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MedKoo Cat#: 574918 | Name: Triapine free base
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Triapine, also known as 3-AP and OCX-191, is a synthetic heterocyclic carboxaldehyde thiosemicarbazone with potential antineoplastic activity. Triapine inhibits the enzyme ribonucleotide reductase, resulting in the inhibition of the conversion of ribonucleoside diphosphates to deoxyribonucleotides necessary for DNA synthesis. This agent has been shown to inhibit tumor growth in vitro.

Chemical Structure

Triapine free base
Triapine free base
CAS#143621-35-6 (free base)

Theoretical Analysis

MedKoo Cat#: 574918

Name: Triapine free base

CAS#: 143621-35-6 (free base)

Chemical Formula: C7H9N5S

Exact Mass: 195.0579

Molecular Weight: 195.24

Elemental Analysis: C, 43.06; H, 4.65; N, 35.87; S, 16.42

Price and Availability

Size Price Availability Quantity
10mg USD 500.00 2 Weeks
25mg USD 1,000.00 2 Weeks
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Related CAS #
200933-27-3 (E-isomer) 143621-35-6 (free base) 236392-56-6 (deleted) 216240-62-9 (HCl) 1938041-34-9 (HCl hydrate)
Synonym
3AP; 3AP; 3Apct; OCX 191; OCX191; OCX191; AIDS179996; AIDS179996; NSC663249. PAN-811; PAN811; PAN 811; Triapine
IUPAC/Chemical Name
(E)-2-((3-aminopyridin-2-yl)methylene)hydrazine-1-carbothioamide
InChi Key
XMYKNCNAZKMVQN-NYYWCZLTSA-N
InChi Code
InChI=1S/C7H9N5S/c8-5-2-1-3-10-6(5)4-11-12-7(9)13/h1-4H,8H2,(H3,9,12,13)/b11-4+
SMILES Code
NC1=C(/C=N/NC(N)=S)N=CC=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 195.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Rodríguez I, Acosta C, Nieves-Escobar C, Strangmark E, Claudio-Ares O, Vargas Figueroa AI, Soto-Millán AM, M Orta-Rivera A, Astashkin AV, Tinoco AD. DefNEtTrp: An Iron Dual Chelator Approach for Anticancer Application. JACS Au. 2024 Dec 4;4(12):4799-4808. doi: 10.1021/jacsau.4c00774. PMID: 39735911; PMCID: PMC11672142. 2: Gufler J, Heffeter P, Kowol CR, Hager S, Marko D. Opposing effects of mycotoxins alternariol and deoxynivalenol on the immunomodulatory effects of oxaliplatin and triapine. Toxicology. 2024 Dec 25;511:154039. doi: 10.1016/j.tox.2024.154039. Epub ahead of print. PMID: 39725263. 3: Taylor SE, Behr S, Cooper KL, Mahdi H, Fabian D, Gallion H, Ueland F, Vargo J, Orr B, Girda E, Courtney-Brooks M, Olawaiye AB, Randall LM, Richardson DL, Sullivan SA, Huang M, Christner SM, Beriwal S, Lin Y, Chauhan A, Chu E, Kohn EC, Kunos C, Ivy SP, Beumer JH. Dose finding, bioavailability, and PK-PD of oral triapine with concurrent chemoradiation for locally advanced cervical cancer and vaginal cancer (ETCTN 9892). Cancer Chemother Pharmacol. 2024 Dec 14;95(1):4. doi: 10.1007/s00280-024-04720-1. PMID: 39673591. 4: Chaudhary U, Kumar P, Sharma P, Chikara A, Barua A, Mahiya K, Adhikari Subin J, Nath Yadav P, Raj Pokharel Y. Synthesis of 5-hydroxyisatin thiosemicarbazones, spectroscopic investigation, protein-ligand docking, and in vitro anticancer activity. Bioorg Chem. 2024 Dec;153:107872. doi: 10.1016/j.bioorg.2024.107872. Epub 2024 Oct 10. PMID: 39442462. 5: Cheng J, Zink J, O'Neill E, Cornelissen B, Nonnekens J, Livieratos L, Terry SYA. Enhancing [177Lu]Lu-DOTA-TATE therapeutic efficacy in vitro by combining it with metronomic chemotherapeutics. EJNMMI Res. 2024 Aug 13;14(1):73. doi: 10.1186/s13550-024-01135-0. PMID: 39136880; PMCID: PMC11322472. 6: Kaya B, Gholam Azad M, Suleymanoglu M, Harmer JR, Wijesinghe TP, Richardson V, Zhao X, Bernhardt PV, Dharmasivam M, Richardson DR. Isosteric Replacement of Sulfur to Selenium in a Thiosemicarbazone: Promotion of Zn(II) Complex Dissociation and Transmetalation to Augment Anticancer Efficacy. J Med Chem. 2024 Jul 25;67(14):12155-12183. doi: 10.1021/acs.jmedchem.4c00884. Epub 2024 Jul 5. PMID: 38967641. 7: Li T, Zheng J, Huang T, Wang X, Li J, Jin F, Wei W, Chen X, Liu C, Bao M, Zhao G, Huang L, Zhao D, Chen J, Bu Z, Weng C. Identification of several African swine fever virus replication inhibitors by screening of a library of FDA- approved drugs. Virology. 2024 May;593:110014. doi: 10.1016/j.virol.2024.110014. Epub 2024 Feb 14. PMID: 38401340. 8: Huang S, Zhang D, Yi X, Liu C, Jian C, Yu A. 3-AP inhibits the growth of human osteosarcoma by decreasing the activity of the iron-dependent pathway. Med Oncol. 2023 Nov 11;40(12):353. doi: 10.1007/s12032-023-02215-2. PMID: 37952032. 9: Wijesinghe TP, Kaya B, Gonzálvez MA, Harmer JR, Gholam Azad M, Bernhardt PV, Dharmasivam M, Richardson DR. Steric Blockade of Oxy-Myoglobin Oxidation by Thiosemicarbazones: Structure-Activity Relationships of the Novel PPP4pT Series. J Med Chem. 2023 Nov 23;66(22):15453-15476. doi: 10.1021/acs.jmedchem.3c01612. Epub 2023 Nov 3. Erratum in: J Med Chem. 2024 Apr 25;67(8):6893. doi: 10.1021/acs.jmedchem.4c00714. PMID: 37922410. 10: Serttas R, Erdogan S. Inhibition of Ribonucleotide Reductase Induces Endoplasmic Reticulum Stress and Apoptosis, Leading to the Death of Docetaxel- resistant Prostate Cancer Cells. Anticancer Agents Med Chem. 2023;23(17):1958-1965. doi: 10.2174/1871520623666230810094635. PMID: 37565554. 11: Schaier M, Falcone E, Prstek T, Vileno B, Hager S, Keppler BK, Heffeter P, Koellensperger G, Faller P, Kowol CR. Human serum albumin as a copper source for anticancer thiosemicarbazones. Metallomics. 2023 Aug 1;15(8):mfad046. doi: 10.1093/mtomcs/mfad046. PMID: 37505477; PMCID: PMC10405564. 12: Corrales-Guerrero S, Cui T, Castro-Aceituno V, Yang L, Nair S, Feng H, Venere M, Yoon S, DeWees T, Shen C, Williams TM. Inhibition of RRM2 radiosensitizes glioblastoma and uncovers synthetic lethality in combination with targeting CHK1. Cancer Lett. 2023 Aug 28;570:216308. doi: 10.1016/j.canlet.2023.216308. Epub 2023 Jul 22. PMID: 37482342. 13: Perrault EN, Shireman JM, Ali ES, Lin P, Preddy I, Park C, Budhiraja S, Baisiwala S, Dixit K, James CD, Heiland DH, Ben-Sahra I, Pott S, Basu A, Miska J, Ahmed AU. Ribonucleotide reductase regulatory subunit M2 drives glioblastoma TMZ resistance through modulation of dNTP production. Sci Adv. 2023 May 19;9(20):eade7236. doi: 10.1126/sciadv.ade7236. Epub 2023 May 17. PMID: 37196077; PMCID: PMC10191446. 14: Sturm MJ, Henao-Restrepo JA, Becker S, Proquitté H, Beck JF, Sonnemann J. Synergistic anticancer activity of combined ATR and ribonucleotide reductase inhibition in Ewing's sarcoma cells. J Cancer Res Clin Oncol. 2023 Sep;149(11):8605-8617. doi: 10.1007/s00432-023-04804-0. Epub 2023 Apr 25. PMID: 37097390; PMCID: PMC10374484. 15: Chung MH, Aimaier R, Yu Q, Li H, Li Y, Wei C, Gu Y, Wang W, Guo Z, Long M, Li Q, Wang Z. RRM2 as a novel prognostic and therapeutic target of NF1-associated MPNST. Cell Oncol (Dordr). 2023 Oct;46(5):1399-1413. doi: 10.1007/s13402-023-00819-4. Epub 2023 Apr 22. PMID: 37086345. 16: Zhao Y, Zheng Y, Zhu Y, Ding K, Zhou M, Liu T. Co-delivery of gemcitabine and Triapine by calcium carbonate nanoparticles against chemoresistant pancreatic cancer. Int J Pharm. 2023 Apr 5;636:122844. doi: 10.1016/j.ijpharm.2023.122844. Epub 2023 Mar 14. PMID: 36925025. 17: Ritacca AG, Falcone E, Doumi I, Vileno B, Faller P, Sicilia E. Dual Role of Glutathione as a Reducing Agent and Cu-Ligand Governs the ROS Production by Anticancer Cu-Thiosemicarbazone Complexes. Inorg Chem. 2023 Mar 6;62(9):3957-3964. doi: 10.1021/acs.inorgchem.2c04392. Epub 2023 Feb 20. PMID: 36802558; PMCID: PMC9996813. 18: Pósa V, Stefanelli A, Nunes JHB, Hager S, Mathuber M, May NV, Berger W, Keppler BK, Kowol CR, Enyedy ÉA, Heffeter P. Thiosemicarbazone Derivatives Developed to Overcome COTI-2 Resistance. Cancers (Basel). 2022 Sep 14;14(18):4455. doi: 10.3390/cancers14184455. PMID: 36139615; PMCID: PMC9497102. 19: Rizwan Ahmad AM, Farooq U, Anees M, Anis RA, Rashid S, Ahmed W. Co- administration of Inulin and Iron Fortificants improves Iron Deficiency Biomarkers in Female Sprague Dawley Rats. Food Sci Nutr. 2022 May 7;10(7):2141-2148. doi: 10.1002/fsn3.2337. Erratum in: Food Sci Nutr. 2022 Oct 09;10(10):3527. doi: 10.1002/fsn3.3086. PMID: 35844906; PMCID: PMC9281937. 20: Huff SE, Winter JM, Dealwis CG. Inhibitors of the Cancer Target Ribonucleotide Reductase, Past and Present. Biomolecules. 2022 Jun 10;12(6):815. doi: 10.3390/biom12060815. PMID: 35740940; PMCID: PMC9221315.