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    CAS-68-96-2

    BUILDING BLOCK

    PharmaCompass
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    2D Structure
    Also known as: 17alpha-hydroxyprogesterone, 68-96-2, 17-hydroxyprogesterone, 17a-hydroxyprogesterone, Prodix, Prodox
    Molecular Formula
    C21H30O3
    Molecular Weight
    330.5  g/mol
    InChI Key
    DBPWSSGDRRHUNT-CEGNMAFCSA-N
    FDA UNII
    21807M87J2
    A metabolite of PROGESTERONE with a hydroxyl group at the 17-alpha position. It serves as an intermediate in the biosynthesis of HYDROCORTISONE and GONADAL STEROID HORMONES.
    Hydroxyprogesterone is a Progestin.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
    2.1.2 InChI
    InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1
    2.1.3 InChI Key
    DBPWSSGDRRHUNT-CEGNMAFCSA-N
    2.1.4 Canonical SMILES
    CC(=O)C1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O
    2.1.5 Isomeric SMILES
    CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O
    2.2 Other Identifiers
    2.2.1 UNII
    21807M87J2
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 17 Alpha Hydroxyprogesterone

    2. 17 Alpha-hydroxyprogesterone

    3. 17 Hydroxyprogesterone

    4. 17-alpha-hydroxyprogesterone

    5. 17-hydroxyprogesterone

    6. 17-hydroxyprogesterone, (17 Alpha)-isomer

    7. 17-hydroxyprogesterone, (9 Beta, 10 Alpha)-isomer

    2.3.2 Depositor-Supplied Synonyms

    1. 17alpha-hydroxyprogesterone

    2. 68-96-2

    3. 17-hydroxyprogesterone

    4. 17a-hydroxyprogesterone

    5. Prodix

    6. Prodox

    7. Gestageno Gador

    8. 17-alpha-hydroxyprogesterone

    9. 17-hydroxypregn-4-ene-3,20-dione

    10. Pregn-4-ene-3,20-dione, 17-hydroxy-

    11. Setaderm

    12. Oxiprogesteronum

    13. 17alpha-hydroxy-progesterone

    14. 17alpha-hydroxy-4-pregnene-3,20-dione

    15. Hidroxiprogesterona

    16. Hydroxyprogesteronum

    17. Pregn-4-ene-3,20-dione-17-ol

    18. Gestageno

    19. Idrossiprogesterone [dcit]

    20. Delta(4)-pregnene-17alpha-ol-3,20-dione

    21. 17

    22. A-hydroxyprogesterone

    23. Hydroxyprogesteronum [inn-latin]

    24. Hidroxiprogesterona [inn-spanish]

    25. 17-oh Progesterone

    26. 17-hydroxypregn-4-en-3,20-dione

    27. 17.alpha.-hydroxyprogesterone

    28. Hsdb 3343

    29. 604-09-1

    30. Chebi:17252

    31. Nsc-15468

    32. Mls000028453

    33. 17-ohp

    34. (8r,9s,10r,13s,14s,17r)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one

    35. 4-pregnen-17a-ol-3,20-dione

    36. U 3096

    37. Pregn-4-ene-3,20-dione, 17-hydroxy-, (17a)-

    38. 4-pregnen-17alpha-ol-3,20-dione

    39. Delta4-pregnen-17alpha-ol-3,20-dione

    40. Ncgc00093949-03

    41. Alpha-17hydroxypregn-4-ene-3,20-dione

    42. Smr000058349

    43. 21807m87j2

    44. Hydroxyprogesterone (inn)

    45. (9beta)-17-hydroxypregn-4-ene-3,20-dione

    46. U-3096

    47. Dsstox_cid_20747

    48. Dsstox_rid_79586

    49. Dsstox_gsid_40747

    50. Hydroxyprogesterone [inn]

    51. Alpha Hydroxy Progesterone

    52. Idrossiprogesterone

    53. Cas-68-96-2

    54. 17ohp

    55. Hydroxyprogesterone [inn:ban]

    56. Einecs 200-699-4

    57. Nsc 15468

    58. 17alpha Hydroxyprogesterone

    59. Brn 2062088

    60. Mfcd00003659

    61. Unii-21807m87j2

    62. 3qz

    63. 17a-hydroxypregn-4-ene-3,20-dione

    64. 17-hydroxy-progesterone

    65. 17-a-hydroxyprogesterone

    66. Opera_id_1812

    67. 17?-hydroxy Progesterone

    68. Bmse000472

    69. Bmse000598

    70. Epitope Id:152220

    71. Schembl8068

    72. Chembl1062

    73. Bidd:pxr0103

    74. Lopac0_000565

    75. 17.alpha.-hydoxyprogesterone

    76. 4-08-00-02189 (beilstein Handbook Reference)

    77. Mls001076300

    78. Mls002695950

    79. Gtpl5104

    80. Progesterone, 17alpha-hydroxy-

    81. Dtxsid6040747

    82. Pregn-4-ene-3,20-dione, 17-hydroxy-, (17.alpha.)-

    83. Pregn-4-ene-3, 17-hydroxy-

    84. Dtxsid00859075

    85. Hydroxyprogesterone [hsdb]

    86. Hms2090m08

    87. Hms2234j04

    88. Hms3261b12

    89. Hydroxyprogesterone [vandf]

    90. D4-pregnen-17a-ol-3,20-dione

    91. Hy-b0891

    92. Nsc15468

    93. Pregn-4-en-17a-ol-3,20-dione

    94. Zinc5434436

    95. Hydroxyprogesterone [who-dd]

    96. Tox21_111233

    97. Tox21_301530

    98. Tox21_500565

    99. Bdbm50423511

    100. Lmst02030161

    101. S4507

    102. 17alpha-hydroxyprogesterone, >=95%

    103. Akos015955623

    104. Tox21_111233_1

    105. Ccg-204655

    106. Cs-4354

    107. Db14570

    108. Fd12004

    109. Ks-5312

    110. Lp00565

    111. Sdccgsbi-0050548.p002

    112. 4-pregnen-17.alpha.-ol-3,20-dione

    113. Ncgc00093949-04

    114. Ncgc00093949-05

    115. Ncgc00093949-08

    116. Ncgc00255425-01

    117. Ncgc00261250-01

    118. 17alpha-hydroxy-pregn-4-ene-3,20-dione

    119. 17.alpha.-hydroxyprogesterone [mi]

    120. 17.alpha.-hydroxypregna-4-ene-3,20-dione

    121. Eu-0100565

    122. H1250

    123. C01176

    124. D08052

    125. H 5752

    126. 17-hydroxypregn-4-ene-3,20-dione, (+/-)-

    127. Ab00490003-08

    128. Q175901

    129. 17.alpha.-hydroxypregn-4-ene-3,20-dione

    130. W-104646

    131. 17-hydroxypregn-4-ene-3,20-dione-, (17.alpha.)-

    132. 7a45bef6-add0-4b3e-a014-2de930d3b67b

    133. 17-alpha-hydroxyprogesterone 100 Microg/ml In Methanol

    134. 17alpha-hydroxyprogesterone, Vetranal(tm), Analytical Standard

    135. (1s,2r,10r,11s,14r,15s)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

    136. (8r,10r,13s,17r)-17-acetyl-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

    137. (8r,9s,10r,13s,14s,17r)-17-acetyl-17-hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3(2h)-one

    138. 110850-01-6

    139. 17alpha-hydroxyprogesterone Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 330.5 g/mol
    Molecular Formula C21H30O3
    XLogP33.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count1
    Exact Mass330.21949481 g/mol
    Monoisotopic Mass330.21949481 g/mol
    Topological Polar Surface Area54.4 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity635
    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 Therapeutic Uses

    THERAPEUTIC USES. ...CONTRACEPTION...FUNCTIONAL UTERINE BLEEDING... DYSMENORRHEA...PREMENSTRUAL TENSION...ENDOMETRIOSIS...THREATENED & HABITUAL ABORTION...EVALUATION OF OVARIAN FUNCTION & DIAGNOSIS OF PREGNANCY...SUPPRESSION OF POST-PARTUM LACTATION...ENDOMETRIAL CARCINOMA. /PROGESTINS/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1439

    CHEMOTHERAPEUTIC AGENTS USEFUL IN NEOPLASTIC DISEASE: HYDROXYPROGESTERONE CAPROATE (DELALUTIN) FOR ENDOMETRIUM, RENAL CELL, BREAST, PROSTATE. /CAPROATE/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1251

    ...IN METASTATIC & RECURRENT ENDOMETRIAL CARCINOMA. THEY PRODUCE REMISSIONS FOR PROLONGED PERIODS IN ABOUT 25% OF PT WHEN METASTASES ARE CONFINED TO PULMONARY AREA. LARGER DOSES...WHEN DISEASE RECURS IN OSSEOUS, INTRA-ABDOMINAL, OR PELVIC SITES. ...USED PARENTERALLY IN RENAL CARCINOMA. /PROGESTAGEUS/

    American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 1142

    WHEN USED TO REGULATE IRREGULAR ESTRUS CYCLE, IT IS USUALLY COMBINED WITH ESTROGEN. /CAPROATE/

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 922

    For more Therapeutic Uses (Complete) data for 17ALPHA-HYDROXYPROGESTERONE (15 total), please visit the HSDB record page.

    4.2 Drug Warning

    VET: AVOID BREEDING TREATED ANIMALS UNTIL SECOND POST-TREATMENT ESTRUS CYCLE. SEVERE PYOMETRA-LIKE SYNDROMES HAVE OCCURRED IN TREATED ANIMALS DEPRIVED OF NORMAL ESTRUS STIMULATING EFFECTS ON UTERINE ENDOMETRIUM...

    Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 269

    WHETHER TAKING ORAL CONTRACEPTIVES OF PROGESTIN-ESTROGEN TYPE PRODUCED HIGHER INCIDENCE OF OCULAR & OPHTHALMO-NEUROLOGIC DISEASES THAN WOULD OCCUR SPONTANEOUSLY IN UNMEDICATED WOMEN OR IN PREGNANT WOMEN WAS NOT ANSWERED CONCLUSIVELY... /PROGESTINS/

    Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 307

    CONTRAINDICATIONS TO THEIR USE ARE THROMBOEMBOLIC DISORDERS OR PAST HISTORY OF THESE CONDITIONS, MARKEDLY IMPAIRED HEPATIC FUNCTION, KNOWN OR SUSPECTED CARCINOMA OF BREAST OR OTHER ESTROGEN-DEPENDENT NEOPLASIA, & UNDIAGNOSED GENITAL BLEEDING. /ORAL CONTRACEPTIVES/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1447

    5 Pharmacology and Biochemistry
    5.1 FDA Pharmacological Classification
    5.1.1 Active Moiety
    HYDROXYPROGESTERONE
    5.1.2 FDA UNII
    21807M87J2
    5.1.3 Pharmacological Classes
    Established Pharmacologic Class [EPC] - Progestin
    5.2 ATC Code

    G - Genito urinary system and sex hormones

    G03 - Sex hormones and modulators of the genital system

    G03D - Progestogens

    G03DA - Pregnen (4) derivatives

    G03DA03 - Hydroxyprogesterone

    5.3 Absorption, Distribution and Excretion

    ...DURATION OF ACTION IS LONGER /THAN PROGESTERONE/, BUT ITS ONSET OF ACTION IS SLOWER. SINGLE INJECTION OF SOLN OF HYDROXYPROGESTERONE CAPROATE IN OIL WILL EXERT PROGESTATIONAL EFFECTS FOR 1-2 WK. /CAPROATE/

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 922

    ABOUT 50-60% OF ADMIN RADIOACTIVE PROGESTERONE APPEARS IN URINE & ABOUT 10% IN FECES. ... WHEN PROGESTERONE IS GIVEN FOR PROLONGED PERIOD, DURING LUTEAL PHASE OF CYCLE, OR DURING PREGNANCY, LARGER PROPORTION (25-30%) APPEARS IN URINE AS PREGUANEDIOL. /PROGESTERONE/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1439

    RATE OF TURNOVER OF ENDOGENOUS PROGESTERONE IS UNUSUALLY RAPID, T/2 IN BLOOD BEING FEW MIN, & DOUBTLESS EXOGENOUS MATERIAL IS HANDLED IN SAME WAY. SMALL AMT...IS STORED IN BODY FAT... PRESUMABLY, ABSORPTION FROM INTESTINAL TRACT IS PROMPT, BUT COMPD IS RAPIDLY TRANSFORMED DURING PASSAGE THROUGH LIVER... /PROGESTERONE/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1439

    5.4 Metabolism/Metabolites

    17alpha-hydroxy-progesterone has known human metabolites that include 17Beta-21-dihydroxyprogesterone.

    17alpha-hydroxy-progesterone is a known human metabolite of progesterone.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.5 Mechanism of Action

    ADMIN OF ESTROGEN & PROGESTIN, AS CONTAINED IN COMBINATION OR SEQUENTIAL PREPN, COULD INTERFERE WITH FERTILITY IN ANY ONE OF SEVERAL WAYS. HOWEVER, IT IS CLEAR THAT, AS CURRENTLY USED, MIXTURE INHIBITS OVULATION. ...CONTINUED ACTION OF PROGESTERONE SERVES TO INHIBIT RELEASE OF LH. /PROGESTINS/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1443

    IT ACTS AS ANTIGONADOTROPHIC AGENT ON ANTERIOR PITUITARY INHIBITING FSH RELEASE &, THUS, FOLLICULAR GROWTH, ESTROGEN PRODUCTION, & ESTRUS. IT ALSO INHIBITS LH RELEASE, THUS PREVENTING OVULATION, CORPORA LUTEA FORMATION, & FURTHER PROGESTERONE SECRETION. BY INHIBITING LH...HOLDS PROGESTERONE LEVELS IN CHECK.

    Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 269