Structure via PubChem · Public domain (PubChem)
eribulin
Sign in to saveAlso known as 2-(3-Amino-2-hydroxypropyl)hexacosahydro-3-methoxy- 26-methyl-20,27-bis(methylene)11,15-18,21-24,28-triepoxy- 7,9-ethano-12,15-methano-9H,15H-furo(3,2-i)furo(2',3'-5,6) pyrano(4,3-b)(1,4)dioxacyclopentacosin-5-(4H)-one, eribulin mesylate, L01XX41, ER-086526, E7389
Eribulin, sold under the brand name Halaven among others, is an anti-cancer medication used to treat breast cancer and liposarcoma.
Key facts
- Drug.Verifiedfields
- changed
- Drug.verifiedrevid
- 461094948
- Drug.image
- Eribulin.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 300
- Drug.USAN
- eribulin mesylate
- Drug.JAN
- eribulin mesilate
- Drug.tradename
- Halaven, Mevlyq
- Drug.MedlinePlus
- a611007
- Drug.DailyMedID
- Eribulin
- Drug.pregnancy_AU
- D
- Drug.routes_of_administration
- Intravenous
- Drug.class
- Antineoplastic
- Drug.ATC_prefix
- L01
- Drug.ATC_suffix
- XX41
- Drug.legal_AU
- S4
- Drug.legal_CA
- Rx-only
- Drug.legal_UK
- POM
via Wikipedia infobox
Chemical data
- Formula
- C40H59NO11
- Molecular weight
- 729.9 g/mol
- IUPAC name
- (1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-dimethylidene-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one
- SMILES
- C[C@@H]1C[C@@H]2CC[C@H]3C(=C)C[C@@H](O3)CC[C@]45C[C@@H]6[C@H](O4)[C@H]7[C@@H](O6)[C@@H](O5)[C@@H]8[C@@H](O7)CC[C@@H](O8)CC(=O)C[C@H]9[C@H](C[C@H](C1=C)O2)O[C@@H]([C@@H]9OC)C[C@@H](CN)O
- InChIKey
- UFNVPOGXISZXJD-JBQZKEIOSA-N
- XLogP
- 1.1
- Polar surface area
- 146 Ų
- H-bond donors
- 2
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2010
- Admin. routes
- parenteral
- Indications
- neoplasm, breast carcinoma, non-small cell lung carcinoma, angiosarcoma
via ChEMBL · EBI
Research
1,184 papers- Eribulin versus dacarbazine in previously treated patients with advanced liposarcoma or leiomyosarcoma: a randomised, open-label, multicentre, phase 3 trial.Lancet (London, England) · 2016
- Eribulin monotherapy versus treatment of physician's choice in patients with metastatic breast cancer (EMBRACE): a phase 3 open-label randomised study.Lancet (London, England) · 2011
- Eribulin.Drugs · 2011
- Eribulin in advanced liposarcoma and leiomyosarcoma.Expert review of anticancer therapy · 2017
- Clinical and preclinical features of eribulin-related peripheral neuropathy.Experimental neurology · 2022
via PubMed
Wikidata facts
- Mass
- 729.409
- Has use
- medication
Show 7 more facts
- chemical formula
- C₄₀H₅₉NO₁₁
- isomeric SMILES
- C[C@@H]1C[C@@H]2CC[C@H]3C(=C)C[C@@H](O3)CC[C@]45C[C@@H]6[C@H](O4)[C@H]7[C@@H](O6)[C@@H](O5)[C@@H]8[C@@H](O7)CC[C@@H](O8)CC(=O)C[C@H]9[C@H](C[C@H](C1=C)O2)O[C@@H]([C@@H]9OC)C[C@@H](CN)O
- canonical SMILES
- CC1CC2CCC3C(=C)CC(O3)CCC45CC6C(O4)C7C(O6)C(O5)C8C(O7)CCC(O8)CC(=O)CC9C(CC(C1=C)O2)OC(C9OC)CC(CN)O
- medical condition treated
- breast cancer
- stylized name
- eriBULin
- significant drug interaction
- anagrelide
- Commons category
- Eribulin
Sources (7)
via Wikidata · CC0
~4 min read
Encyclopedic overview
5 sectionsContents
- Medical uses
- Adverse effects
- Structure and mechanism
- Research
- References
Eribulin, sold under the brand name Halaven among others, is an anti-cancer medication used to treat breast cancer and liposarcoma.
The most common side effects include fatigue, nausea, hair loss (alopecia), constipation, certain nerve damage causing weakness or numbness in the hands and feet (peripheral neuropathy), abdominal pain and fever (pyrexia). Eribulin may also cause low levels of infection-fighting white blood cells (neutropenia) or decreased levels of potassium or calcium.
Excerpted from Wikipedia’s “eribulin” article, available under the CC BY-SA 4.0 licence.