WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H100734
CAS#: 72496-41-4 (free base)
Description: Pirarubicin is an anthracycline drug. An analogue of the anthracycline antineoplastic antibiotic doxorubicin. Pirarubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. This agent is less cardiotoxic than doxorubicin and exhibits activity against some doxorubicin-resistant cell lines.
Hodoodo Cat#: H100734
Name: Pirarubicin
CAS#: 72496-41-4 (free base)
Chemical Formula: C32H37NO12
Exact Mass: 627.23
Molecular Weight: 627.643
Elemental Analysis: C, 61.24; H, 5.94; N, 2.23; O, 30.59
Related CAS #: 95343-20-7 (HCl); 72496-41-4 (free base)
Synonym: Tepirubicin; Tetrahydropyranyl-Doxorubicin; THP-Adriamycin; THP-Doxorubicin. brand names: Pinorubicin; Theprubicine; Therarubicin. THPADM; THPDOX. 1609RB.
IUPAC/Chemical Name: (8S,10S)-10-(((2R,4S,5S,6S)-4-amino-6-methyl-5-(((S)-tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
InChi Key: KMSKQZKKOZQFFG-HSUXVGOQSA-N
InChi Code: InChI=1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19-,21-,22-,31+,32-/m0/s1
SMILES Code: O=C1C2=C(O)C(C[C@](C(CO)=O)(O)C[C@@H]3O[C@H]4C[C@H](N)[C@H](O[C@H]5CCCCO5)[C@H](C)O4)=C3C(O)=C2C(C6=C1C=CC=C6OC)=O
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, not in water
Shelf Life: >2 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: P irarubicin is an analogue of the anthracycline antineoplastic antibiotic doxorubicin. Pirarubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. This agent is less cardiotoxic than doxorubicin and exhibits activity against some doxorubicin-resistant cell lines. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).
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The following data is based on the product molecular weight 627.64 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.
| 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 |
| Formulation protocol: | |
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1: Chen Z, Liu G, Chen M, Chen X, Wu M, Chen X. An instrument-based screening assay for DNA-targeted anticancer drugs using resonance light scattering. Comb Chem High Throughput Screen. 2010 Jun;13(5):383-92. PubMed PMID: 20156144.
2: Vautravers C, Rat P, Cercueil JP, Moreau T, Horiot JC, Chauffert B. Hepatocellular carcinoma presenting as paraneoplastic myasthenia gravis. Eur J Intern Med. 2008 Dec;19(8):e86-7. Epub 2008 Jun 10. PubMed PMID: 19046712.
3: Tanaka T, Toujima S, Utsunomiya T, Yukawa K, Umesaki N. Experimental characterization of recurrent ovarian immature teratoma cells after optimal surgery. Oncol Rep. 2008 Jul;20(1):13-23. PubMed PMID: 18575713.
4: Qiao BM, Sun G, Tang Y, Chang JW, Wang WC, Ma TX. [Overexpression of PTEN gene inhibits proliferation of bladder transitional carcinoma cell line EJ]. Zhonghua Zhong Liu Za Zhi. 2007 Apr;29(4):262-5. Chinese. PubMed PMID: 17760251.
5: Wu XX, Zeng Y, Jin XH, Kakehi Y. Enhanced susceptibility of adriamycin-treated human renal cell carcinoma cells to lysis by peripheral blood lymphocytes and tumor infiltrating lymphocytes. Oncol Rep. 2007 Aug;18(2):353-9. PubMed PMID: 17611656.
6: Benoit L, Favoulet P, Ortega-Deballon P, Cheynel N, Anusca A, Bamourou D, Bonnetain F, Rat P, Favre JP, Chauffert B. Attempts to improve locoregional chemotherapy for the prevention of colonic cancer liver metastasis in the rat. Gastroenterol Clin Biol. 2006 Aug-Sep;30(8-9):1019-25. PubMed PMID: 17075453.
7: Lu YF, Zeng J, Liao QH, Lin J, Huang Y, Chen JQ, Tian L, Xie NC. [Comparative study on clinical effect of postoperative arterial infusion chemotherapy and systemic chemotherapy in gastric cancer]. Zhonghua Wei Chang Wai Ke Za Zhi. 2006 Jul;9(4):317-9. Chinese. PubMed PMID: 16886113.
8: Kokawa K, Mabuchi Y, Tanaka K, Yagi S, Utsunomiya T, Oba N, Yata C, Umesaki N. Apoptosis in cervical cancer after balloon-occluded arterial infusion of anticancer drugs. Anticancer Res. 2006 Mar-Apr;26(2B):1413-8. PubMed PMID: 16619552.
9: Tanaka T, Bai T, Yukawa K, Umesaki N. Optimal combination chemotherapy and chemoradiotherapy with etoposide for advanced cervical squamous cancer cells in vitro. Oncol Rep. 2006 Apr;15(4):939-47. PubMed PMID: 16525683.
10: Greish K, Nagamitsu A, Fang J, Maeda H. Copoly(styrene-maleic acid)-pirarubicin micelles: high tumor-targeting efficiency with little toxicity. Bioconjug Chem. 2005 Jan-Feb;16(1):230-6. PubMed PMID: 15656596.
