Compound Detail

CHEMBL50882

TIRAPAZAMINE

🧪 Phase III

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

Research home View demo workspace

🧪 Phase III

Nc1n[n+]([O-])c2ccccc2[n+]1[O-]

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL50882
Name	TIRAPAZAMINE
Phase	Phase III
Structure Type	MOL
InChI Key	ORYDPOVDJJZGHQ-UHFFFAOYSA-N

Known Names

NSC-130181 SML-0552 SML0552 SR-259075 SR-4233 SR259075 SR4233 Tirapazamina Tirapazamine Tirazone WIN 59075 WIN-59075 +1 more

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

178.2

MW (Da)

-0.92

ALogP

HBA

HBD

92.8

PSA (Å²)

0.42

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

USAN Year

1992

Extended Properties

Molecular Formula	C7H6N4O2
MW	178.15
Aromatic Rings	2
Heavy Atoms	13
NP-Likeness	-0.27

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
DNA disrupting agent	DISRUPTING AGENT	DNA	✓	✓

Indications

Carcinoma, Squamous Cell Carcinoma, Squamous Cell Head and Neck Neoplasms Lung Neoplasms Uterine Cervical Neoplasms Uterine Cervical Neoplasms Carcinoma, Hepatocellular Ovarian Neoplasms Peritoneal Neoplasms Rhabdomyosarcoma Small Cell Lung Carcinoma Neoplasms

Activity Summary

IC50 47 meas. best 5.93

EC50 5 meas. best 4.66

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
PC-3 CHEMBL390	IC50	5.93	5.0867	1170.0	3
SW-620 CHEMBL612262	IC50	5.92	4.98	1200.0	2
MDA-MB-468 CHEMBL614335	IC50	5.88	5.88	1304.0	1
K562 CHEMBL385	IC50	5.74	5.2433	1810.0	3
A549 CHEMBL392	IC50	5.71	5.3333	1930.0	3
HL-60 CHEMBL383	IC50	5.64	5.1875	2310.0	4
SCC-7 CHEMBL614147	IC50	5.62	4.88	2400.0	2
SiHa CHEMBL612542	IC50	5.6	5.6	2500.0	2
MOLT-4 CHEMBL614177	IC50	5.46	5.235	3430.0	4
SMMC-7721 CHEMBL613831	IC50	5.32	4.9	4750.0	2
HT-29 CHEMBL384	IC50	5.29	5.1914	5100.0	7
KB CHEMBL398	IC50	5.2	4.965	6290.0	2
NCI-H460 CHEMBL396	IC50	4.96	4.96	11000.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.92	4.544	11900.0	5
HepG2 CHEMBL395	IC50	4.72	4.72	19100.0	1
MOLM-13 CHEMBL3706572	EC50	4.66	4.34	22000.0	4
NRK CHEMBL613518	EC50	4.46	4.46	35000.0	1
MDCK CHEMBL614068	IC50	4.02	4.02	95000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	8759.64	ng.hr.mL-1	Mus musculus
CL	8.9	mL.min-1.kg-1	Homo sapiens
Cmax	61700.0	nM	Mus musculus
Fu	0.81	-	Homo sapiens
MRT	1.0	hr	Homo sapiens
T1/2	0.465	hr	Mus musculus
T1/2	0.78	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
PC-3	IC50	=	1170.0	nM	5.93	Cytotoxicity against human PC3 cells for 72 hrs under hypoxic condition by MTT a...	21281992
SW-620	IC50	=	1200.0	nM	5.92	Cytotoxicity against human SW620 cells incubated for 4 hrs under hypoxic conditi...	30885680
MDA-MB-468	IC50	=	1304.0	nM	5.88	Cytotoxicity against human MDA-MB-468 cells incubated for 4 hrs under hypoxic co...	30885680
K562	IC50	=	1810.0	nM	5.74	Cytotoxicity against human K562 cells for 72 hrs under hypoxic condition by MTT ...	21281992
A549	IC50	=	1930.0	nM	5.71	Cytotoxicity against human A549 cells for 72 hrs under hypoxic condition by MTT ...	21281992
HL-60	IC50	=	2310.0	nM	5.64	Ratio of cytotoxicity against human HL60 cells in normoxia to hypoxia after 48 h...	16777409
SCC-7	IC50	=	2400.0	nM	5.62	Inhibitory concentration against murine SCCVII cell line under hypoxic condition	12502371
SiHa	IC50	=	2500.0	nM	5.6	Cytotoxicity against human SiHa cells under hypoxic conditions after 4 hrs	18001018
SiHa	IC50	=	2500.0	nM	5.6	Cytotoxicity against human SiHa cells after 4 hrs under strict hypoxic condition	18847185
MOLT-4	IC50	=	3430.0	nM	5.46	Ratio of cytotoxicity against human Molt4 cells in normoxia to hypoxia after 48 ...	16777409
MOLT-4	IC50	=	4600.0	nM	5.34	Cytotoxicity against human Molt4 cells in hypoxia after 48 hrs	16777409
MOLT-4	IC50	=	4600.0	nM	5.34	Cytotoxicity against human Molt4 cells after 48 hrs by MTT assay	16777409
SMMC-7721	IC50	=	4750.0	nM	5.32	Cytotoxicity against human SMMC7721 cells for 72 hrs under hypoxic condition by ...	21281992
HT-29	IC50	=	5100.0	nM	5.29	Cytotoxicity against human HT-29 cells after 4 hrs under strict hypoxic conditio...	18847185
HT-29	IC50	=	5100.0	nM	5.29	Cytotoxicity against human HT29 cells under hypoxic conditions after 4 hrs	18001018
HT-29	IC50	=	5300.0	nM	5.28	Inhibitory concentration against human adenocarcinoma HT-29 cell line under hypo...	12502371
K562	IC50	=	5200.0	nM	5.28	Cytotoxicity against human K562 cells after 48 hrs by MTT assay	16777409
HT-29	IC50	=	6200.0	nM	5.21	Concentration required to kill hypoxic HT-29 human colon carcinoma cells in vitr...	14711317
HT-29	IC50	=	6200.0	nM	5.21	Antiproliferative activity against human HT-29 cells assessed as inhibition of c...	28851503
KB	IC50	=	6290.0	nM	5.2	Cytotoxicity against human KB cells for 72 hrs under normoxic condition by MTT a...	21281992

Literature References

PubMed	DOI	Target Context	# Activities
18001018	10.1021/jm070670g	HT-29	7
18847185	10.1021/jm800967h	HT-29	7
16777409	10.1016/j.bmcl.2006.05.095	MOLT-4	7
12502371	10.1021/jm020367+	NON-PROTEIN TARGET	5
28851503	10.1016/j.ejmech.2017.08.009	Unchecked	5
27140429	10.1021/acs.jnatprod.5b00846	NON-PROTEIN TARGET	4
11585455	10.1021/jm010202l	Mus musculus	4
18426954	10.1124/dmd.108.020479	ADMET	4
18001018	10.1021/jm070670g	Mus musculus	4
27823879	10.1016/j.ejmech.2016.10.037	MDCK	4
16777409	10.1016/j.bmcl.2006.05.095	HL-60	4
12502371	10.1021/jm020367+	HT-29	3
22691154	10.1021/jm300123s	Mycobacterium tuberculosis	3
32196334	10.1021/acs.jnatprod.9b00773	A549	3
18257544	10.1021/jm701028q	NCI-H460	3
18715787	10.1016/j.bmc.2008.07.087	NON-PROTEIN TARGET	3
30885680	10.1016/j.bmcl.2019.03.015	MDA-MB-468	3
12502371	10.1021/jm020367+	SCC-7	3
20371184	10.1016/j.bmc.2010.03.042	V79	3
30885680	10.1016/j.bmcl.2019.03.015	SW-620	3

Data from ChEMBL 36 via Core Engine