Details of the Drug

General Information of Drug (ID: DM1DX4Q)

• Drug Name: Eribulin

Indication

Disease Entry	ICD 11	Status	REF
Breast cancer	2C60-2C65	Approved	[1]
Liposarcoma	2B59	Approved	[2]

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 2:
  Molecular Weight (mw); 729.9
  Logarithm of the Partition Coefficient (xlogp); 1.1
  Rotatable Bond Count (rotbonds); 4
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 12
• ADMET Property: Half-life: The concentration or amount of drug in body reduced by one-half in 40 hours [3]
• Chemical Identifiers:
  Formula: C40H59NO11
  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
  Canonical 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
  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
  InChIKey: UFNVPOGXISZXJD-JBQZKEIOSA-N
• Cross-matching ID:
  PubChem CID: 11354606
  ChEBI ID: CHEBI:63587
  CAS Number: 253128-41-5
  DrugBank ID: DB08871
  TTD ID: D0KK2E
  INTEDE ID: DR0601
• Repurposed Drugs (RPD): Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Tubulin (TUB)	TTML2WA	NOUNIPROTAC	Inhibitor	[4]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4) Main DME	DE4LYSA	CP3A4_HUMAN	Substrate	[5]

Molecular Expression Atlas of This Drug

• The Studied Disease: Breast cancer
• ICD Disease Classification: 2C60-2C65

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Tubulin (TUB)	DTT	NO-GeName	7.94E-02	0.35	0.43
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	2.96E-01	-3.35E-01	-1.10E+00

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Eribulin (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Ivosidenib	DM8S6T7	Major	Increased risk of prolong QT interval by the combination of Eribulin and Ivosidenib.	Acute myeloid leukaemia [2A60]	[6]
Arn-509	DMT81LZ	Moderate	Increased risk of prolong QT interval by the combination of Eribulin and Arn-509.	Acute myeloid leukaemia [2A60]	[7]
Gilteritinib	DMTI0ZO	Moderate	Increased risk of prolong QT interval by the combination of Eribulin and Gilteritinib.	Acute myeloid leukaemia [2A60]	[8]
Oliceridine	DM6MDCF	Moderate	Increased risk of prolong QT interval by the combination of Eribulin and Oliceridine.	Acute pain [MG31]	[9]
Ivabradine	DM0L594	Major	Increased risk of ventricular arrhythmias by the combination of Eribulin and Ivabradine.	Angina pectoris [BA40]	[7]
Bedaquiline	DM3906J	Major	Increased risk of prolong QT interval by the combination of Eribulin and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[10]
Levalbuterol	DM5YBO1	Moderate	Increased risk of prolong QT interval by the combination of Eribulin and Levalbuterol.	Asthma [CA23]	[11]
PF-04449913	DMSB068	Moderate	Increased risk of prolong QT interval by the combination of Eribulin and PF-04449913.	Chronic myelomonocytic leukaemia [2A40]	[12]
Olodaterol	DM62B78	Moderate	Increased risk of ventricular arrhythmias by the combination of Eribulin and Olodaterol.	Chronic obstructive pulmonary disease [CA22]	[13]
Vilanterol	DMF5EK1	Moderate	Increased risk of ventricular arrhythmias by the combination of Eribulin and Vilanterol.	Chronic obstructive pulmonary disease [CA22]	[11]
Osilodrostat	DMIJC9X	Moderate	Increased risk of prolong QT interval by the combination of Eribulin and Osilodrostat.	Cushing syndrome [5A70]	[9]
Deutetrabenazine	DMUPFLI	Moderate	Additive CNS depression effects by the combination of Eribulin and Deutetrabenazine.	Dystonic disorder [8A02]	[14]
Ingrezza	DMVPLNC	Moderate	Additive CNS depression effects by the combination of Eribulin and Ingrezza.	Dystonic disorder [8A02]	[15]
Fostemsavir	DM50ILT	Moderate	Increased risk of prolong QT interval by the combination of Eribulin and Fostemsavir.	Human immunodeficiency virus disease [1C60-1C62]	[9]
Teriflunomide	DMQ2FKJ	Major	Additive myelosuppressive effects by the combination of Eribulin and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[16]
Polyethylene glycol	DM4I1JP	Moderate	Increased risk of ventricular arrhythmias by the combination of Eribulin and Polyethylene glycol.	Irritable bowel syndrome [DD91]	[7]
Ceritinib	DMB920Z	Major	Increased risk of prolong QT interval by the combination of Eribulin and Ceritinib.	Lung cancer [2C25]	[9]
Osimertinib	DMRJLAT	Major	Increased risk of prolong QT interval by the combination of Eribulin and Osimertinib.	Lung cancer [2C25]	[17]
Selpercatinib	DMZR15V	Major	Increased risk of prolong QT interval by the combination of Eribulin and Selpercatinib.	Lung cancer [2C25]	[7]
Arry-162	DM1P6FR	Moderate	Decreased clearance of Eribulin due to the transporter inhibition by Arry-162.	Melanoma [2C30]	[18]
Vemurafenib	DM62UG5	Major	Increased risk of prolong QT interval by the combination of Eribulin and Vemurafenib.	Melanoma [2C30]	[9]
LGX818	DMNQXV8	Moderate	Increased risk of prolong QT interval by the combination of Eribulin and LGX818.	Melanoma [2C30]	[19]
Tecfidera	DM2OVDT	Moderate	Additive immunosuppressive effects by the combination of Eribulin and Tecfidera.	Multiple sclerosis [8A40]	[20]
Siponimod	DM2R86O	Major	Increased risk of ventricular arrhythmias by the combination of Eribulin and Siponimod.	Multiple sclerosis [8A40]	[18]
Ocrelizumab	DMEZ2KH	Moderate	Additive immunosuppressive effects by the combination of Eribulin and Ocrelizumab.	Multiple sclerosis [8A40]	[21]
Ozanimod	DMT6AM2	Major	Increased risk of ventricular arrhythmias by the combination of Eribulin and Ozanimod.	Multiple sclerosis [8A40]	[7]
Entrectinib	DMMPTLH	Moderate	Increased risk of prolong QT interval by the combination of Eribulin and Entrectinib.	Non-small cell lung cancer [2C25]	[18]
Rucaparib	DM9PVX8	Moderate	Increased risk of prolong QT interval by the combination of Eribulin and Rucaparib.	Ovarian cancer [2C73]	[9]
Triclabendazole	DMPWGBR	Moderate	Increased risk of prolong QT interval by the combination of Eribulin and Triclabendazole.	Parasitic worm infestation [1F90]	[9]
Macimorelin	DMQYJIR	Major	Increased risk of prolong QT interval by the combination of Eribulin and Macimorelin.	Pituitary gland disorder [5A60-5A61]	[22]
Lefamulin	DME6G97	Major	Increased risk of prolong QT interval by the combination of Eribulin and Lefamulin.	Pneumonia [CA40]	[23]
Enzalutamide	DMGL19D	Moderate	Increased risk of prolong QT interval by the combination of Eribulin and Enzalutamide.	Prostate cancer [2C82]	[7]
Relugolix	DMK7IWL	Moderate	Increased risk of prolong QT interval by the combination of Eribulin and Relugolix.	Prostate cancer [2C82]	[7]
Anthrax vaccine	DM9GSWY	Moderate	Antagonize the effect of Eribulin when combined with Anthrax vaccine.	Sepsis [1G40-1G41]	[24]
LEE011	DMMX75K	Moderate	Increased risk of prolong QT interval by the combination of Eribulin and LEE011.	Solid tumour/cancer [2A00-2F9Z]	[9]
Pitolisant	DM8RFNJ	Moderate	Increased risk of prolong QT interval by the combination of Eribulin and Pitolisant.	Somnolence [MG42]	[9]
Fostamatinib	DM6AUHV	Moderate	Decreased metabolism of Eribulin caused by Fostamatinib mediated inhibition of CYP450 enzyme.	Thrombocytopenia [3B64]	[25]
Lenvatinib	DMB1IU4	Moderate	Increased risk of prolong QT interval by the combination of Eribulin and Lenvatinib.	Thyroid cancer [2D10]	[9]
Cabozantinib	DMIYDT4	Major	Increased risk of prolong QT interval by the combination of Eribulin and Cabozantinib.	Thyroid cancer [2D10]	[7]

References

• [1] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6813).
• [2] Eribulin FDA Label
• [3] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [4] Mullard A: 2010 FDA drug approvals. Nat Rev Drug Discov. 2011 Feb;10(2):82-5.
• [5] Delineation of the interactions between the chemotherapeutic agent eribulin mesylate (E7389) and human CYP3A4. Cancer Chemother Pharmacol. 2008 Sep;62(4):707-16.
• [6] Product Information. Tibsovo (ivosidenib). Agios Pharmaceuticals, Cambridge, MA.
• [7] Cerner Multum, Inc. "UK Summary of Product Characteristics.".
• [8] Product Information. Xospata (gilteritinib). Astellas Pharma US, Inc, Deerfield, IL.
• [9] Canadian Pharmacists Association.
• [10] Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
• [11] Product Information. Arcapta Neohaler (indacaterol). Novartis Pharmaceuticals, East Hanover, NJ.
• [12] Product Information. Daurismo (glasdegib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
• [13] Bengtsson B, Fagerstrom PO "Extrapulmonary effects of terbutaline during prolonged administration." Clin Pharmacol Ther 31 (1982): 726-32. [PMID: 7042176]
• [14] Product Information. Austedo (deutetrabenazine). Teva Pharmaceuticals USA, North Wales, PA.
• [15] Product Information. Ingrezza (valbenazine). Neurocrine Biosciences, Inc., San Diego, CA.
• [16] Product Information. Arava (leflunomide). Hoechst Marion-Roussel Inc, Kansas City, MO.
• [17] Product Information. Tagrisso (osimertinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
• [18] Cerner Multum, Inc. "Australian Product Information.".
• [19] Product Information. Braftovi (encorafenib). Array BioPharma Inc., Boulder, CO.
• [20] Product Information. Vumerity (diroximel fumarate). Alkermes, Inc, Cambridge, MA.
• [21] Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA.
• [22] Product Information. Macrilen (macimorelin). Aeterna Zentaris, Charleston, SC.
• [23] Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
• [24] CDC. Centers for Disease Control and Prevention/ "Recommendations of the advisory committtee on immunization practices (ACIP): use of vaccines and immune globulins in persons with altered immunocompetence." MMWR Morb Mortal Wkly Rep 42(RR-04) (1993): 1-18. [PMID: 20300058]
• [25] Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.