Amrubicin hydrochloride - CAS 110311-30-3
Catalog number: 110311-30-3
Category: Inhibitor
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Molecular Formula:
C25H26ClNO9
Molecular Weight:
519.93
COA:
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Targets:
Topoisomerase
Description:
Amrubicin hydrochloride is a topoisomerase II inhibitor used in the treatment of lung cancer.
Purity:
>98%
Synonyms:
SM-5887 hydrochloride
MSDS:
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InChIKey:
BHMLHEQFWVQAJS-IITOGVPQSA-N
InChI:
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
Canonical SMILES:
CC(=O)C1(CC(C2=C(C3=C(C(=C2C1)O)C(=O)C4=CC=CC=C4C3=O)O)OC5CC(C(CO5)O)O)N.Cl
1.[Retrospective analysis of amrubicin hydrochloride monotherapy in patients with previously treated small-cell lung cancer].
Nitta T1, Yamasaki M, Kajihara T, Mito A, Awaya H, Ikegami Y, Arita K. Gan To Kagaku Ryoho. 2010 Jun;37(6):1045-9.
We retrospectively investigated amrubicin hydrochloride(AMR)monotherapy as second or thirdline chemotherapy for small-cell lung cancer(SCLC)and assessed its efficacy and safety. AMR was intravenously administered at 25-45mg/m2 for 3 consecutive days every 3-4 weeks. Fifty-three patients were enrolled. Response rates and median survival times were as follows: total cases, 32% and 7. 4 months; sensitive relapse cases, 64% and 16. 4 months; refractory relapse cases, 27% and 5. 9 months. Neutropenia was major toxicity(Grade 3 or 4 was observed in 72% of the subjects), whereas nonhematologic toxicities were mild. Treatment with AMR appeared effective in SCLC patients previously treated with chemotherapy. On the other hand, it must be used carefully because of its relatively severe hematologic toxicities.
2.C609T Polymorphism of NADPH Quinone Oxidoreductase 1 Correlates Clinical Hematological Toxicities in Lung Cancer Patients Treated with Amrubicin.
Nagata M1, Kimura T, Suzumura T, Kira Y, Nakai T, Umekawa K, Tanaka H, Matsuura K, Mitsuoka S, Yoshimura N, Oka T, Kudoh S, Hirata K. Clin Med Insights Oncol. 2013;7:31-9. doi: 10.4137/CMO.S10839. Epub 2013 Feb 13.
BACKGROUND: Amrubicin hydrochloride (AMR) is a key agent for lung cancer. NADPH quinone oxidoreductase 1 (NQO1) metabolizes the quinone structures contained in both amrubicin (AMR) and amrubicinol (AMR-OH). We hypothesized that NQO1 C609T polymorphism may affect AMR-related pharmacokinetics and clinical outcomes.
3.Efficacy and safety of amrubicin hydrochloride for treatment of relapsed small cell lung cancer.
Ogawara D1, Fukuda M, Nakamura Y, Kohno S. Cancer Manag Res. 2010 Aug 11;2:191-5.
Long-term survival is quite uncommon in refractory small cell lung cancer (SCLC) patients, with less than 25% of patients with limited-stage disease and 1%-2% of patients with extensive-stage disease remaining alive at five years. Recent clinical studies have demonstrated the promising efficacy of amrubicin for patients with relapsed SCLC. This review presents the results of clinical studies showing the efficacy and safety of amrubicin for the treatment of relapsed SCLC. Amrubicin is a synthetic anthracycline agent with a similar structure to doxorubicin, in which the hydroxyl group at position 9 in amrubicin is replaced by an amino group to enhance efficacy. It is converted to an active metabolite, amrubicinol, which is 5-54 times more active than amrubicin. Amrubicin and amrubicinol are inhibitors of DNA topoisomerase II, exerting their cytotoxic effects by stabilizing a topoisomerase II-mediated cleavable complex. The toxicity of amrubicin is similar to that of doxorubicin, although amrubicin shows almost no cardiotoxicity.
4.Review of the management of relapsed small-cell lung cancer with amrubicin hydrochloride.
Kimura T1, Kudoh S, Hirata K. Clin Med Insights Oncol. 2011 Mar 3;5:23-34. doi: 10.4137/CMO.S5072.
Lung cancer is the leading cause of cancer death, and approximately 15% of all lung cancer patients have small-cell lung cancer (SCLC). Although second-line chemotherapy can produce tumor regression, the prognosis is poor. Amrubicin hydrochloride (AMR) is a synthetic anthracycline anticancer agent and a potent topoisomerase II inhibitor. Here, we discuss the features of SCLC, the chemistry, pharmacokinetics, and pharmacodynamics of AMR, the results of in vitro and in vivo studies, and the efficacy and safety of AMR monotherapy and combination therapy in clinical trials. With its predictable and manageable toxicities, AMR is one of the most attractive agents for the treatment of chemotherapy-sensitive and -refractory relapsed SCLC. Numerous studies are ongoing to define the applicability of AMR therapy for patients with SCLC. These clinical trials, including phase III studies, will clarify the status of AMR in the treatment of SCLC.
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CAS 110311-30-3 Amrubicin hydrochloride

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