Abiraterone acetate

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

What is the Abiraterone acetate?

The molecule Abiraterone acetate presents a molecular formula of C26H33NO2 and its IUPAC name is [(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate.

Abiraterone acetate (brand name Zytiga) is a drug used in the treatment of metastatic castration-resistant prostate cancer (mCRPC). It is a prodrug of abiraterone, which is a potent androgen receptor antagonist. Abiraterone acetate is a white to off-white powder that is soluble in methanol and slightly soluble in water..

The mechanism of action of abiraterone acetate is similar to that of other androgen receptor antagonists, such as bicalutamide and flutamide. These drugs bind to the androgen receptor, preventing androgens from binding and activating the receptor. This inhibits the growth of prostate cancer cells that are dependent on androgens for growth and survival..

Abiraterone acetate was approved by the US Food and Drug Administration (FDA) in 2011 for the treatment of mCRPC. It is typically used in combination with the steroidal antiandrogen drugsprednisone or prednisolone..

Common side effects of abiraterone acetate include fatigue, joint pain, hot flashes, diarrhea, and nausea. More serious side effects include liver damage, low blood potassium levels, and fluid retention..

Abiraterone acetate is a promising new treatment for mCRPC. It is well tolerated and has shown efficacy in clinical trials. However, long-term data on its efficacy and safety are still needed..

3D structure

Cartesian coordinates

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

2D drawing

 

Abiraterone acetate UVIQSJCZCSLXRZ-UBUQANBQSA-N chemical compound 2D structure molecule svg
Abiraterone acetate

 

Molecule descriptors

 
IUPAC name[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
InChI codeInChI=1S/C26H33NO2/c1-17(28)29-20-10-12-25(2)19(15-20)6-7-21-23-9-8-22(18-5-4-14-27-16-18)26(23,3)13-11-24(21)25/h4-6,8,14,16,20-21,23-24H,7,9-13,15H2,1-3H3/t20-,21-,23-,24-,25-,26+/m0/s1
InChI KeyUVIQSJCZCSLXRZ-UBUQANBQSA-N
SMILESCC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC=C(c5cccnc5)[C@@]4(C)CC[C@@H]32)C1

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,2R,5S,10R,11S,15S)-2,15-dimethyl-14-(pyridin-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,13-dien-5-yl acetate
  • (3?)-17-(3-Pyridinyl)androsta-5,16-dien-3-yl acetate
  • (3S)-3-Acetoxy-17-(pyridin-3-yl)androsta-5,16-diene
  • (3S,8R,9S,10R,13S,14S)-10,13-DIMETHYL-17-(PYRIDIN-3-YL)-2,3,4,7,8,9,10,11,12,13,14,15-DODECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-3-YL ACETATE
  • (3beta)-17-(pyridin-3-yl)androsta-5,16-dien-3-yl acetate
  • 154229-18-2
  • 17-(3-Pyridyl)-5,16-androstadien-3beta-acetate
  • 17-(3-Pyridyl)androsta-5, acetate
  • 17-(PYRIDIN-3-YL)ANDROSTA-5,16-DIEN-3.BETA.-YL ACETATE
  • 17-(pyridin-3-yl)androsta-5,16-dien-3beta-yl acetate
  • 3S,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-ol, 3-acetate
  • 3b-acetoxy-17-(3-pyridyl)androsta-5,16-diene
  • 3beta-17-(3-Pyridyl)androsta-5,16-dien-3-ol Acetate
  • 3beta-Acetoxy-17-(3-pyridyl)androsta-5,16-diene
  • A809510
  • ABIRATERONE (AS ACETATE)
  • AC-25760
  • ANDROSTA-5,16-DIEN-3-OL, 17-(3-PYRIDINYL)-, ACETATE (ESTER), (3.BETA.)-
  • Abiraterone Acetate
  • Abiraterone Acotate
  • Abiraterone (acetate)
  • Abiraterone acetate
  • Abiraterone acetate (JAN/USP)
  • Abiraterone acetate- Bio-X
  • Androsta-5, 17-(3-pyridinyl)-, 3-acetate,
  • Androsta-5,16-dien-3-ol, 17-(3-pyridinyl)-, acetate (ester), (3beta)-
  • BA164133
  • BCP02949
  • BDBM50407398
  • CB 7630
  • CB-7630
  • CB7630
  • CS-0544
  • D09701
  • DS-2007
  • DSSTox_CID_28969
  • DSSTox_GSID_49043
  • DSSTox_RID_83234
  • EM5OCB9YJ6
  • EX-A107
  • GTPL9288
  • HY-75054
  • JNJ 212082
  • JNJ-2012082
  • JNJ-212082
  • MFCD00934213
  • MLS006010090
  • NCGC00186462-01
  • NCGC00379022-06
  • NSC 748121
  • NSC 749227
  • NSC-748121
  • NSC-749227
  • NSC748121
  • NSC749227
  • Q27888393
  • SMR004701235
  • W-201385
  • Yonsa
  • Zytiga
  • [(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
  • [(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] ethanoate
  • abiraterone-acetate
  • acetic acid [(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-(3-pyridinyl)-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] ester
  • s2246

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3809191
  • CAS-154229-18-2
  • UNII-EM5OCB9YJ6
  • AKOS015896502
  • BRD-K24048528-001-02-5
  • DTXSID3049043
  • CHEMBL271227
  • CHEBI:68639
  • Tox21_113589
  • SCHEMBL93715

Physico-Chemical properties

IUPAC name[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Molecular formulaC26H33NO2
Molecular weight391.546
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity117.50
LogP6.0
Topological polar surface area39.2

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.