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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H25NO9
Molecular Weight 483.4673
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMRUBICIN

SMILES

[H][C@@]1(C[C@H](O)[C@H](O)CO1)O[C@H]2C[C@@](N)(CC3=C(O)C4=C(C(=O)C5=CC=CC=C5C4=O)C(O)=C23)C(C)=O

InChI

InChIKey=VJZITPJGSQKZMX-XDPRQOKASA-N
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

HIDE SMILES / InChI

Description

Amrubicin is a totally synthetic 9-aminoanthracycline anticancer drug, which is approved in Japan for the treatment of small cell and non-small cell lung cancer. Upon administration amrubicin is reduced to its C-13 hydroxy metabolite, amrubicinol. The cytotoxicity of amrubicinol in vitro is 10 to 100 times greater than that of amrubicin. Thus, the anticancer activity of amrubicin is considered to derive from this active metabolite. The mechanism of action of the drug is related to the inhibition of topoisomerase II by stabilizing the cleavable complex.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CALSED
Primary
CALSED

PubMed

Sample Use Guides

In Vivo Use Guide
The usual dose is 45 mg/m2 given intravenously once a day for 3 days.
Route of Administration: Intravenous
In Vitro Use Guide
In a cell viability assay, lung cancer cells DMS 114, NCI-H69, NCI-H82, NCI-H526 were incubated with amrubicin at concentrations from 18 nM to 16 uM for 72 h. IC50 values were 0.803, 1.54, 0.746 and 0.818 uM, respectively.