Sulfamethoxazole
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Also known as AcetylsulfamethoxazoleGantanolGantanol-dsNSC-147832STX-608Sulfamethoxazole component of bactrimSulfamethoxazole component of bactrim dsSulfamethoxazole component of cotrimSulfamethoxazole component of septraSulfamethoxazole component of sulfatrimSulfamethoxazole component of sulmeprimSulfamethoxazole component of uroplusSulfamethoxazole sodiumSulfamethoxazolumSulfametoxazolSulphamethoxazoleSinominSuphamethoxazoleUrobak
Summary
Sulfamethoxazole (CHEMBL443) is an approved small-molecule antibacterial agent (ATC J01EC01); indicated across 33 conditions including urinary tract infection and pneumocystosis.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: J01EC01
- Indications: 33 conditions
- Clinical trials: 48
- Chemistry: 253.28 Da · C10H11N3O3S
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL443 |
| Name | Sulfamethoxazole |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 5329 |
| ChEBI | CHEBI:9332 |
| ATC | J01EC01 |
| Molecular formula | C10H11N3O3S |
| Molecular weight | 253.28 |
| InChIKey | JLKIGFTWXXRPMT-UHFFFAOYSA-N |
SMILES: CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N
IUPAC name: 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
ChEBI definition: An isoxazole (1,2-oxazole) compound having a methyl substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 3-position.
Pharmacological roles (ChEBI): antibacterial agent, antiinfective agent, epitope, EC 2.5.1.15 (dihydropteroate synthase) inhibitor, antimicrobial agent, P450 inhibitor, EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor, drug allergen.
Other ChEBI roles (chemical / environmental): environmental contaminant, xenobiotic.
Also known as: Acetylsulfamethoxazole, Gantanol, Gantanol-ds, NSC-147832, STX-608, Sulfamethoxazole, Sulfamethoxazole component of bactrim, Sulfamethoxazole component of bactrim ds, Sulfamethoxazole component of cotrim, Sulfamethoxazole component of septra, Sulfamethoxazole component of sulfatrim, Sulfamethoxazole component of sulmeprim
Patent coverage: 14,038 distinct patent families (41,606 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Broader ChEMBL bioactivity targets: 6 (assay-derived). Sample: Microtubule-associated protein tau, Dihydrofolate reductase, Alpha-1A adrenergic receptor, Aldehyde dehydrogenase 1A1, Dihydropteroate synthase, Endothelin-1 receptor.
Bioactivity
ChEMBL activities: 5 potent at pChembl ≥ 5 of 7 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| P16184 | 7 | IC50 | 100 | nM | CHEMBL_ACT_101558 |
| P26684 | 5.4 | IC50 | 4000 | nM | CHEMBL_ACT_490954 |
| P26684 | 5.4 | IC50 | 4000 | nM | CHEMBL_ACT_492134 |
| P0AC13 | 5.33 | IC50 | 4700 | nM | CHEMBL_ACT_752293 |
| MAPT | 5.05 | Potency | 8912 | nM | CHEMBL_ACT_4512539 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
33 indications (4 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| urinary tract infection | 4 | MONDO:0100338 | EFO:0003103 |
| pneumocystosis | 4 | MONDO:0019121 | EFO:0007448 |
| bacterial infectious disease | 4 | MONDO:0005113 | EFO:0000771 |
| idiopathic pulmonary fibrosis | 3 | MONDO:0800504 | EFO:0000768 |
| malaria | 3 | MONDO:0005136 | EFO:0001068 |
| abscess | 3 | MONDO:0005227 | EFO:0003030 |
| pneumonia | 3 | MONDO:0005249 | EFO:0003106 |
| staphylococcus aureus infection | 3 | MONDO:0005545 | EFO:0005681 |
| ocular toxoplasmosis | 3 | MONDO:0005879 | EFO:0007399 |
| pyelonephritis | 3 | MONDO:0006939 | EFO:1001141 |
| HIV infectious disease | 3 | MONDO:0005109 | EFO:0000764 |
| measles | 3 | MONDO:0004619 | EFO:1002025 |
| tuberculosis | 3 | MONDO:0018076 | MONDO:0018076 |
| type 1 diabetes mellitus | 2 | MONDO:0005147 | MONDO:0005147 |
| cystic fibrosis | 2 | MONDO:0009061 | MONDO:0009061 |
| skin disorder | 2 | MONDO:0005093 | EFO:0000701 |
| dermatitis | 2 | MONDO:0002406 | MONDO:0002406 |
| neoplasm | 1 | MONDO:0005070 | EFO:0000616 |
| kidney disorder | 1 | MONDO:0005240 | EFO:0003086 |
| granulomatosis with polyangiitis | 1 | MONDO:0012105 | EFO:0005297 |
| glioblastoma | 1 | MONDO:0018177 | EFO:0000519 |
| anaplastic astrocytoma | 1 | MONDO:0016684 | EFO:0002499 |
| B-cell acute lymphoblastic leukemia | 1 | MONDO:0004947 | EFO:0000094 |
| brain neoplasm | 1 | MONDO:0021211 | EFO:0003833 |
| chronic obstructive pulmonary disease | 1 | MONDO:0005002 | EFO:0000341 |
| T-cell acute lymphoblastic leukemia | 1 | MONDO:0004963 | EFO:0000209 |
| leukemia | 1 | MONDO:0005059 | EFO:0000565 |
| age-related macular degeneration | 1 | MONDO:0005150 | EFO:0001365 |
| osteomyelitis | 0 | MONDO:0005246 | EFO:0003102 |
4 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 48.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE4 | 11 |
| PHASE2 | 9 |
| Not specified | 9 |
| PHASE3 | 7 |
| PHASE2/PHASE3 | 4 |
| PHASE1/PHASE2 | 4 |
| PHASE1 | 4 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT03014687 | PHASE4 | RECRUITING | Prophylactic Oral Antibiotics on Sinonasal Outcomes Following Endoscopic Transsphenoidal Surgery for Pituitary Lesions |
| NCT05398679 | PHASE4 | RECRUITING | Oral Antimicrobial Treatment vs. Outpatient Parenteral for Infective Endocarditis |
| NCT06499233 | PHASE4 | RECRUITING | Efficacy and Safety of Prophylactic Treatment for Pneumocystis Jirovecii Pneumonia in Patients With Autoimmune Inflammatory Rheumatic Disease |
| NCT06709196 | PHASE4 | RECRUITING | Clinical Trial Testing Whether Targeted Antibiotic Prophylaxis Can Reduce Infections After Cystectomy Compared to Empiric Prophylaxis |
| NCT06982105 | PHASE4 | RECRUITING | Trimethoprim-sulfamethoxazole vs. Clindamycin for the Treatment of Children With Invasive MRSA Infections |
| NCT00382343 | PHASE4 | COMPLETED | A Randomized Controlled Trial on Antibiotic Prophylaxis in Children With Vesico-Ureteral Reflux |
| NCT01167452 | PHASE4 | COMPLETED | Effect of Weight and/or Obesity on Sulfamethoxazole and Trimethoprim Concentrations |
| NCT01723150 | PHASE4 | COMPLETED | Antibiotics for Klebsiella Liver Abscess Study |
| NCT01820897 | PHASE4 | COMPLETED | Efficacy of Fosfomycin-Trometamol in Urinary Tract Infection Prophylaxis After Kidney Transplantation |
| NCT03228108 | PHASE4 | COMPLETED | Culture-guided Antimicrobial Prophylaxis in Men Undergoing Prostate Biopsy. |
| NCT03235947 | PHASE4 | COMPLETED | Perioperative Fosfomycin in the Prophylaxis of Urinary Tract Infection in Kidney Transplant Recipients |
| NCT07202052 | PHASE2/PHASE3 | RECRUITING | Role of Antibiotic Therapy or Immunoglobulin On iNfections in hAematoLogy Platform Trial (RATIONAL-PT) |
| NCT07202078 | PHASE2/PHASE3 | RECRUITING | Role of Antibiotic Therapy or Immunoglobulin On iNfections in hAematoLogy: Starting Immunoglobulin (Start Ig) |
| NCT07202091 | PHASE2/PHASE3 | RECRUITING | Role of Antibiotic Therapy or Immunoglobulin On iNfections in hAematoLogy Immunoglobulin Stopping or Extension (Stop Ig) |
| NCT00000727 | PHASE3 | COMPLETED | A Controlled Comparative Trial of Sulfamethoxazole-Trimethoprim Versus Aerosolized Pentamidine for Secondary Prophylaxis of Pneumocystis Carinii Pneumonia in AIDS Patients Receiving Azidothymidine (AZT) |
| NCT00691600 | PHASE3 | COMPLETED | Management of Skin and Soft Tissue Abscesses in Pediatric Patients After Incision and Drainage |
| NCT00752375 | PHASE3 | WITHDRAWN | Antibiotic Prophylaxis in Children With Pyelonephritis |
| NCT01595438 | PHASE3 | COMPLETED | Ceftazidime-Avibactam Compared With Doripenem Followed by Oral Therapy for Hospitalized Adults With Complicated UTIs (Urinary Tract Infections) |
| NCT01599806 | PHASE3 | COMPLETED | Ceftazidime-Avibactam Compared With Doripenem Followed by Oral Therapy for Hospitalized Adults With Complicated UTIs (Urinary Tract Infections) |
| NCT01747278 | PHASE2/PHASE3 | UNKNOWN | Study of Trimethoprim/Sulfamethoxazole as PCP Prophylaxis in CTD Patients |
| NCT01808755 | PHASE3 | COMPLETED | D Mannose in Recurrent Urinary Tract Infections |
| NCT02021006 | PHASE3 | UNKNOWN | Antibiotic Prophylaxis and Renal Damage In Congenital Abnormalities of the Kidney and Urinary Tract |
| NCT03919435 | PHASE1/PHASE2 | ACTIVE_NOT_RECRUITING | TEMPO Study: Trimethoprim-Sulfamethoxazole in Granulomatosis With Polyangiitis |
| NCT07485010 | PHASE2 | NOT_YET_RECRUITING | Testing a Novel Combination Treatment (Arm D) Versus Standard of Care for Intensive Phase Treatment for Mycobacterium Abscessus Pulmonary Disease in People With or Without Cystic Fibrosis in the Finding the Optimal Regimen for Mycobacterium Abscessus Treatment (FORMaT) Adaptive Platform Trial |
| NCT00014911 | PHASE2 | COMPLETED | Islet Transplantation for Type 1 Diabetes |
| NCT00141037 | PHASE1/PHASE2 | COMPLETED | Steroid-Free Versus Steroid-Based Immunosuppression in Pediatric Renal (Kidney) Transplantation |
| NCT00789464 | PHASE2 | WITHDRAWN | Probiotics for Girls With Recurring Urinary Tract Infections |
| NCT01349192 | PHASE2 | TERMINATED | Early Methicillin-resistant Staphylococcus Aureus (MRSA) Therapy in Cystic Fibrosis (CF) |
| NCT01595529 | PHASE2 | COMPLETED | The SCOUT Study: Short Course Therapy for Urinary Tract Infections in Children |
| NCT01632891 | PHASE1/PHASE2 | COMPLETED | Comparing PI-Based to a nNRTI-based ART for Clearance of Plasmodium Falciparum Parasitemia in HIV-Infected |
| NCT01757236 | PHASE2 | UNKNOWN | Efficacy and Safety Study of Antibiotic Treatment to Treat Hip Prosthetic Joint Infection |
| NCT02624440 | PHASE2 | UNKNOWN | Clarithromycin, Sulfamethoxazole/Trimethoprim or Observation in Newly Diagnosed Multiple Myeloma |
| NCT02640443 | PHASE2 | UNKNOWN | Sulfamethoxazole for the Treatment of Primary PREPL Deficiency |
| NCT02734732 | PHASE2 | UNKNOWN | Antibiotic Prophylaxis for Transrectal Prostate Biopsy-Ciprofloxacin vs. Trimethoprim/Sulfamethoxazole |
| NCT05418777 | PHASE1/PHASE2 | TERMINATED | Treatment of Pneumocystis in COPD (the TOPIC Study) |
| NCT05302531 | PHASE1 | RECRUITING | Absorption of Antibiotics With High Oral Bioavailability in Short-bowel Syndrome |
| NCT07228702 | PHASE1 | ENROLLING_BY_INVITATION | Bacteriophage Therapy for Mycobacterium Abscessus Pulmonary Infection |
| NCT00002120 | PHASE1 | COMPLETED | Randomized Phase I Study of Trimetrexate Glucuronate (TMTX) With Leucovorin (LCV) Protection Plus Dapsone Versus Trimethoprim / Sulfamethoxazole (TMP/SMX) for Treatment of Moderately Severe Episodes of Pneumocystis Carinii Pneumonia |
| NCT01469637 | PHASE1 | COMPLETED | Sulfamethoxazole Drug Interaction Study With MMX® Mesalazine/Mesalamine |
| NCT00002002 | Not specified | COMPLETED | A Randomized, Double-Blind, Placebo Controlled Study of l-Leucovorin in Combination With Trimethoprim / Sulfamethoxazole in the Therapy of Pneumocystis Carinii Pneumonia in Patients With the Acquired Immunodeficiency Syndrome |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
PharmGKB dosing guidelines (1) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):
| Guideline | Source | Gene(s) | Dosing | Recommendation |
|---|---|---|---|---|
| Annotation of CPIC Guideline for aminosalicylic acid, chloramphenicol, | CPIC | G6PD |
PharmGKB also curates 2 clinical and 17 variant annotation(s) for this drug (gene-keyed; see PharmGKB).
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).