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    Also known as: 630-56-8, Delalutin, Primolut depot, Hydroxyprogesterone hexanoate, Hormofort, Proge
    Molecular Formula
    C27H40O4
    Molecular Weight
    428.6  g/mol
    InChI Key
    DOMWKUIIPQCAJU-LJHIYBGHSA-N
    FDA UNII
    276F2O42F5
    Hydroxyprogesterone Caproate
    Hydroxyprogesterone derivative that acts as a PROGESTIN and is used to reduce the risk of recurrent MISCARRIAGE and of PREMATURE BIRTH. It is also used in combination with ESTROGEN in the management of MENSTRUATION DISORDERS.
    1 2D Structure

    Hydroxyprogesterone Caproate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(8R,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] hexanoate
    2.1.2 InChI
    InChI=1S/C27H40O4/c1-5-6-7-8-24(30)31-27(18(2)28)16-13-23-21-10-9-19-17-20(29)11-14-25(19,3)22(21)12-15-26(23,27)4/h17,21-23H,5-16H2,1-4H3/t21-,22+,23+,25+,26+,27+/m1/s1
    2.1.3 InChI Key
    DOMWKUIIPQCAJU-LJHIYBGHSA-N
    2.1.4 Canonical SMILES
    CCCCCC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)C(=O)C
    2.1.5 Isomeric SMILES
    CCCCCC(=O)O[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)C(=O)C
    2.2 Other Identifiers
    2.2.1 UNII
    276F2O42F5
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 17 Alpha Hydroxy Progesterone Caproate

    2. 17 Alpha Hydroxyprogesterone Caproate

    3. 17 Alpha Oxyprogesterone Capronate

    4. 17 Alpha-hydroxyprogesterone Caproate

    5. 17 Alpha-oxyprogesterone Capronate

    6. 17 Hydroxyprogesterone Capronate

    7. 17-alpha-hydroxy-progesterone Caproate

    8. 17-hydroxyprogesterone Capronate

    9. Caproate, 17-alpha-hydroxy-progesterone

    10. Delalutin

    11. Hydroxyprogesterone Hexanoate

    12. Makena

    13. Neolutin

    14. Oxyprogesterone Caproate

    15. Prolutin Depot

    16. Proluton Depot

    2.3.2 Depositor-Supplied Synonyms

    1. 630-56-8

    2. Delalutin

    3. Primolut Depot

    4. Hydroxyprogesterone Hexanoate

    5. Hormofort

    6. Proge

    7. Syngynon

    8. Depo-proluton

    9. Proluton Depot

    10. Hylutin

    11. Teralutil

    12. Makena

    13. Estralutin

    14. Hyproval

    15. Kaprogest

    16. Neolutin

    17. Lutate

    18. Relutin

    19. Progesterone Caproate

    20. Neolutin Forte

    21. 17-caproxyprogesterone

    22. Idrogestene

    23. Duraluton

    24. Hyroxon

    25. Luteocrin

    26. Lutopron

    27. Luteocrin Depot

    28. Hyproval-pa

    29. 17alpha-hydroxyprogesterone Caproate

    30. Nsc-17592

    31. 17-alpha-hydroxy-progesterone Caproate

    32. Corlutin L.a.

    33. Gesterol La 250

    34. 17-ohpc

    35. Procyte Depo

    36. Progesterone Retard Pharlon

    37. 17alpha-caproyloxypregn-4-ene-3,20-dione

    38. 17-alpha-hydroxyprogesterone Caproate

    39. 17-((1-oxohexyl)oxy)pregn-4-ene-3,20-dione

    40. Mls000028438

    41. 17a-hydroxyprogesterone Caproate

    42. Oxiprogesterone Caproate

    43. 17 Alpha-hydroxyprogesterone Caproate

    44. 17alpha-hydroxyprogesterone Hexanoate

    45. 17.alpha.-caproyloxy-p4

    46. Progesterone, 17-hydroxy-, Hexanoate

    47. Smr000058336

    48. Mls001148643

    49. Chebi:5812

    50. 17-hydroxypregn-4-ene-3,20-dione Hexanoate

    51. 17a-hydroxyprogesterone Hexanoate

    52. Pregn-4-ene-3,20-dione, 17-hydroxy-, Hexanoate

    53. Pregn-4-ene-3,20-dione, 17-((1-oxohexyl)oxy)-

    54. 17.alpha.-hydroxyprogesterone Caproate

    55. 276f2o42f5

    56. (8r,9s,10r,13s,14s,17r)-17-acetyl-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl Hexanoate

    57. 17.alpha.-hydroxyprogesterone Hexanoate

    58. Ncgc00021268-03

    59. 17.alpha.-hydroxyprogesterone N-caproate

    60. 3,20-dioxopregn-4-en-17.alpha.-yl Caproate

    61. Dsstox_cid_23915

    62. Dsstox_rid_80089

    63. Dsstox_gsid_43915

    64. [(8r,9s,10r,13s,14s,17r)-17-acetyl-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] Hexanoate

    65. 17.alpha.-hydroxypregn-4-ene-3,20-dione Hexanoate

    66. Pregn-4-ene-3,20-dione, 17-[(1-oxohexyl)oxy]-

    67. Gestiva

    68. Hexanoic Acid, Ester With 17-hydroxypregn-4-ene-3,20-dione

    69. Delalutin (tn)

    70. Cas-630-56-8

    71. 17

    72. A-hydroxyprogesterone Caproate

    73. Idroprogesterone Caproato

    74. Hydroxyprogesteroni Caproas

    75. Lewntogest

    76. Caproate D'hydroxyprogesterone

    77. Caproato De Hidroxiprogesterona

    78. Unii-276f2o42f5

    79. Idroprogesterone Caproato [dcit]

    80. 17

    81. A-hydroxyprogesterone Hexanoate

    82. Hyproval P.a.

    83. Einecs 211-138-8

    84. Hylutin (tn)

    85. Makena (tn)

    86. 17-alpha-hydroxyprogesterone Hexanoate

    87. 17alpha-hydroxyprogesterone N-caproate

    88. Hydroxyprogesteroni Caproas [inn-latin]

    89. Progesterone, Hexanoate

    90. 17-alpha-hydroxy Progesterone N-caproate

    91. 17-caproyloxyprogesterone

    92. 3,20-dioxo-4-pregnen-17alpha-yl Hexanoat

    93. 3,20-dioxopregn-4-en-17alpha-yl Caproate

    94. Caproate D'hydroxyprogesterone [inn-french]

    95. Hydroxyprogesterone Caproate [usp:inn:jan]

    96. Opera_id_1479

    97. 17alpha-hydroxyprogesterone-17alpha Caproate

    98. 17-alpha-hexanoyloxypregn-4-ene-3,20-dione

    99. Caproato De Hidroxiprogesterona [inn-spanish]

    100. Deluteval 2x (salt/mix)

    101. Schembl5330

    102. Mls002207289

    103. 17alpha-caproyloxyprogesterone

    104. 17-hydroxyprogesterone-caproate

    105. Caproic Acid Hydroxyprogesterone

    106. Cid_169870

    107. Chembl1200848

    108. Dtxsid6043915

    109. Bdbm70293

    110. 17alpha-hydroxyprogesteron-caproat

    111. Hms2230l08

    112. Bcp16081

    113. Hy-b0742

    114. Nsc17592

    115. Zinc4083606

    116. Tox21_113502

    117. Tox21_302333

    118. 17-alpha Hydroxyprogesterone Caproate

    119. Mfcd00072134

    120. S4674

    121. Akos005267159

    122. Tox21_113502_1

    123. 17 Alpha -hydroxyprogesterone Caproate

    124. Ccg-268987

    125. Db06789

    126. Gs-3233

    127. Ncgc00021268-04

    128. Ncgc00255784-01

    129. (1s,11s,15s,2r,10r,14r)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0<2,7>.0 <11,15>]heptadec-6-en-14-yl Hexanoate

    130. Hydroxyprogesterone Caproate [inn]

    131. Hydroxyprogesterone Caproate [jan]

    132. Pregn-4-ene-3, 17-hydroxy-, Hexanoate

    133. 17alpha-hexanoyloxy-4pregnene-3,20-dione

    134. Hydroxyprogesterone Caproate (jan/usp/inn)

    135. Hydroxyprogesterone Caproate [mart.]

    136. Hydroxyprogesterone Caproate [vandf]

    137. Pregn-4-ene-3, 17-[(1-oxohexyl)oxy]-

    138. 17-hydroxypregn-4-ene-3,20-dione Caproate

    139. H0994

    140. Hydroxyprogesterone Caproate [usp-rs]

    141. Hydroxyprogesterone Caproate [who-dd]

    142. 17alpha-hydroxyprogesterone Hexanoate, >=98%

    143. C08148

    144. D00949

    145. H10189

    146. 17-.alpha.-hexanoyloxypregn-4-ene-3,20-dione

    147. 17alpha-hydroxypregn-4-ene-3,20-diene Caproate

    148. 17alpha-hydroxyprogesterone Caproate [progestins]

    149. 3,20-dioxopregn-4-en-17.alpha.-yl Hexanoate #

    150. 630h568

    151. A834188

    152. Hydroxyprogesterone Caproate [orange Book]

    153. Sr-01000003075

    154. 17.alpha.-hydroxypregn-4-ene-3,20-dione Caproate

    155. 17.alpha.-hydroxyprogesterone Caproate [mi]

    156. Hydroxyprogesterone Caproate [usp Monograph]

    157. Q-201222

    158. Q3792032

    159. Sr-01000003075-3

    160. Hydroxyprogesterone Caproate, United States Pharmacopeia (usp) Reference Standard

    161. (1s,2r,10r,11s,14r,15s)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl Hexanoate

    162. [(10r,13s,17r)-17-acetyl-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] Hexanoate

    163. [(8r,9s,10r,13s,14s,17r)-17-acetyl-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] Hexanoate;17-caproxyprogesterone

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 428.6 g/mol
    Molecular Formula C27H40O4
    XLogP35.7
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count7
    Exact Mass428.29265975 g/mol
    Monoisotopic Mass428.29265975 g/mol
    Topological Polar Surface Area60.4 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity797
    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 Information
    1 of 2  
    Drug NameMakena
    PubMed HealthHydroxyprogesterone
    Drug ClassesEndocrine-Metabolic Agent, Hydroxyprogesterone
    Drug LabelThe active pharmaceutical ingredient in Makena is hydroxyprogesterone caproate.The chemical name for hydroxyprogesterone caproate is pregn-4-ene-3,20-dione, 17[(1-oxohexyl)oxy]. It has an empirical formula of C27H40O4 and a molecular weight of 428.60...
    Active IngredientHydroxyprogesterone caproate
    Dosage FormSolution
    RouteIntramuscular
    Strength1250mg/5ml (250mg/ml)
    Market StatusPrescription
    CompanyLumara Health

    2 of 2  
    Drug NameMakena
    PubMed HealthHydroxyprogesterone
    Drug ClassesEndocrine-Metabolic Agent, Hydroxyprogesterone
    Drug LabelThe active pharmaceutical ingredient in Makena is hydroxyprogesterone caproate.The chemical name for hydroxyprogesterone caproate is pregn-4-ene-3,20-dione, 17[(1-oxohexyl)oxy]. It has an empirical formula of C27H40O4 and a molecular weight of 428.60...
    Active IngredientHydroxyprogesterone caproate
    Dosage FormSolution
    RouteIntramuscular
    Strength1250mg/5ml (250mg/ml)
    Market StatusPrescription
    CompanyLumara Health

    4.2 Drug Indication

    Hydroxyprogesterone caproate is indicated for the prevention of spontaneous preterm births in singleton pregnancies in women who have previously had a spontaneous preterm birth. (1)

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    No specific pharmacodynamic studies have been performed to assess hydroxyprogesterone caproate injections. (4) However, the mechanism of action is likely related to increased interaction between progesterone and progesterone receptors. (5)

    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.)

    Estrogen Antagonists

    Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds. (See all compounds classified as Estrogen Antagonists.)

    5.3 FDA Pharmacological Classification
    5.3.1 Pharmacological Classes
    Progestin [EPC]; Progesterone Congeners [CS]
    5.4 Absorption, Distribution and Excretion

    Absorption

    Absorption of 17-hydroxyprogesteron caproate is slow, occurring over a long period of time. (3)

    Route of Elimination

    Following intramuscular injection, approximately 50% of hydroxyprogesterone caproate metabolites are eliminated in the feces, while approximately 30% of metabolites are eliminated in the urine. (3)

    Volume of Distribution

    Hydroxyprogesterone caproate has a high volume of distribution. (3)

    Clearance

    Clearance is highly variable from patient to patient. (3)

    5.5 Metabolism/Metabolites

    The main enzymes involved in metabolism of hydroxyprogesterone caproate are cytochrome P450 (CYP) 3A4 and to a lesser extent CYP3A5. (3)

    5.6 Biological Half-Life

    Half-life = 16 days (6 days). (3)

    5.7 Mechanism of Action

    The mechanism by which progesterone prevents preterm birth is not well understood, but many pathways are likely involved. (1) Progesterone plays a vital role in regulation of the female reproductive system and is important for successful implantation of the embryo and maintenance of pregnancy. It acts by binding to progesterone receptors in the uterus, ovaries, breasts and in the central nervous system. These receptors exist in 2 isoforms, PR-A and PR-B. Progesterone binding to these receptors ultimately leads to regulation of gene transcription. (2) This results in an anti-inflammatory effect which blunts the proinflammatory state that occurs with initiation of labor, and maintains uterine queiscence by stabilizing progesterone acting on the myometrium. (2)

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    06-Feb-2021
    28-Aug-2024
    KGS
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    Average Price (USD/KGS)

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    (USD/KGS)    		 Number of Transactions

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