Amrubicin

Topoisomerase II inhibitor, anthracycline agent CAS# 110267-81-7

Amrubicin

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Chemical structure

Amrubicin

3D structure

Chemical Properties of Amrubicin

Cas No. 110267-81-7 SDF Download SDF
PubChem ID 178149 Appearance Powder
Formula C25H25NO9 M.Wt 483.47
Type of Compound N/A Storage Desiccate at -20°C
Synonyms AMR
Solubility >16.45mg/mL in DMSO
Chemical Name (7S,9S)-9-acetyl-9-amino-7-(4,5-dihydroxyoxan-2-yl)oxy-6,11-dihydroxy-8,10-dihydro-7H-tetracene-5,12-dione
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
Standard InChIKey VJZITPJGSQKZMX-HUVCIAIMSA-N
Standard InChI InChI=1S/C25H25NO9/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/t14?,15?,16-,17?,25-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Amrubicin

DescriptionAmrubicin ia an inhibitor of Topoisomerase II Amrubicin.
TargetsTopoisomerase II    

Protocol

Cell experiment: [1]

Cell lines

CCRF-CEM cells

Preparation method

The solubility of this compound in DMSO is >10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while.Stock solution can be stored below -20°C for several months.

Reacting condition

IC 50: 3.3 µM, 1 hour

Applications

Amrubicin induced DNA-protein complex formation in cultured CCRF-CEM cells in a dose-dependent manner. The IC50 value of amrubicin required to inhibit the growth of CCRF-CEM cells was 3.3 µM. Accordingly, under conditions where cell growth was inhibited by amrubicin, considerable amounts of DNA-protein complexes were formed.

Animal experiment: [2]

Animal models

BALB/c nu/nu mice bearing Lu-24 or Lu-134 cells

Dosage form

Intravenous injection, 25 mg/kg

Application

Amrubicin showed significant antitumor activities against both SCLC tumors tested, Lu-24 and Lu-134, with T/C-values at day 14 of 17% and 9%, respectively.

Other notes

Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.

References:

[1] Hanada M, Mizuno S, Fukushima A, et al. A New Antitumor Agent Amrubicin Induces Cell Growth Inhibition by Stabilizing Topoisomerase II-DNA Complex. Cancer Science, 1998, 89(11): 1229-1238.

[2] Hanada M, Noguchi T, Yamaoka T. Amrubicin, a novel 9-aminoanthracycline, enhances the antitumor activity of chemotherapeutic agents against human cancer cells in vitro and in vivo. Cancer science, 2007, 98(3): 447-454.

Amrubicin Dilution Calculator

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Amrubicin Molarity Calculator

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Preparing Stock Solutions of Amrubicin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.0684 mL 10.3419 mL 20.6838 mL 41.3676 mL 51.7095 mL
5 mM 0.4137 mL 2.0684 mL 4.1368 mL 8.2735 mL 10.3419 mL
10 mM 0.2068 mL 1.0342 mL 2.0684 mL 4.1368 mL 5.171 mL
50 mM 0.0414 mL 0.2068 mL 0.4137 mL 0.8274 mL 1.0342 mL
100 mM 0.0207 mL 0.1034 mL 0.2068 mL 0.4137 mL 0.5171 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Amrubicin

A synthetic anthracycline antibiotic. It inhibits DNA topoisomerase II. Antineoplastic.

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References on Amrubicin

Lactate dehydrogenase and body mass index are prognostic factors in patients with recurrent small cell lung cancer receiving amrubicin.[Pubmed:26429641]

Tumori. 2016 Dec 1;102(6):606-609.

AIMS AND BACKGROUND: Amrubicin monotherapy can be an effective treatment option for patients with recurrent small cell lung cancer (SCLC). We conducted this retrospective study to investigate the prognostic factors in patients with recurrent SCLC receiving Amrubicin monotherapy. METHODS: The associations between survival and clinical data, including the performance status, body mass index (BMI), plasma lactate dehydrogenase (LDH) level, and plasma neuron-specific enolase level, were evaluated in patients with recurrent SCLC, and a subset analysis of patients with platinum-resistant disease was conducted. RESULTS: In all, 37 patients were evaluated. The median survival from the date of initiation of Amrubicin monotherapy was 9.1 months (95% confidence interval 4.7-12.0 months). Multivariate analysis using a Cox proportional hazard model identified the plasma LDH level (p = 0.049), BMI (p = 0.031), and platinum resistance (p = 0.032) as independent factors associated with survival. The same associations were also observed in the subset of patients with platinum-resistant disease. CONCLUSIONS: Our findings suggest that the plasma LDH level and BMI may be useful prognostic factors in patients with SCLC receiving Amrubicin monotherapy, including patients with platinum-resistant disease.

Comparison of Amrubicin and Weekly Cisplatin/Etoposide/Irinotecan in Patients With Relapsed Small-cell Lung Cancer.[Pubmed:27867001]

Clin Lung Cancer. 2017 Mar;18(2):234-240.e2.

BACKGROUND: Although several agents have been introduced for the treatment of relapsed small-cell lung cancer (SCLC), there is still only limited evidence regarding second- and later-line chemotherapies for these patients. PATIENTS AND METHODS: Consecutive patients with relapsed SCLC treated at the National Cancer Center Hospital between 2000 and 2014 were analyzed. Patients' characteristics and treatments to explore factors associated with the survival outcomes were reviewed. RESULTS: A total of 580 patients diagnosed as having SCLC received first-line chemotherapy/chemoradiotherapy, of which 343 (59%) received second-line chemotherapy. Among the 343 patients, 193, 148, and 2 patients were diagnosed sensitive relapse, refractory relapse, and relapse of unknown sensitivity status, respectively. Second-line chemotherapy regimens used were as follows: Amrubicin (AMR) in 188 (55%) patients; weekly cisplatin/etoposide/irinotecan (PEI) in 56 (16%) patients; topotecan in 18 (5.2%) patients; others in 81 (24%) patients. In the analysis including all patients, the following outcomes were obtained for the patients treated with AMR and PEI, respectively: objective response rate: 51% and 73%; median progression-free survival: 4.5 and 4.2 months; median overall survival: 10.0 and 10.8 months. Multivariate analysis identified sensitive relapse to first-line treatment (vs. refractory relapse) (P = .007) and AMR as second-line treatment (vs. PEI) (P = .005) as independent favorable prognostic factors for survival. CONCLUSION: AMR showed a favorable trend compared with PEI in terms of the progression-free survival and feasibility in SCLC patients with relapsed disease. Based on our findings, we suggest that a randomized trial comparing AMR and PEI is warranted.

Potential Activity of Amrubicin as a Salvage Therapy for Merkel Cell Carcinoma.[Pubmed:28250307]

Intern Med. 2017;56(5):567-570.

Merkel cell carcinoma (MCC) is a rare neuroendocrine carcinoma of the skin with an aggressive clinical course. Although anthracycline- and platinum-based regimens are empirically used as first-line treatments for metastatic or unresectable cases, no salvage therapy has been established. A 73-year-old man with platinum-refractory recurrent MCC was treated with Amrubicin. The symptoms improved soon, and a partial response was achieved. A total of nine cycles of Amrubicin were administered in nine months with manageable adverse events until disease progression was finally observed. The present findings suggest the potential of Amrubicin monotherapy as a second-line therapy for patients with advanced/recurrent MCC.

METASTATIC SMALL CELL CARCINOMA OF THE URINARY BLADDER TREATED WITH SYSTEMIC CHEMOTHERAPY INCLUDING AN AMRUBICIN; A CASE REPORT.[Pubmed:28132989]

Nihon Hinyokika Gakkai Zasshi. 2016;107(1):34-38.

We report a 59-year-old male patient with metastatic small cell carcinoma of the bladder treated with systemic chemotherapy including an Amrubicin. The patient was referred to our hospital complaining of macrohematuria. A cytoscopy revealed a non-papillary, broad-based tumor extending from the right to the posterior wall of the bladder. A computed tomography showed bilateral hydronephrosis caused by the bladder tumor and multiple metastases to the para-aortic and common iliac lymph nodes. The histopathological findings following a transurethral resection of the bladder tumor revealed a T2N3M1, LYM, stage IV small cell carcinoma. We administered two courses of systemic chemotherapy consisting of cisplatin (CDDP) plus an etoposide (VP-16), a first-line treatment usually administered to patients with small cell carcinoma of the lung. We then administered second-line chemotherapy consisting of CDDP plus an irinotecan. When the first and second-line therapies failed to halt progression of the disease, we decided to use Amrubicin as the third-line therapy concomitant with radiotherapy for local control. Although the NSE (neuron-specific enolase) value decreased, the patient died 11 months after the initial examination. To our knowledge, this is the first case in which small cell carcinoma of the bladder was treated with Amrubicin.

Description

Amrubicin(SM-5887) is a novel anthracycline derivative for treatment of bladder carcinoma.

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