halichondrin b profile

halichondrin B: from marine sponge Halichondria okadai; binds in the Vinca domain of tubulin [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Flora	Rank	Flora Definition	Family	Family Definition
Vinca	genus	A plant genus of the family Apocynaceae.[MeSH]	Apocynaceae	The dogbane family of the order Gentianales. Members of the family have milky, often poisonous juice, smooth-margined leaves, and flowers in clusters.[MeSH]

ID Source	ID
PubMed CID	10079877
CHEBI ID	80731
MeSH ID	M0192008

Synonym
halichondrin b
103614-76-2
CHEBI:80731

Excerpt	Reference	Relevance
"Halichondrin B is a polyether macrolide of marine origin which binds to tubulin and inhibits microtubule assembly in vitro and in vivo. "	( Interaction of halichondrin B and homohalichondrin B with bovine brain tubulin. Ludueña, RF; Pettit, GR; Prasad, V; Roach, MC, 1993)	2.08
"Halichondrin B is a highly potent anticancer agent originally found in marine sponges. "	( In vitro and in vivo anticancer activities of synthetic macrocyclic ketone analogues of halichondrin B. Aalfs, KK; Budrow, J; Chen, JJ; Davis, A; Dipietro, LV; Habgood, GJ; Kishi, Y; Kuznetsov, G; Littlefield, BA; Palme, MH; Quincy, DA; Salvato, KA; Seletsky, BM; Singer, LA; Towle, MJ; Wang, Y; Wels, BF; Welsh, S; Yoshimatsu, K; Yu, MJ; Zheng, W, 2001)	1.98

Excerpt	Reference	Relevance
"3 and 1 nM, respectively), with accumulation of cells arrested in mitosis at toxic concentrations, that both inhibited the polymerization of purified tubulin, and that both inhibited microtubule assembly dependent on microtubule-associated proteins."	( Halichondrin B and homohalichondrin B, marine natural products binding in the vinca domain of tubulin. Discovery of tubulin-based mechanism of action by analysis of differential cytotoxicity data. Bai, RL; Hamel, E; Herald, CL; Malspeis, L; Paull, KD; Pettit, GR, 1991)	1.72

Excerpt	Reference	Relevance
" This phase I study aimed to determine the maximum tolerated dose (MTD), dose-limiting toxicities (DLTs), and pharmacokinetics in combination with cisplatin (CP) in patients with advanced solid tumours."	( Phase I study of the halichondrin B analogue eribulin mesylate in combination with cisplatin in advanced solid tumors. Carroll, MI; Chung, VM; Cristea, MC; Doyle, LA; El-Khoueiry, AB; Frankel, PH; Gandara, DR; Koczywas, M; Lau, DH; Lenz, HJ; Lim, D; Mortimer, JE; Newman, EM; Reckamp, KL; Ruel, C; Synold, TW, 2014)	0.72
" Eribulin mesylate was administered on days 1, 8, and 15 in combination with CP day 1 every 28-day cycle."	( Phase I study of the halichondrin B analogue eribulin mesylate in combination with cisplatin in advanced solid tumors. Carroll, MI; Chung, VM; Cristea, MC; Doyle, LA; El-Khoueiry, AB; Frankel, PH; Gandara, DR; Koczywas, M; Lau, DH; Lenz, HJ; Lim, D; Mortimer, JE; Newman, EM; Reckamp, KL; Ruel, C; Synold, TW, 2014)	0.72
"2 mg m(-2), administered on days 1 and 8, in combination with CP 75 mg m(-2), administered on day 1 is well tolerated and showed preliminary anticancer activity."	( Phase I study of the halichondrin B analogue eribulin mesylate in combination with cisplatin in advanced solid tumors. Carroll, MI; Chung, VM; Cristea, MC; Doyle, LA; El-Khoueiry, AB; Frankel, PH; Gandara, DR; Koczywas, M; Lau, DH; Lenz, HJ; Lim, D; Mortimer, JE; Newman, EM; Reckamp, KL; Ruel, C; Synold, TW, 2014)	0.72

Excerpt	Relevance	Reference
"Eribulin demonstrated activity with manageable tolerability (including infrequent grade 3 and no grade 4 neuropathy) in heavily pretreated patients with MBC when dosed as a short IV infusion on days 1 and 8 of a 21-day cycle."	( Phase II study of eribulin mesylate, a halichondrin B analog, in patients with metastatic breast cancer previously treated with an anthracycline and a taxane. Ashworth, S; Blum, JL; Chandrawansa, K; Chuang, E; Cole, PE; Dacosta, NA; Fabian, CJ; Fang, F; Meneses, NL; O'Shaughnessy, J; Pruitt, B; Rivera, RR; Shuster, DE; Smith, DA; Smith, J; Tan, AR; Tan-Chiu, E; Vahdat, LT; Wright, J, 2009)	0.62

Class	Description
furopyran	Any organic heterobicyclic compound containing ortho-fused furan and pyran rings.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	7 (11.29)	18.2507
2000's	29 (46.77)	29.6817
2010's	24 (38.71)	24.3611
2020's	2 (3.23)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	5 (8.06%)	5.53%
Reviews	16 (25.81%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	41 (66.13%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (12)

Trial Overview

Trial	Phase	Enrollment	Study Type	Start Date	Status
A Phase III Randomized Trial of Eribulin (NSC #707389) With or Without Gemcitabine Versus Standard of Care (Physician's Choice) for Treatment of Metastatic Urothelial Carcinoma Refractory to, or Ineligible for, Anti PD1/PDL1 Therapy [NCT04579224]	Phase 3	465 participants (Anticipated)	Interventional	2021-06-28	Suspended(stopped due to Other - New treatment available, eliminating Arm 2)
A Phase I/II Trial Evaluating the Safety and Efficacy of Eribulin in Combination With Copanlisib in Patients With Metastatic Triple Negative Breast Cancer [NCT04345913]	Phase 1/Phase 2	106 participants (Anticipated)	Interventional	2021-03-01	Active, not recruiting
A Phase I/II Study of E7389 Halichondrin B Analog (NSC # 707389) in Metastatic Urothelial Tract Cancer and Renal Insufficiency [NCT00365157]	Phase 1/Phase 2	132 participants (Anticipated)	Interventional	2006-10-23	Active, not recruiting
A Phase I Study of Halichondrin B Analog E7389 in Combination With Gemcitabine in Patients With Refractory or Advanced Solid Tumors [NCT00410553]	Phase 1	45 participants (Actual)	Interventional	2006-11-14	Completed
A Randomized Phase III Trial of Eribulin Compared to Standard Weekly Paclitaxel as First- or Second-Line Therapy for Locally Recurrent or Metastatic Breast Cancer [NCT02037529]	Phase 3	201 participants (Actual)	Interventional	2014-01-17	Suspended(stopped due to Total enrollment number is being lowered)
Phase II Trial of Gemcitabine-Eribulin (GE) in Cisplatin Ineligible Patients With Advanced or Unresectable Urothelial Carcinoma of the Bladder [NCT02178241]	Phase 2	26 participants (Actual)	Interventional	2014-12-11	Completed
A Phase Ib Trial of M7824 and Eribulin in Patients With Metastatic Triple Negative Breast Cancer (TNBC) [NCT03579472]	Phase 1	38 participants (Actual)	Interventional	2018-05-30	Terminated(stopped due to Due to the fact that the sponsor decided not to move forward with the development of M7824)
A Randomized, Phase 2 Trial to Evaluate the Safety and Efficacy of Eribulin Mesylate in Combination With Atezolizumab Compared to Atezolizumab Alone in Subjects With Locally Advanced or Metastatic Transitional Cell Urothelial Cancer Where Cisplatin-Based [NCT03237780]	Phase 2	72 participants (Anticipated)	Interventional	2018-07-20	Active, not recruiting
A Phase II Study of Eribulin (NSC# 707389) in Recurrent or Refractory Osteosarcoma [NCT02097238]	Phase 2	19 participants (Actual)	Interventional	2014-08-31	Completed
Phase II Trial of Metronomic Eribulin (Halaven) in Pretreated Metastatic Breast Cancer (MBC) [NCT01908101]	Phase 2	86 participants (Actual)	Interventional	2014-01-08	Completed
A Phase 1B Trial of Preoperative Eribulin and Radiation for Retroperitoneal Liposarcoma [NCT03361436]	Phase 1	15 participants (Actual)	Interventional	2018-03-19	Active, not recruiting
Phase Ib/II Study of Grapiprant (IK-007) and Eribulin Combination Treatment for Metastatic Inflammatory Breast Cancer (mIBC) [NCT05041101]	Phase 1/Phase 2	25 participants (Anticipated)	Interventional	2021-11-04	Active, not recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

Trial	Outcome
NCT01908101 (1) [back to overview]	PFS
NCT02037529 (11) [back to overview]	Cumulative Dose Level Triggering a Grade 2 or Higher Neuropathy Event.
NCT02037529 (11) [back to overview]	Duration of Response
NCT02037529 (11) [back to overview]	Incidence of Treatment Related Adverse Events
NCT02037529 (11) [back to overview]	Mean Change in Patient Reported PRO-CTCAE
NCT02037529 (11) [back to overview]	Objective Tumor Response Rate
NCT02037529 (11) [back to overview]	Overall Survival (OS)
NCT02037529 (11) [back to overview]	Patients With Reported Neurotoxicity
NCT02037529 (11) [back to overview]	Progression Free Survival Assessed by RECIST 1.1 Criteria
NCT02037529 (11) [back to overview]	Time to New Metastasis
NCT02037529 (11) [back to overview]	Time to Treatment Failure
NCT02037529 (11) [back to overview]	Validation of PRO-CTCAE Sensory Neuropathy Item
NCT02097238 (6) [back to overview]	A Half Life of Eribulin Mesylate in hr
NCT02097238 (6) [back to overview]	Area Under the Curve 0-infinity of Eribulin Mesylate in Ng-hr/ml
NCT02097238 (6) [back to overview]	Clearance of Eribulin Mesylate in L/hr
NCT02097238 (6) [back to overview]	Disease Control Success
NCT02097238 (6) [back to overview]	Number of Cycles Where a Dose Limiting Toxicity Was Identified
NCT02097238 (6) [back to overview]	Response Evaluation Criteria in Solid Tumors (RECIST) Response
NCT02178241 (4) [back to overview]	Observed Overall Response Rate
NCT02178241 (4) [back to overview]	Overall Survival
NCT02178241 (4) [back to overview]	Progression-free Survival
NCT02178241 (4) [back to overview]	Incidence of Adverse Events.

PFS

Kaplan-Meier survival curves will be used to describe PFS, overall and stratified by number of prior metastatic treatment regimens. A 95% confidence interval for the median PFS will be calculated using the method of Brookmeyer and Crowley. (NCT01908101)
Timeframe: From study enrollment until the earliest date of disease progression or death, assessed up to 1 year

Intervention	months (Median)
Treatment (Eribulin Mesylate)	3.5

Intervention	Pearson correlation (Number)
	Baseline - Severity	Baseline - interference	Week 12 - severity	Week 12 - interference	Week 24 - severity	Week 24 - interference
All Patients	0.72	0.67	0.71	0.51	0.79	0.85

Intervention	participants (Number)
	Grade 1 or 2 : Anemia	Grade 1 or 2 : Febrile neutropenia	Grade 1 or 2 : Thrombotic microangiopathy	Grade 1 or 2 : Chest pain - cardiac	Grade 1 or 2 : Heart failure	Grade 1 or 2 : Colitis	Grade 1 or 2 : Constipation	Grade 1 or 2 : Diarrhea	Grade 1 or 2 : Dry Mouth	Grade 1 or 2 : Mucositis oral	Grade 1 or 2 : Nausea	Grade 1 or 2 : Vomiting	Grade 1 or 2 : Edema	Grade 1 or 2 : Fatigue	Grade 1 or 2 : Fever	Grade 1 or 2 : Appendicitis perforated	Grade 1 or 2 : Lung infection	Grade 1 or 2 : Sepsis	Grade 1 or 2 : Upper respiratory infection	Grade 1 or 2 : Urinary Tract Infection	Grade 1 or 2 : Electrocardiogram QT	Grade 1 or 2 : Weight Loss	Grade 1 or 2 : Lymphocyte Count Decreased	Grade 1 or 2 : Neutrophil Count Decreased	Grade 1 or 2 : Platelet Count Decreased	Grade 1 or 2 : White Blood Cell Decreased	Grade 1 or 2 : INR increased	Grade 1 or 2 : Alanine Aminotransferase Increased	Grade 1 or 2 : Aspartate Aminotransferase Incr	Grade 1 or 2 : Creatinine Increased	Grade 1 or 2 : Anorexia	Grade 1 or 2 : Hyperglycemia	Grade 1 or 2 : Dehydration	Grade 1 or 2 : Hypoalbuminemia	Grade 1 or 2 : Hypocalcemia	Grade 1 or 2 : Hypokalemia	Grade 1 or 2 : Hypomagnesemia	Grade 1 or 2 : Hyponatremia	Grade 1 or 2 : Hypophosphatemia	Grade 1 or 2 : Generalized Muscle Weakness	Grade 1 or 2 : Grip Weakness	Grade 1 or 2 : Pain in Extremity	Grade 1 or 2 : Dizziness	Grade 1 or 2 : Dysgeusia	Grade 1 or 2 : Paresthesia	Grade 1 or 2 : Peripheral Sensory Neuropathy	Grade 1 or 2 : Insomnia	Grade 1 or 2 : Dyspnea	Grade 1 or 2 : Pneumonitis	Grade 1 or 2 : Sore Throat	Grade 1 or 2 : Alopecia	Grade 1 or 2 : Hypotension	Grade 1 or 2 : Thromboembolic event	Grade 3 or 4 : Anemia	Grade 3 or 4 : Febrile neutropenia	Grade 3 or 4 : Thrombotic microangiopathy	Grade 3 or 4 : Chest pain - cardiac	Grade 3 or 4 : Heart failure	Grade 3 or 4 : Colitis	Grade 3 or 4 : Constipation	Grade 3 or 4 : Diarrhea	Grade 3 or 4 : Dry Mouth	Grade 3 or 4 : Mucositis oral	Grade 3 or 4 : Nausea	Grade 3 or 4 : Vomiting	Grade 3 or 4 : Edema	Grade 3 or 4 : Fatigue	Grade 3 or 4 : Fever	Grade 3 or 4 : Appendicitis perforated	Grade 3 or 4 : Lung infection	Grade 3 or 4 : Sepsis	Grade 3 or 4 : Upper respiratory infection	Grade 3 or 4 : Urinary Tract Infection	Grade 3 or 4 : Electrocardiogram QT	Grade 3 or 4 : Weight Loss	Grade 3 or 4 : Lymphocyte Count Decreased	Grade 3 or 4 : Neutrophil Count Decreased	Grade 3 or 4 : Platelet Count Decreased	Grade 3 or 4 : White Blood Cell Decreased	Grade 3 or 4 : INR increased	Grade 3 or 4 : Alanine Aminotransferase Increased	Grade 3 or 4 : Aspartate Aminotransferase Incr	Grade 3 or 4 : Creatinine Increased	Grade 3 or 4 : Anorexia	Grade 3 or 4 : Hyperglycemia	Grade 3 or 4 : Dehydration	Grade 3 or 4 : Hypoalbuminemia	Grade 3 or 4 : Hypocalcemia	Grade 3 or 4 : Hypokalemia	Grade 3 or 4 : Hypomagnesemia	Grade 3 or 4 : Hyponatremia	Grade 3 or 4 : Hypophosphatemia	Grade 3 or 4 : Generalized Muscle Weakness	Grade 3 or 4 : Grip Weakness	Grade 3 or 4 : Pain in Extremity	Grade 3 or 4 : Dizziness	Grade 3 or 4 : Dysgeusia	Grade 3 or 4 : Paresthesia	Grade 3 or 4 : Peripheral Sensory Neuropathy	Grade 3 or 4 : Insomnia	Grade 3 or 4 : Dyspnea	Grade 3 or 4 : Pneumonitis	Grade 3 or 4 : Sore Throat	Grade 3 or 4 : Alopecia	Grade 3 or 4 : Hypotension	Grade 3 or 4 : Thromboembolic event
Treatment (Eribulin Mesylate and Gemcitabine Hydrochloride)	7	3	1	0	0	0	10	7	4	2	7	2	9	13	4	0	0	0	0	1	2	4	4	4	7	7	1	9	11	4	9	0	3	8	4	4	3	7	4	5	0	3	5	4	4	5	3	0	0	3	12	2	0	8	0	0	1	1	1	0	2	0	2	3	2	1	7	0	1	1	1	1	2	1	0	6	15	3	13	1	0	1	0	0	1	2	1	0	0	0	2	0	1	1	1	0	0	1	0	0	1	1	0	0	1	1

Substance	Relationship Strength	Studies	Trials	Classes	Roles
carbamates [no description available]	2.44	2	0	amino-acid anion
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	2.73	3	0	metal allergen; nickel group element atom	epitope; micronutrient
galactose galactopyranose : The pyranose form of galactose.	2.05	1	0	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	4.04	2	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
colchicine (S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.	2.38	2	0	alkaloid; colchicine	anti-inflammatory agent; gout suppressant; mutagen
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	2.02	1	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	2.21	1	0	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	2.21	1	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
calcium gluconate [no description available]	2.05	1	0	calcium salt	nutraceutical
limestone Calcium Carbonate: Carbonic acid calcium salt (CaCO3). An odorless, tasteless powder or crystal that occurs in nature. It is used therapeutically as a phosphate buffer in hemodialysis patients and as a calcium supplement.. calcium carbonate : A calcium salt with formula CCaO3.	2.03	1	0	calcium salt; carbonate salt; inorganic calcium salt; one-carbon compound	antacid; fertilizer; food colouring; food firming agent
thiazolidines Thiazolidines: Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES.	2.21	1	0	thiazolidine
podophyllotoxin Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.	1.98	1	0	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
deoxycytidine [no description available]	3.46	1	1	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
tetrabutylammonium tetrabutylammonium: lipophilic probe; RN given refers to parent cpd	2.03	1	0	quaternary ammonium ion
n,n'-ethylenebis(iodoacetamide) [no description available]	1.98	1	0
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.42	2	0	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	3.46	1	1	elemental platinum; nickel group element atom; platinum group metal atom
chromium Chromium: A trace element that plays a role in glucose metabolism. It has the atomic symbol Cr, atomic number 24, and atomic weight 52. According to the Fourth Annual Report on Carcinogens (NTP85-002,1985), chromium and some of its compounds have been listed as known carcinogens.. chromium ion : An chromium atom having a net electric charge.. chromium atom : A chromium group element atom that has atomic number 24.	2.95	4	0	chromium group element atom; metal allergen	micronutrient
gemcitabine gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.	8.46	1	1	organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; environmental contaminant; immunosuppressive agent; photosensitizing agent; prodrug; radiosensitizing agent; xenobiotic
avarol avarol: RN given refers to parent cpd; extract from Dysidea avara(sea sponge)	2.02	1	0
fingolimod hydrochloride Fingolimod Hydrochloride: A sphingosine-derivative and IMMUNOSUPPRESSIVE AGENT that blocks the migration and homing of LYMPHOCYTES to the CENTRAL NERVOUS SYSTEM through its action on SPHINGOSINE 1-PHOSPHATE RECEPTORS. It is used in the treatment of MULTIPLE SCLEROSIS.. fingolimod hydrochloride : The hydrochloride salt of 2-amino-2-[2-(4-octylphenyl) ethyl]-1,3-propanediol (fingolimod).	3.16	1	0	hydrochloride	immunosuppressive agent; prodrug; sphingosine-1-phosphate receptor agonist
ecteinascidin 743 [no description available]	4.91	4	0	acetate ester; azaspiro compound; bridged compound; hemiaminal; isoquinoline alkaloid; lactone; organic heteropolycyclic compound; organic sulfide; oxaspiro compound; polyphenol; tertiary amino compound	alkylating agent; angiogenesis modulating agent; anti-inflammatory agent; antineoplastic agent; marine metabolite
patellamide a patellamide A: a cytotoxic cyclic peptide from ascidian Lissoclinum patella; structure given in first source	2.03	1	0	cyclic peptide
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	3.8	2	0	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
epothilone b [no description available]	2.02	1	0	epothilone; epoxide	antineoplastic agent; apoptosis inducer; microtubule-stabilising agent
epothilone a Epothilones: A group of 16-member MACROLIDES which stabilize MICROTUBULES in a manner similar to PACLITAXEL. They were originally found in the myxobacterium Sorangium cellulosum, now renamed to Polyangium (MYXOCOCCALES).	3.56	2	0	epothilone; epoxide	antineoplastic agent; metabolite; microtubule-stabilising agent; tubulin modulator
sesquiterpenes [no description available]	2.02	1	0
galactal galactal: RN given refers to cpd with unspecified isomeric designation; structure	2.05	1	0	anhydrohexose; glycal
sphingosine sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.	3.16	1	0	sphing-4-enine	human metabolite; mouse metabolite
maytansine Maytansine: An ansa macrolide isolated from the MAYTENUS genus of East African shrubs.. maytansine : An organic heterotetracyclic compound and 19-membered macrocyclic lactam antibiotic originally isolated from the Ethiopian shrub Maytenus serrata but also found in other Maytenus species. It exhibits cytotoxicity against many tumour cell lines.	8.48	2	0	alpha-amino acid ester; carbamate ester; epoxide; maytansinoid; organic heterotetracyclic compound; organochlorine compound	antimicrobial agent; antimitotic; antineoplastic agent; plant metabolite; tubulin modulator
thiocillin thiocillin: closely related to microccin P; RN given refers to mono-Na salt(2S-(2alpha,5alpha,6beta(Z)))-isomer	2.21	1	0	azamacrocycle; lactam
psammaplin a psammaplin A: isolated from marine sponges Poecillastra and Jaspis; structure in second source	3.14	1	0
rhizoxin rhizoxin: from Rhizopus chinensis; causal agent of rice seedling blight; structure given in first source. rhizoxin : An macrolide antibiotic isolated from the pathogenic plant fungus Rhizopus microsporus. It also exhibits antitumour and antimitotic activity.	8.08	1	0	1,3-oxazoles; epoxide; macrolide antibiotic	antimitotic; antineoplastic agent; metabolite
thermozymocidin thermozymocidin: a serine palmitoyltransferase inhibitor; FTY720 is an analog	3.16	1	0	alpha-amino fatty acid; hydroxy monocarboxylic acid; non-proteinogenic alpha-amino acid; sphingoid	antifungal agent; antimicrobial agent; antineoplastic agent; apoptosis inducer; EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor; fungal metabolite; immunosuppressive agent
phomopsin phomopsin: RN for cpd not in Chemline 7/18/83	8.08	1	0	oligopeptide
laulimalide laulimalide: isolated from Cacospongia mycofijiensis; structure in first source. laulimalide : A macrolide with formula C30H42O7 that is isolated from the marine sponges, Cacospongia mycofijiensis and Hyattella sp.	3.16	1	0	carboxylic ester; epoxide; macrolide; secondary alcohol; secondary allylic alcohol	animal metabolite; antimitotic; antineoplastic agent; marine metabolite; microtubule-stabilising agent
pep005 3-ingenyl angelate: protein kinase C agonist and antineoplastic; structure in first source	3.23	1	0
taxane taxane: produced by Taxomyces andreanae	6.44	3	3	diterpene; terpenoid fundamental parent
dolastatin 10 dolastatin 10: from mollusk Dolabella auricularia; contains four amino acids, dolavaline, dolaisoleucine, dolaproine, valine and the primary amine dolaphenine; deo-dolastatin 10 is a new dolastatin 10 chiral derivative with MW of 784. dolastatin 10 : A tetrapeptide that is isolated from the sea hare Dolabella auricularia. It is a potent anticancer agent which inhibits tubulin polymerization.	4.51	4	0	1,3-thiazoles; tetrapeptide	animal metabolite; antineoplastic agent; apoptosis inducer; marine metabolite; microtubule-destabilising agent
plitidepsin plitidepsin: a cyclodepsipeptide isolated from Aplidium albicans; has a pyruvoyl-proline residue instead of the lactyl-proline residue found in the linear peptide moiety of didemnin B. plitidepsin : A didemnin that is didemin B in which the hydroxy group of the 1-(2-hydroxypropanoyl)-L-prolinamide moiety has been oxidised to the corresponding ketone. It was originally isolated from the Mediterranean tunicate Aplidium albicans.	2.03	1	0	didemnin	anticoronaviral agent; antineoplastic agent; marine metabolite
dolastatin 15 dolastatin 15: from Dolabella auricularia; seven subunit depsipeptide	3.08	1	0
epoxomicin [no description available]	3.23	1	0	morpholines; tripeptide	proteasome inhibitor
er-086526 eribulin: a halichondrin B derivative that suppresses microtubule growth and acts as an antimitotic agent; structure in first source. eribulin : A fully synthetic macrocyclic ketone analogue of marine sponge natural products. Inhibits growth phase of microtubules via tubulin-based antimitotic mechanism, which leads to G2/M cell-cycle block, disruption of mitotic spindles, and, ultimately, apoptotic cell death after prolonged mitotic blockage	13.14	30	7	cyclic ketal; cyclic ketone; macrocycle; polycyclic ether; polyether; primary amino compound	antineoplastic agent; microtubule-destabilising agent
carfilzomib [no description available]	3.23	1	0	epoxide; morpholines; tetrapeptide	antineoplastic agent; proteasome inhibitor
discodermolide discodermolide: a lactone-bearing polyhydroxylated alkatetraene from the marine sponge Discodermia dissoluta; microtubule-stabilizing agent like taxol	2.44	2	0
neopeltolide neopeltolide: a macrolide from a lithistid sponge of the family Neopeltidae; structure in first source	3.16	1	0
gramicidin a Gramicidin: A group of peptide antibiotics from BACILLUS brevis. Gramicidin C or S is a cyclic, ten-amino acid polypeptide and gramicidins A, B, D are linear. Gramicidin is one of the two principal components of TYROTHRICIN.	2.21	1	0
ziconotide ziconotide: amino acid sequence in first source; from venom of South Pacific sea cone snail, Conus magus; calcium channel blocker; administered by injection into Cerebrospinal Fluid; Prialt is synthetic form. omega-conotoxin MVIIA : A heterodetic cyclic polypeptide consisting of the linear sequence Cys-Lys-Gly-Lys-Gly-Ala-Lys-Cys-Ser-Arg-Leu-Met-Tyr-Asp-Cys-Cys-Thr-Gly-Ser-Cys-Arg-Ser-Gly-Lys-Cys-NH2 with three disulfide bridges between cysteine residues 1-16, 8-20 and 15-25. A neuronal N-type Ca(2+) channel blocker in mammalian and amphibian brain, it blocks release of GABA and glutamate at neuronal synapses. Used as a probe for calcium channel receptors, it is selective for different receptor subtypes. A synthetic form, named ziconotide, is an atypical analgesic agent for the amelioration of severe and chronic pain.	2.21	1	0
largazole largazole: an antiproliferative agent from Symploca; structure in first source	2.21	1	0
bryostatin 1 bryostatin 1: a protein kinase C activator; macrocyclic lactone from marine Bryozoan Bugula neritina; RN given refers to (1S-(1R,3R,5Z,7S,8E,11R,12R(2E,4E),13E,15R,17S(S),21S,23S,25R))-isomer; structure given in first source; activates protein kinase c. bryostatin 1 : A member of the class of bryostatins that is (17E)-2-oxooxacyclohexacos-17-ene which is substituted by hydroxy groups at positions 4, 10, and 20; an acetoxy group at position 8; methyl groups at positions 9, 9, 18, and 19; 2-methoxy-2-oxoethylidene groups at positions 14 and 24; an (E,E)-octa-2,4-dienoyloxy group at position 21; and with oxygen bridges linking positions 6 to 10, 12 to 16, and 20 to 24. It is one of the most abundant member of the class of bryostatins.	4.06	2	0
kahalalide f kahalalide F: a cyclodepsipeptide toxin; isolated from a mollusk, Elysia rubefescens; exhibits antitumoral activity against cell lines of colon cancer and prostatic cancer; structure given in first source	2.05	1	0
okadaic acid Okadaic Acid: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING.. okadaic acid : A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.	3.41	1	0	ketal
laspartomycin c laspartomycin C: an acidic lipopeptide antibiotic with a unique peptide core; structure in first source	2.21	1	0
daptomycin [no description available]	2.21	1	0
lugdunin lugdunin: antibiotic from Staphylococcus lugdunensis. lugdunin : A thiazolidine-containing homodetic cyclic peptide that is isolated from human nasal bacteria. Exhibits bactericidal activity against many major pathogens including methicillin-resistant Staphylococcus aureus (MRSA).	2.21	1	0	homodetic cyclic peptide; indoles; macrocycle; peptide antibiotic; thiazolidines	human metabolite; rat metabolite
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	2.21	1	0
guanosine triphosphate Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.	2.68	3	0	guanosine 5'-phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor

Condition	Relationship Strength	Studies	Trials
Breast Cancer [description not available]	12.29	19	8
Metastase [description not available]	10.13	9	4
Sarcoma, Epithelioid [description not available]	3.06	1	0
Breast Neoplasms Tumors or cancer of the human BREAST.	12.29	19	8
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	10.13	9	4
Sarcoma A connective tissue neoplasm formed by proliferation of mesodermal cells; it is usually highly malignant.	3.06	1	0
Carcinoma, Epidermoid [description not available]	3.91	2	1
Cancer of Head [description not available]	2.21	1	0
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	3.91	2	1
Head and Neck Neoplasms Soft tissue tumors or cancer arising from the mucosal surfaces of the LIP; oral cavity; PHARYNX; LARYNX; and cervical esophagus. Other sites included are the NOSE and PARANASAL SINUSES; SALIVARY GLANDS; THYROID GLAND and PARATHYROID GLANDS; and MELANOMA and non-melanoma skin cancers of the head and neck. (from Holland et al., Cancer Medicine, 4th ed, p1651)	2.21	1	0
Alopecia Cicatrisata [description not available]	3.38	2	0
Carcinoma, Anaplastic [description not available]	3.01	1	0
Lassitude [description not available]	3.38	2	0
Peripheral Nerve Diseases [description not available]	8.74	6	4
Alopecia Absence of hair from areas where it is normally present.	3.38	2	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	3.01	1	0
Fatigue The state of weariness following a period of exertion, mental or physical, characterized by a decreased capacity for work and reduced efficiency to respond to stimuli.	3.38	2	0
Neutropenia A decrease in the number of NEUTROPHILS found in the blood.	4.68	4	0
Peripheral Nervous System Diseases Diseases of the peripheral nerves external to the brain and spinal cord, which includes diseases of the nerve roots, ganglia, plexi, autonomic nerves, sensory nerves, and motor nerves.	8.74	6	4
Benign Neoplasms [description not available]	5.92	5	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	5.92	5	1
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	3.03	1	0
Angiogenesis, Pathologic [description not available]	3.03	1	0
Triple Negative Breast Neoplasms Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.	3.03	1	0
Cancer of Pancreas [description not available]	3.46	1	1
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	3.46	1	1
Adenocarcinoma, Basal Cell [description not available]	3.46	1	1
Carcinoma, Non-Small Cell Lung [description not available]	3.46	1	1
Cancer of Lung [description not available]	3.46	1	1
Local Neoplasm Recurrence [description not available]	3.46	1	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	3.46	1	1
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	3.46	1	1
Lung Neoplasms Tumors or cancer of the LUNG.	3.46	1	1
Degenerative Diseases, Central Nervous System [description not available]	2.02	1	0
Neurodegenerative Diseases Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.	2.02	1	0
Fasting Hypoglycemia HYPOGLYCEMIA expressed in the postabsorptive state, after prolonged FASTING, or an overnight fast.	2.03	1	0
Hypoglycemia A syndrome of abnormally low BLOOD GLUCOSE level. Clinical hypoglycemia has diverse etiologies. Severe hypoglycemia eventually lead to glucose deprivation of the CENTRAL NERVOUS SYSTEM resulting in HUNGER; SWEATING; PARESTHESIA; impaired mental function; SEIZURES; COMA; and even DEATH.	2.03	1	0
Nausea An unpleasant sensation in the stomach usually accompanied by the urge to vomit. Common causes are early pregnancy, sea and motion sickness, emotional stress, intense pain, food poisoning, and various enteroviruses.	2.03	1	0
Hypophosphatemia A condition of an abnormally low level of PHOSPHATES in the blood.	2.03	1	0
Leukemia L 1210 [description not available]	2.38	2	0
Cancer of Colon [description not available]	2	1	0
Leucocythaemia [description not available]	2	1	0
Colonic Neoplasms Tumors or cancer of the COLON.	2	1	0
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	2	1	0
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	1.97	1	0

Intervention	mg/m^2 (Median)
Arm A (Eribulin)	39.25
Arm B (Paclitaxel)	3950

Intervention	Months (Median)
Arm A (Eribulin)	13.7
Arm B (Paclitaxel)	14.1

Intervention	Participants (Count of Participants)
Arm A (Eribulin)	94
Arm B (Paclitaxel)	90

Intervention	score on a scale (Mean)
Arm A (Eribulin)	3.72
Arm B (Paclitaxel)	3.77

halichondrin b

Description

Related Flora

Cross-References

Synonyms (3)

Research Excerpts

Overview

Toxicity

Compound-Compound Interactions

Dosage Studied

Drug Classes (1)

Research

Studies (62)

Market Indicators

Research Demand Index: 38.75

Study Types

Clinical Trials (12)

Trial Overview

Trial Outcomes

PFS

Cumulative Dose Level Triggering a Grade 2 or Higher Neuropathy Event.

Duration of Response

Incidence of Treatment Related Adverse Events

Mean Change in Patient Reported PRO-CTCAE

Objective Tumor Response Rate

Overall Survival (OS)

Patients With Reported Neurotoxicity

Progression Free Survival Assessed by RECIST 1.1 Criteria

Time to New Metastasis

Time to Treatment Failure

Validation of PRO-CTCAE Sensory Neuropathy Item

A Half Life of Eribulin Mesylate in hr

Area Under the Curve 0-infinity of Eribulin Mesylate in Ng-hr/ml

Clearance of Eribulin Mesylate in L/hr

Disease Control Success

Number of Cycles Where a Dose Limiting Toxicity Was Identified

Response Evaluation Criteria in Solid Tumors (RECIST) Response

Observed Overall Response Rate

Overall Survival

Progression-free Survival

Incidence of Adverse Events.

Related Drugs (57)

Related Conditions (45)