Sabarubicin

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MedKoo CAT#: 206223

CAS#: 211100-13-9 (free base)

Description: Sabarubicin, also known as BMS195615 and MEN10755, is a disaccharide analogue of the anthracycline antineoplastic antibiotic doxorubicin. Sabarubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. This agent also induces apoptosis through a p53-independent mechanism. Sabarubicin is less cardiotoxic than doxorubicin.


Chemical Structure

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Sabarubicin
CAS# 211100-13-9 (free base)

Theoretical Analysis

MedKoo Cat#: 206223
Name: Sabarubicin
CAS#: 211100-13-9 (free base)
Chemical Formula: C32H38N2O12
Exact Mass: 642.24247
Molecular Weight: 642.65032
Elemental Analysis: C, 59.81; H, 5.96; N, 4.36; O, 29.88

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 #: 169317-77-5 (HCl)   211100-13-9 (free base)    

Synonym: BMS195615; BMS-195615; BMS 195615; MEN10755; MEN 10755; MEN-10755; Sabarubicin;

IUPAC/Chemical Name: (7S,9S)-7-(((2S,4R,5R,6S)-6-amino-5-(((2S,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-methyltetrahydro-2H-pyran-2-yl)oxy)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7,8,9,10-tetrahydrotetracene-5,12-dione

InChi Key: GDALLDVOCMKLMS-OTEQBJPJSA-N

InChi Code: InChI=1S/C32H38N2O12/c1-12-7-20(46-31(34)30(12)45-21-8-17(33)25(37)13(2)43-21)44-18-10-32(42,19(36)11-35)9-16-22(18)29(41)24-23(28(16)40)26(38)14-5-3-4-6-15(14)27(24)39/h3-6,12-13,17-18,20-21,25,30-31,35,37,40-42H,7-11,33-34H2,1-2H3/t12-,13+,17+,18+,20+,21+,25-,30-,31+,32+/m1/s1

SMILES Code: O=C1C2=C(O)C([C@@H](O[C@@H]3C[C@@H](C)[C@@H](O[C@H]4C[C@H](N)[C@H](O)[C@H](C)O4)[C@@H](N)O3)C[C@@](C(CO)=O)(O)C5)=C5C(O)=C2C(C6=C1C=CC=C6)=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

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 642.65032 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: Manet I, Manoli F, Zambelli B, Andreano G, Masi A, Cellai L, Ottani S, Marconi G, Monti S. Complexes of the antitumoral drugs Doxorubicin and Sabarubicin with telomeric G-quadruplex in basket conformation: ground and excited state properties. Photochem Photobiol Sci. 2011 Aug;10(8):1326-37. Epub 2011 Jun 9. PubMed PMID: 21655621.

2: Manet I, Manoli F, Zambelli B, Andreano G, Masi A, Cellai L, Monti S. Affinity of the anthracycline antitumor drugs Doxorubicin and Sabarubicin for human telomeric G-quadruplex structures. Phys Chem Chem Phys. 2011 Jan 14;13(2):540-51. Epub 2010 Nov 4. PubMed PMID: 21052579.

3: Mazzini S, Scaglioni L, Animati F, Mondelli R. Interaction between double helix DNA fragments and the new antitumor agent sabarubicin, Men10755. Bioorg Med Chem. 2010 Feb 15;18(4):1497-506. Epub 2010 Jan 11. PubMed PMID: 20116264.

4: Bressan A, Nardelli F, Bellarosa D, Bigioni M, Curcurù G, Curatella B, Crea A, Maggi CA, Manzini S, Binaschi M. Sabarubicin (MEN10755)-induced apoptosis is independent from mtDNA in A2780 human ovarian tumor cells. Anticancer Res. 2007 Nov-Dec;27(6B):4039-46. PubMed PMID: 18225568.

5: Bigioni M, Benzo A, Irrissuto C, Lopez G, Curatella B, Maggi CA, Manzini S, Crea A, Caroli S, Cubadda F, Binaschi M. Antitumour effect of combination treatment with Sabarubicin (MEN 10755) and cis-platin (DDP) in human lung tumour xenograft. Cancer Chemother Pharmacol. 2008 Sep;62(4):621-9. Epub 2007 Nov 24. PubMed PMID: 18038274.

6: Fiedler W, Tchen N, Bloch J, Fargeot P, Sorio R, Vermorken JB, Collette L, Lacombe D, Twelves C; EORTC new drug development group. A study from the EORTC new drug development group: open label phase II study of sabarubicin (MEN-10755) in patients with progressive hormone refractory prostate cancer. Eur J Cancer. 2006 Jan;42(2):200-4. Epub 2005 Dec 7. PubMed PMID: 16337787.

7: Bellarosa D, Binaschi M, Maggi CA, Goso C. Sabarubicin- (MEN 10755) and paclitaxel show different kinetics in nuclear factor-kappaB (NF-kB) activation: effect of parthenolide on their cytotoxicity. Anticancer Res. 2005 May-Jun;25(3B):2119-28. PubMed PMID: 16158953.

8: Caponigro F, Willemse P, Sorio R, Floquet A, van Belle S, Demol J, Tambaro R, Comandini A, Capriati A, Adank S, Wanders J. A phase II study of sabarubicin (MEN-10755) as second line therapy in patients with locally advanced or metastatic platinum/taxane resistant ovarian cancer. Invest New Drugs. 2005 Jan;23(1):85-9. PubMed PMID: 15528985.



Additional Information

Sabarubicin (MEN-10755), a disaccharide analog of doxorubicin, is used for the treatment of small cell lung cancer (SCLC). It has been seen to show superior antitumour efficacy, which is purported to be linked to the activation of p53-independent apoptosis.