Amrubicin

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

MedKoo CAT#: 200220

CAS#: 92395-36-3 (HCl salt)

Description: Amrubicin hydrochloride is the hydrochloride salt of a third-generation synthetic 9-amino-anthracycline with antineoplastic activity. Amrubicin intercalates into DNA and inhibits the activity of topoisomerase II, resulting in inhibition of DNA replication, and RNA and protein synthesis, followed by cell growth inhibition and cell death. This agent has demonstrated a higher level of anti-tumor activity than conventional anthracycline drugs without exhibiting any indication of the cumulative cardiac toxicity common to this class of compounds. It is marketed in Japan since 2002 by Sumitomo Pharmaceuticals.


Price and Availability

Size
Price

1g
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Size
Price

2g
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Size
Price

5g
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Amrubicin, purity > 98%, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 200220
Name: Amrubicin
CAS#: 92395-36-3 (HCl salt)
Chemical Formula: C25H26ClNO9
Exact Mass:
Molecular Weight: 519.93
Elemental Analysis: C, 57.75; H, 5.04; Cl, 6.82; N, 2.69; O, 27.70


Synonym: Amirubicin Hydrochloride. Foreign brand name: Calsed. Abbreviation: AMR.

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

InChi Key: BHMLHEQFWVQAJS-IITOGVPQSA-N

InChi Code: InChI=1S/C25H25NO9.ClH/c1-10(27)25(26)7-13-18(16(8-25)35-17-6-14(28)15(29)9-34-17)24(33)20-19(23(13)32)21(30)11-4-2-3-5-12(11)22(20)31;/h2-5,14-17,28-29,32-33H,6-9,26H2,1H3;1H/t14-,15+,16-,17-,25-;/m0./s1

SMILES Code: O=C1C2=C(O)C([C@@H](O[C@H]3C[C@H](O)[C@H](O)CO3)C[C@](N)(C(C)=O)C4)=C4C(O)=C2C(C5=C1C=CC=C5)=O.[H]Cl


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, not in water

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


Additional Information

Related:
92395-36-3 (Amrubicin HCl salt)
110267-81-7 (Amrubicin free base).

Amrubicin (INN; previously known as SM-5887) is an anthracycline used in the treatment of lung cancer. It is marketed in Japan since 2002 by Sumitomo Pharmaceuticals under the brand name Calsed. Amrubicin acts by inhibiting Topoisomerase II, and has been compared in clinical trials with Topotecan, a Topoisomerase I inhibitor. It has also been studied for the treatment of bladder carcinoma and gastric cancer. See: http://en.wikipedia.org/wiki/Amrubicin.
 
 


References

1: Inoue A, Sugawara S, Maemondo M, Mori Y, Oizumi S, Harada M, Taima K, Morikawa N, Ishida T, Kinoshita I, Watanabe H, Suzuki T, Nakagawa T, Saito R, Nukiwa T. Randomized phase II trial comparing amrubicin with re-challenge of platinum doublet in patients with sensitive-relapsed small-cell lung cancer: North Japan Lung Cancer Study Group trial 0702. Lung Cancer. 2015 Jul;89(1):61-5. doi: 10.1016/j.lungcan.2015.04.012. Epub 2015 May 4. PubMed PMID: 26004087.

2: Miura S, Kaira K, Kaira R, Akamatsu H, Ono A, Shukuya T, Tsuya A, Nakamura Y, Kenmotsu H, Naito T, Murakami H, Takahashi T, Endo M, Yamamoto N. The efficacy of amrubicin on central nervous system metastases originating from small-cell lung cancer: a case series of eight patients. Invest New Drugs. 2015 Jun;33(3):755-60. doi: 10.1007/s10637-015-0233-7. Epub 2015 Apr 7. PubMed PMID: 25846908.

3: Ogawara D, Nakamura Y, Fukuda M, Nakatomi K, Yamaguchi H, Motoshima K, Mizoguchi K, Nakano H, Takemoto S, Gyotoku H, Nagashima S, Kohno S. Phase I/II study of amrubicin and nedaplatin in patients with untreated, advanced, non-small cell lung cancer. Chemotherapy. 2014;60(3):180-4. doi: 10.1159/000371870. Epub 2015 Mar 25. PubMed PMID: 25823897.

4: Nio K, Arita S, Isobe T, Kusaba H, Kohashi K, Kajitani T, Tamura S, Hirano G, Mitsugi K, Makiyama A, Esaki T, Ariyama H, Oda Y, Akashi K, Baba E. Amrubicin monotherapy for patients with extrapulmonary neuroendocrine carcinoma after platinum-based chemotherapy. Cancer Chemother Pharmacol. 2015 Apr;75(4):829-35. doi: 10.1007/s00280-015-2706-y. Epub 2015 Feb 22. PubMed PMID: 25702050.

5: Jalal SI, Hanna N, Zon R, Masters GA, Borghaei H, Koneru K, Badve S, Prasad N, Somaiah N, Wu J, Yu Z, Einhorn L. Phase I Study of Amrubicin and Cyclophosphamide in Patients With Advanced Solid Organ Malignancies: HOG LUN 07-130. Am J Clin Oncol. 2014 Dec 10. [Epub ahead of print] PubMed PMID: 25503432.

6: Inoue A, Sugawara S, Harada M, Kobayashi K, Kozuki T, Kuyama S, Maemondo M, Asahina H, Hisamoto A, Nakagawa T, Hotta K, Nukiwa T. Phase II study of Amrubicin combined with carboplatin for thymic carcinoma and invasive thymoma: North Japan Lung Cancer group study 0803. J Thorac Oncol. 2014 Dec;9(12):1805-9. doi: 10.1097/JTO.0000000000000362. PubMed PMID: 25393793.

7: von Pawel J, Jotte R, Spigel DR, O'Brien ME, Socinski MA, Mezger J, Steins M, Bosquée L, Bubis J, Nackaerts K, Trigo JM, Clingan P, Schütte W, Lorigan P, Reck M, Domine M, Shepherd FA, Li S, Renschler MF. Randomized phase III trial of amrubicin versus topotecan as second-line treatment for patients with small-cell lung cancer. J Clin Oncol. 2014 Dec 10;32(35):4012-9. doi: 10.1200/JCO.2013.54.5392. Epub 2014 Nov 10. PubMed PMID: 25385727.

8: Yardley DA, Raefsky E, Hainsworth JD, Burris HA 3rd, Priego V, Inclan A. Amrubicin as second- or third-line treatment for women with metastatic HER2-negative breast cancer: a Sarah Cannon Research Institute phase 1/2 trial. Breast Cancer Res Treat. 2014 Dec;148(3):535-40. doi: 10.1007/s10549-014-3189-y. Epub 2014 Nov 6. PubMed PMID: 25374098.

9: Fukushima T, Gomi D, Kobayashi T, Sekiguchi N, Sakamoto A, Sasaki S, Koizumi T. Successful salvage chemotherapy with amrubicin for invasive thymoma associated with myasthenia gravis. Jpn J Clin Oncol. 2014 Nov;44(11):1120-2. doi: 10.1093/jjco/hyu136. Epub 2014 Sep 19. PubMed PMID: 25240023.

10: Ikeda T, Fukuda M, Nakamura Y, Kinoshita A, Senju H, Nakano H, Kitazaki T, Ogawara D, Taniguchi H, Motoshima K, Yamaguchi H, Nakatomi K, Shimada M, Nagashima S, Tsukamoto K, Kohno S; Nagasaki Thoracic Oncology Group. A phase II study of amrubicin and carboplatin for previously untreated patients with extensive-disease small cell lung cancer. Cancer Chemother Pharmacol. 2014 Sep;74(3):497-502. doi: 10.1007/s00280-014-2527-4. Epub 2014 Jul 18. PubMed PMID: 25034978.