Synonym
Amrubicin; SM-5887; SM 5887; SM5887;
IUPAC/Chemical Name
(+-)-(7S,9S)-9-Acetyl-9-amino-7-((2-deoxy-beta-D-erythro-pentopyranosyl)oxy)-7,8,9,10-tetrahydro-6,11-dihydroxy-5,12-naphthacenedione
InChi Key
VJZITPJGSQKZMX-XDPRQOKASA-N
InChi Code
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
SMILES Code
O=C(C1=C2C(O)=C3C[C@@](N)(C(C)=O)C[C@H](O[C@H]4C[C@@H]([C@@H](CO4)O)O)C3=C1O)C5=CC=CC=C5C2=O
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
Shelf Life
>3 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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
483.47
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: Liu CQ, Tian D, Wang N, Meng XP, Yang JD, Li HW, Zhao N, Zhao S, Liao F, Cui Y. Efficacy and safety of amrubicin-based regimen used as first-line for extensive-disease small-cell lung cancer: A meta-analysis of randomized controlled trials. Asia Pac J Clin Oncol. 2018 Apr;14(2):e81-e87. doi: 10.1111/ajco.12778. Epub 2017 Oct 25. PubMed PMID: 29071806.
2: Imai H, Sugiyama T, Tamura T, Minemura H, Kaira K, Kanazawa K, Yokouchi H, Kasai T, Kaburagi T, Minato K; Gunma-Ibaraki-Fukushima-Tochigi (GIFT) group. A retrospective study of amrubicin monotherapy for the treatment of relapsed small cell lung cancer in elderly patients. Cancer Chemother Pharmacol. 2017 Sep;80(3):615-622. doi: 10.1007/s00280-017-3403-9. Epub 2017 Jul 31. PubMed PMID: 28761968; PubMed Central PMCID: PMC5573757.
3: 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.
