Structure via PubChem · Public domain (PubChem)
epirubicin
Sign in to saveAlso known as Epiadriamycin, 4'-Epiadriamycin, Epirubicina, Epirubicine, Epirubicinum, Pidorubicina, Pidorubicine
Epirubicin is an anthracycline drug used for chemotherapy. It can be used in combination with other medications to treat breast cancer in patients who have had surgery to remove the tumor. It is marketed by Pfizer under the trade name Ellence in the US and Pharmorubicin or Epirubicin Ebewe elsewhere.
In the Vinony graph
Within Vinony's link graph, epirubicin is referenced by 306 other articles, and connects out to type II topoisomerase, tiazofurin and liver.
It sits within the topics Anthracyclines, Drugboxes which contain changes to watched fields and Drugs developed by Pfizer.
Its subject is documented across 23 Wikipedia language editions.
Chemical data
- Formula
- C27H29NO11
- Molecular weight
- 543.5 g/mol
- IUPAC name
- (7S,9S)-7-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
- SMILES
- C[C@H]1[C@@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O
- InChIKey
- AOJJSUZBOXZQNB-VTZDEGQISA-N
- XLogP
- 1.3
- Polar surface area
- 206 Ų
- H-bond donors
- 6
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1999
- Admin. routes
- parenteral
- Indications
- hepatocellular carcinoma, diffuse large B-cell lymphoma, germ cell tumor, neoplasm
via ChEMBL · EBI
Research
8,529 papers- [Epirubicin (4'-epi-adriamycin].Gan to kagaku ryoho. Cancer & chemotherapy · 1990
- Clinical pharmacokinetics of epirubicin.Clinical pharmacokinetics · 1994
- Epirubicin: is it like doxorubicin in breast cancer? A clinical review.Breast (Edinburgh, Scotland) · 2012
- Epirubicin in combination with the taxanes.Seminars in oncology · 2001
- Epirubicin. Clinical pharmacology and dose-effect relationship.Drugs · 1993
via PubMed
Wikidata facts
- Subclass of
- anthracycline antibiotic
- Mass
- 543.174061
- Has use
- medication
Show 8 more facts
- chemical formula
- C₂₇H₂₉NO₁₁
- canonical SMILES
- CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O
- isomeric SMILES
- C[C@H]1[C@@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O
- World Health Organisation international non-proprietary name
- epirubicin
- Commons category
- Epirubicin
- found in taxon
- Streptomyces
- stylized name
- epiRUBicin
- stereoisomer of
- doxorubicin
via Wikidata · CC0
~15 min read
Encyclopedic overview
21 sectionsContents
- Medical uses
- Adjuvant therapy
- Vs standard adjuvant therapy
- Dose response
- Advanced breast cancer
- First-line therapy
- Second-line therapy
- Dose escalation
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Metabolism
- Excretion
- Side effects
- Toxicity
- Chemistry
- Synthesis
- Daunorubicin
- 13-daunorubicinol
- Development history
- References
{{Drugbox | Watchedfields = changed | verifiedrevid = 461094075 | IUPAC_name = (8S,10S)-10-{[(2R,4S,5R,6S)-4-Amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione | image = Epirubicin2DACS.svg | image_class = skin-invert-image | image2 = Epirubicin ball-and-stick.png | image_class2 = bg-transparent
| tradename = Ellence | Drugs.com = | MedlinePlus = a603003 | pregnancy_category = | pregnancy_AU = D | pregnancy_US = D | legal_status = | legal_US = Rx-only | legal_UK = POM | routes_of_administration = Intravenous
Excerpted from Wikipedia’s “epirubicin” article, available under the CC BY-SA 4.0 licence.