BRENDA - Enzyme Database show
show all sequences of 1.14.14.55

Inhibition of CYP3A4 and CYP3A5 catalyzed metabolism of alprazolam and quinine by ketoconazole as racemate and four different enantiomers

Allqvist, A.; Miura, J.; Bertilsson, L.; Mirghani, R.A.; Eur. J. Clin. Pharmacol. 63, 173-179 (2007)

Data extracted from this reference:

Inhibitors
Inhibitors
Commentary
Organism
Structure
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
Homo sapiens
ketoconazole 2R,4R enantiomer
-
Homo sapiens
ketoconazole 2R,4S enantiomer
-
Homo sapiens
ketoconazole 2S,4R enantiomer
-
Homo sapiens
ketoconazole 2S,4S enantiomer
-
Homo sapiens
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
additional information
-
additional information
kinetics
Homo sapiens
Localization
Localization
Commentary
Organism
GeneOntology No.
Textmining
microsome
-
Homo sapiens
-
-
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
quinine + [reduced NADPH-hemoprotein reductase] + O2
Homo sapiens
-
3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Homo sapiens
-
-
-
Purification (Commentary)
Commentary
Organism
native enzyme partially by microsome preparation
Homo sapiens
Source Tissue
Source Tissue
Commentary
Organism
Textmining
liver
-
Homo sapiens
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
quinine + [reduced NADPH-hemoprotein reductase] + O2
-
686501
Homo sapiens
3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
Temperature Optimum [C]
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
37
-
assay at
Homo sapiens
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.4
-
assay at
Homo sapiens
Cofactor
Cofactor
Commentary
Organism
Structure
NADPH
-
Homo sapiens
IC50 Value
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.004
-
pH 7.4, 37C
Homo sapiens
ketoconazole 2S,4S enantiomer
0.01
-
pH 7.4, 37C
Homo sapiens
ketoconazole racemate
0.011
-
pH 7.4, 37C
Homo sapiens
ketoconazole 2S,4R enantiomer
0.014
-
pH 7.4, 37C
Homo sapiens
ketoconazole 2R,4S enantiomer
0.023
-
pH 7.4, 37C
Homo sapiens
ketoconazole 2R,4R enantiomer
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADPH
-
Homo sapiens
IC50 Value (protein specific)
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.004
-
pH 7.4, 37C
Homo sapiens
ketoconazole 2S,4S enantiomer
0.01
-
pH 7.4, 37C
Homo sapiens
ketoconazole racemate
0.011
-
pH 7.4, 37C
Homo sapiens
ketoconazole 2S,4R enantiomer
0.014
-
pH 7.4, 37C
Homo sapiens
ketoconazole 2R,4S enantiomer
0.023
-
pH 7.4, 37C
Homo sapiens
ketoconazole 2R,4R enantiomer
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
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
Homo sapiens
ketoconazole 2R,4R enantiomer
-
Homo sapiens
ketoconazole 2R,4S enantiomer
-
Homo sapiens
ketoconazole 2S,4R enantiomer
-
Homo sapiens
ketoconazole 2S,4S enantiomer
-
Homo sapiens
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
additional information
-
additional information
kinetics
Homo sapiens
Localization (protein specific)
Localization
Commentary
Organism
GeneOntology No.
Textmining
microsome
-
Homo sapiens
-
-
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
quinine + [reduced NADPH-hemoprotein reductase] + O2
Homo sapiens
-
3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
Purification (Commentary) (protein specific)
Commentary
Organism
native enzyme partially by microsome preparation
Homo sapiens
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
liver
-
Homo sapiens
-
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
quinine + [reduced NADPH-hemoprotein reductase] + O2
-
686501
Homo sapiens
3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
Temperature Optimum [C] (protein specific)
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
37
-
assay at
Homo sapiens
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.4
-
assay at
Homo sapiens
Other publictions for EC 1.14.14.55
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [C]
Temperature Range [C]
Temperature Stability [C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [C] (protein specific)
Temperature Range [C] (protein specific)
Temperature Stability [C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
745448
Igbinoba
Influence of a Nigerian honey ...
Homo sapiens
J. Clin. Pharm. Ther.
40
545-549
2015
-
-
-
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1
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1
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2
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1
-
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1
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1
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-
1
-
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-
-
-
-
-
-
-
-
-
-
-
-
-
703423
Wanwimolruk
Variable inhibitory effect of ...
Homo sapiens
Drug Metabol. Drug Interact.
24
17-35
2009
1
1
-
-
-
-
3
-
1
-
-
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-
6
-
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-
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-
1
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1
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-
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1
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1
1
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1
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3
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1
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1
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1
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-
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706089
Diczfalusy
4Beta-hydroxycholesterol is a ...
Homo sapiens
Pharmacogenet. Genomics
18
201-208
2008
-
1
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-
-
-
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2
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1
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1
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1
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1
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1
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1
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-
1
-
-
-
-
-
-
-
-
-
-
1
1
-
-
-
686501
Allqvist
Inhibition of CYP3A4 and CYP3A ...
Homo sapiens
Eur. J. Clin. Pharmacol.
63
173-179
2007
-
-
-
-
-
-
5
1
1
-
-
1
-
2
-
-
1
-
-
1
-
-
1
-
1
-
-
-
1
-
-
1
-
-
5
-
-
-
1
-
-
-
5
5
-
1
1
-
-
1
-
-
-
1
-
1
-
-
1
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
676312
Mirghani
CYP3A5 genotype has significan ...
Homo sapiens
Pharmacogenet. Genomics
16
637-645
2006
-
-
1
-
2
-
-
-
-
-
-
1
-
1
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
1
-
-
-
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-
1
1
-
2
-
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-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
744749
Numata
Ontogeny of hepatic microsoma ...
Pygoscelis adeliae
Comp. Biochem. Physiol. C
138
53-58
2004
-
-
-
-
-
-
3
-
1
-
-
1
-
3
-
-
-
-
-
3
-
-
1
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3
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1
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1
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3
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-
1
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-
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-
-
-
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-
-
-
-
-
-
-
-
744838
Mirghani
Quinine 3-hydroxylation as a ...
Homo sapiens
Eur. J. Clin. Pharmacol.
59
23-28
2003
-
-
-
-
-
-
1
-
-
-
-
1
-
2
-
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-
1
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1
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1
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1
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1
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1
-
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-
-
-
-
-
-
-
-
-
-
-
-
-
744611
Wanwimolruk
Is quinine a suitable probe t ...
Homo sapiens
Br. J. Clin. Pharmacol.
54
643-651
2002
-
-
-
-
-
-
1
-
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1
-
1
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1
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1
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1
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1
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1
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1
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-
-
-
-
-
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-
-
-
-
744769
Mirghani
Enzyme kinetics for the forma ...
Homo sapiens
Drug Metab. Dispos.
30
1368-1371
2002
-
-
-
-
-
-
3
-
1
-
-
1
-
2
-
-
-
-
-
2
-
-
1
-
-
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-
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3
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1
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1
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2
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
744743
Mirghani
The roles of cytochrome P450 ...
Homo sapiens
Clin. Pharmacol. Ther.
66
454-460
1999
-
-
-
-
-
-
2
-
-
-
-
1
-
1
-
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-
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-
2
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1
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2
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1
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-
2
-
-
1
-
-
-
-
-
-
-
-
-
-
-
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-
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-
285328
Zhao
Mutual inhibition between quin ...
Homo sapiens
Drug Metab. Dispos.
26
188-191
1997
-
-
-
-
-
-
4
-
1
-
-
-
-
2
-
-
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-
-
1
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-
2
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4
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1
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1
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2
-
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-
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-
-
-
-
285329
Zhao
The in vitro hepatic metabolis ...
Canis lupus familiaris, Homo sapiens, Mus musculus, Rattus norvegicus
J. Pharmacol. Exp. Ther.
283
1168-1176
1997
4
-
-
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-
32
4
4
-
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-
10
-
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-
4
-
-
4
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4
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32
-
4
4
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4
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4
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744608
Zhang
Evidence for involvement of h ...
Homo sapiens
Br. J. Clin. Pharmacol.
43
245-252
1997
1
-
-
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-
4
1
1
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1
-
2
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1
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1
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1
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1
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4
1
1
1
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1
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1
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1
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-
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-
-
-
744609
Zhao
Metabolic interactions of sel ...
Homo sapiens
Br. J. Clin. Pharmacol.
44
505-511
1997
1
-
-
-
-
-
14
-
1
-
-
1
-
1
-
-
-
-
-
1
-
-
2
-
-
-
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13
1
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13
14
-
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1
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1
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1
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2
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285327
Zhao
Identification of human cytoch ...
Homo sapiens
J. Pharmacol. Exp. Ther.
279
1327-1334
1996
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1
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5
3
1
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1
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285330
Relling
Human cytochrome P450 metaboli ...
Homo sapiens
J. Pharmacol. Exp. Ther.
261
491-496
1992
-
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2
1
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1
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1
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