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Compound Detail

CHEMBL671

THIOTEPA
💊 Approved Drug
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💊 Approved Drug
S=P(N1CC1)(N1CC1)N1CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL671
Name THIOTEPA
Phase Approved
Structure Type MOL
InChI Key FOCVUCIESVLUNU-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

NSC-6396 Tepadina Tepylute Thioplex Thiotepa Thiotepa riemser Tiotepa
12
Targets
16
Activities
2
Assay Types
5
PK Parameters
20
Publications
7
Known Names
20
Indications
1
Mechanisms

Molecular Properties

189.2
MW (Da)
0.16
ALogP
1
HBA
0
HBD
9.0
PSA (Ų)
0.46
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1959
Availability Prescription
Chirality Achiral

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -tepa

Extended Properties

Molecular Formula C6H12N3PS
MW 189.22
Aromatic Rings 0
Heavy Atoms 11
NP-Likeness -0.06

Mechanism of Action

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

Indications

Adenocarcinoma Carcinoma Hematopoietic Stem Cell Transplantation Hodgkin Disease Neoplasms Neoplasms Brain Neoplasms Breast Neoplasms Breast Neoplasms Central Nervous System Neoplasms Ganglioneuroblastoma Graft vs Host Disease Leukemia Medulloblastoma Neuroblastoma Neuroectodermal Tumors, Primitive Precursor Cell Lymphoblastic Leukemia-Lymphoma Retinoblastoma Anemia, Sickle Cell Breast Neoplasms, Male

ATC Classification

L01AC01
thiotepa
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

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

Activity Summary

IC50 12 meas. best 5.85
Ki 4 meas. best 5.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
SISO
CHEMBL613527
 IC50 5.85 5.85 1400.0 1
A-427
CHEMBL614515
 IC50 5.8 5.8 1580.0 1
DAN-G
CHEMBL614033
 IC50 5.78 5.78 1660.0 1
5637
CHEMBL612565
 IC50 5.7 5.7 2000.0 1
Cytochrome P450 2B6
CHEMBL4729
 Ki 5.66 5.1267 2200.0 3
YAPC
CHEMBL612815
 IC50 5.58 5.58 2660.0 1
MCF7
CHEMBL387
 IC50 5.49 5.49 3230.0 1
RT-112
CHEMBL614145
 IC50 5.47 5.47 3400.0 1
KYSE-510
CHEMBL613868
 IC50 5.37 5.37 4310.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.27 5.2067 5400.0 3
RT-4
CHEMBL614884
 IC50 4.74 4.74 18270.0 1
Cytochrome P450 2B1
CHEMBL3335
 Ki 4.51 4.51 31000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 6.7 mL.min-1.kg-1 Homo sapiens
CL 6.7 mL.min-1.kg-1 Homo sapiens
Fu 0.9 - Homo sapiens
MRT 4.0 hr Homo sapiens
T1/2 2.7 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
SISO IC50 = 1400.0 nM 5.85 Cytotoxicity against human SISO cells after 96 hrs by microtiter assay 18187237
A-427 IC50 = 1580.0 nM 5.8 Cytotoxicity against human A427 cells after 96 hrs by microtiter assay 18187237
DAN-G IC50 = 1660.0 nM 5.78 Cytotoxicity against human DAN-G cells after 96 hrs by microtiter assay 18187237
5637 IC50 = 2000.0 nM 5.7 Cytotoxicity against human 5637 cells after 96 hrs by microtiter assay 18187237
Cytochrome P450 2B6 Ki = 2200.0 nM 5.66 Mechanism based inhibition of human cytochrome P450 2B6 measured by bupropion hy... 16248836
YAPC IC50 = 2660.0 nM 5.58 Cytotoxicity against human YAPC cells after 96 hrs by microtiter assay 18187237
MCF7 IC50 = 3230.0 nM 5.49 Cytotoxicity against human MCF7 cells after 96 hrs by microtiter assay 18187237
RT-112 IC50 = 3400.0 nM 5.47 Cytotoxicity against human RT112 cells after 96 hrs by microtiter assay 18187237
Cytochrome P450 2B6 Ki = 3800.0 nM 5.42 Mechanism based inhibition of human cytochrome P450 2B6 measured by bupropion hy... 16248836
KYSE-510 IC50 = 4310.0 nM 5.37 Cytotoxicity against human KYSE510 cells after 96 hrs by microtiter assay 18187237
NON-PROTEIN TARGET IC50 = 5400.0 nM 5.27 Cytotoxicity against human KYSE70 cells after 96 hrs by microtiter assay 18187237
NON-PROTEIN TARGET IC50 = 6440.0 nM 5.19 Cytotoxicity against human KYSE520 cells after 96 hrs by microtiter assay 18187237
NON-PROTEIN TARGET IC50 = 6970.0 nM 5.16 Cytotoxicity against human LCLC-103H cells after 96 hrs by microtiter assay 18187237
RT-4 IC50 = 18270.0 nM 4.74 Cytotoxicity against human RT4 cells after 96 hrs by microtiter assay 18187237
Cytochrome P450 2B1 Ki = 31000.0 nM 4.51 Mechanism based inhibition of rat cytochrome P450 2B1 16248836
Cytochrome P450 2B6 Ki = 50000.0 nM 4.3 Mechanism based inhibition of human cytochrome P450 2B6 16248836

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
16248836 10.2174/138920005774330639 Cytochrome P450 2B6 7
2431142 10.1021/jm00161a016 P388 6
6204051 10.1021/jm00372a014 Mus musculus 6
3806574 10.1021/jm00157a023 Mus musculus 4
18426954 10.1124/dmd.108.020479 ADMET 4
16248836 10.2174/138920005774330639 Cytochrome P450 2B1 3
2431142 10.1021/jm00161a016 L1210 3
8568824 10.1021/jm9500885 Mus musculus 3
18187237 10.1016/j.ejmech.2007.11.017 NON-PROTEIN TARGET 3
19445515 10.1021/jm900403j Homo sapiens 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Glucocorticoid receptor 2
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2

Data from ChEMBL 36 via Core Engine