amrubicin

Also known as SM-5887

Amrubicin (INN; previously known as SM-5887) is an anthracycline used in the treatment of lung cancer. It is marketed in Japan since 2002 by Sumitomo under the brand name Calsed.

In the Vinony graph

Vinony's link graph records 275 inbound references to amrubicin, and connects out to type II topoisomerase, tiazofurin and medication.

It is catalogued under topics including 3-Hydroxypropenals within hydroxyquinones, Anthracyclines and Chemical pages without DrugBank identifier.

Vinony links it to 8 Wikipedia language editions.

Chemical data

Formula: C25H25NO9
Molecular weight: 483.5 g/mol
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
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
InChIKey: VJZITPJGSQKZMX-XDPRQOKASA-N
XLogP: 0.9
Polar surface area: 177 Å²
H-bond donors: 5
H-bond acceptors: 10
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 3
Molecule type: Small molecule
Indications: neoplasm, small cell lung carcinoma, multiple myeloma, soft tissue sarcoma

via ChEMBL · EBI

Research

384 papers

Tarlatamab in Small-Cell Lung Cancer after Platinum-Based Chemotherapy.The New England journal of medicine · 2025
[Amrubicin].Nihon rinsho. Japanese journal of clinical medicine · 2002
Amrubicin for non-small-cell lung cancer and small-cell lung cancer.Investigational new drugs · 2007
Amrubicin for relapsed small-cell lung cancer: a systematic review and meta-analysis of 803 patients.Scientific reports · 2016
Amrubicin for the treatment of small cell lung cancer: does effectiveness cross the Pacific?Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer · 2007

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 483.153
Has use: medication

Show 4 more facts

chemical formula: C₂₅H₂₅NO₉
canonical 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
isomeric SMILES: CC(=O)[C@]1(C[C@@H](C2=C(C3=C(C(=C2C1)O)C(=O)C4=CC=CC=C4C3=O)O)O[C@H]5C[C@@H]([C@@H](CO5)O)O)N
subject has role: antineoplastic

Sources (2)

via Wikidata · CC0

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Encyclopedic overview

1 sections

Contents

References

Amrubicin (INN; previously known as SM-5887) is an anthracycline used in the treatment of lung cancer. It is marketed in Japan since 2002 by Sumitomo under the brand name Calsed.

Amrubicin acts by inhibiting topoisomerase II, and has been compared in clinical trials with topotecan, a Topoisomerase I inhibitor.

Excerpted from Wikipedia’s “amrubicin” article, available under the CC BY-SA 4.0 licence.