trimethoprim indications/contra

Stem definitionDrug idCAS RN
antibacterials, dihydrofolate reductase (DHFR) inhibitors, trimethoprim derivatives 2755 738-70-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • trimethoprim
  • trimethoprim sulfate
  • trimethoprim hydrochloride
  • trimethioprim
  • trimetoprim
  • trimopan
  • trimethoprim HCl
A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.
  • Molecular weight: 290.32
  • Formula: C14H18N4O3
  • CLOGP: 0.98
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 2
  • TPSA: 105.51
  • ALOGS: -2.67
  • ROTB: 5

Drug dosage:

DoseUnitRoute
0.40 g O
0.40 g P

Approvals:

DateAgencyCompanyOrphan
July 30, 1973 FDA MUTUAL PHARM

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 2732.98 32.18 804 5968 34876 3344211
Acute kidney injury 1715.36 32.18 614 6158 49069 3330018
Pyrexia 1210.62 32.18 549 6223 80566 3298521
Hyperkalaemia 1029.88 32.18 294 6478 11000 3368087
Rash 1021.74 32.18 469 6303 70352 3308735
Drug reaction with eosinophilia and systemic symptoms 904.64 32.18 246 6526 7649 3371438
Stevens-Johnson syndrome 710.33 32.18 197 6575 6575 3372512
Agranulocytosis 709.48 32.18 187 6585 5125 3373962
Pancytopenia 678.85 32.18 242 6530 18578 3360509
Neutropenia 619.63 32.18 265 6507 33121 3345966
Rash maculo-papular 602.78 32.18 168 6604 5699 3373388
Thrombocytopenia 599.11 32.18 263 6509 35005 3344082
Nausea 444.93 32.18 340 6432 129305 3249782
Vomiting 443.56 32.18 294 6478 89237 3289850
Toxic epidermal necrolysis 425.01 32.18 121 6651 4424 3374663
Pruritus 417.83 32.18 225 6547 46608 3332479
Hepatitis 400.78 32.18 138 6634 9487 3369600
Hepatocellular injury 348.67 32.18 103 6669 4292 3374795
Leukopenia 344.21 32.18 141 6631 15682 3363405
Drug interaction 330.40 32.18 193 6579 46619 3332468
Renal failure 326.54 32.18 170 6602 32770 3346317
Blood creatinine increased 319.37 32.18 147 6625 21671 3357416
Hyponatraemia 317.47 32.18 139 6633 18220 3360867
Eosinophilia 304.28 32.18 95 6677 4778 3374309
Pneumocystis jirovecii pneumonia 292.63 32.18 87 6685 3703 3375384
Cholestasis 291.68 32.18 94 6678 5243 3373844
Anaemia 279.05 32.18 183 6589 54150 3324937
Diarrhoea 276.57 32.18 236 6536 104112 3274975
Urticaria 272.39 32.18 144 6628 28583 3350504
Asthenia 263.64 32.18 190 6582 65475 3313612

Pharmacologic Action:

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SourceCodeDescription
ATC J01EA01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Trimethoprim and derivatives
ATC J01EE01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Combinations of sulfonamides and trimethoprim, incl. derivatives
ATC J01EE02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Combinations of sulfonamides and trimethoprim, incl. derivatives
ATC J01EE03 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Combinations of sulfonamides and trimethoprim, incl. derivatives
ATC J01EE04 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Combinations of sulfonamides and trimethoprim, incl. derivatives
ATC J01EE05 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Combinations of sulfonamides and trimethoprim, incl. derivatives
ATC J01EE07 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Combinations of sulfonamides and trimethoprim, incl. derivatives
FDA EPC N0000175489 Dihydrofolate Reductase Inhibitor Antibacterial
FDA MoA N0000000191 Dihydrofolate Reductase Inhibitors
FDA MoA N0000187062 Cytochrome P450 2C8 Inhibitors
FDA MoA N0000187061 Organic Cation Transporter 2 Inhibitors
CHEBI has role CHEBI:88188 drug allergen
CHEBI has role CHEBI:36047 antibacterial drug
CHEBI has role CHEBI:35498 diuretic
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000892 Anti-Infective Agents, Urinary
MeSH PA D000962 Antimalarials
MeSH PA D000977 Antiparasitic Agents
MeSH PA D000981 Antiprotozoal Agents
MeSH PA D065687 Cytochrome P-450 CYP2C8 Inhibitors
MeSH PA D065607 Cytochrome P-450 Enzyme Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D005493 Folic Acid Antagonists
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
MeSH PA D012076 Renal Agents

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Acute otitis media indication 3110003
Shigellosis indication 36188001 DOID:12385
Klebsiella cystitis indication 60867007
Urinary tract infectious disease indication 68566005
Blepharoconjunctivitis indication 68659002 DOID:2456
Bacterial conjunctivitis indication 128350005 DOID:9700
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
Haemophilus Influenzae Acute Otitis Media indication
Haemophilus Influenzae Chronic Bronchitis indication
Streptococcus Pneumoniae Chronic Bronchitis indication
Morganella Morganii Urinary Tract Infection indication
Staphylococcus Aureus Urinary Tract Infection indication
Pneumocystis Carinii Pneumonia Prevention indication
Third trimester pregnancy contraindication 41587001
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
Nocardiosis off-label use 29227009 DOID:2312
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
Chronic Bacterial Prostatitis off-label use
Diabetic Foot Infection off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.01 Basic
pKa2 0.6 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
Dihydrofolate reductase Enzyme Ki 8 CHEMBL
Solute carrier family 22 member 1 Transporter IC50 4.25 CHEMBL
Dihydrofolate reductase Enzyme INHIBITOR IC50 5.57 CHEMBL CHEMBL
Dihydrofolate reductase Enzyme Ki 6.82 CHEMBL
Dihydrofolate reductase Enzyme Ki 8.92 CHEMBL
Dihydrofolate reductase Enzyme Ki 6.88 CHEMBL
Dihydrofolate reductase Enzyme IC50 6.35 CHEMBL
Bifunctional dihydrofolate reductase-thymidylate synthase Enzyme IC50 6.92 CHEMBL
Bifunctional dihydrofolate reductase-thymidylate synthase Enzyme IC50 8.14 CHEMBL
Dihydrofolate reductase Enzyme IC50 4.92 CHEMBL
Dihydrofolate reductase Enzyme IC50 8.66 CHEMBL
Bifunctional dihydrofolate reductase-thymidylate synthase Unclassified IC50 5.40 CHEMBL
Dihydrofolate reductase Enzyme Ki 6.30 CHEMBL
Dihydrofolate reductase Enzyme Ki 4.84 CHEMBL
Dihydrofolate reductase Enzyme Ki 4.62 CHEMBL
Dihydrofolate reductase Enzyme IC50 6.35 CHEMBL
Dihydrofolate reductase Unclassified Ki 8.89 CHEMBL
Dihydrofolate reductase type 1 Unclassified IC50 6.30 CHEMBL
Dihydrofolate reductase Enzyme IC50 6.72 CHEMBL
Bifunctional dihydrofolate reductase-thymidylate synthase Enzyme Ki 8 WOMBAT-PK
Bifunctional dihydrofolate reductase-thymidylate synthase Enzyme Ki 6 WOMBAT-PK
Bifunctional dihydrofolate reductase-thymidylate synthase Enzyme Ki 6.92 WOMBAT-PK
Bifunctional dihydrofolate reductase-thymidylate synthase Enzyme Ki 7.99 CHEMBL
Dihydrofolate reductase Unclassified Ki 8.08 CHEMBL

External reference:

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IDSource
DB00440 DRUGBANK_ID
4017735 VUID
N0000146103 NUI
C0041041 UMLSCUI
D00145 KEGG_DRUG
CHEMBL22 ChEMBL_ID
5578 PUBCHEM_CID
4017735 VANDF
N0000006193 NDFRT
N0000146103 NDFRT
3055 MMSL
10829 RXNORM
32792001 SNOMEDCT_US
387179001 SNOMEDCT_US
5633 MMSL
d00123 MMSL
002873 NDDF
9XE000OU9B UNII
60834-30-2 SECONDARY_CAS_RN
1047 INN_ID
CHEBI:45924 CHEBI
CHEMBL1200915 ChEMBL_ID
CHEMBL1201080 ChEMBL_ID
D014295 MESH_DESCRIPTOR_UI
TOP PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Polytrim HUMAN PRESCRIPTION DRUG LABEL 2 0023-7824 SOLUTION/ DROPS 1 mg OPHTHALMIC NDA 11 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0121-4793 SUSPENSION 40 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0179-0138 TABLET 160 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0179-0206 TABLET 80 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0440-2406 TABLET 160 mg ORAL ANDA 13 sections
Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 1 0591-5571 TABLET 100 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0615-0170 TABLET 160 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0703-9503 INJECTION, SOLUTION, CONCENTRATE 16 mg INTRAVENOUS ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0703-9514 INJECTION, SOLUTION, CONCENTRATE 16 mg INTRAVENOUS ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0703-9526 INJECTION, SOLUTION, CONCENTRATE 16 mg INTRAVENOUS ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 0904-2725 TABLET 160 mg ORAL ANDA 12 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 10544-053 TABLET 160 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 10544-092 TABLET 160 mg ORAL ANDA 14 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 10544-525 TABLET 160 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 10544-926 TABLET 160 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 10544-940 TABLET 160 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim DS HUMAN PRESCRIPTION DRUG LABEL 2 12634-177 TABLET 160 mg ORAL ANDA 12 sections
SULFAMETHOXAZOLE and TRIMETHOPRIM HUMAN PRESCRIPTION DRUG LABEL 2 12634-779 SUSPENSION 40 mg ORAL ANDA 12 sections
Bactrim HUMAN PRESCRIPTION DRUG LABEL 2 13310-145 TABLET 80 mg ORAL NDA 13 sections
Bactrim DS HUMAN PRESCRIPTION DRUG LABEL 2 13310-146 TABLET 160 mg ORAL NDA 13 sections
Primsol HUMAN PRESCRIPTION DRUG LABEL 1 13551-501 SOLUTION 50 mg ORAL NDA 14 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 16590-210 TABLET 160 mg ORAL ANDA 13 sections
Polymyxin B Sulfate and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 16590-233 SOLUTION 1 mg OPHTHALMIC ANDA 10 sections
Trimethoprim sulfate and Polymyxin B sulfate HUMAN PRESCRIPTION DRUG LABEL 2 17478-703 SOLUTION 1 mg OPHTHALMIC ANDA 11 sections
SULFATRIM HUMAN PRESCRIPTION DRUG LABEL 2 17856-0007 SUSPENSION 40 mg ORAL NDA 11 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 17856-0496 SUSPENSION 40 mg ORAL ANDA 13 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 17856-0823 SUSPENSION 40 mg ORAL ANDA 11 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 21695-125 TABLET 160 mg ORAL ANDA 13 sections
Polymyxin B Sulfate and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 21695-335 SOLUTION 1 mg OPHTHALMIC ANDA 10 sections
Sulfamethoxazole and Trimethoprim HUMAN PRESCRIPTION DRUG LABEL 2 21695-701 SUSPENSION 40 mg ORAL ANDA 11 sections