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17-alpha-Hydroxyprogesterone Hexanoate

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Symbiotec Hydroxyprogesterone Caproate

Synopsis

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Chemistry

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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 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 Formula	C₂₇H₄₀O₄
Molecular Weight	428.6 g/mol
XLogP3	5.7
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	7
Exact Mass	428.29265975 g/mol
Monoisotopic Mass	428.29265975 g/mol
Topological Polar Surface Area	60.4 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	797
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Makena
PubMed Health	Hydroxyprogesterone
Drug Classes	Endocrine-Metabolic Agent, Hydroxyprogesterone
Drug Label	The 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 Ingredient	Hydroxyprogesterone caproate
Dosage Form	Solution
Route	Intramuscular
Strength	1250mg/5ml (250mg/ml)
Market Status	Prescription
Company	Lumara Health

2 of 2
Drug Name	Makena
PubMed Health	Hydroxyprogesterone
Drug Classes	Endocrine-Metabolic Agent, Hydroxyprogesterone
Drug Label	The 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 Ingredient	Hydroxyprogesterone caproate
Dosage Form	Solution
Route	Intramuscular
Strength	1250mg/5ml (250mg/ml)
Market Status	Prescription
Company	Lumara 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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