We're sorry, but BRENDA doesn't work properly without JavaScript. Please make sure you have JavaScript enabled in your browser settings.
Information on EC 1.14.14.55 - quinine 3-monooxygenase for references in articles please use BRENDA:EC1.14.14.55
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
EC Tree
The enzyme appears in viruses and cellular organisms
Synonyms
CYP2C19, CYP3A, CYP3A4, CYPIIIA4, cytochrome P450 isoform, NF-25, Nifedipine oxidase, P450-PCN1, quinine 3-hydroxylase, Quinine 3-monooxygenase,
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
cytochrome P450 isoform
-
-
-
-
Nifedipine oxidase
-
-
-
-
quinine 3-hydroxylase
-
-
-
-
Quinine 3-monooxygenase
-
-
-
-
quinine monooxygenase
-
-
CYP3A4
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
quinine + [reduced NADPH-hemoprotein reductase] + O2 = 3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
quinine,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase
A cytochrome P-450 (heme-thiolate) protein.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
-
-
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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 + [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
-
-
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
-
not inhibited by lignocaine, pyrimethamine, dapsone, chloroquine, diazepam, norfloxacin, proguanil, cycloguanil, and 4-chlorophenylbiguanide
-
additional information
-
not inhibited by fluvoxamine
-
additional information
-
enzyme activity is not significantly altered following low or high dose of Nigeria honey
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
2-naphthoflavone
-
0.05 mM 2-naphthoflavone activates the enzyme (about 40%) in the presence of high substrate concentrations (0.5 mM)
grape seed extract
-
some brands cause minor activation of CYP3A4
-
additional information
-
not activated by 0.025 mM 2-naphthoflavone
-
alpha-naphthoflavone
-
-
diazepam
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
additional information
etoposide
0.00083
Quinine
-
at pH 7.4 and 37°C
0.046
Quinine
-
recombinant CYP2C19
0.106
Quinine
-
between 0.08 mM and 0.145 mM in 10 different human livers
0.114
Quinine
-
recombinant CYP3A4
additional information
etoposide
-
between 0.0421 mM and 0.1151 mM
additional information
additional information
-
kinetics
-
additional information
tenoposide
-
between 0.0197 mM and 0.0435 mM
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
0.00327
Quinine
-
recombinant CYP2C19
0.125
Quinine
-
recombinant CYP3A4
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
0.11
midazolam
-
at pH 7.4 and 37°C
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
0.097
cimetidine
Homo sapiens
-
at pH 7.4 and 37°C
0.127
diltiazem
Homo sapiens
-
at pH 7.4 and 37°C
0.017
doxycycline
Homo sapiens
-
at pH 7.4 and 37°C
0.061
erythromycin
Homo sapiens
-
at pH 7.4 and 37°C
0.197
hydralazine
Homo sapiens
-
at pH 7.4 and 37°C
0.000026
ketoconazole
Homo sapiens
-
at pH 7.4 and 37°C
0.023
ketoconazole 2R,4R enantiomer
Homo sapiens
-
pH 7.4, 37°C
0.014
ketoconazole 2R,4S enantiomer
Homo sapiens
-
pH 7.4, 37°C
0.011
ketoconazole 2S,4R enantiomer
Homo sapiens
-
pH 7.4, 37°C
0.004
ketoconazole 2S,4S enantiomer
Homo sapiens
-
pH 7.4, 37°C
0.01
ketoconazole racemate
Homo sapiens
-
pH 7.4, 37°C
0.038
nifepidine
Homo sapiens
-
at pH 7.4 and 37°C
0.143
oleandomycin
Homo sapiens
-
at pH 7.4 and 37°C
0.018
Omeprazole
Homo sapiens
-
at pH 7.4 and 37°C
0.02
primaquine
Homo sapiens
-
at pH 7.4 and 37°C
0.029
tetracycline
Homo sapiens
-
at pH 7.4 and 37°C
0.0083
troleandomycin
Homo sapiens
-
at pH 7.4 and 37°C
0.064
verapamil
Homo sapiens
-
at pH 7.4 and 37°C
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
dog
-
-
brenda
mouse
-
-
brenda
-
-
-
brenda
rat
-
-
brenda
-
-
-
brenda
-
UniProt
brenda
human
-
-
brenda
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
-
-
brenda
-
-
brenda
-
-
brenda
-
-
brenda
-
-
285327 , 285328 , 285329 , 285330 , 686501 , 703423 , 744608 , 744609 , 744611 , 744769 , 744838
brenda
-
-
brenda
-
-
brenda
-
-
brenda
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
-
-
-
brenda
-
-
-
brenda
-
-
-
brenda
-
-
-
brenda
-
-
-
brenda
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
physiological function
-
differences in the activity of both CYP3A4 and CYP3A5 in Koreans, Swedes and Tanzanians. Both 4beta-hydroxycholesterol and quinine/3-hydroxyquinine metabolic ratio show a higher CYP3A activity in women than in men
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CP3A4_HUMAN
503
2
57343
Swiss-Prot
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
A6986AG
-
single nucleotide polymorphism responsible for different CYP3A genotypes, CYP3A5 allele and genotype frequency in the populations, overview
additional information
-
the CYP3A5 genotype has significant effect on quinine 3-hydroxylation in black Tanzanians, who have lower total CYP3A activity compared to a population of Swedish caucasians, overview
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
native enzyme partially by microsome preparation
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
expression of CYP3A4 in human B lymphoblastoid cell line AHH-1
-
genes CYP3A5 and CYP3A4, DNA sequence determination, genotyping of two different human populations revealing the CYP3A5 and the CYP3A4 genotypes
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
medicine
-
green tea extract use may cause significant interactions with drugs metabolized by CYP3A4. Effect on CYP3A4 varies among different brands of green tea extract, possibly due to variations in their content of the herbal product's active ingredients
medicine
-
plasma concentration of 4beta-hydroxycholesterol may be used as an endogenous marker of CYP3A activity
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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, Homo sapiens (P08684)
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, Homo sapiens (P08684)
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
Select items on the left to see more content.
html completed
HOME
login
history
all enzymes
BRENDA home
History
1.14.14.55 quinine 3-monooxygenase
more
top
Information
