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MedKoo Cat#: 414312 | Name: Nemorubicin HCl

Description:

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

Nemorubicin is the salt form of Nemorubicin, also known as PNU152243A, a doxorubicin derivative that differs significantly from its parent drug in terms of spectrum of antitumor activity, metabolism and toxicity profile. The drug is active on tumors resistant to alkylating agents, topoisomerase II inhibitors and platinum derivatives. It works primarily through topoisomerase I inhibition. Of note, Nemorubicin is active in cells with upregulation of the nucleotide excision repair (NER) pathway, where current therapies fail. Nemorubicin is biotransformed in the liver into cytotoxic metabolites that may further contribute to render this drug highly active against primary liver tumors or liver metastases.

Chemical Structure

Nemorubicin HCl
Nemorubicin HCl
CAS#108943-08-4 (HCl)

Theoretical Analysis

MedKoo Cat#: 414312

Name: Nemorubicin HCl

CAS#: 108943-08-4 (HCl)

Chemical Formula: C32H38ClNO13

Exact Mass: 679.2032

Molecular Weight: 680.10

Elemental Analysis: C, 56.51; H, 5.63; Cl, 5.21; N, 2.06; O, 30.58

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 #
108943-08-4 (HCl) 108852-90-0 (free base)
Synonym
Nemorubicin hydrochloride; Nemorubicin HCl; PNU152243A; PNU-152243A; PNU 152243A;
IUPAC/Chemical Name
(8S,10S)-6,8,11-trihydroxy-10-(((2R,4S,5S,6S)-5-hydroxy-4-((S)-2-methoxymorpholino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride
InChi Key
DSXDXWLGVADASF-QQFKZXDBSA-N
InChi Code
InChI=1S/C32H37NO13.ClH/c1-14-27(36)17(33-7-8-44-22(12-33)43-3)9-21(45-14)46-19-11-32(41,20(35)13-34)10-16-24(19)31(40)26-25(29(16)38)28(37)15-5-4-6-18(42-2)23(15)30(26)39;/h4-6,14,17,19,21-22,27,34,36,38,40-41H,7-13H2,1-3H3;1H/t14-,17-,19-,21-,22-,27+,32-;/m0./s1
SMILES Code
CO[C@@H]1CN([C@H]2C[C@@H](O[C@H]([C@H]2O)C)O[C@H]3C[C@@](Cc4c3c(O)c5c(C(c6c(C5=O)c(OC)ccc6)=O)c4O)(C(CO)=O)O)CCO1.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 680.10 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: Mazzini S, Scaglioni L, Mondelli R, Caruso M, Sirtori FR. The interaction of nemorubicin metabolite PNU-159682 with DNA fragments d(CGTACG)(2), d(CGATCG)(2) and d(CGCGCG)(2) shows a strong but reversible binding to G:C base pairs. Bioorg Med Chem. 2012 Dec 15;20(24):6979-88. doi: 10.1016/j.bmc.2012.10.033. Epub 2012 Nov 3. PubMed PMID: 23154079. 2: Sabatino MA, Marabese M, Ganzinelli M, Caiola E, Geroni C, Broggini M. Down-regulation of the nucleotide excision repair gene XPG as a new mechanism of drug resistance in human and murine cancer cells. Mol Cancer. 2010 Sep 24;9:259. doi: 10.1186/1476-4598-9-259. PubMed PMID: 20868484; PubMed Central PMCID: PMC2955619. 3: Lu H, Chen CS, Waxman DJ. Potentiation of methoxymorpholinyl doxorubicin antitumor activity by P450 3A4 gene transfer. Cancer Gene Ther. 2009 May;16(5):393-404. doi: 10.1038/cgt.2008.93. Epub 2008 Nov 14. PubMed PMID: 19011599; PubMed Central PMCID: PMC2669851. 4: Quintieri L, Fantin M, Palatini P, De Martin S, Rosato A, Caruso M, Geroni C, Floreani M. In vitro hepatic conversion of the anticancer agent nemorubicin to its active metabolite PNU-159682 in mice, rats and dogs: a comparison with human liver microsomes. Biochem Pharmacol. 2008 Sep 15;76(6):784-95. doi: 10.1016/j.bcp.2008.07.003. Epub 2008 Jul 11. PubMed PMID: 18671948. 5: Broggini M. Nemorubicin. Top Curr Chem. 2008;283:191-206. doi: 10.1007/128_2007_6. PubMed PMID: 23605633. 6: Sessa C, Valota O, Geroni C. Ongoing phase I and II studies of novel anthracyclines. Cardiovasc Toxicol. 2007;7(2):75-9. Review. PubMed PMID: 17652808. 7: Quintieri L, Geroni C, Fantin M, Battaglia R, Rosato A, Speed W, Zanovello P, Floreani M. Formation and antitumor activity of PNU-159682, a major metabolite of nemorubicin in human liver microsomes. Clin Cancer Res. 2005 Feb 15;11(4):1608-17. PubMed PMID: 15746066. 8: Fraier D, Frigerio E, Brianceschi G, James CA. LC-MS-MS determination of nemorubicin (methoxymorpholinyldoxorubicin, PNU-152243A) and its 13-OH metabolite (PNU-155051A) in human plasma. J Pharm Biomed Anal. 2002 Oct 15;30(3):377-89. PubMed PMID: 12367663.