Pirarubicin
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MedKoo CAT#: 100734

CAS#: 72496-41-4

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.


Chemical Structure

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Pirarubicin
CAS# 72496-41-4

Theoretical Analysis

MedKoo Cat#: 100734
Name: Pirarubicin
CAS#: 72496-41-4
Chemical Formula: C32H37NO12
Exact Mass: 627.23158
Molecular Weight: 627.63
Elemental Analysis: C, 61.24; H, 5.94; N, 2.23; O, 30.59

Price and Availability

Size Price Availability Quantity
10.0mg USD 150.0 2 Weeks
25.0mg USD 250.0 2 Weeks
50.0mg USD 450.0 2 Weeks
100.0mg USD 850.0 2 Weeks
200.0mg USD 1250.0 2 Weeks
500.0mg USD 1950.0 2 Weeks
1.0g USD 3250.0 2 Weeks
2.0g USD 5350.0 2 Weeks
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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

Preparing Stock Solutions

The following data is based on the product molecular weight 627.63 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

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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.



Additional Information

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).