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Compound Detail

CHEMBL3989843

TRANYLCYPROMINE
💊 Approved Drug
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💊 Approved Drug
N[C@@H]1C[C@H]1c1ccccc1.N[C@H]1C[C@@H]1c1ccccc1

Basic Information

ChEMBL ID CHEMBL3989843
Name TRANYLCYPROMINE
Phase Approved
Structure Type MOL
InChI Key IGLYMJRIWWIQQE-QUOODJBBSA-N
Therapeutic ✓ Yes

Known Names

NSC-80664 Tranilcipromina Tranylcypromine
16
Targets
141
Activities
4
Assay Types
11
PK Parameters
20
Publications
3
Known Names
9
Indications

Molecular Properties

266.4
MW (Da)

Drug Information

Molecule Type Small molecule
First Approval 1961
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning

Extended Properties

Molecular Formula C18H22N2
MW 266.39

Indications

Depressive Disorder Depressive Disorder Anxiety Dementia Schizophrenia Hypotension, Orthostatic Leukemia Leukemia, Myeloid, Acute Myelodysplastic Syndromes

ATC Classification

N06AF04
tranylcypromine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 107 meas. best 8.35
Ki 30 meas. best 7.58
Kd 3 meas. best 5.7
EC50 1 meas. best 5.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Lysine-specific histone demethylase 1A
CHEMBL6136
IC50 8.35 4.7888 4.5 26
Amine oxidase [flavin-containing] B
CHEMBL2039
IC50 8.03 5.738 9.4 20
Amine oxidase [flavin-containing] B
CHEMBL2039
Ki 7.58 5.3075 26.0 4
Cytochrome P450 2A6
CHEMBL5282
IC50 7.1 6.446 80.0 5
Amine oxidase [flavin-containing] A
CHEMBL1951
IC50 7.07 5.6242 85.0 19
Cytochrome P450 2A6
CHEMBL5282
Ki 6.89 6.89 130.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL4153
Ki 5.75 5.75 1800.0 1
Cytochrome P450 2C19
CHEMBL3622
IC50 5.72 5.2716 1900.0 19
Cytochrome P450 2A6
CHEMBL5282
Kd 5.7 5.7 2000.0 1
Cytochrome P450 2A13
CHEMBL3542436
Kd 5.64 5.64 2300.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
EC50 5.57 5.57 2697.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
Ki 5.3 5.3 5000.0 1
Sigma intracellular receptor 2
CHEMBL4105864
Ki 5.21 5.21 6200.0 1
Cytochrome P450 2B6
CHEMBL4729
IC50 5.21 5.1957 6200.0 7
Cytochrome P450 2A13
CHEMBL3542436
Ki 5.19 5.19 6500.0 1
7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase
CHEMBL4523494
IC50 5.11 5.11 7800.0 1
LSD1/CoREST complex
CHEMBL3137262
IC50 5.06 4.75 8800.0 3
D(3) dopamine receptor
CHEMBL3138
Ki 4.89 4.89 12793.0 1
Serine protease 1
CHEMBL3769
Ki 4.88 4.88 13300.0 1
Lysine-specific histone demethylase 1A
CHEMBL6136
Ki 4.68 4.496 21000.0 5
D(2) dopamine receptor
CHEMBL339
Ki 4.23 4.23 58737.0 1
Lysine-specific histone demethylase 1A/REST corepressor
CHEMBL4296114
IC50 4.05 4.05 89080.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 490.0 nM Homo sapiens
Fu 0.49 - Not specified
Fu 0.53 - Not specified
Fu 0.612 - Not specified
Fu 0.63 - Not specified
Inhibition 97.0 % Homo sapiens
Inhibition 98.0 % Homo sapiens
Inhibition 99.0 % Homo sapiens
Inhibition 96.0 % Homo sapiens
Inhibition 99.0 % Homo sapiens
Inhibition 97.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Lysine-specific histone demethylase 1A IC50 = 4.5 nM 8.35 Inhibition of LSD1 (unknown origin) 36537915
Amine oxidase [flavin-containing] B IC50 = 9.4 nM 8.03 Inhibition of recombinant human MAOB expressed in baculovirus infected BTI insec... 30611617
Amine oxidase [flavin-containing] B Ki = 26.0 nM 7.58 Inhibition of human recombinant soluble MAO-B expressed in Pichia pastoris incub... 25600407
Cytochrome P450 2A6 IC50 = 80.0 nM 7.1 Inhibition Assay: The inhibition of human CYP2A6-mediated 7-hydroxy coumarin for... -
Cytochrome P450 2A6 IC50 = 80.0 nM 7.1 Inhibition of CYP2A6 in human liver microsomes assessed as reduction in CYP2A6-m... -
Amine oxidase [flavin-containing] A IC50 = 85.0 nM 7.07 Inhibition of recombinant human MAOA expressed in baculovirus infected BTI insec... 30611617
Cytochrome P450 2A6 Ki = 130.0 nM 6.89 Mixed inhibition of CYP2A6 (unknown origin) 22696418
Amine oxidase [flavin-containing] A IC50 = 240.0 nM 6.62 Inhibition of human recombinant MAO-A assessed as kynuramine oxidation to 4-hydr... 24393810
Amine oxidase [flavin-containing] B IC50 = 250.0 nM 6.6 Inhibition of human recombinant MAO-B assessed as kynuramine oxidation to 4-hydr... 24393810
Amine oxidase [flavin-containing] B IC50 = 560.0 nM 6.25 Inhibition of MAOB (unknown origin) by Promega MAO-Glo assay 30713023
Amine oxidase [flavin-containing] B IC50 = 600.0 nM 6.22 Fluorescent-Based (Inhibitor) Screening Assay: Human recombinant monoamine oxida... -
Amine oxidase [flavin-containing] B IC50 = 600.0 nM 6.22 Fluorescent-Based (Inhibitor) Screening Assay: Human recombinant monoamine oxida... -
Amine oxidase [flavin-containing] B IC50 = 800.0 nM 6.1 Inhibition of recombinant human MAOB incubated for 15 mins measured after 30 min... 28186755
Amine oxidase [flavin-containing] B IC50 = 890.0 nM 6.05 Inhibition of human recombinant MAOB expressed in Pichia pastoris incubated for ... 25768700
Cytochrome P450 2A6 IC50 = 970.0 nM 6.01 Inhibition of human CYP2A6 expressed in insect cell microsomes assessed as reduc... -
Cytochrome P450 2A6 IC50 = 970.0 nM 6.01 Inhibition Assay: The inhibition of human CYP2A6-mediated 7-hydroxy coumarin for... -
Cytochrome P450 2A6 IC50 = 970.0 nM 6.01 Inhibition Assay: The inhibition of human CYP2A6-mediated 7-hydroxy coumarin for... -
Amine oxidase [flavin-containing] A IC50 = 1020.0 nM 5.99 Inhibition of MAOA (unknown origin) by Promega MAO-Glo assay 30713023
Amine oxidase [flavin-containing] B IC50 = 1050.0 nM 5.98 Inhibition of human recombinant MAOB expressed in Pichia pastoris incubated for ... 25173853
Amine oxidase [flavin-containing] A IC50 = 1060.0 nM 5.97 Inhibition of recombinant human MAOA incubated for 15 mins measured after 30 min... 28186755

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.1007/s00044-009-9176-x Mus musculus 8
21098647 10.1124/dmd.110.036988 ADMET 5
6716406 10.1021/jm00371a023 Mus musculus 4
7265121 10.1021/jm00135a020 Mus musculus 4
36537915 10.1021/acs.jmedchem.2c01324 Lysine-specific histone demethylase 1A 4
24237195 10.1021/jm400870h Lysine-specific histone demethylase 1A 4
- 10.1039/C6MD00170J NON-PROTEIN TARGET 4
25725609 10.1016/j.bmc.2015.01.049 Lysine-specific histone demethylase 1A 4
20014752 10.1021/tx900326k Hepatotoxicity 3
32283297 10.1016/j.ejmech.2020.112281 Lysine-specific histone demethylase 1A 3
21382717 10.1016/j.bmc.2011.02.017 Lysine-specific histone demethylase 1A 3
36537915 10.1021/acs.jmedchem.2c01324 Amine oxidase [flavin-containing] B 3
24848155 10.1021/jm401798r Unchecked 3
28186755 10.1021/acs.jmedchem.6b01018 LSD1/CoREST complex 3
- 10.1039/C4MD00031E Lysine-specific histone demethylase 1A 3
24393810 10.1016/j.ejmech.2013.11.035 Rattus norvegicus 3

Data from ChEMBL 36 via Core Engine