Details of the Drug

General Information of Drug (ID: DM6SGUB)

Drug Name

Amrubicin

Synonyms

110267-81-7; Amrubicin [INN]; SCHEMBL119022; AC1L4374; (+-)-(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; BC677604; AN-16624; LS-183761; FT-0662134; ( -)-(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; (7S,9S)-9-acetyl-9-amino-7-(4,5-dihydroxytetrahydropyran-2-yl)oxy-6,11-dihydroxy-8,10-dihydro-7H-tetracene-5,12-dione

Indication

Disease Entry	ICD 11	Status	REF
Small-cell lung cancer	2C25.Y	Phase 3	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

483.5

Logarithm of the Partition Coefficient (xlogp)

0.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Elimination: In one study, urinary excretion of amrubicin and amrubicinol after ingestion of amrubicin accounted for 2.7% to 19.6% of the administered dose [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 0.06 +/- 0.01 hours (alpha), and 2.0 +/- 0.3 hours (beta) [3]
Metabolism: The drug is metabolized via the cytoplasmic carbonyl reductase at the C-13 carbonyl group [2]

Chemical Identifiers

Formula: C25H25NO9
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
Canonical 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
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
InChIKey: VJZITPJGSQKZMX-XDPRQOKASA-N

Cross-matching ID

PubChem CID: 3035016
ChEBI ID: CHEBI:135779
CAS Number: 110267-81-7
DrugBank ID: DB06263
TTD ID: D04BEN
INTEDE ID: DR0108

Combinatorial Drugs (CBD)

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Molecular Interaction Atlas of This Drug

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
NADPH-cytochrome P450 reductase (CPR)_{Main DME}	DE3N2FM	NCPR_HUMAN	Substrate	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

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References

1	ClinicalTrials.gov (NCT00547651) AMR PH GL 2007 CL001 Phase 3 Trial in Patients With Small Cell Lung Cancer After Failure of First-Line Chemotherapy. U.S. National Institutes of Health.
2	Amrubicin for the Treatment of Small Cell Lung Cancer: Does Effectiveness Cross the Pacific?
3	Pharmacokinetics of anthracyclines. Acta Oncol. 1989;28(6):873-6.
4	Characterization of the enzymes involved in the in vitro metabolism of amrubicin hydrochloride. Xenobiotica. 2005 Dec;35(12):1121-33.