Tirapazamine

Summary

Tirapazamine (CHEMBL50882) is a phase-3 clinical-stage small-molecule antineoplastic agent; indicated across 12 conditions including head and neck squamous cell carcinoma and upper aerodigestive tract neoplasm.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• Indications: 12 conditions
• Clinical trials: 19
• Chemistry: 178.15 Da · C7H6N4O2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL50882
Name	Tirapazamine
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	135413511
ChEBI	CHEBI:78887
Molecular formula	C7H6N4O2
Molecular weight	178.15
InChIKey	ORYDPOVDJJZGHQ-UHFFFAOYSA-N

SMILES: C1=CC=C2C(=C1)[N+](=C(N=[N+]2[O-])N)[O-]

IUPAC name: 1,4-dioxido-1,2,4-benzotriazine-1,4-diium-3-amine

ChEBI definition: A member of the class of benzotriazines that is 1,2,4-benzotriazine carrying an amino substituent at position 3 and two oxido substituents at positions 1 and 4.

Pharmacological roles (ChEBI): antineoplastic agent, apoptosis inducer, antibacterial agent.

Also known as: NSC-130181, SML-0552, SML0552, SR-259075, SR-4233, SR259075, SR4233, Tirapazamina, Tirapazamine, Tirazone, WIN 59075, WIN-59075

Patent coverage: 5,081 distinct patent families (20,712 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 20,383 (98%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

No target linkage available.

Bioactivity

No ChEMBL bioactivity rows at pChembl ≥ 5 (expected for biologics / antibodies).

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

11 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
head and neck squamous cell carcinoma	3	MONDO:0010150	EFO:0000181
upper aerodigestive tract neoplasm	3	MONDO:0005398	EFO:0004284
lung neoplasm	3	MONDO:0021117	MONDO:0008903
cervical adenocarcinoma	3	MONDO:0005153	EFO:0001416
squamous cell carcinoma	3	MONDO:0005096	EFO:0000707
hepatocellular carcinoma	2	MONDO:0007256	EFO:0000182
small cell lung carcinoma	2	MONDO:0008433	EFO:0000702
rhabdomyosarcoma	2	MONDO:0005212	EFO:0002918
peritoneal neoplasm	2	MONDO:0006901	MONDO:0002087
ovarian cancer	2	MONDO:0008170	MONDO:0008170
neoplasm	1	MONDO:0005070	EFO:0000616

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 19.

Phase distribution

Phase	Trials
PHASE2	6
PHASE3	5
PHASE1	5
PHASE1/PHASE2	2
PHASE2/PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT06844357	PHASE2/PHASE3	RECRUITING	A Phase II/III Trial Comparing Transarterial Tirapazamine Embolization (TATE) With cTACE for Intermediate-stage Liver Cancer.
NCT00006484	PHASE3	COMPLETED	Combination Chemotherapy With or Without Tirapazamine in Treating Patients With Stage IIIB or Stage IV Non-small Cell Lung Cancer
NCT00017459	PHASE3	COMPLETED	Cisplatin Plus Vinorelbine With or Without Tirapazamine in Treating Patients With Stage IIIB or Stage IV Non-Small Cell Lung Cancer
NCT00094081	PHASE3	COMPLETED	Concomitant Radiation and Cisplatin With and Without Tirapazamine in Treatment of Advanced Head and Neck Cancer
NCT00174837	PHASE3	COMPLETED	TRACE: Tirapazamine-Radiation And Cisplatin Evaluation
NCT00262821	PHASE3	TERMINATED	Cisplatin and Radiation Therapy With or Without Tirapazamine in Treating Patients With Cervical Cancer
NCT02174549	PHASE1/PHASE2	RECRUITING	Dose-defining Study of Tirapazamine Combined With Embolization in Liver Cancer
NCT00002774	PHASE2	COMPLETED	Radiation Therapy and Combination Chemotherapy in Treating Patients With Stage III or Stage IV Head and Neck Cancer
NCT00003369	PHASE2	COMPLETED	S9717 Tirapazamine Plus Cisplatin in Treating Patients With Metastatic, Recurrent, or Refractory Cervical Cancer
NCT00020696	PHASE2	COMPLETED	Tirapazamine Plus Cisplatin in Treating Patients With Persistent or Recurrent Ovarian Epithelial or Primary Peritoneal Cancer
NCT00025363	PHASE2	COMPLETED	Comparison of Chemotherapy Regimens in Treating Children With Relapsed or Progressive Rhabdomyosarcoma
NCT00066742	PHASE2	COMPLETED	Tirapazamine Combined With Chemo and RT in Limited-Stage Small Cell Lung Cancer
NCT03145558	PHASE2	TERMINATED	TATE Versus TACE in Intermediate Stage HCC
NCT06848556	PHASE1/PHASE2	TERMINATED	Evaluate the Effect of Tirazamine on Primary Liver Cancer.
NCT00003288	PHASE1	COMPLETED	Tirapazamine Plus Cyclophosphamide in Treating Children With Refractory Solid Tumors
NCT00005078	PHASE1	COMPLETED	Tirapazamine, Carboplatin, and Paclitaxel in Treating Patients With Advanced Malignant Solid Tumors
NCT00006487	PHASE1	COMPLETED	S0004: Combination Chemotherapy Plus Radiation Therapy in Treating Patients With Limited-stage Small Cell Lung Cancer
NCT00033410	PHASE1	COMPLETED	Chemotherapy, Tirapazamine, and Radiation Therapy in Treating Patients With Non-Small Cell Lung Cancer
NCT00098995	PHASE1	COMPLETED	Tirapazamine, Cisplatin, and Radiation Therapy in Treating Patients With Stage IB, Stage II, Stage III, or Stage IVA Cervical Cancer

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).