Structure via PubChem · Public domain (PubChem)
trimethoprim
Sign in to saveAlso known as Monotrim, Proloprin, Trimpex 200, Trimpex, 5-[(3,4,5-Trimethoxyphenyl)methyl]-2,4-pyrimidinediamine, Proloprim, 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine, BW-56-72
Trimethoprim (TMP) is an antibiotic used mainly in the treatment of bladder infections. Other uses include for middle ear infections and travellers' diarrhoea. With sulfamethoxazole or dapsone it may be used for Pneumocystis pneumonia in people with HIV/AIDS. It is taken orally (swallowed by mouth).
OverviewAI-generated
Trimethoprim is a chemical compound with the molecular formula C₁₄H₁₈N₄O₃. Its IUPAC name is 5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine. The substance has a mass of 290.138 and a weight of 290.32. It possesses a charge of 0, an xlogp value of 0.9, and a topological polar surface area of 106. The molecule contains two hydrogen bond donors and seven hydrogen bond acceptors.
The compound is associated with the MCN code 2933.59.41. In scientific literature, it is the subject of 28807 PubMed entries. Additionally, the topic is referenced by 228 other encyclopedia articles.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 470615131
- Drug.image
- Trimethoprim.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 240
- Drug.alt
- Structural formula of trimethoprim
- Drug.image2
- Trimethoprim-from-hydrochloride-xtal-1984-3D-balls.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 250
- Drug.alt2
- Ball-and-stick model of the trimethoprim molecule
- Drug.tradename
- Proloprim, Monotrim, Triprim, others
- Drug.MedlinePlus
- a684025
- Drug.DailyMedID
- Trimethoprim
- Drug.pregnancy_AU
- B3
- Drug.routes_of_administration
- By mouth
- Drug.class
- Diaminopyrimidines
- Drug.ATC_prefix
- J01
- Drug.ATC_suffix
- EA01
via Wikipedia infobox
Chemical data
- Formula
- C14H18N4O3
- Molecular weight
- 290.32 g/mol
- IUPAC name
- 5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
- SMILES
- COC1=CC(=CC(=C1OC)OC)CC2=CN=C(N=C2N)N
- InChIKey
- IEDVJHCEMCRBQM-UHFFFAOYSA-N
- XLogP
- 0.9
- Polar surface area
- 106 Ų
- H-bond donors
- 2
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1973
- Admin. routes
- oral, parenteral, topical
- Indications
- infection, neoplasm, idiopathic pulmonary fibrosis, malaria
via ChEMBL · EBI
Research
28,807 papers- Trimethoprim-sulphamethoxazole.Drugs · 1971
- Trimethoprim: mechanisms of action, antimicrobial activity, bacterial resistance, pharmacokinetics, adverse reactions, and therapeutic indications.Pharmacotherapy · 1981
- Trimethoprim-sulphamethoxazole.Drugs · 1971
- Trimethoprim-sulfamethoxazole.The Medical clinics of North America · 1982
- Trimethoprim-sulfamethoxazole for bacterial meningitis.Annals of internal medicine · 1984
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 290.138
- Has use
- medication
Show 10 more facts
- MCN code
- 2933.59.41
- subject has role
- bactericide
- chemical formula
- C₁₄H₁₈N₄O₃
- World Health Organisation international non-proprietary name
- trimethoprim
- medical condition treated
- staphylococcal infection
- canonical SMILES
- COC1=CC(=CC(=C1OC)OC)CC2=CN=C(N=C2N)N
- Commons category
- Trimethoprim
- different from
- thymidine monophosphate
- significant drug interaction
- pyrimethamine
- has characteristic
- bitterness
via Wikidata · CC0
~5 min read
Encyclopedic overview
10 sectionsContents
- Medical uses
- Spectrum of susceptibility
- Side effects
- Common
- Rare
- Contraindications
- Pregnancy
- Mechanism of action
- History
- References
Trimethoprim (TMP) is an antibiotic used mainly in the treatment of bladder infections. Other uses include for middle ear infections and travellers' diarrhoea. With sulfamethoxazole or dapsone it may be used for Pneumocystis pneumonia in people with HIV/AIDS. It is taken orally (swallowed by mouth).
Common side effects include nausea, changes in taste, and rash. Rarely it may result in blood problems such as not enough platelets or white blood cells. Trimethoprim may cause sun sensitivity. There is evidence of potential harm during pregnancy in some animals but not humans. It works by blocking folate metabolism via dihydrofolate reductase in some bacteria, preventing creation of bacterial DNA and RNA and leading to bacterial cell death.
Excerpted from Wikipedia’s “trimethoprim” article, available under the CC BY-SA 4.0 licence.