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MedKoo Cat#: 100954 | Name: Carubicin HCl
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Description:

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

Carubicin (IDN-540), a semisynthetic anthracycline analog of doxorubicin, exhibits potent antitumor activity by intercalating DNA and inhibiting topoisomerase II, leading to DNA strand breaks and apoptosis. In preclinical studies, Carubicin demonstrated strong cytotoxicity against various human cancer cell lines, including colon, lung, and breast carcinomas, with IC₅₀ values typically in the low micromolar range (e.g., 0.2–1.5 μM depending on the cell line). Notably, Carubicin showed less cardiotoxicity compared to doxorubicin in animal models while retaining comparable efficacy. It has been evaluated in clinical settings, particularly for bladder cancer via intravesical administration, showing favorable tolerability and antitumor response rates in patients with superficial transitional cell carcinoma. NOTE: This product has purity ~90%, the ~10% impurity is sodium chloride

Chemical Structure

Carubicin HCl
Carubicin HCl
CAS#52794-97-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 100954

Name: Carubicin HCl

CAS#: 52794-97-5 (HCl)

Chemical Formula: C26H28ClNO10

Exact Mass: 0.0000

Molecular Weight: 549.96

Elemental Analysis: C, 56.78; H, 5.13; Cl, 6.45; N, 2.55; O, 29.09

Price and Availability

Size Price Availability Quantity
5mg USD 250.00 Ready to Ship
10mg USD 450.00 Ready to Ship
25mg USD 950.00 Ready to Ship
50mg USD 1,650.00 Ready to ship
100mg USD 2,950.00 Ready to Ship
200mg USD 5,250.00 Ready to ship
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Related CAS #
52794-97-5 (HCl) 50935-04-1 (free base)
Synonym
Carubicin HCl; Carubicin hydrochloride; Karminomycin hydrochloride; NSC 275649; IDN-540; IDN 540; IDN540;
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
Appearance
Red solid powder
Purity
Purity ~90%, the ~10% impurity is sodium chloride
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
More Info
Product Data
Product Data
Certificate of Analysis
CoA-Carubicin HCl-B7B06C19
QC Data
View QC data: current batch, Lot#B7B06C19
Safety Data Sheet (SDS)
SDS-Carubicin HCl
Instruction
View handling instruction
Biological target:
Carubicin HCl is an anthracycline antineoplastic antibiotic which inhibits topoisomerase II.
In vitro activity:
CA (Carubicin) induced apoptosis in CCRCC (clear cell renal cell carcinoma) cells by a mechanism independent of p53 or hypoxia-inducible factor 2. P-glycoprotein (P-gp) sequestered CA within the Golgi complex. Interestingly, Golgi sequestration was critical for the antiproliferative effects of CA and P-gp inhibitors abrogated this activity. Furthermore, CA induced cleavage of the Golgi protein p115 and the translocation of its C-terminal fragment to the nucleus. Finally, examination of the activity of the VHL-interacting Golgi protein, endoplasmic reticulum-Golgi intermediate compartment, ERGIC-53 showed that VHL could mediate protection from CA in CCRCC cells. Reference: Cancer Res. 2011 Jan 1;71(1):134-42. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3074515/
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 549.96 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:
1. 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. PMID: 21199801; PMCID: PMC3074515.
In vitro protocol:
1. 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. PMID: 21199801; PMCID: PMC3074515.
In vivo protocol:
TBD
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.