Sulfamethoxazole

Highest phase reached

Approved

www.ebi.ac.uk

Drug type

Small molecule

www.ebi.ac.uk

First approval year

1973

www.ebi.ac.uk

First approval year: 1973
www.ebi.ac.uk

Listing at source: Listed

Highest phase reached: Approved
www.ebi.ac.uk

Drug type: Small molecule
www.ebi.ac.uk

Drug name: Sulfamethoxazole
www.ebi.ac.uk

Molecular weight: 253.28
www.ebi.ac.uk

Structure (SMILES): Cc1cc(NS(=O)(=O)c2ccc(N)cc2)no1
www.ebi.ac.uk

gantanol
Gantanol
gantanol ds
Gantanol-ds
sinomin
Sinomin
sulfamethoxazole
Sulfamethoxazole
sulfamethoxazole component of azo gantanol
Sulfamethoxazole component of azo gantanol
sulfamethoxazole component of bactrim
Sulfamethoxazole component of bactrim
sulfamethoxazole component of bactrim ds
Sulfamethoxazole component of bactrim ds
sulfamethoxazole component of bactrim pediatric
Sulfamethoxazole component of bactrim pediatric
sulfamethoxazole component of co trimethoxazole
Sulfamethoxazole component of co-trimethoxazole
sulfamethoxazole component of cotrim
Sulfamethoxazole component of cotrim
sulfamethoxazole component of cotrim d s
Sulfamethoxazole component of cotrim d.s.
sulfamethoxazole component of septra
Sulfamethoxazole component of septra
sulfamethoxazole component of sulfamethoprim

And 11 more, listed on the interactive page.

acetylsulfamethoxazole
Acetylsulfamethoxazole
azo gantanol component sulfamethoxazole
AZO GANTANOL COMPONENT SULFAMETHOXAZOLE
bactrim component sulfamethoxazole
BACTRIM COMPONENT SULFAMETHOXAZOLE
bactrim ds component sulfamethoxazole
BACTRIM DS COMPONENT SULFAMETHOXAZOLE
bactrim pediatric component sulfamethoxazole
BACTRIM PEDIATRIC COMPONENT SULFAMETHOXAZOLE
co trimethoxazole component sulfamethoxazole
Co-trimethoxazole component sulfamethoxazole
cotrim component sulfamethoxazole
COTRIM COMPONENT SULFAMETHOXAZOLE
cotrim d s component sulfamethoxazole
COTRIM D.S. COMPONENT SULFAMETHOXAZOLE
nsc 147832
NSC-147832
ro 4 2130
RO 4-2130
RO-4-2130
septra component sulfamethoxazole
SEPTRA COMPONENT SULFAMETHOXAZOLE
smx
SMX

And 50 more, listed on the interactive page.

ATC classification codes

J01EC01

Sources for recorded values

www.ebi.ac.uk

CAS registry numbers

723-46-6

ChEMBL ID: CHEMBL443
www.ebi.ac.uk

InChIKey: JLKIGFTWXXRPMT-UHFFFAOYSA-N
www.ebi.ac.uk

PubChem compound IDs

5329

FDA ingredient codes (UNII)

JE42381TNV

10178
10180

Applicant: SUN PHARM INDUSTRIES
Approval date: 30 Jul 1973
Application number: NDA017377

First in class: No
Orphan designation: No
Availability: Prescription only

Pharmacology name: sulfamethoxazole
Type: Synthetic organic
Drug name stem: sulfa-
Approval recorded by Guide to Pharmacology: Yes

Administration routes

Oral
Parenteral

Mechanisms of action

Mechanism
Bacterial dihydropteroate synthase inhibitor
Action type
Inhibitor
Target
Dihydropteroate synthase
Protein identifier
P0AC13

Open Targets mechanisms

Mechanism
Bacterial dihydropteroate synthase inhibitor
Action type
Inhibitor
Target
Dihydropteroate synthase

DrugCentral mechanisms

Action type
Inhibitor
Gene symbol
folP
Protein identifier
P0AC13
Organism
Escherichia coli (strain K12)

Condition
Leukemia, Biphenotypic, Acute
Highest recorded phase
1
Condition identifier
EFO:0000094
Subject identifier
D015456
Condition
Leukemia, Biphenotypic, Acute
Highest recorded phase
1
Condition identifier
EFO:0000209
Subject identifier
D015456
Condition
Pulmonary Disease, Chronic Obstructive
Highest recorded phase
1
Condition identifier
EFO:0000341
Subject identifier
D029424
Condition
Glioblastoma
Highest recorded phase
1
Condition identifier
EFO:0000519
Subject identifier
D005909
Condition
Infections
Highest recorded phase
4
Condition identifier
EFO:0000544
Subject identifier
D007239
Condition
Leukemia
Highest recorded phase
1
Condition identifier
EFO:0000565
Subject identifier
D007938
Condition
Neoplasms
Highest recorded phase
1
Condition identifier
EFO:0000616
Subject identifier
D009369
Condition
Skin Diseases
Highest recorded phase
2
Condition identifier
EFO:0000701
Subject identifier
D012871
Condition
HIV Infections
Highest recorded phase
3
Condition identifier
EFO:0000764
Subject identifier
D015658
Condition
Idiopathic Pulmonary Fibrosis
Highest recorded phase
3
Condition identifier
EFO:0000768
Subject identifier
D054990
Condition
Bacterial Infections
Highest recorded phase
4
Condition identifier
EFO:0000771
Subject identifier
D001424
Condition
Malaria
Highest recorded phase
3
Condition identifier
EFO:0001068
Subject identifier
D008288
Condition
Macular Degeneration
Highest recorded phase
1
Condition identifier
EFO:0001365
Subject identifier
D008268
Condition
Astrocytoma
Highest recorded phase
1
Condition identifier
EFO:0002499
Subject identifier
D001254
Condition
Abscess
Highest recorded phase
3
Condition identifier
EFO:0003030
Subject identifier
D000038
Condition
Kidney Diseases
Highest recorded phase
1
Condition identifier
EFO:0003086
Subject identifier
D007674
Condition
Osteomyelitis
Highest recorded phase
0.5
Condition identifier
EFO:0003102
Subject identifier
D010019
Condition
Urinary Tract Infections
Highest recorded phase
4
Condition identifier
EFO:0003103
Subject identifier
D014552
Condition
Pneumonia
Highest recorded phase
3
Condition identifier
EFO:0003106
Subject identifier
D011014
Condition
Brain Neoplasms
Highest recorded phase
1
Condition identifier
EFO:0003833
Subject identifier
D001932
Condition
Granulomatosis with Polyangiitis
Highest recorded phase
1
Condition identifier
EFO:0005297
Subject identifier
D014890
Condition
Staphylococcal Infections
Highest recorded phase
3
Condition identifier
EFO:0005681
Subject identifier
D013203
Condition
Toxoplasmosis, Ocular
Highest recorded phase
3
Condition identifier
EFO:0007399
Subject identifier
D014126
Condition
Pneumonia, Pneumocystis
Highest recorded phase
4
Condition identifier
EFO:0007448
Subject identifier
D011020
Condition
Pyelonephritis
Highest recorded phase
3
Condition identifier
EFO:1001141
Subject identifier
D011704

And 8 more, listed on the interactive page.

Condition identifier
EFO_0000341
Highest recorded phase
3
Condition identifier
EFO_0000544
Condition identifier
EFO_0000544
Highest recorded phase
4
Condition identifier
EFO_0000764
Highest recorded phase
3
Condition identifier
EFO_0000768
Highest recorded phase
3
Condition identifier
EFO_0000771
Condition identifier
EFO_0003030
Highest recorded phase
3
Condition identifier
EFO_0003102
Highest recorded phase
3
Condition identifier
EFO_0003103
Condition identifier
EFO_0003106
Highest recorded phase
3
Condition identifier
EFO_0004209
Condition identifier
EFO_0004992
Condition identifier
EFO_0005297
Condition identifier
EFO_0005681
Highest recorded phase
3
Condition identifier
EFO_0007399
Highest recorded phase
3
Condition identifier
EFO_0007448
Condition identifier
EFO_0009909
Condition identifier
EFO_1001141
Highest recorded phase
3
Condition identifier
EFO_1001365
Highest recorded phase
2
Condition identifier
EFO_1001865
Highest recorded phase
3
Condition identifier
EFO_1002025
Highest recorded phase
3
Condition identifier
HP_0002789
Highest recorded phase
3
Condition identifier
HP_0011947
Highest recorded phase
2
Condition identifier
HP_0012388
Condition identifier
HP_0031292
Highest recorded phase
2

And 20 more, listed on the interactive page.

Event
abdominal discomfort
Reports
359
Reporting signal score
263.826
Event
acute kidney injury
Reports
541
Reporting signal score
381.753
Event
agranulocytosis
Reports
399
Reporting signal score
788.156
Event
anti-cyclic citrullinated peptide antibody positive
Reports
254
Reporting signal score
828.557
Event
arthralgia
Reports
702
Reporting signal score
297.507
Event
arthropathy
Reports
322
Reporting signal score
402.012
Event
blister
Reports
556
Reporting signal score
1,045.26
Event
cholestasis
Reports
255
Reporting signal score
387.179
Event
confusional state
Reports
615
Reporting signal score
542.268
Event
contusion
Reports
300
Reporting signal score
272.604
Event
dermatitis exfoliative generalised
Reports
72
Reporting signal score
152.478
Event
discomfort
Reports
265
Reporting signal score
376.257
Event
drug hypersensitivity
Reports
1,690
Reporting signal score
2,187.22
Event
drug intolerance
Reports
367
Reporting signal score
260.511
Event
drug reaction with eosinophilia and systemic symptoms
Reports
527
Reporting signal score
1,024.3
Event
duodenal ulcer perforation
Reports
257
Reporting signal score
891.937
Event
dyspnoea
Reports
747
Reporting signal score
151.52
Event
eosinophilia
Reports
264
Reporting signal score
448.278
Event
folliculitis
Reports
518
Reporting signal score
1,836.99
Event
gastrointestinal disorder
Reports
564
Reporting signal score
904.483
Event
glossodynia
Reports
260
Reporting signal score
561.42
Event
hand deformity
Reports
262
Reporting signal score
671.973
Event
helicobacter infection
Reports
262
Reporting signal score
777.091
Event
hepatic enzyme increased
Reports
331
Reporting signal score
333.714
Event
hepatocellular injury
Reports
296
Reporting signal score
471.652

And 38 more, listed on the interactive page.

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And 31 more, listed on the interactive page.

Dose: 1 or 2 tablets
How often: Every 12 hours

Hydrogen bond acceptors: 5
Hydrogen bond donors: 2
Polar surface area: 98.22
Calculated partition coefficient (ALogP): 1.37
Calculated partition coefficient (XLogP): 0.9
Prodrug: No
Chirality: Achiral
Inorganic: No
Rule-of-five violations: 0
Rotatable bonds: 3
Heavy atoms: 17
Molecular formula: C10H11N3O3S
Monoisotopic mass: 253.05211239
Natural product: Yes

0121-0853
0121-0854
0615-8121
0703-9503
0703-9514
0703-9526
0904-2725
42291-758
42291-759
42708-053
49708-145
49708-146
50268-728
51655-188
51655-307
53489-145
53489-146
53746-271
53746-272
54348-625
55700-611
57237-232
57237-233
60429-259
60687-442

And 76 more, listed on the interactive page.

Recorded assays: 4,206
Active assays: 39

Confirmatory
Other
Screening

Anti-Infective Agents
id.nlm.nih.gov

These details could not be displayed.

Related records

Trials (77)

A Comparison of Dapsone and Trimethoprim-Sulfamethoxazole in the Treatment of Pneumocystis Carinii Pneumonia (PCP) in Patients With AIDS
A Controlled Comparative Trial of Sulfamethoxazole-Trimethoprim Versus Aerosolized Pentamidine for Secondary Prophylaxis of Pneumocystis Carinii Pneumonia in AIDS Patients Receiving Azidothymidine (AZT)
A Controlled Trial Comparing the Efficacy of Aerosolized Pentamidine and Parenteral/Oral Sulfamethoxazole-Trimethoprim in the Treatment of Pneumocystis Carinii Pneumonia in AIDS
A Non-Interventional Safety Study of Balsamic Bactrim
A Phase III Comparative Study of Dapsone / Trimethoprim and Clindamycin / Primaquine Versus Sulfamethoxazole / Trimethoprim in the Treatment of Mild-to-Moderate PCP in Patients With AIDS
A Randomized Controlled Trial on Antibiotic Prophylaxis in Children With Vesico-Ureteral Reflux
A Randomized, Comparative, Prospective Study of Daily Trimethoprim / Sulfamethoxazole (TMS) and Thrice-Weekly TMS for Prophylaxis Against PCP in HIV-Infected Patients
A Randomized, Double-Blind Study of 566C80 Versus Septra (Sulfamethoxazole/Trimethoprim) for the Treatment of Pneumocystis Carinii Pneumonia in AIDS Patients
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
A Safety Study of Balsamic Bactrim in Pediatric Participants With Acute Bronchitis
A Study of LBP-EC01 in the Treatment of Acute Uncomplicated UTI Caused by Drug Resistant E. Coli (ELIMINATE Trial)
A Study of Three Drugs Plus Zidovudine in the Prevention of Infections in HIV-Infected Patients
A Study to Compare Different Drugs Used to Prevent Serious Bacterial Infections in HIV-Positive Children
Absorption of Antibiotics With High Oral Bioavailability in Short-bowel Syndrome
Antibiotic Prophylaxis and Renal Damage In Congenital Abnormalities of the Kidney and Urinary Tract
Antibiotic Prophylaxis for Transrectal Prostate Biopsy-Ciprofloxacin vs. Trimethoprim/Sulfamethoxazole
Antibiotic Prophylaxis When Removing Ureteric Stent After Stone Surgery
Antibiotic Prophylaxis With Routine Ureteral Stent Removal
Antibiotic Therapy After Incision and Drainage for Abscess
Antibiotic Therapy in Preventing Early Infection in Patients With Multiple Myeloma Who Are Receiving Chemotherapy

Approved for (3)

In development for (26)

Abscess Phase 3
Age-related macular degeneration Phase 1
Anaplastic astrocytoma Phase 1
B-cell acute lymphoblastic leukemia Phase 1
Brain neoplasm Phase 1
Chronic obstructive pulmonary disease Phase 1
Cystic fibrosis Phase 2
Dermatitis Phase 2
Glioblastoma Phase 1
Granulomatosis with polyangiitis Phase 1
HIV infectious disease Phase 3
Idiopathic pulmonary fibrosis Phase 3
Kidney disorder Phase 1
Leukemia Phase 1
Malaria Phase 3
Measles Phase 3
Neoplasm Phase 1
Ocular toxoplasmosis Phase 3
Osteomyelitis Early phase 1
Pneumonia Phase 3

Sulfamethoxazole

Development status

Names and chemistry

Brand names (36)

Other names (75)

Identifiers

RxNorm IDs (RxCUI) (2)

Regulatory information

United States

Other regulatory facts

Pharmacology

Drug classification

Administration routes

Mechanisms of action

Open Targets mechanisms

DrugCentral mechanisms

Investigated indications (33)

Open Targets indications (45)

Reported adverse events (63)

Trial references (56)

Dosing

Chemical properties

National Drug Codes

Evidence counts

Active assay types (3)

Pharmacologic actions

Biological measurements

Related records

Trials (77)

Approved for (3)

In development for (26)

Other linked conditions (3)