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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:55 UTC
HMDB IDHMDB0014583
Secondary Accession Numbers
  • HMDB14583
Metabolite Identification
Common NameTrimethoprim
DescriptionTrimethoprim, also known as proloprim or trimpex, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Trimethoprim is a very strong basic compound (based on its pKa). An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.
Structure
Data?1582753195
Synonyms
ValueSource
2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidineChEBI
5-[(3,4,5-Trimethoxyphenyl)methyl]-2,4-pyrimidinediamineChEBI
ProloprimChEBI
TrimpexChEBI
CO-TrimoxazoleHMDB
Chemical FormulaC14H18N4O3
Average Molecular Weight290.3177
Monoisotopic Molecular Weight290.137890462
IUPAC Name5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
Traditional Nametrimethoprim
CAS Registry Number738-70-5
SMILES
COC1=CC(CC2=CN=C(N)N=C2N)=CC(OC)=C1OC
InChI Identifier
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)
InChI KeyIEDVJHCEMCRBQM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
Substituents
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Alkyl aryl ether
  • Aminopyrimidine
  • Monocyclic benzene moiety
  • Pyrimidine
  • Imidolactam
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Ether
  • Azacycle
  • Organic oxygen compound
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point199 - 203 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.62 g/LNot Available
LogP0.6Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM170.830932474
[M+H]+Not Available171.225http://allccs.zhulab.cn/database/detail?ID=AllCCS00000787
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.62 g/LALOGPS
logP10(1.26) g/LALOGPS
logP10(1.28) g/LChemAxon
logS10(-2.7) g/LALOGPS
pKa (Strongest Acidic)17.33ChemAxon
pKa (Strongest Basic)7.16ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.51 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity81.51 m³·mol⁻¹ChemAxon
Polarizability29.71 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+170.29631661259
DarkChem[M-H]-169.60831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TrimethoprimCOC1=CC(CC2=CN=C(N)N=C2N)=CC(OC)=C1OC3800.3Standard polar33892256
TrimethoprimCOC1=CC(CC2=CN=C(N)N=C2N)=CC(OC)=C1OC2577.3Standard non polar33892256
TrimethoprimCOC1=CC(CC2=CN=C(N)N=C2N)=CC(OC)=C1OC2638.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Trimethoprim,1TMS,isomer #1COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N)=CC(OC)=C1OC2666.2Semi standard non polar33892256
Trimethoprim,1TMS,isomer #1COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N)=CC(OC)=C1OC2610.4Standard non polar33892256
Trimethoprim,1TMS,isomer #1COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N)=CC(OC)=C1OC4269.8Standard polar33892256
Trimethoprim,1TMS,isomer #2COC1=CC(CC2=CN=C(N)N=C2N[Si](C)(C)C)=CC(OC)=C1OC2679.4Semi standard non polar33892256
Trimethoprim,1TMS,isomer #2COC1=CC(CC2=CN=C(N)N=C2N[Si](C)(C)C)=CC(OC)=C1OC2606.6Standard non polar33892256
Trimethoprim,1TMS,isomer #2COC1=CC(CC2=CN=C(N)N=C2N[Si](C)(C)C)=CC(OC)=C1OC4121.0Standard polar33892256
Trimethoprim,2TMS,isomer #1COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N[Si](C)(C)C)=CC(OC)=C1OC2632.7Semi standard non polar33892256
Trimethoprim,2TMS,isomer #1COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N[Si](C)(C)C)=CC(OC)=C1OC2623.0Standard non polar33892256
Trimethoprim,2TMS,isomer #1COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N[Si](C)(C)C)=CC(OC)=C1OC4011.1Standard polar33892256
Trimethoprim,2TMS,isomer #2COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N)=CC(OC)=C1OC2599.1Semi standard non polar33892256
Trimethoprim,2TMS,isomer #2COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N)=CC(OC)=C1OC2659.9Standard non polar33892256
Trimethoprim,2TMS,isomer #2COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N)=CC(OC)=C1OC3946.1Standard polar33892256
Trimethoprim,2TMS,isomer #3COC1=CC(CC2=CN=C(N)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC2553.6Semi standard non polar33892256
Trimethoprim,2TMS,isomer #3COC1=CC(CC2=CN=C(N)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC2709.4Standard non polar33892256
Trimethoprim,2TMS,isomer #3COC1=CC(CC2=CN=C(N)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC3870.4Standard polar33892256
Trimethoprim,3TMS,isomer #1COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N[Si](C)(C)C)=CC(OC)=C1OC2610.6Semi standard non polar33892256
Trimethoprim,3TMS,isomer #1COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N[Si](C)(C)C)=CC(OC)=C1OC2621.2Standard non polar33892256
Trimethoprim,3TMS,isomer #1COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N[Si](C)(C)C)=CC(OC)=C1OC3579.4Standard polar33892256
Trimethoprim,3TMS,isomer #2COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC2604.1Semi standard non polar33892256
Trimethoprim,3TMS,isomer #2COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC2674.5Standard non polar33892256
Trimethoprim,3TMS,isomer #2COC1=CC(CC2=CN=C(N[Si](C)(C)C)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC3678.5Standard polar33892256
Trimethoprim,4TMS,isomer #1COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC2649.8Semi standard non polar33892256
Trimethoprim,4TMS,isomer #1COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC2655.1Standard non polar33892256
Trimethoprim,4TMS,isomer #1COC1=CC(CC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C2N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC3287.5Standard polar33892256
Trimethoprim,1TBDMS,isomer #1COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N)=CC(OC)=C1OC2853.9Semi standard non polar33892256
Trimethoprim,1TBDMS,isomer #1COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N)=CC(OC)=C1OC2825.4Standard non polar33892256
Trimethoprim,1TBDMS,isomer #1COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N)=CC(OC)=C1OC4235.7Standard polar33892256
Trimethoprim,1TBDMS,isomer #2COC1=CC(CC2=CN=C(N)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC2873.4Semi standard non polar33892256
Trimethoprim,1TBDMS,isomer #2COC1=CC(CC2=CN=C(N)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC2817.2Standard non polar33892256
Trimethoprim,1TBDMS,isomer #2COC1=CC(CC2=CN=C(N)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC4105.2Standard polar33892256
Trimethoprim,2TBDMS,isomer #1COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3031.7Semi standard non polar33892256
Trimethoprim,2TBDMS,isomer #1COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3020.8Standard non polar33892256
Trimethoprim,2TBDMS,isomer #1COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3981.5Standard polar33892256
Trimethoprim,2TBDMS,isomer #2COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N)=CC(OC)=C1OC3033.6Semi standard non polar33892256
Trimethoprim,2TBDMS,isomer #2COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N)=CC(OC)=C1OC3086.2Standard non polar33892256
Trimethoprim,2TBDMS,isomer #2COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N)=CC(OC)=C1OC3916.1Standard polar33892256
Trimethoprim,2TBDMS,isomer #3COC1=CC(CC2=CN=C(N)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC2988.0Semi standard non polar33892256
Trimethoprim,2TBDMS,isomer #3COC1=CC(CC2=CN=C(N)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3084.9Standard non polar33892256
Trimethoprim,2TBDMS,isomer #3COC1=CC(CC2=CN=C(N)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3876.2Standard polar33892256
Trimethoprim,3TBDMS,isomer #1COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3159.7Semi standard non polar33892256
Trimethoprim,3TBDMS,isomer #1COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3230.2Standard non polar33892256
Trimethoprim,3TBDMS,isomer #1COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3689.2Standard polar33892256
Trimethoprim,3TBDMS,isomer #2COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3177.4Semi standard non polar33892256
Trimethoprim,3TBDMS,isomer #2COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3220.9Standard non polar33892256
Trimethoprim,3TBDMS,isomer #2COC1=CC(CC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3774.4Standard polar33892256
Trimethoprim,4TBDMS,isomer #1COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3362.7Semi standard non polar33892256
Trimethoprim,4TBDMS,isomer #1COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3434.3Standard non polar33892256
Trimethoprim,4TBDMS,isomer #1COC1=CC(CC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3533.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Trimethoprim EI-B (Non-derivatized)splash10-0006-5390000000-e68103f64cbb997e57762017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Trimethoprim EI-B (Non-derivatized)splash10-0006-5390000000-e68103f64cbb997e57762018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trimethoprim GC-MS (Non-derivatized) - 70eV, Positivesplash10-072c-0390000000-14ead3ead386e06ae4542017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trimethoprim GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-qTof , Positive-QTOFsplash10-03na-2690000000-39babdc7b45a0aa0adf72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOFsplash10-0089-0290000000-32000410829186ca112c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOFsplash10-0006-0090000000-44ccaa9725303a7db8a42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOFsplash10-0006-0090000000-af77a44791c8867aad662017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOFsplash10-0006-0190000000-8eb1449e3f800368c8632017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOFsplash10-03n9-0190000000-deb1664d211c2227b0482017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOFsplash10-077i-0590000000-ae48b54f4879c15516702017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOFsplash10-0089-1950000000-5084ea4b328a585b675d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOFsplash10-0006-0090000000-fb9fa4e4130917b6e6ff2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOFsplash10-0006-0090000000-15d83f92b30f466cd5872017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOFsplash10-0006-0190000000-f95e0c038a6aa70dc02e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOFsplash10-03na-0190000000-72c88d8f9739c7d297142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOFsplash10-077i-0590000000-9c0f5662b9713adab9cb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOFsplash10-0089-1950000000-8b16041ba3b127d299ba2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-ITFT , positive-QTOFsplash10-0089-0290000000-6a16da6c03a03fd87f342017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-QQ , positive-QTOFsplash10-0006-0090000000-145bf44afce31ab82f642017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-QQ , positive-QTOFsplash10-0006-0090000000-68ca013641f0c338b3a22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-QQ , positive-QTOFsplash10-008c-0290000000-d56028ecf88d373b83bd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethoprim LC-ESI-QQ , positive-QTOFsplash10-03n9-0590000000-15246e14a33089adf87d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethoprim 10V, Positive-QTOFsplash10-0006-0090000000-ab604617a206ca2115582016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethoprim 20V, Positive-QTOFsplash10-006x-0190000000-20fc4fb0fdca747b84f82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethoprim 40V, Positive-QTOFsplash10-00dj-3690000000-0ec38b6068b0db0dfb832016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethoprim 10V, Negative-QTOFsplash10-000i-0090000000-8e413946db77cf7ccfea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethoprim 20V, Negative-QTOFsplash10-000i-1090000000-691ddb4fa4a66277fa2e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethoprim 40V, Negative-QTOFsplash10-0006-7390000000-a01859f18f535ce1b0962016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00440 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00440 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00440
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5376
KEGG Compound IDC01965
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrimethoprim
METLIN IDNot Available
PubChem Compound5578
PDB IDNot Available
ChEBI ID45924
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Brumfitt W, Hamilton-Miller JM: Limitations of and indications for the use of co-trimoxazole. J Chemother. 1994 Feb;6(1):3-11. [PubMed:8071675 ]
  2. Brumfitt W, Hamilton-Miller JM: Reassessment of the rationale for the combinations of sulphonamides with diaminopyrimidines. J Chemother. 1993 Dec;5(6):465-9. [PubMed:8195839 ]
  3. Johnson JR, Manges AR, O'Bryan TT, Riley LW: A disseminated multidrug-resistant clonal group of uropathogenic Escherichia coli in pyelonephritis. Lancet. 2002 Jun 29;359(9325):2249-51. [PubMed:12103291 ]
  4. Felmingham D, Reinert RR, Hirakata Y, Rodloff A: Increasing prevalence of antimicrobial resistance among isolates of Streptococcus pneumoniae from the PROTEKT surveillance study, and compatative in vitro activity of the ketolide, telithromycin. J Antimicrob Chemother. 2002 Sep;50 Suppl S1:25-37. [PubMed:12239226 ]
  5. Bean DC, Livermore DM, Papa I, Hall LM: Resistance among Escherichia coli to sulphonamides and other antimicrobials now little used in man. J Antimicrob Chemother. 2005 Nov;56(5):962-4. Epub 2005 Sep 8. [PubMed:16150859 ]

Enzymes

General function:
Involved in dihydrofolate reductase activity
Specific function:
Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis. Binds its own mRNA and that of DHFRL1.
Gene Name:
DHFR
Uniprot ID:
P00374
Molecular weight:
21452.61
References
  1. Laskowska E, Kuczynska-Wisnik D, Bak M, Lipinska B: Trimethoprim induces heat shock proteins and protein aggregation in E. coli cells. Curr Microbiol. 2003 Oct;47(4):286-9. [PubMed:14629008 ]
  2. Floris-Moore MA, Amodio-Groton MI, Catalano MT: Adverse reactions to trimethoprim/sulfamethoxazole in AIDS. Ann Pharmacother. 2003 Dec;37(12):1810-3. [PubMed:14632594 ]
  3. Rosowsky A, Fu H, Chan DC, Queener SF: Synthesis of 2,4-diamino-6-[2'-O-(omega-carboxyalkyl)oxydibenz[b,f]azepin-5-yl]methylpteridine s as potent and selective inhibitors of Pneumocystis carinii, Toxoplasma gondii, and Mycobacterium avium dihydrofolate reductase. J Med Chem. 2004 May 6;47(10):2475-85. [PubMed:15115391 ]
  4. Nahimana A, Rabodonirina M, Bille J, Francioli P, Hauser PM: Mutations of Pneumocystis jirovecii dihydrofolate reductase associated with failure of prophylaxis. Antimicrob Agents Chemother. 2004 Nov;48(11):4301-5. [PubMed:15504856 ]
  5. Barrow EW, Bourne PC, Barrow WW: Functional cloning of Bacillus anthracis dihydrofolate reductase and confirmation of natural resistance to trimethoprim. Antimicrob Agents Chemother. 2004 Dec;48(12):4643-9. [PubMed:15561838 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in thymidylate synthase activity
Specific function:
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
Gene Name:
TYMS
Uniprot ID:
P04818
Molecular weight:
35715.65
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Gamarro F, Yu PL, Zhao J, Edman U, Greene PJ, Santi D: Trypanosoma brucei dihydrofolate reductase-thymidylate synthase: gene isolation and expression and characterization of the enzyme. Mol Biochem Parasitol. 1995 Jun;72(1-2):11-22. [PubMed:8538681 ]
  4. Rosowsky A, Papoulis AT, Forsch RA, Queener SF: Synthesis and antiparasitic and antitumor activity of 2, 4-diamino-6-(arylmethyl)-5,6,7,8-tetrahydroquinazoline analogues of piritrexim. J Med Chem. 1999 Mar 25;42(6):1007-17. [PubMed:10090784 ]
  5. Reche P, Arrebola R, Santi DV, Gonzalez-Pacanowska D, Ruiz-Perez LM: Expression and characterization of the Trypanosoma cruzi dihydrofolate reductase domain. Mol Biochem Parasitol. 1996 Feb-Mar;76(1-2):175-85. [PubMed:8920005 ]
  6. Oefner C, Parisi S, Schulz H, Lociuro S, Dale GE: Inhibitory properties and X-ray crystallographic study of the binding of AR-101, AR-102 and iclaprim in ternary complexes with NADPH and dihydrofolate reductase from Staphylococcus aureus. Acta Crystallogr D Biol Crystallogr. 2009 Aug;65(Pt 8):751-7. doi: 10.1107/S0907444909013936. Epub 2009 Jul 10. [PubMed:19622858 ]
  7. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Romiti N, Tramonti G, Chieli E: Influence of different chemicals on MDR-1 P-glycoprotein expression and activity in the HK-2 proximal tubular cell line. Toxicol Appl Pharmacol. 2002 Sep 1;183(2):83-91. [PubMed:12387747 ]
  2. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]