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Amrubicin (hydrochloride)

CAT: 0804-HY-B0067A-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-B0067A-01Size:1 mg
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Description
Amrubicin (SM-5887) hydrochloride is a DNA topoisomerase II inhibitor, used for the research of cancer.
CAS Number
110311-30-3
Product Name Alternative
SM-5887 (hydrochloride)
UNSPSC
12352005
Target
Bacterial; Topoisomerase
Related Pathways
Anti-infection; Cell Cycle/DNA Damage
Field of Research
Cancer
Purity
98.78
Solubility
DMSO : 100 mg/mL
Smiles
CC([C@@](C1)(N)C[C@H](O[C@@H]2OC[C@@H](O)[C@@H](O)C2)C(C1=C3O)=C(O)C4=C3C(C5=CC=CC=C5C4=O)=O)=O.Cl
Molecular Formula
C25H26ClNO9
Molecular Weight
519.93
References & Citations
[1]Hayashi S, et al. Enhancement of radiosensitivity by topoisomerase II inhibitor, amrubicin and amrubicinol, in human lung adenocarcinoma A549 cells and kinetics of apoptosis and necrosis induction. Int J Mol Med. 2006 Nov;18 (5) :909-15.|[2]Hanada M, et al. Amrubicin, a novel 9-aminoanthracycline, enhances the antitumor activity of chemotherapeutic agents against human cancer cells in vitro and in vivo. Cancer Sci. 2007 Mar;98 (3) :447-54.|[3]Hanada M, et al. Amrubicin induces apoptosis in human tumor cells mediated by the activation of caspase-3/7 preceding a loss of mitochondrial membrane potential. Cancer Sci. 2006 Dec;97 (12) :1396-403. Epub 2006 Sep 21.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C (Powder, protect from light, stored under nitrogen)
Scientific Category
Reference compound1
Clinical Information
Launched
Isoform
Topo II

Chemical Information

Amrubicin Hydrochloride

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.

CAS Number110311-30-3
PubChem CID114897
IUPAC Name(7S,9S)-9-acetyl-9-amino-7-[(2S,4S,5R)-4,5-dihydroxyoxan-2-yl]oxy-6,11-dihydroxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
Molecular FormulaC25H26ClNO9
Molecular Weight519.9
Topological Polar Surface Area177
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count10
Rotatable Bond Count3
Heavy Atom Count36
Formal Charge0
Complexity881
SMILES
CC(=O)[C@]1(C[C@@H](C2=C(C1)C(=C3C(=C2O)C(=O)C4=CC=CC=C4C3=O)O)O[C@H]5C[C@@H]([C@@H](CO5)O)O)N.Cl
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
InChIKey
BHMLHEQFWVQAJS-IITOGVPQSA-N
Chemical Structure
2D Structure
2D structure of Amrubicin Hydrochloride
CAS: 110311-30-3
CID: 114897
Formula: C25H26ClNO9
MW: 519.9
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight519.9
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count10
Rotatable Bond Count3
Exact Mass519.1296091
Monoisotopic Mass519.1296091
Topological Polar Surface Area177 Ų
Heavy Atom Count36
Formal Charge0
Complexity881
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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