Carubicin HCl
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MedKoo CAT#: 100954

CAS#: 52794-97-5 (HCl)

Description: Carubicin HCl is an anthracycline antineoplastic antibiotic isolated from the bacterium Actinomadura carminata. Carubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis.


Price and Availability

Size
Price

100mg
USD 1650
1g
USD 6450
Size
Price

200mg
USD 2250
2g
USD 11850
Size
Price

500mg
USD 4250
5g
Ask price

Carubicin HCl, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100954
Name: Carubicin HCl
CAS#: 52794-97-5 (HCl)
Chemical Formula: C26H28ClNO10
Exact Mass:
Molecular Weight: 549.957
Elemental Analysis: C, 56.78; H, 5.13; Cl, 6.45; N, 2.55; O, 29.09


Related CAS #: 52794-97-5 (HCl)   50935-04-1 (free base)    

Synonym: Carubicin HCl; Carubicin hydrochloride; Karminomycin hydrochloride; NSC 275649.

IUPAC/Chemical Name: (8S,10S)-8-acetyl-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-1,6,8,11-tetrahydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride

InChi Key: WYVYEIZFAUXWKW-SHUUXQFMSA-N

InChi Code: InChI=1S/C26H27NO10.ClH/c1-9-21(30)13(27)6-16(36-9)37-15-8-26(35,10(2)28)7-12-18(15)25(34)20-19(23(12)32)22(31)11-4-3-5-14(29)17(11)24(20)33;/h3-5,9,13,15-16,21,29-30,32,34-35H,6-8,27H2,1-2H3;1H/t9-,13-,15-,16-,21+,26-;/m0./s1

SMILES Code: [H]Cl.CC([C@@](C[C@@H]1O[C@@H]2O[C@H]([C@H]([C@H](C2)N)O)C)(CC(C(O)=C3C(C4=C5C(O)=CC=C4)=O)=C1C(O)=C3C5=O)O)=O


Technical Data

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).

Harmonized System Code:
293490


References

1: Dezhenkova LG, Teviashova AN, Olsuf'eva EN, Treshchalin ID, Shtil' AA, Preobrazhenskaia MN. [Anthracycline antibiotics and their derivatives--inhibitors of topoisomerase I]. Bioorg Khim. 2008 May-Jun;34(3):430-2. Russian. PubMed PMID: 18672696.

2: Woldemichael GM, Turbyville TJ, Linehan WM, McMahon JB. Carminomycin I is an apoptosis inducer that targets the Golgi complex in clear cell renal carcinoma cells. Cancer Res. 2011 Jan 1;71(1):134-42. doi: 10.1158/0008-5472.CAN-10-0757. PubMed PMID: 21199801; PubMed Central PMCID: PMC3074515.

3: Asano T, Nakamura K, Fujii H, Horichi N, Ohmori T, Hasegawa K, Isoe T, Adachi M, Otake N, Fukunaga Y. Altered expression of topoisomerase IIalpha contributes to cross-resistant to etoposide K562/MX2 cell line by aberrant methylation. Br J Cancer. 2005 Apr 25;92(8):1486-92. PubMed PMID: 15798770; PubMed Central PMCID: PMC2362017.

4: Tevyashova AN, Shtil AA, Olsufyeva EN, Simonova VS, Samusenko AV, Preobrazhenskaya MN. Carminomycin, 14-hydroxycarminomycin and its novel carbohydrate derivatives potently kill human tumor cells and their multidrug resistant variants. J Antibiot (Tokyo). 2004 Feb;57(2):143-50. PubMed PMID: 15112963.

5: Mizumatsu S, Matsumoto K, Ono Y, Tamiya T, Furuta T, Ohmoto T. Intrathecal chemotherapy with MX2 for treating glioma dissemination in vivo. J Neurooncol. 2000 Aug;49(1):41-7. PubMed PMID: 11131985.

6: Kuratsu JI, Arita N, Kayama T, Kubo N, Mori T, Sawamura Y, Ushio Y. Phase II trial of pre-irradiation KRN8602 (MX2) in malignant glioma patients. J Neurooncol. 2000 Jun;48(2):145-9. PubMed PMID: 11083079.

7: Capobianco ML, De Champdoré M, Francini L, Lena S, Garbesi A, Arcamone F. New TFO conjugates containing a carminomycinone-derived chromophore. Bioconjug Chem. 2001 Jul-Aug;12(4):523-8. PubMed PMID: 11459456.

8: Park SJ, Kaye AH, Hill JS. An investigation of the cytotoxicity of the morpholino anthracycline MX2 against glioma cells in vitro. J Clin Neurosci. 2000 Jan;7(1):42-7. PubMed PMID: 10847650.

9: Lutsenko SV, Feldman NB, Finakova GV, Gukasova NV, Petukhov SP, Posypanova GA, Skryabin KG, Severin SE. Antitumor activity of alpha fetoprotein and epidermal growth factor conjugates in vitro and in vivo. Tumour Biol. 2000 Nov-Dec;21(6):367-74. PubMed PMID: 11006577.

10: Takemoto Y, Sampi K, Kuraishi Y, Okabe K, Tamura K, Mizoguchi H, Saito H, Masaoka T, Ogawa M. A prospective randomized trial of KRN8602 and cytosine arabinoside vs. daunorubicin and cytosine arabinoside in adult patients with newly diagnosed acute myelogenous leukemia. The KRN8602 Leukemia Study Group. Int J Hematol. 1999 Jul;70(1):20-5. PubMed PMID: 10446490.

11: Clarke K, Basser RL, Maher D, Morgan DJ, Cebon J, Fox RM, Hill JS, Alt C, Bartlett J, Geldard H, Kaye AH, Green MD. Phase I and pharmacokinetic study of KRN8602 alone and with filgrastim in patients with advanced cancer. J Clin Oncol. 1998 Jun;16(6):2181-7. PubMed PMID: 9626219.

12: Okabe K, Sampi K, Kuraishi Y, Takemoto Y, Tamura K, Ogawa M. [Phase II study of KRN8602 (MX2) for malignant lymphoma]. Gan To Kagaku Ryoho. 1998 Jun;25(7):1001-6. Japanese. PubMed PMID: 9644314.

13: Clarke K, Basser RL, Underhill C, Mitchell P, Bartlett J, Cher L, Findlay M, Dalley D, Pell M, Byrne M, Geldard H, Hill JS, Maher D, Fox RM, Green MD, Kaye AH. KRN8602 (MX2-hydrochloride): an active new agent for the treatment of recurrent high-grade glioma. J Clin Oncol. 1999 Aug;17(8):2579-84. PubMed PMID: 10561325.

14: Mima T, Mostafa MG, Mori K. Antitumor effect and peritumoral brain edema formation in relation to MX2, ACNU, and doxorubicin therapy: a comparative analysis using rodent models of gliomas. Neurol Res. 2000 Dec;22(8):819-24. PubMed PMID: 11149245.

15: Kuratsu J, Arita N, Kurisu K, Uozumi T, Hayakawa T, Ushio Y. A phase II study of KRN8602(MX2), a novel morpholino anthracycline derivative, in patients with recurrent malignant glioma. J Neurooncol. 1999 Apr;42(2):177-81. PubMed PMID: 10421076.

16: Katsumata N, Watanabe T, Tominaga T, Ogawa M, Adachi I, Enomoto K, Kajiwara T, Kusama M, Yamada Y, Abe O. Phase II study of KRN8602, 3'-deamino-3'-morpholino-13-deoxo-10-hydroxycarminomycin hydrochloride, MX2 x HCl in patients with metastatic breast cancer. Cancer Chemother Pharmacol. 1999;43(6):441-4. PubMed PMID: 10321502.

17: Hiraoka A, Sampi K, Kuraishi Y, Takemoto Y, Okabe K, Tamura K, Ogawa M. [Pilot late phase II study of KRN8602 (MX2), a novel anthracycline derivative, for acute leukemia--a dose finding study in combination]. Gan To Kagaku Ryoho. 1999 Jan;26(1):93-9. Japanese. PubMed PMID: 9987504.

18: Toshchevikova AIu, Pisarev OA. [Optimization of conditions of preparative chromatography of carminomycin on a carboxylic cation exchanger]. Prikl Biokhim Mikrobiol. 2002 Mar-Apr;38(2):128-31. Russian. PubMed PMID: 11962206.

19: Takemoto Y, Sampi K, Kuraishi Y, Toki H, Tamura K, Ogawa M. [Early phase II study of KRN8602 (MX2), a novel anthracycline derivative for acute leukemia]. Gan To Kagaku Ryoho. 1998 Dec;25(14):2243-8. Japanese. PubMed PMID: 9881081.

20: Morgan DJ, Hill JS, Clarke K, Stylli SS, Park SJ, Cebon J, Basser RL, Kaye AH, Geldard H, Maher DW, Green MD. Pharmacokinetics and pharmacodynamics of MX2 hydrochloride in patients with advanced malignant disease. Cancer Chemother Pharmacol. 1997;40(3):202-8. PubMed PMID: 9219502.