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Compound Detail

CHEMBL476

DACARBAZINE
💊 Approved Drug
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💊 Approved Drug
CN(C)/N=N/c1[nH]cnc1C(N)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL476
Name DACARBAZINE
Phase Approved
Structure Type MOL
InChI Key FDKXTQMXEQVLRF-ZHACJKMWSA-N
Therapeutic ✓ Yes

Known Names

Biocarbazine r Dacarbasine Dacarbazina Dacarbazine Dacarbazinum Decarbazine DIC Dicarbazine DTIC Dtic-dome NCI C04717 NSC-45388
5
Targets
7
Activities
1
Assay Types
4
PK Parameters
20
Publications
12
Known Names
20
Indications
1
Mechanisms

Molecular Properties

182.2
MW (Da)
0.07
ALogP
4
HBA
2
HBD
99.7
PSA (Ų)
0.51
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1975
Availability Prescription
Chirality Achiral

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product
USAN Year 1972

Extended Properties

Molecular Formula C6H10N6O
MW 182.19
Aromatic Rings 1
Heavy Atoms 13
NP-Likeness -0.95

Mechanism of Action

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

Indications

Hodgkin Disease Hodgkin Disease Melanoma Melanoma Melanoma Neoplasms Neoplasms Leiomyosarcoma Lymphoma Lymphoma, T-Cell, Peripheral Neuroblastoma Sarcoma Sarcoma Sarcoma, Alveolar Soft Part Sarcoma, Synovial Skin Neoplasms Uveal Melanoma Uveal Melanoma Neuroendocrine Tumors Neuroendocrine Tumors

ATC Classification

L01AX04
dacarbazine
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning
teratogenicity
Country: United States
Black Box Warning
carcinogenicity
Country: United States
Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
hematological toxicity
Country: United States
Black Box Warning
nephrotoxicity
Country: United States

Activity Summary

IC50 7 meas. best 6.25

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Matrix metalloproteinase-9
CHEMBL321
 IC50 6.25 6.25 556.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.12 5.12 7670.0 1
UACC-62
CHEMBL614610
 IC50 4.93 4.93 11830.0 1
GM892A cell line
CHEMBL614505
 IC50 4.85 4.85 14000.0 1
OVCAR-3
CHEMBL614213
 IC50 4.75 4.75 17670.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 2.6 mL.min-1.kg-1 Homo sapiens
Fu 1.0 - Homo sapiens
MRT 7.8 hr Homo sapiens
T1/2 6.2 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Matrix metalloproteinase-9 IC50 = 556.0 nM 6.25 DRUGMATRIX: Protease, Matrix Metalloprotease-9 (MMP-9) enzyme inhibition (substr... -
NON-PROTEIN TARGET IC50 = 7670.0 nM 5.12 Cytotoxicity against human GC3/C1 cells after 6 days by MTT assay 21131205
UACC-62 IC50 = 11830.0 nM 4.93 Cytotoxicity against human UACC62 cells after 6 days by MTT assay 21131205
GM892A cell line IC50 = 14000.0 nM 4.85 In vitro cytotoxicity against human lymphoblastoid cell (GM892 A) 7739008
OVCAR-3 IC50 = 17670.0 nM 4.75 Cytotoxicity against human OVCAR3 cells after 6 days by MTT assay 21131205

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
533891 10.1021/jm00197a028 L1210 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
3746822 10.1021/jm00159a036 B16 6
628002 10.1021/jm00201a006 B16 6
7411549 10.1021/jm00183a017 Mus musculus 6
533891 10.1021/jm00197a028 Mus musculus 5
36961300 10.1021/acs.jmedchem.3c00094 SK-MEL-2 4
6502603 10.1021/jm00378a033 Mus musculus 4
18426954 10.1124/dmd.108.020479 ADMET 4
628002 10.1021/jm00201a006 Mus musculus 3
35818137 10.1021/acs.jmedchem.2c00640 A-375 3
20014752 10.1021/tx900326k Hepatotoxicity 3
20919720 10.1021/jm100884b Mus musculus 3
22931300 10.1021/tx300075j Liver microsomes 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
18834112 10.1021/jm800656v Amine oxidase [flavin-containing] A 2
18834112 10.1021/jm800656v Amine oxidase [flavin-containing] B 2
671453 10.1021/jm00204a012 No relevant target 2

Data from ChEMBL 36 via Core Engine