Triapine

Summary

Triapine (CHEMBL231616) is a phase-3 clinical-stage small molecule; indicated across 11 conditions including exocrine pancreatic carcinoma and non-small cell lung carcinoma.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• Indications: 11 conditions
• Clinical trials: 34
• Chemistry: 195.25 Da · C7H9N5S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL231616
Name	Triapine
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	9571836
Molecular formula	C7H9N5S
Molecular weight	195.25
InChIKey	XMYKNCNAZKMVQN-NYYWCZLTSA-N

SMILES: C1=CC(=C(N=C1)/C=N/NC(=S)N)N

IUPAC name: [(E)-(3-amino-2-pyridinyl)methylideneamino]thiourea

Also known as: NSC-663249, Ocx 191, OCX-0191, OCX-191, PAN-811, Triapine, SID510133, triapine, TRIAPINE, C0088779

Patent coverage: 1,343 distinct patent families (4,524 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 3,569 (79%) 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

Broader ChEMBL bioactivity targets: 3 (assay-derived). Sample: CDGSH iron-sulfur domain-containing protein 1, Ribonucleoside-diphosphate reductase subunit M2, Ribonucleotide reductase.

Bioactivity

ChEMBL activities: 4 potent at pChembl ≥ 5 of 4 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
RRM2	6.73	IC50	185	nM	CHEMBL_ACT_18125581
CISD1	6.41	Ki	388	nM	CHEMBL_ACT_16766187
RRM1	5.92	IC50	1200	nM	CHEMBL_ACT_27081902
CISD1	5.04	IC50	9078	nM	CHEMBL_ACT_16766186

Target pathways

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

Indications & clinical

Indications

11 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
exocrine pancreatic carcinoma	2	MONDO:0005192	EFO:0002618
non-small cell lung carcinoma	2	MONDO:0005233	EFO:0003060
male breast carcinoma	2	MONDO:0005628	EFO:0006861
kidney cancer	2	MONDO:0002367	MONDO:0002367
gallbladder neoplasm	2	MONDO:0021253	MONDO:0005411
lung neoplasm	2	MONDO:0021117	MONDO:0008903
neuroendocrine neoplasm	2	MONDO:0019496	EFO:1001901
breast neoplasm	2	MONDO:0021100	MONDO:0007254
neoplasm	1	MONDO:0005070	EFO:0000616
malignant endocrine neoplasm	1	MONDO:0021069	MONDO:0021069

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

Clinical trials

Total trials: 34.

Phase distribution

Phase	Trials
PHASE1	17
PHASE2	15
PHASE3	1
EARLY_PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT02466971	PHASE3	ACTIVE_NOT_RECRUITING	Testing the Addition of a New Anti-Cancer Drug, Triapine, to the Usual Chemotherapy Treatment (Cisplatin) During Radiation Therapy for Advanced-stage Cervical and Vaginal Cancers
NCT05724108	PHASE2	ACTIVE_NOT_RECRUITING	Testing the Effectiveness of an Anti-cancer Drug, Triapine, When Used With Targeted Radiation-based Treatment (Lutetium Lu 177 Dotatate), Compared to Lutetium Lu 177 Dotatate Alone for Metastatic Neuroendocrine Tumors
NCT00054015	PHASE2	COMPLETED	3-AP in Treating Patients With Advanced Prostate Cancer
NCT00064051	PHASE2	COMPLETED	3-AP and Gemcitabine in Treating Patients With Unresectable or Metastatic Pancreatic Cancer
NCT00064064	PHASE2	COMPLETED	3-AP and Gemcitabine in Treating Patients With Metastatic Non-Small Cell Lung Cancer
NCT00075504	PHASE2	COMPLETED	Triapine and Gemcitabine Hydrochloride in Gallbladder Cancer
NCT00075660	PHASE2	COMPLETED	3-AP in Treating Patients With Previously Untreated Locally Recurrent or Metastatic Renal Cell Carcinoma
NCT00077350	PHASE2	COMPLETED	A Phase II Trial of Triapine (NSC #663249) in Combination With Gemcitabine as Second Line Treatment of Non-Small Cell Lung Cancer
NCT00077415	PHASE2	COMPLETED	3-AP and Gemcitabine as Second-Line Therapy in Treating Patients With Stage III or Stage IV Recurrent Non-Small Cell Lung Cancer
NCT00077545	PHASE2	COMPLETED	3-AP Plus Cisplatin in Treating Patients With Recurrent or Metastatic Adenocarcinoma of the Esophagus or Gastroesophageal Junction
NCT00078975	PHASE2	COMPLETED	3-AP and Gemcitabine in Treating Patients With Recurrent, Unresectable, or Metastatic Pancreatic Cancer
NCT00081276	PHASE2	COMPLETED	3-AP and Cisplatin in Treating Patients With Recurrent or Persistent Platinum-Resistant Ovarian Epithelial or Primary Peritoneal Cancer
NCT00085371	PHASE2	COMPLETED	Triapine as First-Line or Second-Line Therapy in Treating Patients With Locally Advanced or Metastatic Cancer of the Pancreas
NCT00095888	PHASE2	TERMINATED	3-AP and Gemcitabine in Treating Patients With Refractory Metastatic Breast Cancer
NCT00381550	PHASE2	COMPLETED	3-AP and Fludarabine in Treating Patients With Myeloproliferative Disorders, Chronic Myelomonocytic Leukemia, or Accelerated Phase or Blastic Phase Chronic Myelogenous Leukemia
NCT00941070	PHASE2	COMPLETED	Triapine, Cisplatin, and Radiation Therapy in Treating Patients With Cervical Cancer or Vaginal Cancer
NCT02595879	PHASE1	ACTIVE_NOT_RECRUITING	Triapine With Chemotherapy and Radiation Therapy in Treating Patients With IB2-IVA Cervical or Vaginal Cancer
NCT04234568	PHASE1	ACTIVE_NOT_RECRUITING	Testing the Addition of an Anti-cancer Drug, Triapine, to the Usual Radiation-Based Treatment (Lutetium Lu 177 Dotatate) for Neuroendocrine Tumors
NCT06410248	PHASE1	RECRUITING	Triapine in Combination With Temozolomide for the Treatment of Patients With Recurrent Glioblastoma
NCT00004213	PHASE1	COMPLETED	3-Aminopyridine-2-carboxaldehyde Thiosemicarbazone in Treating Patients With Solid Tumors
NCT00006218	PHASE1	COMPLETED	3-AP in Treating Patients With Advanced Cancer
NCT00016874	PHASE1	COMPLETED	3-AP Plus Cisplatin and Paclitaxel in Treating Patients With Advanced or Metastatic Cancer
NCT00024323	PHASE1	COMPLETED	Combination Chemotherapy in Treating Patients With Advanced Cancer
NCT00064090	PHASE1	COMPLETED	3-AP and Cytarabine in Treating Patients With Hematologic Cancer
NCT00077181	PHASE1	COMPLETED	3-AP and High-Dose Cytarabine in Treating Patients With Advanced Hematologic Malignancies
NCT00077558	PHASE1	COMPLETED	3-AP Followed By Fludarabine In Treating Patients With Relapsed or Refractory Acute or Chronic Leukemia or High-Risk Myelodysplastic Syndrome
NCT00079014	PHASE1	COMPLETED	3-AP and Doxorubicin In Treating Patients With Metastatic or Refractory Solid Tumors
NCT00084877	PHASE1	COMPLETED	Irinotecan and 3-AP in Treating Patients With Metastatic or Unresectable Solid Tumors
NCT00288093	PHASE1	COMPLETED	3-AP and Radiation Therapy in Treating Patients With Stage III Pancreatic Cancer That Cannot Be Removed By Surgery
NCT00293345	PHASE1	COMPLETED	3-AP and Gemcitabine in Treating Patients With Advanced Solid Tumors or Lymphoma
NCT00335998	PHASE1	COMPLETED	Phase I Study of Intravenous Triapine (IND # 68338) in Combination With Pelvic Radiation Therapy With or Without Weekly Intravenous Cisplatin Chemotherapy for Locally Advanced Cervical, Vaginal, or Pelvic Gynecologic Malignancies
NCT00390052	PHASE1	COMPLETED	3-AP in Treating Patients With Advanced or Metastatic Solid Tumors
NCT06860594	PHASE1	SUSPENDED	Testing the Addition of an Anti-Cancer Drug, Triapine, to the Usual Radiation Therapy for Recurrent Glioblastoma or Astrocytoma
NCT04494113	EARLY_PHASE1	ACTIVE_NOT_RECRUITING	Testing the Response to the Anti-cancer Drug, Triapine, in Uterine Cancers Using Markers From the Tissue at the Time of Hysterectomy

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

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