eribulin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
antineoplastics; mitotic inhibitors, tubulin binders	4171	253128-41-5

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: eribulin mesylate eribulin halaven E7389 eribulin mesilate	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. In addition, eribulin treatment of human breast cancer cells caused changes in morphology and gene expression as well as decreased migration and invasiveness in vitro. In mouse xenograft models of human breast cancer, eribulin treatment was associated with increased vascular perfusion and permeability in the tumor cores, resulting in reduced tumor hypoxia, and changes in the expression of genes in tumor specimens associated with a change in phenotype. Molecular weight: 729.91 Formula: C40H59NO11 CLOGP: 0.14 LIPINSKI: 2 HAC: 12 HDO: 2 TPSA: 146.39 ALOGS: -3.96 ROTB: 4 Status: ONP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

eribulin mesylate
eribulin
halaven
E7389
eribulin mesilate

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. In addition, eribulin treatment of human breast cancer cells caused changes in morphology and gene expression as well as decreased migration and invasiveness in vitro. In mouse xenograft models of human breast cancer, eribulin treatment was associated with increased vascular perfusion and permeability in the tumor cores, resulting in reduced tumor hypoxia, and changes in the expression of genes in tumor specimens associated with a change in phenotype.

Molecular weight: 729.91
Formula: C40H59NO11
CLOGP: 0.14
LIPINSKI: 2
HAC: 12
HDO: 2
TPSA: 146.39
ALOGS: -3.96
ROTB: 4

Status: ONP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

None

ADMET properties:

Property	Value	Reference
Vd (Volume of distribution)	1.46 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	0.75 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.43 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	37.80 hours	Lombardo F, Berellini G, Obach RS
S (Water solubility)	10.40 mg/mL	Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Bocci G, Oprea TI, Benet LZ

Approvals:

Date	Agency	Company	Orphan
March 17, 2011	EMA
Nov. 15, 2010	FDA	EISAI INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Neutropenia	1361.69	32.44	638	10213	174367	63303804
Malignant neoplasm progression	1304.38	32.44	498	10353	81623	63396548
Febrile neutropenia	832.52	32.44	404	10447	118045	63360126
Neuropathy peripheral	405.45	32.44	248	10603	113419	63364752
Myelosuppression	396.78	32.44	150	10701	23553	63454618
Metastases to liver	361.25	32.44	140	10711	23499	63454672
Metastases to bone	358.96	32.44	135	10716	20884	63457287
Leukopenia	331.21	32.44	190	10661	77100	63401071
Interstitial lung disease	267.24	32.44	153	10698	61755	63416416
Neutrophil count decreased	210.71	32.44	127	10724	56279	63421892
Disease progression	157.00	32.44	145	10706	122613	63355558
Neoplasm progression	148.96	32.44	87	10764	36341	63441830
Pseudocirrhosis	141.13	32.44	31	10820	676	63477495
Mucosal inflammation	140.81	32.44	92	10759	46836	63431335
Metastases to lung	137.95	32.44	59	10792	12691	63465480
Breast cancer metastatic	131.30	32.44	56	10795	11962	63466209
Palmar-plantar erythrodysaesthesia syndrome	129.92	32.44	68	10783	22947	63455224
Osteonecrosis of jaw	115.58	32.44	73	10778	35050	63443121
Metastases to central nervous system	110.75	32.44	51	10800	13054	63465117
Metastases to lymph nodes	109.36	32.44	44	10807	8114	63470057
Thrombocytopenia	98.37	32.44	125	10726	151032	63327139
White blood cell count decreased	90.44	32.44	115	10736	138989	63339182
Haematotoxicity	90.36	32.44	40	10811	9336	63468835
Pyrexia	85.83	32.44	223	10628	470255	63007916
Stomatitis	79.79	32.44	108	10743	138617	63339554
Pleural effusion	73.48	32.44	85	10766	93125	63385046
Drug ineffective	66.98	32.44	49	10802	1044716	62433455
Hormone receptor positive breast cancer	66.47	32.44	16	10835	528	63477643
Anaemia	62.76	32.44	148	10703	293282	63184889
Breast cancer	61.42	32.44	57	10794	48326	63429845
Metastases to skin	61.15	32.44	19	10832	1644	63476527
Hyperchlorhydria	59.21	32.44	19	10832	1825	63476346
Folate deficiency	53.73	32.44	19	10832	2456	63475715
Lymphopenia	52.66	32.44	35	10816	18292	63459879
Decreased appetite	51.88	32.44	125	10726	250927	63227244
PIK3CA-activated mutation	51.45	32.44	15	10836	1044	63477127
Tumour marker increased	47.45	32.44	21	10830	4894	63473277
Odynophagia	44.75	32.44	23	10828	7463	63470708
Metastases to the mediastinum	42.79	32.44	11	10840	477	63477694
Ascites	42.32	32.44	43	10808	40685	63437486
Abdominal discomfort	40.49	32.44	4	10847	320881	63157290
Polyneuropathy	39.84	32.44	27	10824	14562	63463609
Metastases to spinal cord	38.93	32.44	8	10843	125	63478046
Arthralgia	37.28	32.44	26	10825	569684	62908487
Breast cancer recurrent	36.99	32.44	17	10834	4324	63473847
Drug hypersensitivity	36.39	32.44	5	10846	310682	63167489
Peripheral sensory neuropathy	36.37	32.44	20	10831	7431	63470740
Hypersensitivity	36.02	32.44	4	10847	292681	63185490
Protein total increased	33.86	32.44	14	10837	2763	63475408
Metastases to pleura	33.77	32.44	12	10839	1573	63476598
Hepatic function abnormal	32.86	32.44	36	10815	37106	63441065
Hyperglycaemia	32.65	32.44	38	10813	41829	63436342
Bile duct stenosis	32.52	32.44	11	10840	1245	63476926

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Febrile neutropenia	120.92	53.32	48	350	136801	34819732
Neutropenia	94.55	53.32	42	356	156736	34799797

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Neutropenia	1096.40	30.66	566	8500	287144	79448178
Malignant neoplasm progression	820.90	30.66	368	8698	135622	79599700
Febrile neutropenia	607.02	30.66	357	8709	230642	79504680
Myelosuppression	375.56	30.66	149	8917	40147	79695175
Neuropathy peripheral	319.75	30.66	199	8867	141106	79594216
Leukopenia	260.63	30.66	163	8903	116350	79618972
Metastases to bone	215.84	30.66	87	8979	24340	79710982
Neutrophil count decreased	208.85	30.66	131	8935	93828	79641494
Interstitial lung disease	189.58	30.66	132	8934	112468	79622854
Metastases to liver	167.80	30.66	76	8990	28238	79707084
Pseudocirrhosis	137.10	30.66	28	9038	652	79734670
White blood cell count decreased	103.64	30.66	117	8949	188171	79547151
Osteonecrosis of jaw	102.81	30.66	63	9003	43163	79692159
Metastases to lung	102.05	30.66	47	9019	18116	79717206
Disease progression	87.17	30.66	106	8960	184256	79551066
Metastases to lymph nodes	84.83	30.66	35	9031	10362	79724960
Breast cancer metastatic	84.16	30.66	33	9033	8569	79726753
Stomatitis	82.07	30.66	92	8974	146665	79588657
Mucosal inflammation	81.45	30.66	68	8998	75512	79659810
Neoplasm progression	78.54	30.66	57	9009	51625	79683697
Thrombocytopenia	76.34	30.66	120	8946	265139	79470183
Pyrexia	73.38	30.66	205	8861	678504	79056818
Metastases to central nervous system	69.61	30.66	35	9031	16340	79718982
Metastases to skin	63.42	30.66	18	9048	1721	79733601
Hyperchlorhydria	60.24	30.66	18	9048	2061	79733261
Decreased appetite	53.25	30.66	119	8947	342299	79393023
Folate deficiency	51.75	30.66	18	9048	3342	79731980
Haematotoxicity	51.21	30.66	28	9038	15491	79719831
Pleural effusion	47.77	30.66	70	8996	145192	79590130
Hormone receptor positive breast cancer	44.84	30.66	10	9056	357	79734965
Palmar-plantar erythrodysaesthesia syndrome	42.43	30.66	33	9033	33101	79702221
Anaemia	41.74	30.66	128	8938	444887	79290435
Metastases to the mediastinum	39.79	30.66	10	9056	600	79734722
Breast cancer	39.73	30.66	32	9034	33749	79701573
Odynophagia	38.93	30.66	21	9045	11306	79724016
Pneumothorax	35.81	30.66	28	9038	28295	79707027
Protein total increased	35.21	30.66	14	9052	3765	79731557
Breast cancer recurrent	34.78	30.66	13	9053	2964	79732358
Lymphopenia	33.94	30.66	28	9038	30529	79704793
Drug ineffective	33.02	30.66	45	9021	1080868	78654454

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	L01XX41	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS OTHER ANTINEOPLASTIC AGENTS Other antineoplastic agents
FDA PE	N0000175085	Microtubule Inhibition
FDA EPC	N0000175592	Microtubule Inhibitor
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:61951	microtubule destabilizing role

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
Liposarcoma	indication	254829001	DOID:3382
Metastatic Breast Carcinoma	indication
Constipation	contraindication	14760008	DOID:2089
Hypokalemia	contraindication	43339004
Chronic heart failure	contraindication	48447003
Bradycardia	contraindication	48867003
Prolonged QT interval	contraindication	111975006
Hypomagnesemia	contraindication	190855004
Pregnancy, function	contraindication	289908002
Thrombocytopenic disorder	contraindication	302215000	DOID:1588
Peripheral nerve disease	contraindication	302226006
Neutropenic disorder	contraindication	303011007	DOID:1227
Congenital long QT syndrome	contraindication	442917000

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.2	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
1MG/2ML (0.5MG/ML)	HALAVEN	EISAI INC	N201532	Nov. 15, 2010	RX	SOLUTION	INTRAVENOUS	Jan. 28, 2023	TREATMENT OF PATIENTS WITH UNRESECTABLE OR METASTATIC LIPOSARCOMA WHO HAVE RECEIVED A PRIOR ANTHRACYCLNE-CONTAINING REGIMEN
1MG/2ML (0.5MG/ML)	HALAVEN	EISAI INC	N201532	Nov. 15, 2010	RX	SOLUTION	INTRAVENOUS	Sept. 13, 2025	REVISIONS TO THE PEDIATRIC USE SUBSECTION OF LABELING TO INCLUDE THE RESULTS FROM CLINICAL STUDIES E7389-G000-223 AND E7389-G000-213, CONDUCTED TO FULFILL A PEDIATRIC WRITTEN REQUEST
1MG/2ML (0.5MG/ML)	HALAVEN	EISAI INC	N201532	Nov. 15, 2010	RX	SOLUTION	INTRAVENOUS	March 13, 2026	PEDIATRIC EXCLUSIVITY

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Tubulin beta	Tumour-associated antigen	P07437 Q9H4B7 Q13885 Q9BVA1 Q13509 P04350 P68371 Q9BUF5 Q3ZCM7	TBB5_HUMAN TBB1_HUMAN TBB2A_HUMAN TBB2B_HUMAN TBB3_HUMAN TBB4A_HUMAN TBB4B_HUMAN TBB6_HUMAN TBB8_HUMAN	INHIBITOR	IC50	8.23		IUPHAR	SCIENTIFIC LITERATURE

External reference:

ID	Source
4030296	VUID
N0000182254	NUI
D08914	KEGG_DRUG
441045-17-6	SECONDARY_CAS_RN
4030296	VANDF
4030302	VANDF
C2350866	UMLSCUI
CHEBI:70710	CHEBI
CHEMBL1683590	ChEMBL_ID
CHEMBL1683544	ChEMBL_ID
DB08871	DRUGBANK_ID
C490954	MESH_SUPPLEMENTAL_RECORD_UI
6813	IUPHAR_LIGAND_ID
8854	INN_ID
LR24G6354G	UNII
11354606	PUBCHEM_CID
1045452	RXNORM
178296	MMSL
27619	MMSL
d07716	MMSL
013558	NDDF
013559	NDDF
448800004	SNOMEDCT_US
708166000	SNOMEDCT_US
767582004	SNOMEDCT_US
6K9	PDB_CHEM_ID

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Halaven	HUMAN PRESCRIPTION DRUG LABEL	1	43624-002	INJECTION	0.50 mg	INTRAVENOUS	NDA	2 sections
Halaven	HUMAN PRESCRIPTION DRUG LABEL	1	43624-002	INJECTION	0.50 mg	INTRAVENOUS	NDA	2 sections
Halaven	HUMAN PRESCRIPTION DRUG LABEL	1	62856-389	INJECTION	0.50 mg	INTRAVENOUS	NDA	33 sections
Halaven	HUMAN PRESCRIPTION DRUG LABEL	1	62856-389	INJECTION	0.50 mg	INTRAVENOUS	NDA	33 sections