Eribulin

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Eribulin are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Eribulin?

The molecule Eribulin presents a molecular formula of C40H59NO11 and its IUPAC name is (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.

Eribulin is a chemotherapy drug that is used to treat certain types of cancer, including breast cancer and liposarcoma. It belongs to a class of drugs known as microtubule inhibitors, which work by disrupting the normal function of microtubules in cancer cells. Microtubules are protein structures that play a key role in cell division and the maintenance of the cell's structure. By inhibiting the function of microtubules, eribulin can effectively kill cancer cells or inhibit their growth, leading to reduced tumor size and improved clinical outcomes..

Eribulin is usually administered intravenously (through a vein) as an injection. It is typically given once a week for two weeks, followed by a one-week break, in a cycle that is repeated until the cancer progresses or the patient experiences unacceptable side effects. Eribulin has a relatively long half-life, which means that it remains in the body for a long time after administration..

Eribulin has been shown to be effective in the treatment of advanced breast cancer and liposarcoma in clinical trials. In one large study, eribulin was shown to significantly improve overall survival in patients with advanced breast cancer compared to treatment with a different chemotherapy drug. In another study, eribulin was shown to significantly improve progression-free survival in patients with liposarcoma..

Eribulin can cause side effects in some patients, including fatigue, nausea, hair loss, and anemia. It can also affect the bone marrow and lead to a decrease in white blood cells, red blood cells, and platelets. It is important to follow the dosing and usage instructions provided by a healthcare provider and report any side effects to a healthcare professional..

Summary

From all the above, eribulin is a promising chemotherapy drug that has demonstrated significant clinical activity in the treatment of advanced breast cancer and liposarcoma. Its ability to disrupt the function of microtubules in cancer cells makes it a valuable treatment option for these types of cancer..

3D structure

Cartesian coordinates

Geometry of Eribulin in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Eribulin UFNVPOGXISZXJD-JBQZKEIOSA-N chemical compound 2D structure molecule svg
Eribulin

 

Molecule descriptors

 
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
InChI codeInChI=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
InChI KeyUFNVPOGXISZXJD-JBQZKEIOSA-N
SMILESC=C1C[C@@H]2CC[C@@]34C[C@H]5O[C@H]6[C@@H](O3)[C@H]3O[C@H](CC[C@@H]3O[C@H]6[C@H]5O4)CC(=O)C[C@H]3[C@H](C[C@H]4O[C@@H](CC[C@@H]1O2)C[C@@H](C)C4=C)O[C@H](C[C@H](O)CN)[C@@H]3OC

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (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-o
  • (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
  • (1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,35R,36S)-20-[(2S)-3-amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.1(3,32).1(3,33).1(6,9).1(12,16).0(18,22).0(29,36).0(31,35)]hentetracontan-24-one
  • (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[24.9.2.1~3,32~.1~3,33~.1~6,9~.1~12,16~.0~18,22~.0~29,36~.0~31,35~]hentetracontan-24-One (Non-Preferred Name)
  • 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)dioxacyclopentacosin-5-(4H)-one
  • 253128-41-5
  • B 1939
  • DB08871
  • ER 086526
  • ER-086526
  • EX-A4873D
  • Eribulin
  • Eribulin mesylate
  • GTPL6813
  • HY-13442
  • LR24G6354G
  • NCGC00510497-02
  • NSC-707389
  • Q408717
  • e7389-lf

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC169344691
  • UNII-LR24G6354G
  • DTXSID101009321
  • CHEMBL1683590
  • CHEBI:63587
  • SCHEMBL15783821

Physico-Chemical properties

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
Molecular formulaC40H59NO11
Molecular weight729.897
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity188.29
LogP4.1
Topological polar surface area146.4

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.