WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 200220
CAS#: 92395-36-3 (HCl)
Description: Amrubicin, also known as SM-5887, is an anthracycline used in the treatment of lung cancer. 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.
MedKoo Cat#: 200220
Name: Amrubicin HCl
CAS#: 92395-36-3 (HCl)
Chemical Formula: C25H26ClNO9
Molecular Weight: 519.93
Elemental Analysis: C, 57.75; H, 5.04; Cl, 6.82; N, 2.69; O, 27.70
This product is not in stock, which may be available by custom synthesis.
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Related CAS #: 92395-36-3 (HCl) 110267-81-7 (free base) 110311-30-3
Synonym: Amirubicin Hydrochloride; (±)-AMPA hydrobromide; SM-5887; SM 5887; SM5887;
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
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).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 519.93 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.
|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|
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.
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.