Tibolone

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

What is the Tibolone?

The molecule Tibolone presents a molecular formula of C21H28O2 and its IUPAC name is (7R,8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-7,13-dimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one.

Tibolone is a synthetic steroid hormone drug that is used in menopausal hormone therapy. The drug has tissue-selective estrogenic and androgenic activity. It is used in the treatment of menopausal symptoms such as hot flashes, vaginal atrophy, and osteoporosis. Tibolone has been shown to have a beneficial effect on mood and well-being. The drug exists in Europe and other countries, but is not approved for use in the United States..

3D structure

Cartesian coordinates

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

2D drawing

 

Tibolone WZDGZWOAQTVYBX-XOINTXKNSA-N chemical compound 2D structure molecule svg
Tibolone

 

Molecule descriptors

 
IUPAC name(7R,8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-7,13-dimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
InChI codeInChI=1S/C21H28O2/c1-4-21(23)10-8-18-19-13(2)11-14-12-15(22)5-6-16(14)17(19)7-9-20(18,21)3/h1,13,17-19,23H,5-12H2,2-3H3/t13-,17-,18+,19-,20+,21+/m1/s1
InChI KeyWZDGZWOAQTVYBX-XOINTXKNSA-N
SMILESC#C[C@]1(O)CC[C@H]2[C@H]3[C@H](CC[C@@]21C)C1=C(CC(=O)CC1)C[C@H]3C

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.

  • (17R)-17-hydroxy-7alpha-methyl-19-norpregn-5(10)-en-20-yn-3-one
  • (1S,9R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-9,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-2(7)-en-5-one
  • (7R,8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-7,13-dimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
  • (7alpha,17alpha)-17-hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3-one
  • (7alpha,17beta)-17-ethynyl-17-hydroxy-7-methylestr-5(10)en-3-one
  • (7beta,8xi,9beta,13alpha,14beta,17alpha)-17-ethynyl-17-hydroxy-7-methylestr-5(10)-en-3-one
  • 17-Hydroxy-7.alpha.-methyl-19-nor-17.alpha.-pregn-5(10)-en-20-yn-3-one
  • 17-Hydroxy-7alpha-methyl-19-nor-17alpha-pregn-5(10)-en-20-yn-3-one
  • 17.alpha.-Hydroxy-7.alpha.-methyl-19-norpregn-5(10)-en-20-yn-3-one
  • 17alpha-ethynyl-17beta-hydroxy-7alpha-methylestr-5(10)-en-3-one
  • 19-Norpregn-5(10)-en-20-yn-3-one, 17-hydroxy-7-methyl-, (7.alpha.,17.alpha.)-
  • 19-Norpregn-5(10)-en-20-yn-3-one, 17-hydroxy-7-methyl-, (7alpha,17alpha)-
  • 5630-53-5
  • 630T535
  • AB00698273-05
  • AC-20036
  • AC-31722
  • Boltin
  • CCG-101148
  • CPD000469219
  • D01639
  • DB09070
  • DSSTox_CID_3667
  • DSSTox_GSID_23667
  • DSSTox_RID_77135
  • FF9X0205V2
  • GS-3562
  • GTPL9711
  • HMS2052K21
  • HMS2090B10
  • HMS2232B13
  • HMS3649J14
  • HMS3712J15
  • KB-889
  • Livial
  • Liviella
  • MLS001424234
  • NC00398
  • NCGC00164632-01
  • NCGC00164632-02
  • NSC 759898
  • NSC-759898
  • ORG-OD 14
  • Org OD 14
  • Org OD 14;Org OD14
  • Org-OD14
  • Q413805
  • SMR000469219
  • SR-01000763531
  • SR-01000763531-3
  • SR-01000946727
  • SR-01000946727-1
  • T-3854
  • Tibofem
  • Tibolona
  • Tibolone
  • Tibolone (JAN/USAN/INN)
  • Tibolonum
  • Xyvion
  • tibolone

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3812889
  • CAS-5630-53-5
  • UNII-FF9X0205V2
  • AKOS015963197
  • DTXSID5023667
  • CHEMBL2103774
  • CHEBI:32223
  • Tox21_112250
  • Tox21_112250_1
  • EINECS 227-069-1
  • SCHEMBL41172

Physico-Chemical properties

IUPAC name(7R,8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-7,13-dimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Molecular formulaC21H28O2
Molecular weight312.446
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity93.43
LogP3.9
Topological polar surface area37.3

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.