Home
Drugs
Targets
Pathways
Ontologies
Cyp450s
Adv.search
Help/FAQ

Drug-Target Interaction

Drug

show drug details
PubChem ID:5578
Structure:
Synonyms:
"trimethoprim (8064-90-2 (trimethoprim/sulfamethoxazole); tmp/smx (mixture))"
2,4-Diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidine
2,4-diamino-5-(3,4,5-trimethoxybenzyl) pyrimidine
2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine
2,4-Diamino-5-(3,4,5-trimethoxyphenzyl)pyrimidine
2,4-Diamino-5-[3,4,5-trimethoxy-benzyl]pyrimidine
2,4-Pyrimidinediamine, 5-((3,4,5-trimethoxyphenyl)-methyl)-
2,4-Pyrimidinediamine, 5-((3,4,5-trimethoxyphenyl)methyl)-
2,4-Pyrimidinediamine, 5-[(3,4,5-trimethoxyphenyl)methyl]-
46984_FLUKA
46984_RIEDEL
5-((3,4,5-Trimethoxyphenyl)methyl)-2,4-pyrimidinediamine
5-(3,4,5-Trimethoxy-benzyl)-pyrimidine-2,4-diamine
5-(3,4,5-Trimethoxybenzyl)-2,4-diaminopyrimidine
5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine
5-25-13-00429 (Beilstein Handbook Reference)
5-[(3,4,5-trimethoxyphenyl)methyl]-2,4-pyrimidinediamine
5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
5-{[3,4,5-tris(methyloxy)phenyl]methyl}pyrimidine-2,4-diamine
738-70-5
8064-90-2
92131_FLUKA
92131_SIGMA
AB00052118
AB1004879
Abaprim
AC-13572
AC1L1KNQ
AC1Q48DF
Acuco
AI3-52594
AIDS-010922
AIDS-110808
AIDS010922
AIDS110808
AKOS001650069
Alcorim-F
Alprim
Anitrim
Antrima
Antrimox
Apo-Sulfatrim
ARONIS24118
AZT + TMP/SMX (mixture) combination
Bacdan
Bacidal
Bacide
Bacin
Bacta
Bacterial
Bacterial [Antibiotic]
Bacticel
Bactifor
Bactin
Bactoprim
Bactramin
Bactrim
Bactrim DS
BACTRIM PEDIATRIC
BB_SC-2116
Bencole
Bethaprim
BIDD:GT0190
Biosulten
BPBio1_000215
BRD-K07208025-001-06-5
Briscotrim
BRN 0625127
BSPBio_000195
BSPBio_002245
BW 56-72
BW 5672
BW-56-72
C01965
C14H18N4O3
CAS-738-70-5
CCG-40335
CCRIS 2410
Centrim
CHEBI:45924
CHEMBL22
Chemotrin
Cidal
Co-Trimoxizole
Colizole
Colizole DS
component of Bactrim
component of Septra
Conprim
Cotrim
COTRIM D.S
Cotrimel
CPD0-1581
CPD000035999
D00145
D014295
DB00440
Deprim
Diseptyl
DivK1c_000589
Dosulfin
DRG-0030
Duocide
EINECS 212-006-2
Esbesul
Espectrin
EU-0101271
Euctrim
Exbesul
Fermagex
Fortrim
Futin
HMS1568J17
HMS1921I03
HMS2090D14
HMS2092A10
HMS2095J17
HMS2230L06
HMS3259I11
HMS3263P04
HMS501N11
HSDB 6781
I06-0086
IDI1_000589
Idotrim
Ikaprim
Instalac
Ipral
KBio1_000589
KBio2_000647
KBio2_003215
KBio2_005783
KBio3_001465
KBioGR_000863
KBioSS_000647
Kombinax
KSC-4-158
KUC103659N
Lagatrim
Lagatrim Forte
Lastrim
Lescot
Lopac-T-7883
Lopac0_001271
LS-1627
Methoprim
Metoprim
Mixture Name
MLS000079023
MLS001201740
MLS002303068
Monoprim
Monotrim
Monotrimin
NCGC00016055-01
NCGC00016055-02
NCGC00016055-03
NCGC00016055-04
NCGC00016055-05
NCGC00016055-06
NCGC00016055-07
NCGC00016055-08
NCGC00016055-09
NCGC00016055-10
NCGC00016055-11
NCGC00016055-12
NCGC00016055-13
NCGC00016055-14
NCGC00024707-01
NCGC00024707-03
NCGC00024707-04
NCGC00024707-05
NCGC00024707-06
NCGC00024707-07
NCGC00024707-08
nchembio.108-comp1
nchembio.215-comp11
nchembio.221-comp23
NIH 204
NIH 204 (VAN)
NINDS_000589
Novotrimel
NSC 106568
NSC-106568
NSC106568
Omstat
Oprea1_495058
Oraprim
Pancidim
Polytrim
Prestwick0_000208
Prestwick1_000208
Prestwick2_000208
Prestwick3_000208
Prestwick_485
Priloprim
Primosept
Primsol
Proloprim
Proloprim (TN)
Protrin
Purbal
Pyrimidine, 2,4-diamino-5-(3,4,5-trimethoxybenzyl)-
Resprim
Resprim Forte
Roubac
Roubal
Salvatrim
SAM002264649
Septra
SEPTRA DS
SEPTRA GRAPE
Septrin DS
Septrin Forte
Septrin S
Setprin
Sinotrim
SMP2_000262
SMR000035999
Smz-Tmp
SMZ/TMP
SPBio_000874
SPBio_002116
SPECTRUM1500595
Spectrum2_000937
Spectrum3_000643
Spectrum4_000372
Spectrum5_001559
Spectrum_000167
ST024737
STK177322
Stopan
Streptoplus
Sugaprim
Sulfamar
Sulfamethoprim
SULFAMETHOPRIM-DS
SULFAMETHOXAZOLE & TRIMETHOPRIM
SULFAMETHOXAZOLE AND TRIMETHOPRIM
SULFAMETHOXAZOLE AND TRIMETHOPRIM AND PENAZOPYRIDINE HCL
SULFAMETHOXAZOLE AND TRIMETHOPRIM DOUBLE STRENGTH
SULFAMETHOXAZOLE AND TRIMETHOPRIM SINGLE STRENGTH
Sulfamethoxazole Trimethoprim
Sulfatrim
SULFATRIM PEDIATRIC
SULFATRIM-DS
SULFATRIM-SS
Sulfoxaprim
Sulmeprim
SULMEPRIM PEDIATRIC
Sulthrim
Sultrex
Syraprim
T 7883
T2286
T7883_SIGMA
TCMDC-125538
Tiempe
TL8005108
TMP
Tmp Smx
Tmp-Ratiopharm
TMP/SMX
Tocris-0650
TOP
Toprim
Trimanyl
Trimeth/Sulfa
Trimethioprim
Trimethopim(TMP)
Trimethoprim
Trimethoprim & VRC3375
TRIMETHOPRIM (8064-90-2 (TRIMETHOPRIM/SULFAMETHOXAZOLE)
TRIMETHOPRIM (8064-90-2 (TRIMETHOPRIM/SULFAMETHOXAZOLE); TMP/SMX (MIXTURE))
Trimethoprim (JAN/USP/INN)
TRIMETHOPRIM SULFATE AND POLYMYXIN B SULFATE
Trimethoprim [USAN:BAN:INN:JAN]
Trimethoprim/sulfamethoxazole (commercial)
Trimethoprime
Trimethoprime [INN-French]
Trimethoprimum
Trimethoprimum [INN-Latin]
Trimethopriom
Trimetoprim
Trimetoprim [DCIT]
Trimetoprim [Polish]
Trimetoprima
Trimetoprima [INN-Spanish]
Trimexazole
Trimexol
Trimez-IFSA
Trimezol
Trimogal
Trimono
Trimopan
Trimpex
Trimpex (TN)
TRIMPEX 200
Triprim
Trisul
Trisulcom
Trisulfam
Trisural
U-Prin
UNII-AN164J8Y0X
UPCMLD-DP132
UPCMLD-DP132:001
Uretrim
Uro-D S
Urobactrim
UROPLUS DS
UROPLUS SS
Utetrin
Velaten
Veltrim
Wellcoprim
Wellcoprin
WLN: T6N CNJ BZ DZ E1R CO1 DO1 EO1
WR 5949
Xeroprim
Zamboprim
ZINC06627681
ATC-Codes:
Side-Effects:
Side-EffectFrequency
methemoglobinemia0
anemia0
exfoliative dermatitis0
vomiting0
hyperkalemia0
anaphylaxis0
nausea0
hyponatremia0
glossitis0
megaloblastic anemia0
pruritus0
neutropenia0
stevens - johnson syndrome0
erythema0
rash0
erythema multiforme0
jaundice0
toxic epidermal necrolysis0
fever0
aseptic meningitis0
hypersensitivity0
thrombocytopenia0
leukopenia0

Target

show target details
Uniprot ID:CP2C9_HUMAN
Synonyms:
(R)-limonene 6-monooxygenase
(S)-limonene 6-monooxygenase
(S)-limonene 7-monooxygenase
CYPIIC9
Cytochrome P450 2C9
P-450MP
P450 MP-4/MP-8
P450 PB-1
S-mephenytoin 4-hydroxylase
EC-Numbers:1.14.13.48
1.14.13.49
1.14.13.80
Organism:Homo sapiens
Human
PDB IDs:1OG2 1OG5 1R9O
Structure:
1R9O

Binding Affinities:

Ki: Kd:Ic 50:Ec50/Ic50:
----
----

References:

11996015
12019187
Trimethoprim and sulfamethoxazole are selective inhibitors of CYP2C8 and CYP2C9, respectively.. Xia Wen; Jun-Sheng Wang; Janne T Backman; Jouko Laitila; Pertti J Neuvonen (2002) Drug metabolism and disposition: the biological fate of chemicals display abstract
To evaluate the inhibitory effects of trimethoprim and sulfamethoxazole on cytochrome P450 (P450) isoforms, selective marker reactions for CYP1A2, CYP2A6, CYP2C8, CYP2C9, CYP2C19, CYP2D6, CYP2E1, and CYP3A4 were examined in human liver microsomes and recombinant CYP2C8 and CYP2C9. The in vivo drug interactions of trimethoprim and sulfamethoxazole were predicted in vitro using [I]/([I] + K(i)) values. With concentrations ranging from 5 to 100 microM, trimethoprim exhibited a selective inhibitory effect on CYP2C8-mediated paclitaxel 6alpha-hydroxylation in human liver microsomes and recombinant CYP2C8, with apparent IC(50) (K(i)) values of 54 microM (32 microM) and 75 microM, respectively. With concentrations ranging from 50 to 500 microM, sulfamethoxazole was a selective inhibitor of CYP2C9-mediated tolbutamide hydroxylation in human liver microsomes and recombinant CYP2C9, with apparent IC(50) (K(i)) values of 544 microM (271 microM) and 456 microM, respectively. With concentrations higher than 100 microM trimethoprim and 500 microM sulfamethoxazole, both drugs lost their selectivity for the P450 isoforms. Based on estimated total hepatic concentrations (or free plasma concentrations) of the drugs and the scaling model, one would expect in vivo in humans 80% (26%) and 13% (24%) inhibition of the metabolic clearance of CYP2C8 and CYP2C9 substrates by trimethoprim and sulfamethoxazole, respectively. In conclusion, trimethoprim and sulfamethoxazole can be used as selective inhibitors of CYP2C8 and CYP2C9 in in vitro studies. In humans, trimethoprim and sulfamethoxazole may inhibit the activities of CYP2C8 and CYP2C9, respectively.