC-MS/MS	splash10-0a4i-0940000000-88c5b1ef2f503737ca9a
LC-MS/MS Spectrum - LC-ESI-QTOF , negative	LC-MS/MS	splash10-0a4i-0900000000-b1b1b8e70ec8043bb89b
LC-MS/MS Spectrum - LC-ESI-QTOF , negative	LC-MS/MS	splash10-0a4i-0900000000-f9d7f50685c7e96eefcd
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0a4i-0900000000-465bcb56920d86311f93
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0udi-0390000000-5dac2c73d05262cd10c0
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0a4i-0900000000-754d521e9fa8d49057e7
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0a4i-0900000000-5dea192ddf68e39f5c6c
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0a4i-5900000000-f376319dc72913e8db61
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-08fu-9300000000-275ed92901e4719e8eb0
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0udi-0290000000-b02c397c2d2954785c81
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0a4i-0900000000-c61eade368561111e908
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0a4i-0900000000-c85d502fd299d3c8942c
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0a4i-4900000000-c8c24b18f27b59f6e693
LC-MS/MS Spectrum - LC-ESI-ITFT , negative	LC-MS/MS	splash10-0a4i-0900000000-c61eade368561111e908
LC-MS/MS Spectrum - LC-ESI-QTOF , negative	LC-MS/MS	splash10-0a4i-0910000000-64449078c4fdd8bf4614
LC-MS/MS Spectrum - LC-ESI-QTOF , negative	LC-MS/MS	splash10-0a4i-3900000000-58869a5ce23e7feeeedf
LC-MS/MS Spectrum - LC-ESI-QTOF , negative	LC-MS/MS	splash10-03di-9000000000-c388b00730b45caa4648
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0a4i-3910000000-a82697559a690c6121ea
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0a4i-0910000000-44dbcbdfb3ce5df0ba57
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0a4i-0900000000-181bb6cd1b54b2b6495c
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-052b-0900000000-ef143045595a430e870d
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0002-0900000000-c3682226c90f2e2715a0
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0udi-0190000000-24d764d31dded89ff00f
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-052v-0900000000-2bfa4615b96e29115a6b
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0udi-0090000000-64a7ff77c37052fd7340
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0pb9-2940000000-0ca0de185b8cef9d025b
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0a4i-4900000000-7fa1e7f1e8a16439e36b
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0a4l-7900000000-8584244d965e9da53c66
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-052f-9500000000-00c6bdb3c2f34a8492b6
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-05mo-9400000000-914135419173af598f05
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0udi-0090000000-cf49e6fbc7d210f2db82
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0pb9-2940000000-cf1c49b6edd74e0db359
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0a4i-4900000000-be7ef446a6f0292a0c15
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0a4l-7900000000-96c9b596ad5235d5e8fd
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-052f-9600000000-c5bd253f35dc1f56f173
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-05mo-9400000000-68dc3bc1422a652b6c43
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0a4v-0900000000-e147c7f66af9a39125b4
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0zfr-2970000000-6fea429d8717a3a0e019
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0a4l-6900000000-b134f68352446228a2de
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-00kf-9200000000-f766fcb18caedb6dc7b8
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0a4l-6900000000-55bf55718dd534098430
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-052f-9500000000-6adbdcc86fd0c4aac92a
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0a4r-0900000000-e69bb2beedb2b53adcda
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0a4r-0900000000-c7d050466aea7503baaf
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0zfr-1970000000-cbfc43ff8e81c2553da0
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0zfr-2960000000-9e8c6c452dea7906eac4
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0a4i-4901000000-b25f2b64f82210ccef6f
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0pb9-4930000000-0673f294c7ef0fcc9fc5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0udi-0090000000-4b4609c9128e4994f9b0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0udi-0490000000-180b218861b0ab122ba8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0zfr-1390000000-e6124e8be182abe507cd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-1920000000-8c9aaeaabbef41914c1b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014l-9000000000-dadd16f2204c9a4f76d4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-8900000000-08e1a649030af387a5a9
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	166.7118588	predicted	DarkChem Lite v0.1.0
[M-H]-	166.4601588	predicted	DarkChem Lite v0.1.0
[M-H]-	152.98816	predicted	DeepCCS 1.0 (2019)
[M+H]+	167.7469588	predicted	DarkChem Lite v0.1.0
[M+H]+	167.7867588	predicted	DarkChem Lite v0.1.0
[M+H]+	155.34618	predicted	DeepCCS 1.0 (2019)
[M+Na]+	167.1032588	predicted	DarkChem Lite v0.1.0
[M+Na]+	161.43932	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Dihydropteroate synthase

Kind: Protein
Organism: Escherichia coli (strain K12)
Pharmacological action: Yes
Actions: Antagonist
Curator comments: Note: The above was chosen as a representative target protein in a representative bacterium, and does not encompass all proteins/bacteria affected by this agent.

General Function: Metal ion binding
Specific Function: Catalyzes the condensation of para-aminobenzoate (pABA) with 6-hydroxymethyl-7,8-dihydropterin diphosphate (DHPt-PP) to form 7,8-dihydropteroate (H2Pte), the immediate precursor of folate derivatives.
Gene Name: folP
Uniprot ID: P0AC13
Uniprot Name: Dihydropteroate synthase
Molecular Weight: 30614.855 Da

References

Bushby SR: Synergy of trimethoprim-sulfamethoxazole. Can Med Assoc J. 1975 Jun 14;112(13 Spec No):63-6. [Article]

Enzymes

Details1. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

References

Cribb AE, Spielberg SP, Griffin GP: N4-hydroxylation of sulfamethoxazole by cytochrome P450 of the cytochrome P4502C subfamily and reduction of sulfamethoxazole hydroxylamine in human and rat hepatic microsomes. Drug Metab Dispos. 1995 Mar;23(3):406-14. [Article]
Wen X, Wang JS, Backman JT, Laitila J, Neuvonen PJ: Trimethoprim and sulfamethoxazole are selective inhibitors of CYP2C8 and CYP2C9, respectively. Drug Metab Dispos. 2002 Jun;30(6):631-5. doi: 10.1124/dmd.30.6.631. [Article]
Miners JO, Birkett DJ: Cytochrome P4502C9: an enzyme of major importance in human drug metabolism. Br J Clin Pharmacol. 1998 Jun;45(6):525-38. [Article]
Kagaya H, Miura M, Niioka T, Saito M, Numakura K, Habuchi T, Satoh S: Influence of NAT2 polymorphisms on sulfamethoxazole pharmacokinetics in renal transplant recipients. Antimicrob Agents Chemother. 2012 Feb;56(2):825-9. doi: 10.1128/AAC.05037-11. Epub 2011 Nov 21. [Article]
Flockhart Table of Drug Interactions [Link]

Details2. Arylamine N-acetyltransferase 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Arylamine n-acetyltransferase activity
Specific Function: Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivat...
Gene Name: NAT1
Uniprot ID: P18440
Uniprot Name: Arylamine N-acetyltransferase 1
Molecular Weight: 33898.445 Da

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]

Details3. Arylamine N-acetyltransferase 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Arylamine n-acetyltransferase activity
Specific Function: Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivat...
Gene Name: NAT2
Uniprot ID: P11245
Uniprot Name: Arylamine N-acetyltransferase 2
Molecular Weight: 33542.235 Da

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]

Details4. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Lehmann DF, Newman N, Morse PD: The effect of cimetidine on the formation of sulfamethoxazole hydroxylamine in patients with human immunodeficiency virus. J Clin Pharmacol. 1998 May;38(5):463-6. [Article]
Ribera E, Pou L, Fernandez-Sola A, Campos F, Lopez RM, Ocana I, Ruiz I, Pahissa A: Rifampin reduces concentrations of trimethoprim and sulfamethoxazole in serum in human immunodeficiency virus-infected patients. Antimicrob Agents Chemother. 2001 Nov;45(11):3238-41. doi: 10.1128/AAC.45.11.3238-3241.2001. [Article]
Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]

Carriers

Details1. Serum albumin

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
Molecular Weight: 69365.94 Da

References

Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. doi: 10.1159/000136629. [Article]
Angelakou A, Valsami G, Koupparis M, Macheras P: Use of 1-anilino-8-napthalenesulphonate as an ion probe for the potentiometric study of the binding of sulphonamides to bovine serum albumin and plasma. J Pharm Pharmacol. 1993 May;45(5):434-8. [Article]
Health Canada Product Monograph: Septra (sulfamethoxazole/trimethoprim) for intravenous injection [Link]

Transporters

Details1. Bile salt export pump

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Inhibitor

General Function: Transporter activity
Specific Function: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name: ABCB11
Uniprot ID: O95342
Uniprot Name: Bile salt export pump
Molecular Weight: 146405.83 Da

References

Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54

Sulfamethoxazole

Identification

Structure for Sulfamethoxazole (DB01015)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

Enzymes

References

References

References

References

Carriers

References

Transporters

References