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    Allylestrenol

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    MARKET PLACE

    PharmaCompass
    $ API Ref.Price (USD/KG) : 1,862Xls

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    2D Structure
    Also known as: 432-60-0, Gestanin, Gestanon, Allyloestrenol, Gestanol, Orageston
    Molecular Formula
    C21H32O
    Molecular Weight
    300.5  g/mol
    InChI Key
    ATXHVCQZZJYMCF-XUDSTZEESA-N
    FDA UNII
    I47VB5DZ8O
    A synthetic steroid with progestational activity.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 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
    2.1.2 InChI
    InChI=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
    2.1.3 InChI Key
    ATXHVCQZZJYMCF-XUDSTZEESA-N
    2.1.4 Canonical SMILES
    CC12CCC3C(C1CCC2(CC=C)O)CCC4=CCCCC34
    2.1.5 Isomeric SMILES
    C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(CC=C)O)CCC4=CCCC[C@H]34
    2.2 Other Identifiers
    2.2.1 UNII
    I47VB5DZ8O
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Allyloestrenol

    2. Gestanin

    3. Gestanon

    4. Turinal

    2.3.2 Depositor-Supplied Synonyms

    1. 432-60-0

    2. Gestanin

    3. Gestanon

    4. Allyloestrenol

    5. Gestanol

    6. Orageston

    7. Turinal

    8. Organon

    9. Gestanyn

    10. Estrenol, Allyl-

    11. 17-allylestr-4-en-17-beta-ol

    12. 17alpha-allyl-4-estren-17beta-ol

    13. 17alpha-allylestr-4-en-17beta-ol

    14. Perselin

    15. I47vb5dz8o

    16. 17.alpha.-allylestr-4-en-17.beta.-ol

    17. (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

    18. Chebi:31189

    19. Estr-4-en-17-ol, 17-(2-propenyl)-, (17b)-

    20. Nsc-37723

    21. 19-norpregn-4-ene-20-yn-17beta-ol

    22. Allyloestrenolum

    23. 17-alpha-allylestr-4-en-17-beta-ol

    24. 17alpha-allylestrenol

    25. Allilestrenolo [dcit]

    26. Gestanon-r

    27. Alilestrenol [inn-spanish]

    28. Allylestrenolum [inn-latin]

    29. Perselin (tn)

    30. 17.alpha.-allylestrenol

    31. 17alpha-allyl-4-destrene-17beta-ol

    32. 17alpha-allyl-4-oestrene-17beta-ol

    33. Allylestrenol (jan/inn)

    34. 17-hydroxy-17-alpha-allyl-4-estrene

    35. 17-alpha-allyl-4-oestrene-17-beta-ol

    36. 17alpha-allyl-17beta-hydroxy-4-estrene

    37. Alilestrenol

    38. Allilestrenolo

    39. Allylestrenolum

    40. 17alpha-allyl-3-deoxy-19-nortestosterone

    41. Allyl Estrenol

    42. 17-alpha-allyl-17-beta-hydroxy-4-estrene

    43. Ccris 9068

    44. 17-alpha-allyl-3-deoxy-19-nortestosterone

    45. 17-alpha-allylhydroxy-19-nor-4-androstene

    46. 3-deoxy-17-alpha-allyl-19-nortestosterone

    47. Ncgc00159497-02

    48. 21-methylene-19-nor-17-alpha-preg-4-en-17-ol

    49. Einecs 207-082-9

    50. Estr-4-en-17beta-ol, 17-allyl-

    51. 17-alpha-allyl-17-beta-hydroxy-delta(sup 4)-estren

    52. 17alpha-allyl-19-nor-delta-4-androstene-17beta-ol

    53. Nsc 37723

    54. Estr-4-en-17-ol, 17-(2-propenyl)-, (17beta)-

    55. Brn 3148038

    56. 17.alpha.-allyl-4-estren-17.beta.-ol

    57. 17.alpha.-allyl-4-destrene-17.beta.-ol

    58. 17.alpha.-allyl-4-oestrene-17.beta.-ol

    59. Estr-4-en-17-beta-ol, 17-allyl-

    60. 17.alpha.-allyl-3-deoxy-19-nortestosterone

    61. Dsstox_cid_2574

    62. 17.alpha.-allyl-17.beta.-hydroxy-4-estrene

    63. Allylestrenol [mi]

    64. Unii-i47vb5dz8o

    65. Allylestrenol [inn]

    66. Allylestrenol [jan]

    67. Dsstox_rid_76637

    68. (17beta)-17-prop-2-en-1-ylestr-4-en-17-ol

    69. Dsstox_gsid_22574

    70. Allylestrenol [mart.]

    71. Schembl329623

    72. 19-nor-17-alpha-preg-4-en-17-ol, 21-methylene-

    73. Allylestrenol [who-dd]

    74. Allylestrenol [inn:ban:jan]

    75. Chembl3185133

    76. Dtxsid9022574

    77. 17.alpha.-allyl-17-.beta.-hydroxy-.delta.(sup 4)-estren

    78. Bcp10809

    79. Nsc37723

    80. Zinc4214767

    81. Tox21_111718

    82. Lmst02030125

    83. Mfcd00198957

    84. S5219

    85. Akos015964938

    86. Db01431

    87. Ds-8255

    88. Estr-4-en-17-ol, (17.beta.)-

    89. Estr-4-en-17.beta.-ol, 17-allyl-

    90. Cas-432-60-0

    91. Hy-17375

    92. 3-deketo-17alpha-allyl-19-nortestosterone

    93. Cs-0006769

    94. Wln: L E5 B666 Mutj E1 Fq F2u1

    95. D01374

    96. 4-06-00-04143 (beilstein Handbook Reference)

    97. 432a600

    98. Q531965

    99. Sr-01000883956

    100. Sr-01000883956-1

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 300.5 g/mol
    Molecular Formula C21H32O
    XLogP35.3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count1
    Rotatable Bond Count2
    Exact Mass300.245315640 g/mol
    Monoisotopic Mass300.245315640 g/mol
    Topological Polar Surface Area20.2 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity492
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Allylestrenol was designed to be used for miscarriage prevention, prevention of premature labour and has been investigated for possible use in men for treatment for benign prostatic hyperplasia.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Allylestrenol is a progestogen structurally related to progesterone that has been given in threatened and recurrent miscarriage, and to prevent premature labour. However, with the exception of proven progesterone deficiency, such use is no longer recommended. In threatened miscarriage in progesterone-deficient women a suggested dose is 5 mg three times daily by mouth for 5 to 7 days.

    5.2 MeSH Pharmacological Classification

    Progestins

    Compounds that interact with PROGESTERONE RECEPTORS in target tissues to bring about the effects similar to those of PROGESTERONE. Primary actions of progestins, including natural and synthetic steroids, are on the UTERUS and the MAMMARY GLAND in preparation for and in maintenance of PREGNANCY. (See all compounds classified as Progestins.)

    5.3 ATC Code

    G - Genito urinary system and sex hormones

    G03 - Sex hormones and modulators of the genital system

    G03D - Progestogens

    G03DC - Estren derivatives

    G03DC01 - Allylestrenol

    5.4 Absorption, Distribution and Excretion

    Route of Elimination

    The glucuronide and sulfate conjugates of pregnanediol and pregnanolone are excreted in the urine and bile. Progesterone metabolites which are excreted in the bile may undergo enterohepatic recycling or may be excreted in the feces. Progesterone metabolites are excreted mainly by the kidneys.

    5.5 Mechanism of Action

    Allylestrenol is similar in structure and function to progesterone. Progesterone shares the pharmacological actions of the progestins. Progesterone binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like Progesterone will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge. In women who have adequate endogenous estrogen, progesterone transforms a proliferative endometrium into a secretory one. Progesterone is essential for the development of decidual tissue and is necessary to increase endometrial receptivity for implantation of an embryo. Once an embryo has been implanted, progesterone acts to maintain the pregnancy. Progesterone also stimulates the growth of mammary alveolar tissue and relaxes uterine smooth muscle. It has little estrogenic and androgenic activity.