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etoposide + NADPH + O2
3'-demethyletoposide + NADP+ + H2O
quinine + NADPH + O2
3-hydroxyquinine + NADP+ + H2O
quinine + [reduced NADPH-hemoprotein reductase] + O2
3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
tacrolimus + [reduced NADPH-hemoprotein reductase] + O2
?
-
-
-
-
?
teniposide + [reduced NADPH-hemoprotein reductase] + O2
teniposide catechol + [oxidized NADPH-hemoprotein reductase] + ?
-
-
-
?
etoposide + NADPH + O2
3'-demethyletoposide + NADP+ + H2O
-
-
-
?
etoposide + NADPH + O2
3'-demethyletoposide + NADP+ + H2O
-
-
-
?
quinine + NADPH + O2
3-hydroxyquinine + NADP+ + H2O
-
-
-
-
?
quinine + NADPH + O2
3-hydroxyquinine + NADP+ + H2O
-
-
-
?
quinine + NADPH + O2
3-hydroxyquinine + NADP+ + H2O
-
-
-
?
quinine + NADPH + O2
3-hydroxyquinine + NADP+ + H2O
-
-
-
-
?
quinine + NADPH + O2
3-hydroxyquinine + NADP+ + H2O
-
quinine is used for treatment of severe forms of Plasmodium falciparum malaria, phenotyping of two different populations, overview
-
-
?
quinine + NADPH + O2
3-hydroxyquinine + NADP+ + H2O
-
-
-
-
?
quinine + NADPH + O2
3-hydroxyquinine + NADP+ + H2O
-
-
-
-
?
quinine + [reduced NADPH-hemoprotein reductase] + O2
3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
quinine + [reduced NADPH-hemoprotein reductase] + O2
3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
quinine + [reduced NADPH-hemoprotein reductase] + O2
3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
quinine + [reduced NADPH-hemoprotein reductase] + O2
3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
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anti-CYP2C antibodies
-
inhibition of 20%
-
etoposide
-
maximum inhibition of quinine 3-hydroxylation of 60% at 0.1 mM
grape seed extract
inhibition ranges from 6.4% to 26.8% dependent on the product
-
green tea extract
most pronounced inhibition of CYP3A4, which ranges from 5.6% to 89.9% dependent on the product
-
ketoconazole 2R,4R enantiomer
-
-
ketoconazole 2R,4S enantiomer
-
-
ketoconazole 2S,4R enantiomer
-
-
ketoconazole 2S,4S enantiomer
-
-
Quinine
-
maximum inhibition of etoposide 3'-demethylation of 52% at 0.1 mM
sulfaphenazole
-
inhibits more than 50% at 0.1 mM
2-naphthoflavone
-
0.05 mM 2-naphthoflavone is inhibitory (about 60%) in the presence of low substrate concentrations (0.1 mM)
2-naphthoflavone
-
about 20% inhibition at 0.05 mM
alpha-naphthoflavone
-
-
anti-CYP3A4 antibodies
-
inhibition of 92%
-
anti-CYP3A4 antibodies
-
inhibition of 72%
-
anti-CYP3A4 antibodies
-
-
-
anti-CYP3A4 antibodies
-
inhibition of 96%
-
anti-CYP3A4 antibodies
-
inhibition of 84%
-
Chloroquin
-
-
diazepam
-
-
doxycyclin
-
-
erythromycin
-
about 45% inhibition at 0.01 mM
ketoconazole
-
maximum inhibition of 88%
ketoconazole
-
maximum inhibition of 90% at 0.0005 mM
ketoconazole
-
maximum inhibition of 90% at 0.001 mM
ketoconazole
-
maximum inhibition of 90%
ketoconazole
-
i.e. KTZ, is a antifungal drug, known as an inhibitor of, especially, the CYP3A subfamily, KTZ racemate and four separate enantiomers are evaluated for their selectivity in inhibiting quinine metabolism
ketoconazole
-
complete inhibition at 0.1 mM
ketoconazole
-
maximum inhibition of 94%
ketoconazole
-
maximum inhibition of 91%
midazolam
-
specific inhibitor, about 25% inhibition at 0.01 mM
midazolam
-
about 75% inhibition at 0.05 mM
p-nitrophenol
-
inhibition observed but not quantified
p-nitrophenol
-
inhibits more than 75% at 10 mM
primaquine
-
-
S-mephenytoin
-
maximum inhibition of 74% at 0.12 mM
S-mephenytoin
-
inhibits more than 70% at 0.5 mM
tetracyclin
-
-
troleandomycin
-
maximum inhibition of 93%
troleandomycin
-
maximum inhibition of 70% at 0.08 mM
troleandomycin
-
maximum inhibition of 80% at 0.1 mM
troleandomycin
-
maximum inhibition of 70%
troleandomycin
-
about 95% inhibition at 0.01 mM
troleandomycin
-
complete inhibition at 0.08 mM
troleandomycin
-
maximum inhibition of 85%
troleandomycin
-
about 10% inhibition at 0.05 mM
troleandomycin
-
maximum inhibition of 66%
additional information
ginseng products have little to no effect on the activity of CYP3A4
-
additional information
-
ginseng products have little to no effect on the activity of CYP3A4
-
additional information
-
not inhibited by lignocaine, pyrimethamine, dapsone, chloroquine, diazepam, norfloxacin, proguanil, cycloguanil, and 4-chlorophenylbiguanide
-
additional information
-
not inhibited by fluvoxamine
-
additional information
-
not inhibited by fluvoxamine
-
additional information
-
enzyme activity is not significantly altered following low or high dose of Nigeria honey
-
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CP3A4_HUMAN
503
2
57343
Swiss-Prot
Secretory Pathway (Reliability: 1)
B7P714_IXOSC
163
0
18794
TrEMBL
other Location (Reliability: 3)
B7PME9_IXOSC
524
2
60217
TrEMBL
Secretory Pathway (Reliability: 2)
B7P1N3_IXOSC
259
1
29542
TrEMBL
Secretory Pathway (Reliability: 1)
B7PKJ0_IXOSC
159
0
18245
TrEMBL
other Location (Reliability: 2)
B7PVW7_IXOSC
508
2
58183
TrEMBL
Secretory Pathway (Reliability: 1)
B7Q1D1_IXOSC
140
0
16124
TrEMBL
Secretory Pathway (Reliability: 4)
B7PVW8_IXOSC
419
0
47479
TrEMBL
other Location (Reliability: 2)
B7Q2U5_IXOSC
498
1
57077
TrEMBL
Secretory Pathway (Reliability: 2)
B7P2B0_IXOSC
208
1
24239
TrEMBL
Mitochondrion (Reliability: 5)
B7PES7_IXOSC
363
0
41726
TrEMBL
Mitochondrion (Reliability: 2)
B7P5J6_IXOSC
278
0
31788
TrEMBL
other Location (Reliability: 3)
B7PSW1_IXOSC
280
1
31440
TrEMBL
other Location (Reliability: 2)
B7PWV9_IXOSC
146
1
16730
TrEMBL
Secretory Pathway (Reliability: 1)
B7PFG4_IXOSC
180
0
20790
TrEMBL
other Location (Reliability: 3)
B7P1N5_IXOSC
189
0
21341
TrEMBL
Mitochondrion (Reliability: 5)
B7Q3W6_IXOSC
135
0
15185
TrEMBL
other Location (Reliability: 2)
B7P0T0_IXOSC
202
1
23253
TrEMBL
Mitochondrion (Reliability: 5)
B7QD99_IXOSC
209
1
24137
TrEMBL
Secretory Pathway (Reliability: 4)
B7QDA0_IXOSC
504
1
57487
TrEMBL
Secretory Pathway (Reliability: 3)
E0VSD4_PEDHC
529
0
61663
TrEMBL
Secretory Pathway (Reliability: 2)
B7P474_IXOSC
185
0
21199
TrEMBL
other Location (Reliability: 3)
B7P0T1_IXOSC
178
0
20949
TrEMBL
Mitochondrion (Reliability: 4)
B7QJP4_IXOSC
135
0
15355
TrEMBL
other Location (Reliability: 2)
B7P2B2_IXOSC
204
2
23463
TrEMBL
Secretory Pathway (Reliability: 2)
CP3A4_HUMAN
503
2
57343
Swiss-Prot
-
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Zhao, X.J.; Yokoyama, H.; Chiba, K.; Wanwimolruk, S.; Ishizaki, T.
Identification of human cytochrome P450 isoforms involved in the hydroxylation of quinine by human liver microsomes and nine recombinant human cytochromes P450
J. Pharmacol. Exp. Ther.
279
1327-1334
1996
Homo sapiens
brenda
Zhao, X.J.; Kawashiro, T.; Ishizaki, T.
Mutual inhibition between quinine and etoposide by human liver microsomes. Evidence for cytochrome P4503A4 involvement in their major metabolic pathways
Drug Metab. Dispos.
26
188-191
1997
Homo sapiens
brenda
Zhao, X.J.; Ishizaki, T.
The in vitro hepatic metabolism of quinine in mice, rats and dogs: comparison with human liver microsomes
J. Pharmacol. Exp. Ther.
283
1168-1176
1997
Canis lupus familiaris, Homo sapiens, Mus musculus, Rattus norvegicus
brenda
Relling, M.V.; Evans, R.; Dass, C.; Desiderio, D.M.; Nemec, J.
Human cytochrome P450 metabolism of teniposide and etoposide
J. Pharmacol. Exp. Ther.
261
491-496
1992
Homo sapiens
brenda
Mirghani, R.A.; Sayi, J.; Aklillu, E.; Allqvist, A.; Jande, M.; Wennerholm, A.; Eriksen, J.; Herben, V.M.; Jones, B.C.; Gustafsson, L.L.; Bertilsson, L.
CYP3A5 genotype has significant effect on quinine 3-hydroxylation in Tanzanians, who have lower total CYP3A activity than a Swedish population
Pharmacogenet. Genomics
16
637-645
2006
Homo sapiens
brenda
Allqvist, A.; Miura, J.; Bertilsson, L.; Mirghani, R.A.
Inhibition of CYP3A4 and CYP3A5 catalyzed metabolism of alprazolam and quinine by ketoconazole as racemate and four different enantiomers
Eur. J. Clin. Pharmacol.
63
173-179
2007
Homo sapiens
brenda
Wanwimolruk, S.; Wong, K.; Wanwimolruk, P.
Variable inhibitory effect of different brands of commercial herbal supplements on human cytochrome P-450 CYP3A4
Drug Metabol. Drug Interact.
24
17-35
2009
Homo sapiens (P08684), Homo sapiens
brenda
Diczfalusy, U.; Miura, J.; Roh, H.K.; Mirghani, R.A.; Sayi, J.; Larsson, H.; Bodin, K.G.; Allqvist, A.; Jande, M.; Kim, J.W.; Aklillu, E.; Gustafsson, L.L.; Bertilsson, L.
4Beta-hydroxycholesterol is a new endogenous CYP3A marker: relationship to CYP3A5 genotype, quinine 3-hydroxylation and sex in Koreans, Swedes and Tanzanians
Pharmacogenet. Genomics
18
201-208
2008
Homo sapiens (P08684), Homo sapiens
brenda
Zhang, H.; Coville, P.F.; Walker, R.J.; Miners, J.O.; Birkett, D.J.; Wanwimolruk, S.
Evidence for involvement of human CYP3A in the 3-hydroxylation of quinine
Br. J. Clin. Pharmacol.
43
245-252
1997
Homo sapiens
brenda
Zhao, X.J.; Ishizaki, T.
Metabolic interactions of selected antimalarial and non-antimalarial drugs with the major pathway (3-hydroxylation) of quinine in human liver microsomes
Br. J. Clin. Pharmacol.
44
505-511
1997
Homo sapiens
brenda
Wanwimolruk, S.; Paine, M.F.; Pusek, S.N.; Watkins, P.B.
Is quinine a suitable probe to assess the hepatic drug-metabolizing enzyme CYP3A4?
Br. J. Clin. Pharmacol.
54
643-651
2002
Homo sapiens
brenda
Mirghani, R.A.; Hellgren, U.; Westerberg, P.A.; Ericsson, O.; Bertilsson, L.; Gustafsson, L.L.
The roles of cytochrome P450 3A4 and 1A2 in the 3-hydroxylation of quinine in vivo
Clin. Pharmacol. Ther.
66
454-460
1999
Homo sapiens
brenda
Numata, M.; Fawcett, J.P.; Rosengren, R.J.; Wanwimolruk, S.
Ontogeny of hepatic microsomal 3-hydroxylation of quinine in Adelie Penguins
Comp. Biochem. Physiol. C
138
53-58
2004
Pygoscelis adeliae
brenda
Mirghani, R.A.; Yasar, U.; Zheng, T.; Cook, J.M.; Gustafsson, L.L.; Tybring, G.; Ericsson, O.
Enzyme kinetics for the formation of 3-hydroxyquinine and three new metabolites of quinine in vitro; 3-hydroxylation by CYP3A4 is indeed the major metabolic pathway
Drug Metab. Dispos.
30
1368-1371
2002
Homo sapiens
brenda
Mirghani, R.A.; Ericsson, O.; Tybring, G.; Gustafsson, L.L.; Bertilsson, L.
Quinine 3-hydroxylation as a biomarker reaction for the activity of CYP3A4 in man
Eur. J. Clin. Pharmacol.
59
23-28
2003
Homo sapiens
brenda
Igbinoba, S.I.; Akanmu, M.A.; Onyeji, C.O.; Soyinka, J.O.; Owolabi, A.R.; Nathaniel, T.I.; Pullela, S.V.; Cook, J.M.
Influence of a Nigerian honey on CYP3A4 biotransformation of quinine in healthy volunteers
J. Clin. Pharm. Ther.
40
545-549
2015
Homo sapiens
brenda