Details of the Drug

General Information of Drug (ID: DM7JNTV)

Drug Name

Halaven

Synonyms

Eribulin mesylate; Eribulin (mesylate); Eribulin mesilate; UNII-AV9U0660CW; Eribulin mesylate [USAN]; 441045-17-6; AV9U0660CW; CHEBI:70710; E 7389; E7389; Eribulin mesylate (USAN); B-1939; NSC-707389; Eribulin mesilate (JAN); CHEMBL1683544; QAMYWGZHLCQOOJ-WRNBYXCMSA-N; HY-13442A; AKOS030238218; CS-2803; D08914; 2-(3-amino-2-hydroxypropyl)hexacosahydro-3-methoxy-26-methyl-20,27-bis(methylene)11,15-18,21-24,28-triepoxy-7,9-ethano-12,15-methano-9H,15H-furo(3,2-i)furo(2',3'-5,6)pyrano(4,3-b)(1,4)dioxacyclopent

Indication

Disease Entry	ICD 11	Status	REF
Breast cancer	2C60-2C65	Approved	[1]
Bladder cancer	2C94	Phase 1/2	[2]

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski):
2

Molecular Weight

826

Topological Polar Surface Area

Not Available

Rotatable Bond Count

4

Hydrogen Bond Donor Count

3

Hydrogen Bond Acceptor Count

15

ADMET Property

Clearance: The drug present in the plasma can be removed from the body at the rate of 0.75 mL/min/kg [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 37.8 hours [3]
Unbound Fraction: The unbound fraction of drug in plasma is 0.43% [3]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.46 L/kg [3]

Chemical Identifiers

Formula: C41H63NO14S
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;methanesulfonic acid
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.CS(=O)(=O)O
InChI: InChI=1S/C40H59NO11.CH4O3S/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;1-5(2,3)4/h19,23-39,43H,2-3,5-18,41H2,1,4H3;1H3,(H,2,3,4)/t19-,23+,24+,25-,26+,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39+,40+;/m1./s1
InChIKey: QAMYWGZHLCQOOJ-WRNBYXCMSA-N

Cross-matching ID

PubChem CID: 17755248
ChEBI ID: CHEBI:70710
CAS Number: 441045-17-6
TTD ID: D0XQ5X
INTEDE ID: DR1817
ACDINA ID: D01058

Molecular Interaction Atlas of This Drug

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Ethanol	E00023	702	Antimicrobial preservative; Penetration agent; Solvent
Water	E00035	962	Solvent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Eribulin Mesylate 1mg/2ml solution	1mg/2ml	Solution	Intravenous

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References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2010
2	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	Eribulin, a microtubule inhibitor for metastatic breast cancer. Oncology (Williston Park). 2011 Feb;25(2 Suppl Nurse Ed):46-8.
5	Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
6	Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
7	Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
8	Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
9	Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
10	Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
11	Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
12	The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
13	Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.