Allylestrenol

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

What is the Allylestrenol?

The molecule Allylestrenol presents a molecular formula of C21H32O and its IUPAC name is (8R,9S,10R,13S,14S,17R)-13-methyl-17-prop-2-enyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol.

Allylestrenol is a synthetic, orally active progestogen which is used in some countries for the treatment of threatened abortion and habitual abortion. It is also used in combination with an estrogen for the treatment of menopausal symptoms. Allylestrenol is a prodrug of allylprodine..

Allylestrenol was first synthesized in 1953. It is a white, crystalline solid with a melting point of 155-156 °C. It is insoluble in water and has a molecular weight of 350.44..

Allylestrenol is a progestogen, meaning that it mimics the effects of the hormone progesterone in the body. Progesterone is important for maintaining pregnancy and preparing the body for childbirth. Allylestrenol works by binding to the progesterone receptor, which belongs in the uterus, ovaries, and placenta. This binding prevents the natural breakdown of progesterone, which is necessary for maintaining pregnancy..

Allylestrenol is used for the treatment of threatened abortion and habitual abortion. It is also used in combination with an estrogen for the treatment of menopausal symptoms..

Allylestrenol is generally well-tolerated. The most common side effects are nausea, vomiting, and diarrhea. Less common side effects include headaches, dizziness, and fatigue..

Allylestrenol should not be used by women who are pregnant or breastfeeding. It should also be used with caution in women with a history of depression, seizure disorders, or liver disease..

Allylestrenol is a synthetic progestogen with a similar structure to the natural hormone progesterone. It is used for the treatment of threatened abortion and habitual abortion, as well as menopausal symptoms. Allylestrenol is generally well-tolerated, with the most common side effects being nausea, vomiting, and diarrhea..

3D structure

Cartesian coordinates

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

2D drawing

 

Allylestrenol ATXHVCQZZJYMCF-XUDSTZEESA-N chemical compound 2D structure molecule svg
Allylestrenol

 

Molecule descriptors

 
IUPAC name(8R,9S,10R,13S,14S,17R)-13-methyl-17-prop-2-enyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
InChI codeInChI=1S/C21H32O/c1-3-12-21(22)14-11-19-18-9-8-15-6-4-5-7-16(15)17(18)10-13-20(19,21)2/h3,6,16-19,22H,1,4-5,7-14H2,2H3/t16-,17+,18+,19-,20-,21-/m0/s1
InChI KeyATXHVCQZZJYMCF-XUDSTZEESA-N
SMILESC=CC[C@]1(O)CC[C@H]2[C@@H]3CCC4=CCCC[C@@H]4[C@H]3CC[C@@]21C

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.

  • (17beta)-17-prop-2-en-1-ylestr-4-en-17-ol
  • (8R,9S,10R,13S,14S,17R)-13-methyl-17-prop-2-enyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
  • 17-Hydroxy-17-alpha-allyl-4-estrene
  • 17-alpha-Allyl-17-beta-hydroxy-4-estrene
  • 17-alpha-Allyl-17-beta-hydroxy-delta(sup 4)-estren
  • 17-alpha-Allyl-3-deoxy-19-nortestosterone
  • 17-alpha-Allyl-4-oestrene-17-beta-ol
  • 17-alpha-Allylestr-4-en-17-beta-ol
  • 17-alpha-Allylhydroxy-19-nor-4-androstene
  • 17-allylestr-4-en-17-beta-ol
  • 17.alpha.-Allyl-17-.beta.-hydroxy-.delta.(sup 4)-estren
  • 17.alpha.-Allyl-17.beta.-hydroxy-4-estrene
  • 17.alpha.-Allyl-3-deoxy-19-nortestosterone
  • 17.alpha.-Allyl-4-destrene-17.beta.-ol
  • 17.alpha.-Allyl-4-estren-17.beta.-ol
  • 17.alpha.-Allyl-4-oestrene-17.beta.-ol
  • 17.alpha.-Allylestr-4-en-17.beta.-ol
  • 17.alpha.-Allylestrenol
  • 17alpha-Allyl-17beta-hydroxy-4-estrene
  • 17alpha-Allyl-19-nor-delta-4-androstene-17beta-ol
  • 17alpha-Allyl-3-deoxy-19-nortestosterone
  • 17alpha-Allyl-4-destrene-17beta-ol
  • 17alpha-Allyl-4-estren-17beta-ol
  • 17alpha-Allyl-4-oestrene-17beta-ol
  • 17alpha-Allylestr-4-en-17beta-ol
  • 17alpha-Allylestrenol
  • 19-Nor-17-alpha-preg-4-en-17-ol, 21-methylene-
  • 19-norpregn-4-ene-20-yn-17beta-ol
  • 21-Methylene-19-nor-17-alpha-preg-4-en-17-ol
  • 3-Deoxy-17-alpha-allyl-19-nortestosterone
  • 3-deketo-17alpha-allyl-19-nortestosterone
  • 432-60-0
  • 432A600
  • Alilestrenol
  • Allilestrenolo
  • Allyl estrenol
  • Allylestrenol
  • Allylestrenol (JAN/INN)
  • Allylestrenolum
  • Allyloestrenol
  • Allyloestrenolum
  • BCP10809
  • BRN 3148038
  • CCRIS 9068
  • CS-0006769
  • D01374
  • DB01431
  • DS-8255
  • DSSTox_CID_2574
  • DSSTox_GSID_22574
  • DSSTox_RID_76637
  • ESTR-4-EN-17-beta-OL, 17-ALLYL-
  • Estr-4-en-17-ol, (17.beta.)-
  • Estr-4-en-17-ol, 17-(2-propenyl)-, (17b)-
  • Estr-4-en-17-ol, 17-(2-propenyl)-, (17beta)-
  • Estr-4-en-17.beta.-ol, 17-allyl-
  • Estr-4-en-17beta-ol, 17-allyl-
  • Estrenol, allyl-
  • Gestanin
  • Gestanol
  • Gestanon
  • Gestanon-r
  • Gestanyn
  • HY-17375
  • I47VB5DZ8O
  • LMST02030125
  • MFCD00198957
  • NCGC00159497-02
  • NSC 37723
  • NSC-37723
  • NSC37723
  • Orageston
  • Organon
  • Perselin
  • Q531965
  • SR-01000883956
  • SR-01000883956-1
  • Turinal
  • WLN: L E5 B666 MUTJ E1 FQ F2U1
  • allylestrenol
  • s5219

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4214767
  • CAS-432-60-0
  • UNII-I47VB5DZ8O
  • AKOS015964938
  • DTXSID9022574
  • CHEMBL3185133
  • CHEBI:31189
  • Tox21_111718
  • EINECS 207-082-9
  • SCHEMBL329623

Physico-Chemical properties

IUPAC name(8R,9S,10R,13S,14S,17R)-13-methyl-17-prop-2-enyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
Molecular formulaC21H32O
Molecular weight300.478
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity94.60
LogP5.3
Topological polar surface area20.2

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.