U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C14H18N4O3
Molecular Weight 290.3177
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIMETHOPRIM

SMILES

COC1=CC(CC2=C(N)N=C(N)N=C2)=CC(OC)=C1OC

InChI

InChIKey=IEDVJHCEMCRBQM-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C14H18N4O3
Molecular Weight 290.3177
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Trimethoprim (TMP) is an antibiotic is used for the treatment of initial episodes of uncomplicated urinary tract infections due to susceptible strains of the following organisms: Escherichia coli, Proteus mirabilis, Klebsiella pneumoniae, Enterobacter species, and coagulase-negative Staphylococcus species, including S. saprophyticus. Cultures and susceptibility tests should be performed to determine the susceptibility of the bacteria to trimethoprim. Therapy may be initiated prior to obtaining the results of these tests. Trimethoprim is rapidly absorbed following oral administration. It exists in the blood as unbound, protein-bound, and metabolized forms. Ten to twenty percent of trimethoprim is metabolized, primarily in the liver; the remainder is excreted unchanged in the urine. The principal metabolites of trimethoprim are the 1- and 3-oxides and the 3'- and 4'-hydroxy derivatives. The free form is considered to be the therapeutically active form. Approximately 44% of trimethoprim is bound to plasma proteins. Trimethoprim blocks the production of tetrahydrofolic acid from dihydrofolic acid by binding to and reversibly inhibiting the required enzyme, dihydrofolate reductase. This binding is very much stronger for the bacterial enzyme than for the corresponding mammalian enzyme

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRIMETHOPRIM
PubMed

PubMed

TitleDatePubMed
HIV and drug allergy.
2001 Aug
Antimicrobial resistance of Shigella spp isolated from diarrheal patients between 1989 and 1998 in Vietnam.
2001 Dec
Rapid detection of Haemophilus influenzae type b in Bangladeshi children with pneumonia and meningitis by PCR and analysis of antimicrobial resistance.
2001 Dec
Pneumocystis carinii pneumonitis in haemophagocytic lymphohistiocytosis.
2001 Dec
Empirical treatment of uncomplicated urinary tract infection by community pharmacist in the Eastern province of Saudi Arabia.
2001 Dec
Gradient diffusion antibiotic susceptibility testing of potentially probiotic lactobacilli.
2001 Dec
Antibiotic failure in the treatment of urinary tract infections in young women.
2001 Dec
Neonatal brucellosis and blood transfusion: case report and review of the literature.
2001 Dec
Prevalence of antimicrobial resistance in Streptococcus pneumoniae circulating in Italy: results of the Italian Epidemiological Observatory Survey (1997-1999).
2001 Fall
Epidemic of Vibrio cholerae serogroup O139 in Berhampur, Orissa.
2001 Jul
Infectious complications in chronic lymphoid malignancy.
2001 Jun
Changing pattern of biotypes, phage types & drug resistance of Salmonella typhi in Ludhiana during 1980-1999.
2001 May
Epidemiology of major respiratory pathogens.
2001 Nov
A common-source water-borne outbreak of multidrug-resistant typhoid fever in a rural Thai community.
2001 Nov
Co-trimoxazole compared with sulfadoxine-pyrimethamine in the treatment of uncomplicated malaria in Kenyan children.
2001 Nov-Dec
Epidemiological analysis of Salmonella enteritidis isolates in Singapore.
2001 Oct
Susceptibility patterns and serotypes of non-typhoidal salmonella in Trinidad.
2001 Oct
Epidemiology of shigellosis in Lagos, Nigeria: trends in antimicrobial resistance.
2001 Sep
Occurrence of enteric redmouth disease in rainbow trout (Oncorhynchus mykiss) on farms in Croatia.
2002
[Antibiotic resistance of staphylococci isolated from outpatients].
2002
Staphylococcus aureus and Wegener's granulomatosis.
2002
Incidence and molecular analysis of Vibrio cholerae associated with cholera outbreak subsequent to the super cyclone in Orissa, India.
2002 Apr
[General antibiotic therapy in acne].
2002 Apr 15
Burkholderia pseudomallei: abscess in an unusual site.
2002 Apr-Jun
Trimethoprim-induced aseptic meningitis in an adolescent male.
2002 Aug
Shigellosis linked to sex venues, Australia.
2002 Aug
Pneumocystis carinii: where are we now?
2002 Feb
Clinical efficacy of co-trimoxazole versus amoxicillin twice daily for treatment of pneumonia: a randomised controlled clinical trial in Pakistan.
2002 Feb
Prophylactic antibiotic use in transurethral prostatic resection: a meta-analysis.
2002 Feb
Clinical and biological evolution of HIV-1 seroconverters in Abidjan, Côte d'Ivoire, 1997-2000.
2002 Feb 1
Allergic adverse reactions to sulfonamides.
2002 Jan
Inhibition of Pneumocystis carinii, Toxoplasma gondii, and Mycobacterium avium dihydrofolate reductases by 2,4-diamino-5-[2-methoxy-5-(omega-carboxyalkyloxy)benzyl]pyrimidines: marked improvement in potency relative to trimethoprim and species selectivity relative to piritrexim.
2002 Jan 3
A double-hand transplant can be worth the effort!
2002 Jul 15
Facilitating changes in perinatal smoking. The impact of a stage-based workshop for care-providers in British Columbia.
2002 Jul-Aug
Prevalence of and resistance to anti-microbial drugs in selected microbial species isolated from bulk milk samples.
2002 Jun
In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species.
2002 Jun
HIV-1/AIDS and maternal and child health in Africa.
2002 Jun 15
A disseminated multidrug-resistant clonal group of uropathogenic Escherichia coli in pyelonephritis.
2002 Jun 29
Modified antimicrobial disc susceptibility testing for nutritionally-variant streptococci.
2002 Mar
The relation between sale of antimicrobial drugs and antibiotic resistance in uropathogens in general practice.
2002 Mar
A European study on the relationship between antimicrobial use and antimicrobial resistance.
2002 Mar
Q fever during pregnancy: diagnosis, treatment, and follow-up.
2002 Mar 25
Changes in Escherichia coli resistance to co-trimoxazole in tuberculosis patients and in relation to co-trimoxazole prophylaxis in Thyolo, Malawi.
2002 Mar-Apr
A simple clinical and paraclinical score predictive of CD4 cells counts below 400/mm3 in HIV-infected adults in Dakar University Hospital, Senegal.
2002 Mar-Apr
Clinical signs and symptoms in the assessment of immunodeficiency in men with subtype C HIV infection in Harare, Zimbabwe.
2002 Mar-Apr
Urinary tract-derived Escherichia coli resistant to co-trimoxazole in Japan, where the drug is seldom used for treating acute urinary tract infections.
2002 May
Rapid increase in macrolide resistance among penicillin non-susceptible pneumococci in Finland, 1996-2000.
2002 May
Emergence of vancomycin-intermediate Staphylococcus aureus and S. sciuri, Greece.
2002 May
Neutropenic enterocolitis (typhlitis) after pediatric bone marrow transplant.
2002 May
First characterization of a cluster of VanA-type glycopeptide-resistant Enterococcus faecium, Colombia.
2002 Sep
Patents

Sample Use Guides

In Vivo Use Guide
The usual oral adult dosage is 100 mg of trimethoprim every 12 hours or 200 mg of trimethoprim every 24 hours, each for 10 days. The use of trimethoprim in patients with a creatinine clearance of less than 15 mL/min is not recommended. For patients with a creatinine clearance of 15 to 30 mL/min, the dose should be 50 mg every 12 hours.
Route of Administration: Oral
In Vitro Use Guide
In vitro susceptibility of bacterial isolates to sulfamethoxazole, trimethoprim and trimethoprim/sulfamethoxazole was determined using disk diffusion. E. coli susceptibility to trimethoprim was 70%, comparable to the 70% of trimethoprim/sulfamethoxazole (p = 0.9)and higher than the 56.9% of sulfamethoxazole (p <0.05).
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:46:19 UTC 2019
Edited
by admin
on Mon Oct 21 19:46:19 UTC 2019
Record UNII
AN164J8Y0X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIMETHOPRIM
EP   GREEN BOOK   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
TRIMETHOPRIM COMPONENT OF SULFAMETHOPRIM
Common Name English
TRIMETHOPRIM COMPONENT OF BACTRIM
Common Name English
NIH-204
Code English
SULMEPRIM COMPONENT TRIMETHOPRIM
Common Name English
BACTRIM DS COMPONENT TRIMETHOPRIM
Common Name English
TRIMETHOPRIM [INN]
Common Name English
2,4-PYRIMIDINEDIAMINE, 5-((3,4,5-TRIMETHOXYPHENYL)METHYL)-
Systematic Name English
NSC-106568
Code English
BACTRIM PEDIATRIC COMPONENT TRIMETHOPRIM
Common Name English
SEPTRA COMPONENT TRIMETHOPRIM
Common Name English
TRIMETHOPRIM COMPONENT OF SEPTRA
Common Name English
WELLCOPRIM
Common Name English
TRIMETHOPRIM [HSDB]
Common Name English
TRIMETHOPRIM COMPONENT OF COTRIM
Common Name English
TRIMETHOPRIM COMPONENT OF UROPLUS
Common Name English
COTRIM D.S. COMPONENT TRIMETHOPRIM
Common Name English
TRIMETHOPRIM COMPONENT OF COTRIM D.S.
Common Name English
TRIMETHOPRIM COMPONENT OF BACTRIM PEDIATRIC
Common Name English
TRIMETHOPRIM [VANDF]
Common Name English
TRIMETHOPRIM [EP]
Common Name English
TRIMETHOPRIM [USAN]
Common Name English
BW-56-72
Code English
TRIMETHOPRIMUM [WHO-IP LATIN]
Common Name English
SULFATRIM COMPONENT TRIMETHOPRIM
Common Name English
TRIMETHOPRIM [JAN]
Common Name English
SULFAMETHOPRIM COMPONENT TRIMETHOPRIM
Common Name English
TRIMETHOPRIM COMPONENT OF SULFATRIM
Common Name English
TRIMETHOPRIM [USP]
Common Name English
TRIMPEX
Brand Name English
TRIMETHOPRIM [ORANGE BOOK]
Common Name English
PROLOPRIM
Brand Name English
TRIMETHOPRIM [MART.]
Common Name English
TMP
Common Name English
TRIMETHOPRIM [GREEN BOOK]
Common Name English
BACTRIM COMPONENT TRIMETHOPRIM
Common Name English
TRIMETHOPRIM COMPONENT OF SULMEPRIM
Common Name English
TRIMETHOPRIM [MI]
Common Name English
COTRIM COMPONENT TRIMETHOPRIM
Common Name English
BW 56-72
Code English
TRIMETHOPRIM [WHO-IP]
Common Name English
TRIMETHOPRIM COMPONENT OF BACTRIM DS
Common Name English
TRIMETHOPRIM [USP-RS]
Common Name English
INFECTOTRIMET
Common Name English
UROPLUS COMPONENT TRIMETHOPRIM
Common Name English
2,4-DIAMINO-5-(3,4,5-TRIMETHOXYBENZYL)PYRIMIDINE
Systematic Name English
TRIMETHOPRIM [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC J01EE07
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
CFR 21 CFR 520.2611
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-VATC QJ01EW09
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-VATC QJ01EW18
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-VATC QJ01EW13
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-ATC J04AM08
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
NDF-RT N0000175489
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
LIVERTOX 1002
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-VATC QJ01EW30
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.2 (SUL/TRI)
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-VATC QJ01EW12
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.2
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-VATC QJ01EW11
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-VATC QJ01EW17
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-VATC QJ01EW16
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-ATC J01EE03
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
CFR 21 CFR 520.2610
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.5.4 (SUL/TRI)
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-VATC QJ01EW10
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-ATC J01EE05
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
NCI_THESAURUS C255
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-ATC J01EE02
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-ATC J01EE01
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
NDF-RT N0000000191
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-VATC QJ01EW15
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-VATC QJ01EA01
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
CFR 21 CFR 522.2610
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-VATC QJ01EW03
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-ATC J01EA01
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-VATC QJ01EW14
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-VATC QJ51RE01
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-VATC QJ51EA01
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
WHO-ATC J01EE04
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
CFR 21 CFR 520.2613
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
NDF-RT N0000000191
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
CFR 21 CFR 520.2612
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
Code System Code Type Description
NDF-RT
N0000187061
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY Organic Cation Transporter 2 Inhibitors [MoA]
INN
1047
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
TRIMETHOPRIM
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY Description: A white, crystalline powder; odourless or almost odourless. Solubility: Sparingly soluble in water; soluble in methanol R; practically insoluble in ether R. Category: Antibacterial. Storage: Trimethoprim should be kept in a well-closed container. Definition: Trimethoprim contains not less than 98.5% and not more than 101.0% of C14H18N4O3, calculated with reference to the dried substance.
MESH
D014295
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY
MERCK INDEX
M11148
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY Merck Index
WIKIPEDIA
TRIMETHOPRIM
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY
NDF-RT
N0000187062
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY Cytochrome P450 2C8 Inhibitors [MoA]
RXCUI
10829
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C908
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY
LactMed
738-70-5
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY
PUBCHEM
5578
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY
CAS
738-70-5
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY
EPA CompTox
738-70-5
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY
ECHA (EC/EINECS)
212-006-2
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY
EVMPD
SUB11310MIG
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY
DRUG BANK
DB00440
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY
ChEMBL
CHEMBL22
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY
HSDB
738-70-5
Created by admin on Mon Oct 21 19:46:19 UTC 2019 , Edited by admin on Mon Oct 21 19:46:19 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
METABOLIC ENZYME -> INHIBITOR
MAJOR
Ki
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UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
UNSPECIFIED
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IMPURITY -> PARENT
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC