Estradiol benzoate

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

What is the Estradiol benzoate?

The molecule Estradiol benzoate presents a molecular formula of C25H28O3 and its IUPAC name is [(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate.

Estradiol benzoate is a synthetic, steroidal estrogen and a prodrug of estradiol. It is used as an intramuscular injectable in the treatment of low estrogen levels, and is also used as an intramuscular implant in the form of a pellet. Estradiol benzoate is marketed under a variety of brand names including Femtrace, Progynon-B, and others..

3D structure

Cartesian coordinates

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

2D drawing

 

Estradiol benzoate UYIFTLBWAOGQBI-BZDYCCQFSA-N chemical compound 2D structure molecule svg
Estradiol benzoate

 

Molecule descriptors

 
IUPAC name[(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate
InChI codeInChI=1S/C25H28O3/c1-25-14-13-20-19-10-8-18(28-24(27)16-5-3-2-4-6-16)15-17(19)7-9-21(20)22(25)11-12-23(25)26/h2-6,8,10,15,20-23,26H,7,9,11-14H2,1H3/t20-,21-,22+,23+,25+/m1/s1
InChI KeyUYIFTLBWAOGQBI-BZDYCCQFSA-N
SMILESC[C@]12CC[C@@H]3c4ccc(OC(=O)c5ccccc5)cc4CC[C@H]3[C@@H]1CC[C@@H]2O

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.

  • (17.beta.)-Estra-1,3,5(10)-triene-3,17-diol 3-benzoate
  • (17?)-17-Hydroxyestra-1(10),2,4-trien-3-yl benzoate
  • (17beta)-17-hydroxyestra-1(10),2,4-trien-3-yl benzoate
  • (17beta)-Estra-1,3,5(10)-triene-3,17-diol 3-benzoate
  • (17beta)Estra-1,3,5(10)triene-3,17-diol-3-benzoate
  • (8R,9S,13S,14S,17S)-17-Hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl benzoate
  • (8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl benzoate;17beta-Estradiol benzoate; 1,3,5(10)-Estratriene-3,17b-diol 3-benzoate; 3,17b-Dihydroxy-1,3,5(10)-estratriene 3-benzoate
  • .beta.-Estradiol 3-benzoate
  • .beta.-Estradiol benzoate
  • .beta.-Oestradiol 3-benzoate
  • .beta.-Oestradiol benzoate
  • 003E692
  • 1,3,5(10)-Estratriene-3,17.beta.-diol 3-benzoate
  • 1,3,5(10)-Oestratriene-3,17-.beta.-diol 3-benzoate
  • 1,5(10)-Estratriene-3,17.beta.-diol 3-benzoate
  • 17-.beta.-Oestradiol 3-benzoate
  • 17-Hydroxyestra-1(10),2,4-trien-3-yl benzoate, (17.beta.)-
  • 17-beta-Estradiol 3-benzoate
  • 17-beta-Estradiol benzoate
  • 17-beta-Oestradiol 3-benzoate
  • 17-estradiol 3-benzoate
  • 17.beta.-Estradiol 3-benzoate
  • 17.beta.-Estradiol benzoate
  • 17.beta.-Estradiol monobenzoate
  • 17beta-Estradiol 3-benzoate
  • 17beta-Estradiol monobenzoate
  • 1S4CJB5ZGN
  • 3,17ss-Dihydroxy-1,3,5(10)-estratriene 3-benzoate
  • 3-Benzoyloxy-17.beta.-hydroxyestra-1,3,5(10)-triene
  • 3-Benzoyloxy-17ss-estrol?
  • 50-50-0
  • A828140
  • AI3-52465
  • AMY22166
  • AS-13030
  • Agofollin Depot
  • BCP09252
  • BDBM56905
  • BIDD:ER0126
  • BRN 3107526
  • Benovocylin
  • Benzestrofol
  • Benzhormovarine
  • Benzo-Gineostril
  • Benzo-Ginestryl
  • Benzo-Gynoestryl
  • Benzoate d'estradiol
  • Benzoate d'oestradiol
  • Benzoato de estradiol
  • Benzoestrofol
  • Benzoestrofol difolliculin
  • Benzofoline
  • Benzogynestryl
  • Benzogynoestryl
  • Benzoic acid estradiol
  • Benztrone
  • CCG-268370
  • CCRIS 281
  • CS-4780
  • D01953
  • D97619
  • DB13953
  • DSSTox_CID_2998
  • DSSTox_GSID_22998
  • DSSTox_RID_76823
  • De graafina
  • Diffolisterol,(S)
  • Diffollisterol
  • Difolliculin
  • Difolliculine
  • Dihydroestrin benzoate
  • Dihydrofolliculin benzoate
  • Dihydrofolliculine benzoate
  • Dimenformon benzoate
  • Dimenformone
  • Diogyn B
  • E0329
  • EBZ
  • ESTRADIOL, 3-BENZOATE
  • Eston-B
  • Estra-1,3,5(10)-triene-3,17-beta-diol, 3-benzoate
  • Estra-1,3,5(10)-triene-3,17-diol (17-beta)-3-benzoate
  • Estra-1,3,5(10)-triene-3,17-diol (17b)-, 3-benzoate
  • Estra-1,3,5(10)-triene-3,17-diol, (17beta)-, 3-benzoate
  • Estra-1,3,5(10)-triene-3,17.beta.-diol, 3-benzoate
  • Estra-1,3,5(10)-triene-3,17beta-diol, 3-benzoate
  • Estra-1,5(10)-triene-3,17-diol (17.beta.)-, 3-benzoate
  • Estra-1,5(10)-triene-3,17.beta.-diol, 3-benzoate
  • Estradiol (benzoate)
  • Estradiol 3-benzoate
  • Estradiol benzoate
  • Estradiol benzoate (JP17/USP)
  • Estradiol monobenzoate
  • Estradiol-17-beta-3-benzoate
  • Estradiol-17.beta. 3-benzoate
  • Estradiol-17.beta. benzoate
  • Estradiol-17beta 3-benzoate
  • Estradioli benzoas
  • Estradiolo Amsa
  • Estradiolo benzoato
  • Estrogin
  • Femestrone
  • Folone
  • Follicormon
  • Follidrin
  • Graafina
  • Gynecormone
  • Gynecormone Gouttes
  • Gynformone
  • HMS2232P14
  • HY-B1192
  • Hidroestron
  • Hormogynon
  • Hydroxyestrin benzoate
  • I(2)-Estradiol 3-benzoate
  • MLS000028477
  • MLS002207215
  • Mesalin
  • Metroval
  • NCGC00021274-03
  • NCGC00021274-04
  • NCGC00021274-05
  • NSC 9566
  • NSC-9566
  • NSC9566
  • Oestradiol 3-benzoate
  • Oestradiol benzoate
  • Oestradiol monobenzoate
  • Oestradioli benzoas
  • Oestradiolum benzoicum
  • Oestradiolum benzoylatum
  • Oestraform
  • Oestraform (BDH)
  • Ostrin
  • Ovahormon benzoate
  • Ovasterol-B
  • Ovocyclin Benzoate
  • Ovocyclin M
  • Ovocyclin-MB
  • Pelanin benzoate
  • Primogyn B
  • Primogyn B oleosum
  • Primogyn I
  • Primogyn boleosum
  • Progynon B
  • Progynon benzoate
  • Progynon-B
  • Q-201505
  • Q11450699
  • Recthormone oestradiol
  • Reglovar
  • SMR000058343
  • SR-01000003080
  • SR-01000003080-3
  • ST075190
  • Solestro
  • Unistradiol
  • WLN: L E5 B666TTT&J E1 FQ OOVR
  • [(13S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate
  • [(8R,9S,13S,14S,17S)-13-methyl-17-oxidanyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate
  • [(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate
  • benzoic acid [(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] ester
  • beta-Estradiol 3-benzoate
  • cid_222757
  • estra-1,3,5(10)-triene-3,17beta-diol 3-benzoate
  • estradiol benzoate
  • estradiol-benzoate
  • s4110
  • ss-Estradiol 3-benzoate

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3881345
  • CAS-50-50-0
  • UNII-1S4CJB5ZGN
  • AKOS015955542
  • DTXSID9022998
  • CHEMBL282575
  • CHEBI:77006
  • Tox21_110868
  • EINECS 200-043-7
  • SCHEMBL174896

Physico-Chemical properties

IUPAC name[(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate
Molecular formulaC25H28O3
Molecular weight376.488
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity110.40
LogP5.1
Topological polar surface area46.5

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.