General Information of Drug (ID: DMM7CHK)

Drug Name
Trimethoprim
Synonyms
Abaprim; Alprim; Anitrim; Antrima; Antrimox; Bacdan; Bacidal; Bacide; Bacin; Bacta; Bacterial; Bacticel; Bactin; Bactoprim; Bactramin; Bencole; Bethaprim; Biosulten; Briscotrim; Chemotrin; Cidal; Colizole; Conprim; Cotrimel; Deprim; Duocide; Esbesul; Espectrin; Euctrim; Exbesul; Fermagex; Fortrim; Futin; Idotrim; Ikaprim; Instalac; Kombinax; Lagatrim; Lastrim; Methoprim; Metoprim; Monoprim; Monotrim; Monotrimin; Novotrimel; Omstat; Oraprim; Pancidim; Polytrim; Priloprim; Primosept; Primsol; Proloprim; Protrin; Purbal; Resprim; Roubac; Roubal; Salvatrim; Setprin; Sinotrim; Stopan; Streptoplus; Sugaprim; Sulfamar; Sulfamethoprim; Sulfoxaprim; Sulmeprim; Sulthrim; Sultrex; Syraprim; Tiempe; Toprim; Trimanyl; Trimethioprim; Trimethoprime; Trimethoprimum; Trimethopriom; Trimetoprim; Trimetoprima; Trimexazole; Trimexol; Trimezol; Trimogal; Trimono; Trimopan; Trimpex; Triprim; Trisul; Trisulcom; Trisulfam; Trisural; Uretrim; Urobactrim; Utetrin; Velaten; Wellcoprim; Wellcoprin; Xeroprim; Zamboprim; Bacterial [Antibiotic]; Colizole DS; Component of Bactrim; Component of Septra; Lagatrim Forte; ResprimForte; Septrin DS; Septrin Forte; Septrin S; Trimetoprim [DCIT]; Trimetoprim [Polish]; BW 5672; KUC103659N; NIH 204; T 7883; Trimpex 200; WR 5949; Alcorim-F; Apo-Sulfatrim; BW 56-72; Co-Trimoxizole; Monotrim (TN); NIH 204 (VAN); Proloprim (TN); Smz-Tmp; Sulfamethoxazole & Trimethoprim; TCMDC-125538; Tmp-Ratiopharm; Trimeth/Sulfa; Trimethopim(TMP); Trimethoprim & VRC3375; Trimethoprime [INN-French]; Trimethoprimum [INN-Latin]; Trimetoprima [INN-Spanish]; Trimez-IFSA; Trimpex (TN); Triprim (TN); U-Prin; Uro-D S; BW-56-72; KSC-4-158; AZT + TMP/SMX (mixture) combination; Trimethoprim (JAN/USP/INN); Trimethoprim [USAN:BAN:INN:JAN]
Indication
Disease Entry ICD 11 Status REF
Acute otitis media AB00 Approved [1]
Bacillary dysentery 1A02 Approved [1]
Blepharoconjunctivitis N.A. Approved [1]
Pneumocystis pneumonia CA40.20 Approved [1]
Tuberculosis 1B10-1B14 Approved [1]
Urinary tract infection GC08 Approved [2]
⏷ Show the Full List of Indication(s)
Therapeutic Class
Antiinfective Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 290.32
Logarithm of the Partition Coefficient (xlogp) 0.9
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 1 mg/L [3]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1-4 h [3]
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [4]
Bioavailability
98% of drug becomes completely available to its intended biological destination(s) [5]
Clearance
The renal clearance of drug is 51.7-91.3 mL/min [3]
Elimination
Approximately 10-20% of an ingested trimethoprim dose is metabolized, primarily in the liver, while a large portion of the remainder is excreted unchanged in the urine [6]
Half-life
The concentration or amount of drug in body reduced by one-half in 8 - 10 hours [7]
Metabolism
The drug is metabolized via oxidative metabolism to a number of metabolites, the most abundant of which are the demethylated 3'- and 4'- metabolites [8]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 15.7461 micromolar/kg/day [9]
Unbound Fraction
The unbound fraction of drug in plasma is 0.5% [10]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.5 L/kg [10]
Water Solubility
The ability of drug to dissolve in water is measured as 1.37 mg/mL [4]
Chemical Identifiers
Formula
C14H18N4O3
IUPAC Name
5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
Canonical SMILES
COC1=CC(=CC(=C1OC)OC)CC2=CN=C(N=C2N)N
InChI
InChI=1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18)
InChIKey
IEDVJHCEMCRBQM-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5578
ChEBI ID
CHEBI:45924
CAS Number
738-70-5
DrugBank ID
DB00440
TTD ID
D0AO5H
VARIDT ID
DR00590
INTEDE ID
DR1648
ACDINA ID
D00707
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Dihydrofolate reductase (DHFR) TTYZVDJ DYR_HUMAN Modulator [11]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic cation transporter 1 (SLC22A1) DTT79CX S22A1_HUMAN Substrate [12]
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [13]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME
DE4LYSA CP3A4_HUMAN Substrate [14]
Cytochrome P450 2C9 (CYP2C9)
Main DME
DE5IED8 CP2C9_HUMAN Substrate [15]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [16]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Gene/Protein Processing [17]
HLA class II histocompatibility antigen gamma chain (CD74) OTO16X4Q HG2A_HUMAN Gene/Protein Processing [18]
HLA class II histocompatibility antigen, DO beta chain (HLA-DOB) OTKADDUB DOB_HUMAN Gene/Protein Processing [18]
Solute carrier family 22 member 3 (SLC22A3) OTQYGVXX S22A3_HUMAN Regulation of Drug Effects [19]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Trimethoprim
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Plazomicin DMKMBES Moderate Increased risk of nephrotoxicity by the combination of Trimethoprim and Plazomicin. Urinary tract infection [GC08] [20]
Coadministration of a Drug Treating the Disease Different from Trimethoprim (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Repaglinide DM5SXUV Moderate Decreased metabolism of Trimethoprim caused by Repaglinide mediated inhibition of CYP450 enzyme. Acute diabete complication [5A2Y] [21]
Pioglitazone DMKJ485 Moderate Decreased metabolism of Trimethoprim caused by Pioglitazone mediated inhibition of CYP450 enzyme. Acute diabete complication [5A2Y] [22]
Bedaquiline DM3906J Minor Increased risk of prolong QT interval by the combination of Trimethoprim and Bedaquiline. Antimicrobial drug resistance [MG50-MG52] [23]
Montelukast DMD157S Moderate Decreased metabolism of Trimethoprim caused by Montelukast mediated inhibition of CYP450 enzyme. Asthma [CA23] [24]
Tucatinib DMBESUA Moderate Decreased metabolism of Trimethoprim caused by Tucatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [25]
Anisindione DM2C48U Moderate Increased risk of bleeding by the combination of Trimethoprim and Anisindione. Coagulation defect [3B10] [26]
Drospirenone DM1A9W3 Moderate Increased risk of hyperkalemia by the combination of Trimethoprim and Drospirenone. Contraceptive management [QA21] [27]
Lumacaftor DMCLWDJ Moderate Increased metabolism of Trimethoprim caused by Lumacaftor mediated induction of CYP450 enzyme. Cystic fibrosis [CA25] [28]
Primidone DM0WX6I Moderate Increased metabolism of Trimethoprim caused by Primidone mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [28]
Mephenytoin DM5UGDK Moderate Decreased metabolism of Trimethoprim caused by Mephenytoin mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [29]
Fosphenytoin DMOX3LB Moderate Decreased metabolism of Trimethoprim caused by Fosphenytoin mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [30]
Ethotoin DMXWOCP Moderate Decreased metabolism of Trimethoprim caused by Ethotoin mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [29]
Phenobarbital DMXZOCG Moderate Increased metabolism of Trimethoprim caused by Phenobarbital mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [28]
Carbamazepine DMZOLBI Moderate Increased metabolism of Trimethoprim caused by Carbamazepine mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [28]
Eplerenone DMF0NQR Major Increased risk of hyperkalemia by the combination of Trimethoprim and Eplerenone. Heart failure [BD10-BD1Z] [31]
Amiloride DMRTSGP Major Increased risk of hyperkalemia by the combination of Trimethoprim and Amiloride. Heart failure [BD10-BD1Z] [31]
Rifapentine DMCHV4I Moderate Increased metabolism of Trimethoprim caused by Rifapentine mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [28]
Efavirenz DMC0GSJ Minor Increased risk of prolong QT interval by the combination of Trimethoprim and Efavirenz. Human immunodeficiency virus disease [1C60-1C62] [23]
Eprosartan DM07K2I Major Increased risk of hyperkalemia by the combination of Trimethoprim and Eprosartan. Hypertension [BA00-BA04] [31]
Moexipril DM26E4B Major Increased risk of hyperkalemia by the combination of Trimethoprim and Moexipril. Hypertension [BA00-BA04] [31]
Captopril DM458UM Major Increased risk of hyperkalemia by the combination of Trimethoprim and Captopril. Hypertension [BA00-BA04] [31]
Trandolapril DM4L6EU Major Increased risk of hyperkalemia by the combination of Trimethoprim and Trandolapril. Hypertension [BA00-BA04] [31]
Losartan DM72JXH Major Increased risk of hyperkalemia by the combination of Trimethoprim and Losartan. Hypertension [BA00-BA04] [31]
Fosinopril DM9NJ52 Major Increased risk of hyperkalemia by the combination of Trimethoprim and Fosinopril. Hypertension [BA00-BA04] [31]
TAK-491 DMCF6SX Major Increased risk of hyperkalemia by the combination of Trimethoprim and TAK-491. Hypertension [BA00-BA04] [31]
Pindolol DMD2NV7 Minor Decreased renal excretion of Trimethoprim caused by Pindolol. Hypertension [BA00-BA04] [32]
Benazepril DMH1M9B Major Increased risk of hyperkalemia by the combination of Trimethoprim and Benazepril. Hypertension [BA00-BA04] [31]
Enalapril DMNFUZR Major Increased risk of hyperkalemia by the combination of Trimethoprim and Enalapril. Hypertension [BA00-BA04] [31]
Perindopril DMOPZDT Major Increased risk of hyperkalemia by the combination of Trimethoprim and Perindopril. Hypertension [BA00-BA04] [31]
Quinapril DMR8H31 Major Increased risk of hyperkalemia by the combination of Trimethoprim and Quinapril. Hypertension [BA00-BA04] [31]
Telmisartan DMS3GX2 Major Increased risk of hyperkalemia by the combination of Trimethoprim and Telmisartan. Hypertension [BA00-BA04] [31]
Irbesartan DMTP1DC Major Increased risk of hyperkalemia by the combination of Trimethoprim and Irbesartan. Hypertension [BA00-BA04] [31]
Lisinopril DMUOK4C Major Increased risk of hyperkalemia by the combination of Trimethoprim and Lisinopril. Hypertension [BA00-BA04] [31]
Potassium chloride DMMTAJC Major Increased risk of hyperkalemia by the combination of Trimethoprim and Potassium chloride. Hypo-kalaemia [5C77] [31]
Tolvaptan DMIWFRL Moderate Increased risk of hyperkalemia by the combination of Trimethoprim and Tolvaptan. Hypo-osmolality/hyponatraemia [5C72] [33]
Givosiran DM5PFIJ Moderate Increased risk of nephrotoxicity by the combination of Trimethoprim and Givosiran. Inborn porphyrin/heme metabolism error [5C58] [20]
Porfimer Sodium DM7ZWNY Moderate Increased risk of photosensitivity reactions by the combination of Trimethoprim and Porfimer Sodium. Lung cancer [2C25] [34]
Mercaptopurine DMTM2IK Moderate Additive myelosuppressive effects by the combination of Trimethoprim and Mercaptopurine. Mature B-cell lymphoma [2A85] [35]
Arry-162 DM1P6FR Moderate Decreased clearance of Trimethoprim due to the transporter inhibition by Arry-162. Melanoma [2C30] [20]
Enzalutamide DMGL19D Moderate Increased metabolism of Trimethoprim caused by Enzalutamide mediated induction of CYP450 enzyme. Prostate cancer [2C82] [28]
Selexipag DMAHSU0 Moderate Decreased metabolism of Trimethoprim caused by Selexipag mediated inhibition of CYP450 enzyme. Pulmonary hypertension [BB01] [36]
Vardenafil DMTBGW8 Minor Increased risk of prolong QT interval by the combination of Trimethoprim and Vardenafil. Sexual dysfunction [HA00-HA01] [23]
Taxol DMUOT9V Moderate Decreased metabolism of Trimethoprim caused by Taxol mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [37]
Warfarin DMJYCVW Moderate Increased risk of bleeding by the combination of Trimethoprim and Warfarin. Supraventricular tachyarrhythmia [BC81] [26]
Lusutrombopag DMH6IKO Moderate Decreased clearance of Trimethoprim due to the transporter inhibition by Lusutrombopag. Thrombocytopenia [3B64] [38]
Azathioprine DMMZSXQ Moderate Additive myelosuppressive effects by the combination of Trimethoprim and Azathioprine. Transplant rejection [NE84] [35]
Tacrolimus DMZ7XNQ Moderate Increased risk of nephrotoxicity by the combination of Trimethoprim and Tacrolimus. Transplant rejection [NE84] [20]
⏷ Show the Full List of 47 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Stearic acid E00079 5281 Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Beta-D-lactose E00099 6134 Diluent; Dry powder inhaler carrier; Lyophilization aid
Brushite E00392 104805 Diluent
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate E00208 11177 lubricant
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Water E00035 962 Solvent
⏷ Show the Full List of 8 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Trimethoprim 100 mg tablet 100 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Trimethoprim FDA Label
2 Has nature already identified all useful antibacterial targets Curr Opin Microbiol. 2008 Oct;11(5):387-92.
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5 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
6 FDA Approved Drug Products: Trimethoprim oral tablets
7 Health Canada Product Monograph: Trimethoprim oral tablets
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