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Compound Detail

CHEMBL488

AMINOGLUTETHIMIDE
💊 Approved Drug
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💊 Approved Drug
CCC1(c2ccc(N)cc2)CCC(=O)NC1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL488
Name AMINOGLUTETHIMIDE
Phase Approved
Structure Type MOL
InChI Key ROBVIMPUHSLWNV-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Aminoglutethimide Aminoglutetimida Cytadren NSC-330915 Orimeten
9
Targets
65
Activities
3
Assay Types
0
PK Parameters
20
Publications
5
Known Names
3
Indications
2
Mechanisms

Molecular Properties

232.3
MW (Da)
1.35
ALogP
3
HBA
2
HBD
72.2
PSA (Ų)
0.60
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1980
Availability Discontinued
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product

Extended Properties

Molecular Formula C13H16N2O2
MW 232.28
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness 0.08

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cytochrome P450 19A1 inhibitor INHIBITOR Aromatase ✓ ✓
Cytochrome P450 11A1 inhibitor INHIBITOR Cholesterol side-chain cleavage enzyme, mitochondrial ✓ ✓

Indications

Neoplasms Breast Neoplasms Prostatic Neoplasms, Castration-Resistant

ATC Classification

L02BG01
aminoglutethimide
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ENDOCRINE THERAPY

Activity Summary

IC50 54 meas. best 7.08
Ki 10 meas. best 6.33
EC50 1 meas. best 6.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 7.08 7.08 82.9 1
Aromatase
CHEMBL3859
 EC50 6.58 6.58 260.0 1
Aromatase
CHEMBL1978
 IC50 6.57 5.03 270.0 39
Aromatase
CHEMBL1978
 Ki 6.33 5.975 470.0 10
Aromatase
CHEMBL3859
 IC50 5.21 4.84 6200.0 2
Thromboxane-A synthase
CHEMBL1835
 IC50 4.73 4.73 18500.0 1
Cholesterol side-chain cleavage enzyme, mitochondrial
CHEMBL4813
 IC50 4.54 4.5267 29000.0 3
Cytochrome P450 11B2, mitochondrial
CHEMBL3237
 IC50 4.3 4.2 50000.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.3 4.3 50000.0 1
Steroid 17-alpha-hydroxylase/17,20 lyase
CHEMBL3522
 IC50 4.22 4.22 60000.0 1
Cholesterol side-chain cleavage enzyme, mitochondrial
CHEMBL2033
 IC50 4.1 4.1 80000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 82.9 nM 7.08 Displacement of [131I]IMTO from CYP450c 11 in Wistar rat adrenal membrane 18348518
Aromatase EC50 = 260.0 nM 6.58 In vitro inhibition of cytochrome P450 19A1 by rat ovarian microsomes incubated ... 3612685
Aromatase IC50 = 270.0 nM 6.57 Inhibition of human aromatase 17511439
Aromatase IC50 = 270.0 nM 6.57 Inhibition of aromatase after 30 mins by fluorescence assay 19265439
Aromatase Ki = 470.0 nM 6.33 Competitive inhibition of human placental Cytochrome P450 19A1 1825337
Aromatase Ki = 600.0 nM 6.22 Inhibitory constant (Ki) for Cytochrome P450 19A1 3968684
Aromatase Ki = 600.0 nM 6.22 Inhibition of human placental cytochrome P450 19A1 with testosterone 3625703
Aromatase Ki = 600.0 nM 6.22 Binding affinity was measured on Cytochrome P450 19A1 2231592
Aromatase Ki = 680.0 nM 6.17 Inhibition of Cytochrome P450 19A1 against testosterone at 1.5 uM (Km=0.13 uM) 3754286
Aromatase Ki = 1410.0 nM 5.85 Apparent Ki against human aromatase 15267241
Aromatase Ki = 1410.0 nM 5.85 Inhibitory constant against human placental atomatase at pH 7.0 and 37 degree C 15911319
Aromatase IC50 = 1700.0 nM 5.77 Inhibition of human placental microsome cytochrome P450 19A1 1825337
Aromatase Ki = 1800.0 nM 5.75 Apparent inhibition constant (Ki) for cytochrome P450 19A1 3361583
Aromatase Ki = 1800.0 nM 5.75 Inhibition of human placental cytochrome P450 19A1 with androstenedione 3625703
Aromatase IC50 = 1900.0 nM 5.72 In vitro inhibition of human placental Cytochrome P450 19A1 8496907
Aromatase IC50 = 1900.0 nM 5.72 In vitro inhibition of cytochrome P450 19A1 Aromatase 2016706
Aromatase IC50 = 2800.0 nM 5.55 Inhibitory concentration against human placental aromatase by deutirium oxide re... 15911319
Aromatase IC50 = 2800.0 nM 5.55 Inhibitory concentration against human placental aromatase 15267241
Aromatase Ki = 4100.0 nM 5.39 Inhibition of human aromatase extracted from placental microsomes using [1,2-3H]... 26469743
Aromatase IC50 = 5200.0 nM 5.28 In vitro inhibition of [1,2,6,7-3H]-androstenedione binding to human placental m... 11909717

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 173
- 10.5281/zenodo.13943903 ADMET 79
31158845 10.1038/s41586-019-1291-3 ADMET 59
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
2016706 10.1021/jm00108a013 Rattus norvegicus 10
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
8176705 10.1021/jm00035a007 Rattus norvegicus 7
1895288 10.1021/jm00113a004 Rattus norvegicus 6
15911319 10.1016/j.bmc.2005.03.050 Aromatase 5
7783141 10.1021/jm00012a009 Aromatase 5
15267241 10.1021/jm0306024 Aromatase 5
1895288 10.1021/jm00113a004 Aromatase 5
3625703 10.1021/jm00392a004 Aromatase 5
2016706 10.1021/jm00108a013 Aromatase 4
3361583 10.1021/jm00400a014 Aromatase 4
1825337 10.1021/jm00106a038 Aromatase 4
3735304 10.1021/jm00158a007 Aromatase 3
10450990 10.1016/s0960-894x(99)00328-5 Aromatase 3

Data from ChEMBL 36 via Core Engine