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Identification
- Summary
Eribulin is a microtubule inhibitor used to treat metastatic breast cancer and metastatic or unresectable liposarcoma.
- Brand Names
- Halaven
- Generic Name
- Eribulin
- DrugBank Accession Number
- DB08871
- Background
Eribulin is a microtubule inhibitor indicated for the treatment of patients with metastatic breast cancer who have previously received at least two chemotherapeutic regimens for the treatment of metastatic disease. Eribulin was isolated from the marine sponge Halichondria okadai. Eribulin is also being investigated for use in the treatment of advanced solid tumors 2.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Eribulin (DB08871)
- Weight
- Average: 729.908
Monoisotopic: 729.408811724 - Chemical Formula
- C40H59NO11
- Synonyms
- Eribulin
- Eribulina
- External IDs
- ER-086526
Pharmacology
- Indication
For the treatment of patients with metastatic breast cancer who have previously received at least two chemotherapeutic regimens for the treatment of metastatic cancer.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Metastatic liposarcoma •••••••••••• Treatment of Refractory, metastatic breast cancer •••••••••••• Treatment of Unresectable liposarcoma •••••••••••• - Contraindications & Blackbox Warnings
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Linear
- Mechanism of action
Eribulin inhibits the growth phase of microtubules without affecting the shortening phase and sequesters tubulin into nonproductive aggregates. Eribulin exerts its effects via a tubulin-based antimitotic mechanism leading to G2/M cell-cycle block, disruption of mitotic spindles, and, ultimately, apoptotic cell death after prolonged mitotic blockage. [FDA]
Target Actions Organism UApoptosis regulator Bcl-2 Not Available Humans ATubulin beta-1 chain Not Available Humans - Absorption
Not Available
- Volume of distribution
43 L/m2 to 114 L/m2
- Protein binding
49 to 65%.
- Metabolism
There are no major human metabolites of eribulin, CYP3A4 negligibly metabolizes eribulin in vitro.
- Route of elimination
Eribulin is eliminated primarily in feces unchanged.
- Half-life
about 40 hours
- Clearance
1.16 L/hr/m2 to 2.42 L/hr/m2 (dose range of 0.25 mg/m2 to 4.0 mg/m2). [FDA]
- Adverse Effects
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Peripheral neuropathy was the most common toxicity leading to discontinuation of eribulin (5 percent). [Richard Pazdur, M.D., director of the FDA's Division of Oncology Drug Products.] Single doses of 0.75 mg/kg were lethal to rats and two doses of 0.075 mg/kg were lethal to dogs. The no-observed-adverse-effect level (NOAEL) in rats and dogs were 0.015 and 0.0045 mg/kg/day, respectively.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The risk or severity of adverse effects can be increased when Abatacept is combined with Eribulin. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Eribulin. Acenocoumarol The risk or severity of bleeding can be increased when Acenocoumarol is combined with Eribulin. Acetylsalicylic acid The risk or severity of bleeding can be increased when Acetylsalicylic acid is combined with Eribulin. Acrivastine The risk or severity of QTc prolongation can be increased when Eribulin is combined with Acrivastine. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Eribulin mesylate AV9U0660CW 441045-17-6 QAMYWGZHLCQOOJ-WRNBYXCMSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Eribulin Mesylate Injection Solution 0.5 mg / mL Intravenous Dr Reddy's Laboratories Ltd Not applicable Not applicable Canada 
Halaven Injection, solution 0.44 mg/ml Intravenous Eisai Limited 2016-09-08 Not applicable EU 
Halaven Solution 0.5 mg / mL Intravenous Eisai Limited 2012-03-19 Not applicable Canada Halaven Injection, solution 0.44 mg/ml Intravenous Eisai Limited 2016-09-08 Not applicable EU Halaven Injection, solution 0.44 mg/ml Intravenous Eisai Limited 2016-09-08 Not applicable EU - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Eribulin Mesylate Injection 0.5 mg/1mL Intravenous Apotex Corp. 2024-05-06 Not applicable US 
Eribulin Mesylate Solution 0.5 mg/1mL Intravenous Long Grove Pharmaceuticals, LLC 2024-07-22 Not applicable US Eribulin Mesylate Injection 0.5 mg/1mL Intravenous Gland Pharma Limited 2024-04-05 Not applicable US Eribulin Mesylate Injection 0.5 mg/1mL Intravenous Hikma Pharmaceuticals USA Inc. 2024-06-28 Not applicable US Nat-eribulin Solution 0.5 mg / mL Intravenous Natco Pharma Limited 2024-01-08 Not applicable Canada
Categories
- ATC Codes
- L01XX41 — Eribulin
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- LR24G6354G
- CAS number
- 253128-41-5
- InChI Key
- UFNVPOGXISZXJD-JBQZKEIOSA-N
- InChI
- InChI=1S/C40H59NO11/c1-19-11-24-5-7-28-20(2)12-26(45-28)9-10-40-17-33-36(51-40)37-38(50-33)39(52-40)35-29(49-37)8-6-25(47-35)13-22(42)14-27-31(16-30(46-24)21(19)3)48-32(34(27)44-4)15-23(43)18-41/h19,23-39,43H,2-3,5-18,41H2,1,4H3/t19-,23+,24+,25-,26+,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39+,40+/m1/s1
- IUPAC Name
- (1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33S,35R,36S)-20-[(2S)-3-amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-dimethylidene-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.1^{3,32}.1^{3,33}.1^{6,9}.1^{12,16}.0^{18,22}.0^{29,36}.0^{31,35}]hentetracontan-24-one
- SMILES
- [H][C@@]12CC(=C)[C@]([H])(CC[C@@]3([H])C[C@@H](C)C(=C)[C@@]([H])(C[C@]4([H])O[C@H](C[C@H](O)CN)[C@H](OC)[C@@]4([H])CC(=O)C[C@@]4([H])CC[C@]5([H])O[C@@]6([H])[C@H]7O[C@@]8(C[C@]7([H])O[C@@]6([H])[C@@]([H])(O8)[C@@]5([H])O4)CC1)O3)O2
References
- General References
- Shablak A: Eribulin for advanced breast cancer: a drug evaluation. J Breast Cancer. 2013 Mar;16(1):12-5. doi: 10.4048/jbc.2013.16.1.12. Epub 2013 Mar 31. [Article]
- Devriese LA, Witteveen PO, Marchetti S, Mergui-Roelvink M, Reyderman L, Wanders J, Jenner A, Edwards G, Beijnen JH, Voest EE, Schellens JH: Pharmacokinetics of eribulin mesylate in patients with solid tumors and hepatic impairment. Cancer Chemother Pharmacol. 2012 Dec;70(6):823-32. doi: 10.1007/s00280-012-1976-x. Epub 2012 Sep 26. [Article]
- Nieder C, Aandahl G, Dalhaug A: A case of brain metastases from breast cancer treated with whole-brain radiotherapy and eribulin mesylate. Case Rep Oncol Med. 2012;2012:537183. doi: 10.1155/2012/537183. Epub 2012 Aug 16. [Article]
- Jordan MA, Kamath K, Manna T, Okouneva T, Miller HP, Davis C, Littlefield BA, Wilson L: The primary antimitotic mechanism of action of the synthetic halichondrin E7389 is suppression of microtubule growth. Mol Cancer Ther. 2005 Jul;4(7):1086-95. [Article]
- External Links
- KEGG Drug
- D08914
- PubChem Compound
- 73425383
- PubChem Substance
- 175427126
- ChemSpider
- 24721813
- 1045453
- ChEBI
- 63587
- ChEMBL
- CHEMBL1683590
- ZINC
- ZINC000169344691
- PDBe Ligand
- 6K9
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Eribulin
- PDB Entries
- 5jh7 / 7dp8
- FDA label
- Download (194 KB)
- MSDS
- Download (120 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Not Available Breast Cancer 1 somestatus stop reason just information to hide Not Available Approved for Marketing Not Available Metastatic Breast Cancer 1 somestatus stop reason just information to hide Not Available Completed Not Available Breast Cancer 1 somestatus stop reason just information to hide Not Available Completed Not Available Inoperable or Recurrent Breast Cancer 1 somestatus stop reason just information to hide Not Available Completed Not Available Metastatic or Locally Advanced Breast Cancer 2 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Parenteral 0.44 mg/ml Solution Intravenous 0.5 mg/1mL Injection, solution 0.44 MG/ML Injection Intravenous 0.5 mg/1mL Injection, solution Intravenous; Parenteral 0.44 MG/ML Injection; injection, solution Intravenous 0.44 mg/ml Solution Intravenous 0.5 mg / mL Solution Parenteral 1.130 mg Solution Intravenous 0.5 mg/ml Injection, solution Intravenous bolus 1.0 mg Injection, solution Intravenous 0.44 mg/ml Injection, solution 1 mg/2ml Solution Intravenous 1 mg/2ml - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8097648 No 2012-01-17 2021-01-22 US US6469182 No 2002-10-22 2019-06-16 US US7470720 No 2008-12-30 2019-06-16 US US6214865 Yes 2001-04-10 2024-01-20 US USRE46965 Yes 2018-07-24 2027-07-08 US
Properties
- State
- Liquid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0798 mg/mL ALOGPS logP 1.26 ALOGPS logP 2.31 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 14.82 Chemaxon pKa (Strongest Basic) 9.56 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 12 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 146.39 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 186 m3·mol-1 Chemaxon Polarizability 82.15 Å3 Chemaxon Number of Rings 9 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6417 Blood Brain Barrier - 0.7893 Caco-2 permeable - 0.646 P-glycoprotein substrate Substrate 0.8239 P-glycoprotein inhibitor I Inhibitor 0.5443 P-glycoprotein inhibitor II Non-inhibitor 0.6565 Renal organic cation transporter Non-inhibitor 0.7978 CYP450 2C9 substrate Non-substrate 0.9256 CYP450 2D6 substrate Non-substrate 0.7965 CYP450 3A4 substrate Substrate 0.6412 CYP450 1A2 substrate Non-inhibitor 0.8332 CYP450 2C9 inhibitor Non-inhibitor 0.8636 CYP450 2D6 inhibitor Non-inhibitor 0.8939 CYP450 2C19 inhibitor Non-inhibitor 0.7838 CYP450 3A4 inhibitor Non-inhibitor 0.7094 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9246 Ames test Non AMES toxic 0.7043 Carcinogenicity Non-carcinogens 0.9719 Biodegradation Not ready biodegradable 0.9841 Rat acute toxicity 2.9429 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9408 hERG inhibition (predictor II) Inhibitor 0.5065
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Suppresses apoptosis in a variety of cell systems including factor-dependent lymphohematopoietic and neural cells (PubMed:1508712, PubMed:8183370). Regulates cell death by controlling the mitochondrial membrane permeability (PubMed:11368354). Appears to function in a feedback loop system with caspases (PubMed:11368354). Inhibits caspase activity either by preventing the release of cytochrome c from the mitochondria and/or by binding to the apoptosis-activating factor (APAF-1) (PubMed:11368354). Also acts as an inhibitor of autophagy: interacts with BECN1 and AMBRA1 during non-starvation conditions and inhibits their autophagy function (PubMed:18570871, PubMed:20889974, PubMed:21358617). May attenuate inflammation by impairing NLRP1-inflammasome activation, hence CASP1 activation and IL1B release (PubMed:17418785)
- Specific Function
- BH domain binding
- Gene Name
- BCL2
- Uniprot ID
- P10415
- Uniprot Name
- Apoptosis regulator Bcl-2
- Molecular Weight
- 26265.66 Da
References
- Kuznetsov G, Towle MJ, Cheng H, Kawamura T, TenDyke K, Liu D, Kishi Y, Yu MJ, Littlefield BA: Induction of morphological and biochemical apoptosis following prolonged mitotic blockage by halichondrin B macrocyclic ketone analog E7389. Cancer Res. 2004 Aug 15;64(16):5760-6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- General Function
- Tubulin is the major constituent of microtubules, a cylinder consisting of laterally associated linear protofilaments composed of alpha- and beta-tubulin heterodimers. Microtubules grow by the addition of GTP-tubulin dimers to the microtubule end, where a stabilizing cap forms. Below the cap, tubulin dimers are in GDP-bound state, owing to GTPase activity of alpha-tubulin
- Specific Function
- GTP binding
- Gene Name
- TUBB1
- Uniprot ID
- Q9H4B7
- Uniprot Name
- Tubulin beta-1 chain
- Molecular Weight
- 50326.56 Da
References
- Dabydeen DA, Burnett JC, Bai R, Verdier-Pinard P, Hickford SJ, Pettit GR, Blunt JW, Munro MH, Gussio R, Hamel E: Comparison of the activities of the truncated halichondrin B analog NSC 707389 (E7389) with those of the parent compound and a proposed binding site on tubulin. Mol Pharmacol. 2006 Dec;70(6):1866-75. Epub 2006 Aug 29. [Article]
Drug created at May 02, 2013 19:55 / Updated at October 08, 2024 09:29