sulfamethoxazole indications/contra

Stem definitionDrug idCAS RN
anti-infectives, sulfonamides 2514 723-46-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • sulfamethoxazole
  • sulfamethalazole
  • sulfamethoxazol
  • sulfisomezole
  • sulphamethoxazole
A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208)
  • Molecular weight: 253.28
  • Formula: C10H11N3O3S
  • CLOGP: 0.56
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 2
  • TPSA: 98.22
  • ALOGS: -2.74
  • ROTB: 2

Drug dosage:

DoseUnitRoute
2 g O

Approvals:

DateAgencyCompanyOrphan
July 30, 1973 FDA MONARCH PHARMS

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 2817.83 33.91 799 5166 34881 3345013
Acute kidney injury 1431.86 33.91 520 5445 49163 3330731
Pyrexia 1174.67 33.91 517 5448 80598 3299296
Rash 1008.86 33.91 447 5518 70374 3309520
Drug reaction with eosinophilia and systemic symptoms 883.45 33.91 235 5730 7660 3372234
Hyperkalaemia 795.76 33.91 234 5731 11060 3368834
Agranulocytosis 699.00 33.91 180 5785 5132 3374762
Stevens-Johnson syndrome 688.34 33.91 187 5778 6585 3373309
Pancytopenia 624.05 33.91 220 5745 18600 3361294
Neutropenia 601.44 33.91 250 5715 33136 3346758
Rash maculo-papular 600.65 33.91 163 5802 5704 3374190
Thrombocytopenia 578.21 33.91 247 5718 35021 3344873
Toxic epidermal necrolysis 398.94 33.91 112 5853 4433 3375461
Pruritus 395.88 33.91 208 5757 46625 3333269
Hepatocellular injury 366.20 33.91 104 5861 4291 3375603
Vomiting 359.41 33.91 246 5719 89285 3290609
Hepatitis 358.66 33.91 123 5842 9502 3370392
Renal failure 341.23 33.91 168 5797 32772 3347122
Nausea 336.49 33.91 274 5691 129371 3250523
Leukopenia 323.17 33.91 130 5835 15693 3364201
Blood creatinine increased 305.14 33.91 137 5828 21681 3358213
Cholestasis 299.29 33.91 93 5872 5244 3374650
Anaemia 298.10 33.91 182 5783 54151 3325743
Eosinophilia 286.26 33.91 88 5877 4785 3375109
Pneumocystis jirovecii pneumonia 259.36 33.91 77 5888 3713 3376181
Asthenia 249.96 33.91 175 5790 65490 3314404
Dermatitis exfoliative 246.93 33.91 69 5896 2674 3377220
Alanine aminotransferase increased 245.74 33.91 121 5844 23519 3356375
Urticaria 240.39 33.91 127 5838 28600 3351294
Aspartate aminotransferase increased 231.19 33.91 112 5853 21001 3358893

Pharmacologic Action:

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SourceCodeDescription
ATC J01EC01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Intermediate-acting sulfonamides
ATC J01EE01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Combinations of sulfonamides and trimethoprim, incl. derivatives
FDA EPC N0000175504 Sulfonamide Antimicrobial
FDA Chemical/Ingredient N0000008048 Sulfonamides
FDA MoA N0000185504 Cytochrome P450 2C9 Inhibitors
CHEBI has role CHEBI:88188 drug allergen
CHEBI has role CHEBI:35441 antiinfective agent
MeSH PA D000890 Anti-Infective Agents

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Acute otitis media indication 3110003
Nocardiosis indication 29227009 DOID:2312
Shigellosis indication 36188001 DOID:12385
Klebsiella cystitis indication 60867007
Toxoplasmosis indication 187192000 DOID:9965
Chlamydial conjunctivitis indication 231861005 DOID:13800
Escherichia coli urinary tract infection indication 301011002
Proteus urinary tract infection indication 301012009
Bacterial urinary infection indication 312124009
Infective otitis media indication 312218008
Pneumocystosis jiroveci pneumonia indication 415125002 DOID:11339
Acute exacerbation of chronic bronchitis indication 425748003
Morganella Morganii Urinary Tract Infection indication
Pneumocystis Carinii Pneumonia Prevention indication
Haemophilus Influenzae Chronic Bronchitis indication
Aerobic Gram-Negative Bacillary Infection indication
Haemophilus Influenzae Acute Otitis Media indication
Aerobic Gram-Positive Cocci Infection indication
Streptococcus Pneumoniae Chronic Bronchitis indication
Glomerulonephritis contraindication 36171008 DOID:2921
Acute hepatitis contraindication 37871000
Third trimester pregnancy contraindication 41587001
Uremia contraindication 44730006 DOID:4676
Megaloblastic anemia due to folate deficiency contraindication 85649008 DOID:14026
Kidney disease contraindication 90708001 DOID:2527
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
Folic acid deficiency contraindication 190633005
Disease of liver contraindication 235856003 DOID:409
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Pseudomembranous enterocolitis contraindication 397683000 DOID:0060185
Porphyria contraindication 418470004 DOID:13268
Typhoid fever off-label use 4834000 DOID:13258
Infection of skin AND/OR subcutaneous tissue off-label use 19824006
Pertussis off-label use 27836007
Granuloma inguinale off-label use 28867007 DOID:9113
Listeria meningitis off-label use 31568009 DOID:11572
Sinusitis off-label use 36971009
Whipple's disease off-label use 41545003 DOID:8476
Bacterial pneumonia off-label use 53084003 DOID:874
Paracoccidioidomycosis off-label use 59925007 DOID:12662
Cholera off-label use 63650001 DOID:1498
Brucellosis off-label use 75702008 DOID:11077
Paratyphoid fever off-label use 85904008 DOID:3055
Chlamydial infection off-label use 105629000
Infection of bone off-label use 111253001
Meningococcus carrier off-label use 170486006
Lymphogranuloma venereum off-label use 186946009 DOID:13819
Chancroid off-label use 266143009 DOID:13778
Diverticulitis of gastrointestinal tract off-label use 271366000
Bacterial endocarditis off-label use 301183007
Toxoplasmosis associated with acquired immunodeficiency syndrome off-label use 421666009
Postexposure Plague Prophylaxis off-label use
Toxoplasmosis Prevention off-label use
Diabetic Foot Infection off-label use
Chronic Bacterial Prostatitis off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 5.79 acidic
pKa2 2.08 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Dihydropteroate synthase Enzyme INHIBITOR IC50 5.33 CHEMBL CHEMBL
Bifunctional protein FolC Enzyme WOMBAT-PK
Dihydrofolate reductase Enzyme IC50 7 CHEMBL
Endothelin-1 receptor GPCR IC50 5.40 CHEMBL
Pol polyprotein Enzyme Ki 8 CHEMBL

External reference:

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IDSource
4017734 VUID
N0000146102 NUI
C0038689 UMLSCUI
D00447 KEGG_DRUG
CHEMBL443 ChEMBL_ID
DB01015 DRUGBANK_ID
5329 PUBCHEM_CID
4017734 VANDF
363528007 SNOMEDCT_US
N0000006904 NDFRT
N0000146102 NDFRT
2035 MMSL
10180 RXNORM
70047000 SNOMEDCT_US
5526 MMSL
d00119 MMSL
002827 NDDF
CHEBI:9332 CHEBI
JE42381TNV UNII
1386 INN_ID
D013420 MESH_DESCRIPTOR_UI
08D PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0121-4793 SUSPENSION 200 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0179-0138 TABLET 800 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0179-0206 TABLET 400 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0440-2406 TABLET 800 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0615-0170 TABLET 800 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0703-9503 INJECTION, SOLUTION, CONCENTRATE 80 mg INTRAVENOUS ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0703-9514 INJECTION, SOLUTION, CONCENTRATE 80 mg INTRAVENOUS ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0703-9526 INJECTION, SOLUTION, CONCENTRATE 80 mg INTRAVENOUS ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0904-2725 TABLET 800 mg ORAL ANDA 12 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 10544-053 TABLET 800 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 10544-092 TABLET 800 mg ORAL ANDA 14 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 10544-525 TABLET 800 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 10544-926 TABLET 800 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 10544-940 TABLET 800 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim DS HUMAN PRESCRIPTION DRUG LABEL 2 12634-177 TABLET 800 mg ORAL ANDA 12 sections
SULFAMETHOXAZOLE and TRIMETHOPRIM HUMAN PRESCRIPTION DRUG LABEL 2 12634-779 SUSPENSION 200 mg ORAL ANDA 12 sections
Bactrim HUMAN PRESCRIPTION DRUG LABEL 2 13310-145 TABLET 400 mg ORAL NDA 13 sections
Bactrim DS HUMAN PRESCRIPTION DRUG LABEL 2 13310-146 TABLET 800 mg ORAL NDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 16590-210 TABLET 800 mg ORAL ANDA 13 sections
SULFATRIM HUMAN PRESCRIPTION DRUG LABEL 2 17856-0007 SUSPENSION 200 mg ORAL NDA 11 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 17856-0496 SUSPENSION 200 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 17856-0823 SUSPENSION 200 mg ORAL ANDA 11 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 21695-125 TABLET 800 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 21695-701 SUSPENSION 200 mg ORAL ANDA 11 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 33261-148 TABLET 800 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 33261-396 TABLET 400 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 35356-666 TABLET 800 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 42291-758 TABLET 400 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 42291-759 TABLET 800 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 42292-028 TABLET 800 mg ORAL ANDA 13 sections