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Compound Detail

CHEMBL427

MECHLORETHAMINE
💊 Approved Drug
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💊 Approved Drug

Basic Information

ChEMBL ID CHEMBL427
Name MECHLORETHAMINE
Phase Approved
Structure Type MOL
InChI Key HAWPXGHAZFHHAD-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Chlorethazine Chlormethine Clormetina Ledaga Mechlorethamine Nitrogen mustard (hn 2) NSC-10107 NSC-128663 NSC-757087
7
Targets
10
Activities
1
Assay Types
2
PK Parameters
20
Publications
9
Known Names
6
Indications
1
Mechanisms

Molecular Properties

156.1
MW (Da)
1.40
ALogP
1
HBA
0
HBD
3.2
PSA (Ų)
0.56
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1949
Availability Prescription
Chirality Achiral

Routes of Administration

Parenteral Topical

Flags

Black Box Warning Natural Product

Extended Properties

Molecular Formula C5H11Cl2N
MW 156.06
Aromatic Rings 0
Heavy Atoms 8
NP-Likeness -0.71

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA inhibitor INHIBITOR DNA ✓ ✓

Indications

Mycosis Fungoides Neoplasms Lymphoma Hodgkin Disease Lichen Planus Lymphoma, T-Cell, Cutaneous

ATC Classification

L01AA05
chlormethine
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 10 meas. best 7.54

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
ADMET
CHEMBL612558
 IC50 7.54 6.2667 29.0 3
EMT6
CHEMBL614294
 IC50 6.82 6.82 150.0 1
SK-OV-3
CHEMBL614925
 IC50 5.96 5.96 1090.0 1
CHO-AA8
CHEMBL614555
 IC50 5.7 5.7 2000.0 1
DU-145
CHEMBL613508
 IC50 5.12 5.12 7600.0 2
LNCaP
CHEMBL612518
 IC50 4.19 4.19 64000.0 1
MCF7
CHEMBL387
 IC50 4.16 4.16 70000.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.092 hr -
T1/2 0.09067 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
ADMET IC50 = 29.0 nM 7.54 Ability to reduce cell density of UV4 cells to 50% after 4 hr of exposure to air 11585455
EMT6 IC50 = 150.0 nM 6.82 Ability to reduce cell density of EMT6 cells to 50% after 4 hr of exposure to ai... 11585455
SK-OV-3 IC50 = 1090.0 nM 5.96 Ability to reduce cell density of SKOV3 cells to 50% after 4 hr of exposure to a... 11585455
CHO-AA8 IC50 = 2000.0 nM 5.7 Cytotoxicity against AA8 cell and IC50 values were determined as drug concentrat... 8676343
ADMET IC50 = 2200.0 nM 5.66 Concentration for 50% inhibition of AA8 cells growth under aerobic conditions af... 8355257
ADMET IC50 = 2500.0 nM 5.6 Ability to reduce cell density of AA8 cells to 50% after 4 hr of exposure to air 11585455
DU-145 IC50 = 7600.0 nM 5.12 Growth inhibition of human DU145 cells after 3 days by SRB assay 17472358
DU-145 IC50 = 7600.0 nM 5.12 Induction of cell cycle arrest in human DU145 cells assessed as accumulation at ... 17472358
LNCaP IC50 = 64000.0 nM 4.19 The compound was evaluated for cytotoxicity by assessing 3H thymidine uptake in ... 10987433
MCF7 IC50 = 70000.0 nM 4.16 The compound was evaluated for cytotoxicity by assessing 3H thymidine uptake in ... 10987433

Literature References

PubMed DOI Target Context # Activities
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
11585455 10.1021/jm010202l EMT6 4
11585455 10.1021/jm010202l Mus musculus 4
18834112 10.1021/jm800656v Amine oxidase [flavin-containing] A 3
21449610 10.1021/jm101595p Mus musculus 2
18834112 10.1021/jm800656v Amine oxidase [flavin-containing] B 2
17472358 10.1021/jm070144p DU-145 2
1271405 10.1021/jm00227a012 No relevant target 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
2308133 10.1021/jm00165a019 ADMET 2
11585455 10.1021/jm010202l ADMET 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
2362268 10.1021/jm00169a014 No relevant target 2
8676343 10.1021/jm9507791 CHO-AA8 1
11585455 10.1021/jm010202l SK-OV-3 1
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1
10987433 10.1016/s0960-894x(00)00386-3 MCF7 1

Data from ChEMBL 36 via Core Engine