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Compound Detail

CHEMBL105

MITOMYCIN
💊 Approved Drug
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💊 Approved Drug
CO[C@@]12[C@H](COC(N)=O)C3=C(C(=O)C(C)=C(N)C3=O)N1C[C@@H]1N[C@@H]12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL105
Name MITOMYCIN
Phase Approved
Structure Type MOL
InChI Key NWIBSHFKIJFRCO-WUDYKRTCSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL6068323

Known Names

Ametycine Jelmyto Mitocin-c Mitomicina Mitomycin Mitomycin c Mitomycin-c Mitomycine Mitosol Mitozytrex Muamycin Mutamycin +4 more
706
Targets
883
Activities
3
Assay Types
0
PK Parameters
20
Publications
16
Known Names
20
Indications
1
Mechanisms

Molecular Properties

334.3
MW (Da)
-1.65
ALogP
8
HBA
3
HBD
146.9
PSA (Ų)
0.41
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1981
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral Topical

Flags

Black Box Warning Natural Product Prodrug
USAN Stem -mycin
USAN Year 1972

Extended Properties

Molecular Formula C15H18N4O5
MW 334.33
Aromatic Rings 0
Heavy Atoms 24
NP-Likeness 2.07

Mechanism of Action

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

Indications

Adenocarcinoma Glaucoma Neoplasms Neoplasms Anus Neoplasms Anus Neoplasms Anus Neoplasms Breast Neoplasms Carcinoma Carcinoma in Situ Carcinoma, Hepatocellular Carcinoma, Non-Small-Cell Lung Carcinoma, Transitional Cell Colorectal Neoplasms Head and Neck Neoplasms Lung Neoplasms Lung Neoplasms Mesothelioma Nasopharyngeal Carcinoma Pancreatic Neoplasms

ATC Classification

L01DC03
mitomycin
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning
hematological toxicity
Country: United States
Black Box Warning
nephrotoxicity
Country: United States

Activity Summary

IC50 861 meas. best 10.66
EC50 20 meas. best 6.99
Ki 2 meas. best 4.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NTERA-2-cl-D1
CHEMBL614206
 IC50 10.66 10.66 0.0 1
MOLT-4
CHEMBL614177
 IC50 10.49 10.49 0.0 1
J82
CHEMBL614586
 IC50 9.92 9.92 0.1 1
697
CHEMBL2366253
 IC50 9.89 9.89 0.1 1
KYSE-510
CHEMBL613868
 IC50 9.83 9.83 0.1 1
NCI-H2170
CHEMBL1075534
 IC50 9.82 9.82 0.2 1
BE-13
CHEMBL2366303
 IC50 9.78 9.78 0.2 1
LC-2-ad
CHEMBL2366260
 IC50 9.6 9.6 0.2 1
IMR-5
CHEMBL2366209
 IC50 9.51 9.51 0.3 1
EW-16
CHEMBL2366358
 IC50 9.51 9.51 0.3 1
MC-IXC
CHEMBL1075495
 IC50 9.2 9.2 0.6 1
SW872
CHEMBL2366302
 IC50 9.17 9.17 0.7 1
NCI-H2228
CHEMBL1075536
 IC50 9.1 9.1 0.8 1
K562
CHEMBL385
 IC50 9.0 7.2075 1.0 4
NALM-6
CHEMBL614187
 IC50 8.97 8.97 1.1 1
CHO-AA8
CHEMBL614555
 IC50 8.97 8.97 1.1 1
ES4
CHEMBL2366118
 IC50 8.81 8.81 1.6 1
KE-37
CHEMBL2366287
 IC50 8.79 8.79 1.6 1
ES8
CHEMBL2366069
 IC50 8.77 8.77 1.7 1
IST-MEL1
CHEMBL2366094
 IC50 8.77 8.77 1.7 1
639-V
CHEMBL1075383
 IC50 8.76 8.76 1.8 1
MV4-11
CHEMBL613835
 IC50 8.76 8.76 1.7 1
OCI-AML2
CHEMBL2366220
 IC50 8.72 8.72 1.9 1
SK-LU-1
CHEMBL614913
 IC50 8.65 8.65 2.2 1
REH
CHEMBL2366320
 IC50 8.59 8.59 2.5 1
PSN1
CHEMBL614241
 IC50 8.59 8.59 2.6 1
SBC-5
CHEMBL614896
 IC50 8.59 8.59 2.6 1
HT-3
CHEMBL1075470
 IC50 8.53 8.53 2.9 1
SIG-M5
CHEMBL2366251
 IC50 8.45 8.45 3.5 1
ES7
CHEMBL2366297
 IC50 8.44 8.44 3.7 1
CHP-212
CHEMBL1075423
 IC50 8.36 8.36 4.4 1
HuTu80
CHEMBL614582
 IC50 8.32 8.32 4.8 1
P12-Ichikawa
CHEMBL614660
 IC50 8.32 8.32 4.8 1
P30-OHK
CHEMBL2366165
 IC50 8.31 8.31 4.8 1
NCI-H1651
CHEMBL1075519
 IC50 8.3 8.3 5.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.3 6.2642 5.0 12
COR-L279
CHEMBL2366352
 IC50 8.26 8.26 5.5 1
CMK
CHEMBL2366177
 IC50 8.23 8.23 5.8 1
BV-173
CHEMBL2366145
 IC50 8.22 8.22 6.1 1
MHH-CALL-2
CHEMBL2366286
 IC50 8.22 8.22 6.1 1
NCI-H209
CHEMBL2366365
 IC50 8.21 8.21 6.2 1
NCI-H460
CHEMBL396
 IC50 8.19 8.19 6.5 1
DU-145
CHEMBL613508
 IC50 8.19 6.87 6.5 4
769-P
CHEMBL1075385
 IC50 8.15 8.15 7.1 1
SW480
CHEMBL612544
 IC50 8.15 7.125 7.0 2
ES1
CHEMBL2366146
 IC50 8.14 8.14 7.3 1
COLO-668
CHEMBL2366215
 IC50 8.12 8.12 7.5 1
NKM-1
CHEMBL2366133
 IC50 8.11 8.11 7.8 1
ES3
CHEMBL2366135
 IC50 8.1 8.1 7.9 1
SCC-3
CHEMBL2366081
 IC50 8.07 8.07 8.5 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NTERA-2-cl-D1 IC50 = 0.02213 nM 10.66 SANGER: Inhibition of human NTERA-S-cl-D1 cell growth in a cell viability assay. -
MOLT-4 IC50 = 0.03248 nM 10.49 SANGER: Inhibition of human MOLT-4 cell growth in a cell viability assay. -
J82 IC50 = 0.119 nM 9.92 SANGER: Inhibition of human J82 cell growth in a cell viability assay. -
697 IC50 = 0.1283 nM 9.89 SANGER: Inhibition of human 697 cell growth in a cell viability assay. -
KYSE-510 IC50 = 0.1486 nM 9.83 SANGER: Inhibition of human KYSE-510 cell growth in a cell viability assay. -
NCI-H2170 IC50 = 0.1513 nM 9.82 SANGER: Inhibition of human NCI-H2170 cell growth in a cell viability assay. -
BE-13 IC50 = 0.1673 nM 9.78 SANGER: Inhibition of human BE-13 cell growth in a cell viability assay. -
LC-2-ad IC50 = 0.2492 nM 9.6 SANGER: Inhibition of human LC-2-ad cell growth in a cell viability assay. -
EW-16 IC50 = 0.31 nM 9.51 SANGER: Inhibition of human EW-16 cell growth in a cell viability assay. -
IMR-5 IC50 = 0.3076 nM 9.51 SANGER: Inhibition of human IMR-5 cell growth in a cell viability assay. -
MC-IXC IC50 = 0.638 nM 9.2 SANGER: Inhibition of human MC-IXC cell growth in a cell viability assay. -
SW872 IC50 = 0.676 nM 9.17 SANGER: Inhibition of human SW872 cell growth in a cell viability assay. -
NCI-H2228 IC50 = 0.7963 nM 9.1 SANGER: Inhibition of human NCI-H2228 cell growth in a cell viability assay. -
K562 IC50 = 1.0 nM 9.0 In vitro inhibitory activity against K562 leukemia cells 12699386
NALM-6 IC50 = 1.066 nM 8.97 SANGER: Inhibition of human NALM-6 cell growth in a cell viability assay. -
CHO-AA8 IC50 = 1.08 nM 8.97 Inhibitory activity of compound for AA8 cells to reduce cell density by 50% (exp... 2909741
ES4 IC50 = 1.555 nM 8.81 SANGER: Inhibition of human ES4 cell growth in a cell viability assay. -
KE-37 IC50 = 1.636 nM 8.79 SANGER: Inhibition of human KE-37 cell growth in a cell viability assay. -
ES8 IC50 = 1.712 nM 8.77 SANGER: Inhibition of human ES8 cell growth in a cell viability assay. -
IST-MEL1 IC50 = 1.684 nM 8.77 SANGER: Inhibition of human IST-MEL1 cell growth in a cell viability assay. -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 459
10509925 10.1016/s0960-894x(99)00472-2 Mus musculus 41
18845441 10.1016/j.bmc.2008.09.055 HCT-8 26
2500528 10.1021/jm00127a035 Mus musculus 25
7328599 10.1021/jm00140a012 Mus musculus 24
- 10.1016/0960-894X(95)00098-E Mus musculus 20
36561066 10.1039/d2md00194b Caulobacter vibrioides 17
874953 10.1021/jm00216a006 P388 16
8709111 10.1021/jm950881y Mus musculus 14
6425501 10.1021/jm00371a026 Mus musculus 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
6620304 10.1021/jm00364a018 B16 12
3925147 10.1021/jm00145a013 Mus musculus 12
3397995 10.1021/jm00403a016 L1210 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
6827524 10.1021/jm00355a004 B16 9
19029320 10.1128/aac.00132-08 Escherichia coli 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
96254 10.1021/jm00203a020 Bacillus subtilis 7
7328580 10.1021/jm00142a013 L1210 7

Data from ChEMBL 36 via Core Engine