Eribulin

Identification

Name
Eribulin
Accession Number
DB08871  (DB04940)
Type
Small Molecule
Groups
Approved, Investigational
Description

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].

Structure
Thumb
Synonyms
Not Available
External IDs
ER-086526
Product Ingredients
IngredientUNIICASInChI Key
Eribulin mesylateAV9U0660CW441045-17-6QAMYWGZHLCQOOJ-WRNBYXCMSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
HalavenInjection, solution0.44 mg/mlIntravenousEisai Europe Ltd2011-03-17Not applicableEu
HalavenSolution0.5 mgIntravenousEisai Limited2012-03-19Not applicableCanada
HalavenInjection0.5 mg/1mLIntravenousEisai Limited2010-11-15Not applicableUs
HalavenInjection, solution0.44 mg/mlIntravenousEisai Europe Ltd2011-03-17Not applicableEu
HalavenInjection, solution0.44 mg/mlIntravenousEisai Europe Ltd2011-03-17Not applicableEu
HalavenInjection, solution0.44 mg/mlIntravenousEisai Europe Ltd2011-03-17Not applicableEu
Categories
UNII
LR24G6354G
CAS number
253128-41-5
Weight
Average: 729.8966
Monoisotopic: 729.408811735
Chemical Formula
C40H59NO11
InChI Key
UFNVPOGXISZXJD-WVMZDRIUSA-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,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
[H][C@@]12O[C@@]3([H])CCC4CC(=O)C[C@H]5[C@H](C[C@H]6O[C@H](C[C@@H](C)C6=C)CC[C@@H]6O[C@H](CC6=C)CC[C@@]67C[C@@H](O[C@H]1[C@@H](O6)[C@@]3([H])O4)[C@@H]2O7)O[C@H](C[C@H](O)CN)[C@@H]5OC

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.

Associated Conditions
Pharmacodynamics

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]

TargetActionsOrganism
UApoptosis regulator Bcl-2Not AvailableHuman
UTubulin beta-1 chainNot AvailableHuman
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]

Toxicity

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.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Eribulin.
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Eribulin.
AdalimumabThe risk or severity of adverse effects can be increased when Adalimumab is combined with Eribulin.
AlclometasoneThe risk or severity of adverse effects can be increased when Eribulin is combined with Alclometasone.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Eribulin.
AlemtuzumabThe risk or severity of adverse effects can be increased when Alemtuzumab is combined with Eribulin.
AlfuzosinThe risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Eribulin.
AlimemazineThe risk or severity of QTc prolongation can be increased when Eribulin is combined with Alimemazine.
AltretamineThe risk or severity of adverse effects can be increased when Altretamine is combined with Eribulin.
AmantadineThe risk or severity of QTc prolongation can be increased when Amantadine is combined with Eribulin.
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:23593076]
  2. 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. [PubMed:23010853]
  3. 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. [PubMed:22953094]
  4. 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. [PubMed:16020666]
External Links
KEGG Drug
D08914
PubChem Compound
73425383
PubChem Substance
175427126
ChemSpider
32813307
ChEBI
63587
ChEMBL
CHEMBL1683590
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Eribulin
ATC Codes
L01XX41 — Eribulin
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
FDA label
Download (194 KB)
MSDS
Download (120 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingTreatmentBreast Carcinoma Metastatic to the Brain / Lung Carcinoma Metastatic to the Brain / Metastatic Bladder Cancer / Metastatic Malignant Neoplasm in the Adult Brain / Metastatic Malignant Neoplasm to the Adult Brain / Primary Brain Tumors / Stage IV Non-Small Cell Lung Cancer1
1Active Not RecruitingTreatmentBreast Adenocarcinoma / Estrogen Receptor Negative / HER2/Neu Negative / Progesterone Receptor-negative / Stage IV Breast Cancer / Triple-Negative Breast Carcinoma1
1Active Not RecruitingTreatmentCancer, Breast1
1CompletedTreatmentAdult Solid Neoplasm / Recurrent Ovarian Carcinoma / Recurrent Uterine Corpus Carcinoma / Stage III Ovarian Cancer / Stage III Ovarian Cancer AJCC v6 and v7 / Stage III Uterine Corpus Cancer / Stage III Uterine Corpus Cancer AJCC v7 / Stage IV Ovarian Cancer / Stage IV Ovarian Cancer AJCC v6 and v7 / Stage IV Uterine Corpus Cancer / Stage IV Uterine Corpus Cancer AJCC v71
1CompletedTreatmentAdvanced Solid Tumors3
1CompletedTreatmentCancer, Breast1
1CompletedTreatmentCancer, Breast / Lung Cancer Non-Small Cell Cancer (NSCLC) / Prostate Cancer / Prostatic Neoplasms / Recurrent Ovarian Epithelial Cancer / Sarcomas / Transitional Cell Carcinoma1
1CompletedTreatmentCancers3
1CompletedTreatmentNeoplasms1
1CompletedTreatmentPediatrics / Tumors, Solid1
1CompletedTreatmentTumors1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific3
1RecruitingBasic ScienceSoft Tissue Sarcoma Adult1
1RecruitingTreatmentAdvanced Cancers1
1RecruitingTreatmentAnatomic Stage IV Breast Cancer AJCC v8 / Estrogen Receptor Negative / HER2/Neu Negative / Progesterone Receptor Negative / Prognostic Stage IV Breast Cancer AJCC v8 / Triple-Negative Breast Carcinoma1
1RecruitingTreatmentBreast Adenocarcinoma / Cancer, Breast / Human Epidermal Growth Factor 2 Negative Carcinoma of Breast / Recurrent Breast Carcinoma / Stage IV Breast Cancer1
1RecruitingTreatmentHer2-negative Metastatic Breast Cancer / Recurrent Ovarian Cancer1
1RecruitingTreatmentLiposarcoma / Retroperitoneal Neoplasms1
1RecruitingTreatmentMalignant Lymphomas / Pediatric Cancer / Tumors, Solid1
1RecruitingTreatmentMetastatic Urothelial Cell Cancer1
1RecruitingTreatmentRefractory Solid Tumors / Relapsed Solid Tumors1
1RecruitingTreatmentTriple Negative Breast Cancer (TNBC)1
1RecruitingTreatmentTumors, Solid1
1, 2Active Not RecruitingTreatmentDistal Urethral Carcinoma / Infiltrating Bladder Urothelial Carcinoma Associated With Urethral Carcinoma / Metastatic Bladder Cancer / Metastatic Urothelial Carcinoma of the Renal Pelvis and Ureter / Proximal Urethral Carcinoma / Recurrent Bladder Carcinoma / Recurrent Bladder Urothelial Carcinoma / Recurrent Urethra Carcinoma / Recurrent Urethral Urothelial Carcinoma / Recurrent Urothelial Carcinoma of the Renal Pelvis and Ureter / Regional Urothelial Carcinoma of the Renal Pelvis and Ureter / Renal Failure / Stage III Bladder Cancer / Stage III Bladder Urothelial Carcinoma / Stage III Bladder Urothelial Carcinoma AJCC v6 and v7 / Stage III Urethral Cancer / Stage IV Bladder Urothelial Carcinoma / Stage IV Bladder Urothelial Carcinoma AJCC v7 / Stage IV Urethral Cancer / Ureter Carcinoma / Urothelial carcinoma ureter metastatic1
1, 2Active Not RecruitingTreatmentMetastatic Breast Cancer (MBC)1
1, 2RecruitingTreatmentCancer, Advanced / Leiomyosarcomas / Liposarcoma / Soft Tissue Sarcoma Adult1
1, 2RecruitingTreatmentCancer, Breast1
1, 2RecruitingTreatmentEwing's Sarcoma (ES) / Non-rhabdomyosarcoma Soft Tissue Sarcomas / Refractory or Recurrent Solid Tumors / Rhabdomyosarcomas1
1, 2RecruitingTreatmentMetastatic Breast Cancer (MBC)2
1, 2TerminatedTreatmentHER-2 Positive Breast Cancer1
1, 2Unknown StatusTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
1, 2WithdrawnTreatmentCancer of the Breast1
2Active Not RecruitingTreatmentCancer, Breast3
2Active Not RecruitingTreatmentEstrogen Receptor-negative Breast Cancer / HER2-Negative Breast Cancer / Male Breast Cancer / Progesterone Receptor-negative Breast Cancer / Stage IA Breast Cancer / Stage IB Breast Cancer / Stage II Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer / Triple-Negative Breast Cancer (TNBC)1
2Active Not RecruitingTreatmentHER-2 Positive Breast Cancer1
2Active Not RecruitingTreatmentMetastatic Brain Tumors / Metastatic Breast Cancer (MBC)1
2Active Not RecruitingTreatmentMetastatic Breast Cancer (MBC)1
2Active Not RecruitingTreatmentMetastatic Ureter Carcinoma / Metastatic Ureteral Neoplasm / Metastatic Urethral Carcinoma / Metastatic Urethral Neoplasm / Stage III Bladder Urothelial Carcinoma / Stage III Bladder Urothelial Carcinoma AJCC v6 and v7 / Stage III Ureter Cancer / Stage III Ureter Cancer AJCC v7 / Stage III Urethral Cancer / Stage III Urethral Cancer AJCC v7 / Stage IV Bladder Urothelial Carcinoma / Stage IV Bladder Urothelial Carcinoma AJCC v7 / Stage IV Ureter Cancer / Stage IV Ureter Cancer AJCC v7 / Stage IV Urethral Cancer / Stage IV Urethral Cancer AJCC v7 / Ureter Urothelial Carcinoma / Urethral Urothelial Carcinoma1
2Active Not RecruitingTreatmentRecurrent Breast Carcinoma / Stage IV Breast Cancer1
2Active Not RecruitingTreatmentRecurrent Cervical Cancer / Stage IIIA Cervical Cancer / Stage IIIB Cervical Cancer / Stage IVA Cervical Cancer / Stage IVB Cervical Cancer1
2CompletedTreatmentAdenocarcinoma of the Pancreas / Malignant Neoplasm of Pancreas / Recurrent Pancreatic Cancer / Stage II Pancreatic Cancer / Stage III Pancreatic Cancer / Stage IV Pancreatic Cancer1
2CompletedTreatmentAdenocarcinoma of the Prostate / Hormone-Refractory Prostate Cancer / Recurrent Prostate Cancer / Stage IV Prostate Cancer1
2CompletedTreatmentCancer, Breast6
2CompletedTreatmentCancer, Breast / Estrogen Receptor Positive Tumor1
2CompletedTreatmentCancer, Breast / HER2-Negative Breast Cancer1
2CompletedTreatmentFallopian Tube Cancer / Primary Peritoneal Cavity Cancer / Recurrent Ovarian Epithelial Cancer1
2CompletedTreatmentHER2 Negative Breast Cancer1
2CompletedTreatmentHead and Neck Carcinoma1
2CompletedTreatmentHer2normal1
2CompletedTreatmentLocally Recurrent / Metastatic Breast Cancer ( HER2 Negative)1
2CompletedTreatmentMetastatic Breast Cancer (MBC)2
2CompletedTreatmentNeoplasms, Breast1
2CompletedTreatmentNon-Small Cell Lung Cancer Recurrent / Stage IIIb Non-small Cell Lung Cancer / Stage IV Non-Small Cell Lung Cancer1
2CompletedTreatmentProstate Cancer1
2CompletedTreatmentRecurrent Osteosarcoma1
2CompletedTreatmentRecurrent Salivary Gland Cancer / Stage IVA Salivary Gland Cancer / Stage IVB Salivary Gland Cancer / Stage IVC Salivary Gland Cancer1
2CompletedTreatmentSoft Tissue Sarcoma (STS)2
2Not Yet RecruitingTreatmentMetastatic Breast Cancer (MBC)1
2RecruitingTreatmentAdenocarcinomas / Cancer, Breast1
2RecruitingTreatmentCancer, Breast3
2RecruitingTreatmentCancers / Tumors, Solid1
2RecruitingTreatmentEpithelioid Hemangioendothelioma / Hemangiosarcoma1
2RecruitingTreatmentEwing's Sarcoma (ES) / Non-rhabdomyosarcoma Soft Tissue Sarcomas / Relapsed/Refractory Rhabdomyosarcoma1
2RecruitingTreatmentHER2-negative Circulating Tumor Cells / HER2-negative Und Hormone-receptor Positive Metastatic Breast Cancer / Postmenopausal Female Patients1
2RecruitingTreatmentHuman Epidermal Growth Factor 2 Negative Carcinoma of Breast / Inflammatory carcinoma of the breast1
2RecruitingTreatmentHuman Epidermal Growth Factor 2 Negative Carcinoma of Breast / Metastatic Breast Cancer (MBC)1
2RecruitingTreatmentMalignant Neoplasm of Breast1
2RecruitingTreatmentMetastatic Breast Cancer (MBC)1
2RecruitingTreatmentRecurrent Bladder Urothelial Carcinoma / Recurrent Urethral Urothelial Carcinoma / Recurrent Urothelial Carcinoma of the Renal Pelvis and Ureter / Renal Pelvis Urothelial Carcinoma / Stage III Bladder Urothelial Carcinoma / Stage III Bladder Urothelial Carcinoma AJCC v6 and v7 / Stage III Renal Pelvis Cancer AJCC v7 / Stage III Renal Pelvis Carcinoma / Stage III Ureter Cancer / Stage III Ureter Cancer AJCC v7 / Stage III Urethral Cancer / Stage III Urethral Cancer AJCC v7 / Stage IV Bladder Urothelial Carcinoma / Stage IV Bladder Urothelial Carcinoma AJCC v7 / Stage IV Renal Pelvis Cancer AJCC v7 / Stage IV Renal Pelvis Carcinoma / Stage IV Ureter Cancer / Stage IV Ureter Cancer AJCC v7 / Stage IV Urethral Cancer / Stage IV Urethral Cancer AJCC v7 / Ureter Urothelial Carcinoma / Urothelial carcinoma ureter metastatic1
2TerminatedTreatmentCancer of the Breast / Cancer, Breast / Neoplasms, Breast / Tumors, Breast1
2TerminatedTreatmentCancer, Breast1
2WithdrawnTreatmentBRCA1 Mutations / BRCA2 Mutation / Breast Cancer Metastatic / Cancer of the Ovary1
2WithdrawnTreatmentCancer, Breast1
3Active Not RecruitingTreatmentBreast Adenocarcinoma / HER2/Neu Negative / Invasive Breast Carcinoma / Locally Recurrent Breast Cancer / Metastatic Breast Cancer (MBC) / Stage IIIC Breast Cancer AJCC v7 / Stage IV Breast Cancer AJCC v6 and v71
3Active Not RecruitingTreatmentHER-2 Positive Breast Cancer / Neoplasms, Metastatic1
3Active Not RecruitingTreatmentMetastatic Triple Negative Breast Cancer1
3CompletedTreatmentCancer of the Breast / Cancer, Breast / HER2-Negative Breast Cancer / Triple Negative Breast Cancer (TNBC) / Tumors, Breast1
3CompletedTreatmentCancer, Breast1
3CompletedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
3CompletedTreatmentMetastatic Breast Cancer (MBC)1
3Not Yet RecruitingTreatmentHER2-Negative Breast Cancer / Leptomeningeal Carcinomatosis / Leptomeningeal Metastases / Metastatic Brain Tumors1
3RecruitingTreatmentCancer, Breast2
3RecruitingTreatmentCancer, Breast / Metastasis1
3RecruitingTreatmentHER2-positive Locally Advanced or Metastatic Breast Cancer1
3RecruitingTreatmentMetastatic Breast Cancer (MBC)1
4Active Not RecruitingHealth Services ResearchAdverse Drug Events / Metastatic Breast Cancer (MBC) / Neurotoxicity / Therapeutic Agent Toxicity / Toxicity1
4CompletedTreatmentCancer, Breast / Neoplasms, Breast1
4RecruitingTreatmentNeoplasms, Breast1
Not AvailableActive Not RecruitingNot AvailableCancer, Breast1
Not AvailableActive Not RecruitingNot AvailableSoft Tissue Sarcoma (STS)1
Not AvailableApproved for MarketingNot AvailableMetastatic Breast Cancer (MBC)1
Not AvailableCompletedNot AvailableInoperable or Recurrent Breast Cancer1
Not AvailableCompletedTreatmentCancer, Breast1
Not AvailableRecruitingNot AvailableAdvanced Breast Cancer / Metastatic Breast Cancer (MBC)1
Not AvailableRecruitingNot AvailableCancer, Breast / Neoplasms, Breast1
Not AvailableRecruitingNot AvailableLocally Advanced or Metastatic Breast Cancer2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
InjectionIntravenous0.5 mg/1mL
Injection, solutionIntravenous0.44 mg/ml
SolutionIntravenous0.5 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8097648No2001-01-222021-01-22Us
US6469182No1999-06-162019-06-16Us
US7470720No1999-06-162019-06-16Us
US6214865No2003-07-202023-07-20Us
USRE46965No2007-01-082027-01-08Us

Properties

State
Liquid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0798 mg/mLALOGPS
logP1.26ALOGPS
logP2.31ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)14.81ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area146.39 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity186 m3·mol-1ChemAxon
Polarizability77.52 Å3ChemAxon
Number of Rings9ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6417
Blood Brain Barrier-0.7893
Caco-2 permeable-0.646
P-glycoprotein substrateSubstrate0.8239
P-glycoprotein inhibitor IInhibitor0.5443
P-glycoprotein inhibitor IINon-inhibitor0.6565
Renal organic cation transporterNon-inhibitor0.7978
CYP450 2C9 substrateNon-substrate0.9256
CYP450 2D6 substrateNon-substrate0.7965
CYP450 3A4 substrateSubstrate0.6412
CYP450 1A2 substrateNon-inhibitor0.8332
CYP450 2C9 inhibitorNon-inhibitor0.8636
CYP450 2D6 inhibitorNon-inhibitor0.8939
CYP450 2C19 inhibitorNon-inhibitor0.7838
CYP450 3A4 inhibitorNon-inhibitor0.7094
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9246
Ames testNon AMES toxic0.7043
CarcinogenicityNon-carcinogens0.9719
BiodegradationNot ready biodegradable0.9841
Rat acute toxicity2.9429 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9408
hERG inhibition (predictor II)Inhibitor0.5065
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Furopyrans
Sub Class
Not Available
Direct Parent
Furopyrans
Alternative Parents
Furofurans / 1,3-dioxepanes / 1,4-dioxepanes / Ketals / Pyrans / Oxanes / Monosaccharides / Tetrahydrofurans / Furans / Secondary alcohols
show 8 more
Substituents
Furopyran / Furofuran / 1,3-dioxepane / 1,4-dioxepane / Dioxepane / Ketal / Monosaccharide / Oxane / Pyran / Furan
show 22 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Suppresses apoptosis in a variety of cell systems including factor-dependent lymphohematopoietic and neural cells. Regulates cell death by controlling the mitochondrial membrane permeability. Appea...
Gene Name
BCL2
Uniprot ID
P10415
Uniprot Name
Apoptosis regulator Bcl-2
Molecular Weight
26265.66 Da
References
  1. 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. [PubMed:15313917]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Structural constituent of cytoskeleton
Specific Function
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain (By similarity).
Gene Name
TUBB1
Uniprot ID
Q9H4B7
Uniprot Name
Tubulin beta-1 chain
Molecular Weight
50326.56 Da
References
  1. 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. [PubMed:16940412]

Drug created on May 02, 2013 13:55 / Updated on October 15, 2018 04:36