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Drug-Target Interaction

Drug

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PubChem ID:441233
Structure:
Synonyms:
(1R)-2-phenylcyclopropan-1-amine
155-09-9
AC1L9ASR
C07155
D08625
DB00752
Parnate
Tranylcypromine
Tranylcypromine (INN)
ATC-Codes:
Side-Effects:
Side-EffectFrequency
insomnia0
thrombocytopenia0
tachycardia0
spasm0
scleroderma0
paresthesia0
weakness0
palpitations0
numbness0
tinnitus0
tremor0
urinary incontinence0
memory loss0
urinary frequency0
manic0
blurred vision0
chills0
urinary retention0
dry mouth0
urticaria0
nausea0
leukopenia0
constipation0
confusion0
ataxia0
anxiety0
anorexia0
anemia0
alopecia0
agranulocytosis0
cystic acne0
diarrhea0
dizziness0
siadh0
impotence0
hepatitis0
blood dyscrasia0
headache0
rash0
edema0
somnolence0
abdominal pain0

Target

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Uniprot ID:CP3A4_HUMAN
Synonyms:
Albendazole monooxygenase
Albendazole sulfoxidase
CYPIIIA3
CYPIIIA4
Cytochrome P450 3A3
Cytochrome P450 3A4
HLp
NF-25
Nifedipine oxidase
P450-PCN1
Quinine 3-monooxygenase
Taurochenodeoxycholate 6-alpha-hydroxylase
EC-Numbers:1.14.13.32
1.14.13.67
1.14.13.97
Organism:Homo sapiens
Human
PDB IDs:1TQN 1W0E 1W0F 1W0G 2J0D 2V0M
Structure:
2V0M

Binding Affinities:

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

References:

11181487
In vitro inhibition of cytochrome P450 enzymes in human liver microsomes by a potent CYP2A6 inhibitor, trans-2-phenylcyclopropylamine (tranylcypromine), and its nonamine analog, cyclopropylbenzene.. P Taavitsainen; R Juvonen; O Pelkonen (2001) Drug metabolism and disposition: the biological fate of chemicals display abstract
Currently, there are no selective, well characterized inhibitors for CYP2A6. Therefore, the effects of trans-(+/-)-2-phenylcyclopropylamine (tranylcypromine), a potent CYP2A6 inhibitor, on human liver microsomal cytochromes P450 (CYP) were studied to elucidate its selectivity. The IC50 value of tranylcypromine in coumarin 7-hydroxylation (CYP2A6 model activity) was 0.42 +/- 0.07 microM and in chlorzoxazone 6-hydroxylation (CYP2E1 model activity) 3.0 +/- 1.1 microM. The IC50 values for CYP1A2, CYP2C9, CYP2C19, CYP2D6, and CYP3A4 activities were >10 microM. Potency and selectivity of tranylcypromine were strongly dependent on the amine group, because its nonamine analog cyclopropylbenzene was much less potent inhibitor of CYP1A, CYP2A6, CYP2C19, and CYP2E1 activities and did not inhibit at all CYP2C9, CYP2D6, or CYP3A4 activities. In human liver microsomes tranylcypromine induced type II and cyclopropylbenzene type I difference spectrum. According to the double reciprocal analysis of these spectral responses both tranylcypromine and cyclopropylbenzene may have at least two P450-related binding sites in liver microsomes. The K(a) values of tranylcypromine varied from 4.5 to 15.1 microM and -34.3 to 167 microM in microsomes derived from three different livers and of cyclopropylbenzene from -1.6 to 10.1 microM and -34.6 and 75.2 microM in the same liver microsomes. Based on these results, tranylcypromine seems an adequately selective CYP2A6 inhibitor for in vitro use.