Nemorubicin HCl

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MedKoo CAT#: 414312

CAS#: 108943-08-4 (HCl)

Description: 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

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

Theoretical Analysis

MedKoo Cat#: 414312
Name: Nemorubicin HCl
CAS#: 108943-08-4 (HCl)
Chemical Formula: C32H38ClNO13
Exact Mass: 679.20
Molecular Weight: 680.100
Elemental Analysis: C, 56.51; H, 5.63; Cl, 5.21; N, 2.06; O, 30.58

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.