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MedKoo Cat#: 414989 | Name: Pirarubicin HCl

Description:

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

Pirarubicin HCl is the hydrochloride salt form of pirarubicin, an analogue of the anthracycline antineoplastic antibiotic doxorubicin with antineoplastic activity. Pirarubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair as well as RNA and protein synthesis. This agent is less cardiotoxic than doxorubicin and exhibits activity against some doxorubicin-resistant cell lines.

Chemical Structure

Pirarubicin HCl
Pirarubicin HCl
CAS#95343-20-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 414989

Name: Pirarubicin HCl

CAS#: 95343-20-7 (HCl)

Chemical Formula: C32H38ClNO12

Exact Mass: 663.2083

Molecular Weight: 664.10

Elemental Analysis: C, 57.88; H, 5.77; Cl, 5.34; N, 2.11; O, 28.91

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
95343-20-7 (HCl); 72496-41-4 (free base)
Synonym
Pirarubicin hydrochloride; Pirarubicin HCl
IUPAC/Chemical Name
(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2R)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
InChi Key
ZPHYPKKFSHAVOE-YZIXBPQXSA-N
InChi Code
InChI=1S/C32H37NO12.ClH/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;1H/t14-,17-,19-,21+,22-,31+,32-;/m0./s1
SMILES Code
O=C1C2=C(O)C([C@@H](O[C@@H]3O[C@@H](C)[C@@H](O[C@H]4OCCCC4)[C@@H](N)C3)C[C@@](C(CO)=O)(O)C5)=C5C(O)=C2C(C6=C1C(OC)=CC=C6)=O.[H]Cl
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 664.10 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: 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.

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