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Chemistry

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Also known as: Prostaglandin e2, Pge2, 363-24-6, Prostin e2, Prepidil, Minprostin e2
Molecular Formula
C20H32O5
Molecular Weight
352.5  g/mol
InChI Key
XEYBRNLFEZDVAW-ARSRFYASSA-N
FDA UNII
K7Q1JQR04M

Dinoprostone
The most common and most biologically active of the mammalian prostaglandins. It exhibits most biological activities characteristic of prostaglandins and has been used extensively as an oxytocic agent. The compound also displays a protective effect on the intestinal mucosa.
Dinoprostone is a Prostaglandin Analog.
1 2D Structure

Dinoprostone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid
2.1.2 InChI
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1
2.1.3 InChI Key
XEYBRNLFEZDVAW-ARSRFYASSA-N
2.1.4 Canonical SMILES
CCCCCC(C=CC1C(CC(=O)C1CC=CCCCC(=O)O)O)O
2.1.5 Isomeric SMILES
CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O)O
2.2 Other Identifiers
2.2.1 UNII
K7Q1JQR04M
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Alpha, Pge2

2. Alpha, Prostaglandin E2

3. E2 Alpha, Prostaglandin

4. E2, Prostaglandin

5. E2alpha, Prostaglandin

6. Gel, Prepidil

7. Pge2

8. Pge2 Alpha

9. Pge2alpha

10. Prepidil Gel

11. Prostaglandin E2

12. Prostaglandin E2 Alpha

13. Prostaglandin E2alpha

14. Prostenon

2.3.2 Depositor-Supplied Synonyms

1. Prostaglandin E2

2. Pge2

3. 363-24-6

4. Prostin E2

5. Prepidil

6. Minprostin E2

7. Cervidil

8. Propess

9. Minprositin E2

10. Dinoproston

11. Prostin

12. (15s)-prostaglandin E2

13. Prostarmon E

14. Dinoprostonum

15. L-prostaglandin E2

16. Dinoprostona

17. Glandin

18. Enzaprost E

19. L-pge2

20. (5z,11alpha,13e,15s)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic Acid

21. U-12062

22. (e,z)-(1r,2r,3r)-7-(3-hydroxy-2-((3s)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic Acid

23. (-)-prostaglandin E2

24. Prostaglandin E

25. Nsc 165560

26. [3h]pge2

27. U 12062

28. [3h]prostaglandin E2

29. (z)-7-((1r,2r,3r)-3-hydroxy-2-((s,e)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)hept-5-enoic Acid

30. (z)-7-[(1r,2r,3r)-3-hydroxy-2-[(e,3s)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic Acid

31. Chembl548

32. Nsc 196514

33. Nsc-165560

34. Nsc-196514

35. K7q1jqr04m

36. 7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoic Acid

37. L-7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoic Acid

38. (5z,13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoate

39. Chebi:15551

40. (5z,13e)-(15s)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate

41. U-12,062

42. 5-heptenoic Acid, 7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-

43. 5-heptenoic Acid, 7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-, L-

44. Pge2alpha

45. Prosta-5,13-dien-1-oic Acid, 11,15-dihydroxy-9-oxo-, (5z,11alpha,13e,15s)-

46. Prostaglandin E(2)

47. (z)-7-[(1r,2r,3r)-3-hydroxy-2-[(e,3s)-3-hydroxyoct-1-enyl]-5-oxo-cyclopentyl]hept-5-enoic Acid

48. Ncgc00092361-05

49. Prostaglandin E2alpha

50. Prostaglandin E2.alpha.

51. (5z,13e,15s)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic Acid

52. Dsstox_cid_2947

53. Dsstox_rid_76801

54. Dsstox_gsid_22947

55. Dinoprostonum [inn-latin]

56. 9-oxo-11r,15s-dihydroxy-5z,13e-prostadienoic Acid

57. Dinoprostona [inn-spanish]

58. Cerviprime

59. Prostenone

60. 7-[3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-5-heptenoic Acid

61. Prostarmon E2

62. Prosta-5,13-dien-1-oic Acid, 11,15-dihydroxy-9-oxo-, (5z,11.alpha.,13e,15s)-

63. Cervidil (tn)

64. Prepidil (tn)

65. Cas-363-24-6

66. Dinoprostone Prostaglandin E2

67. U,062

68. Prostin E2 (tn)

69. Pge2-[3,3,4,4-d4]

70. Sr-05000001459

71. Einecs 206-656-6

72. Unii-k7q1jqr04m

73. Dinoprostone (jan/usp/inn)

74. (5z,13e,15s)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic Acid

75. Bml1-f07

76. Prosta-5, (5z,11.alpha.,13e,15s)-11,15-dihydroxy-9-oxo-

77. Prosta-5, 11,15-dihydroxy-9-oxo-, (5z,11.alpha.,13e,15s)-

78. Prosta-5, 11,5-dihydroxy-9-oxo-, (5z,11.alpha.,13e,15s)-

79. [3h]dinoprostone

80. 5-heptenoic Acid, 7-[3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-

81. Prosta-glandin E2

82. Ncgc00092361-06

83. (e,2r,3r)-7-[3-hydroxy-2-[(3s)-(3-hydroxy-1-octenyl)]-5-oxocyclopentyl]-5-heptenoic Acid

84. P2e

85. Prestwick_793

86. (5z,11-alpha,13e,15s)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic Acid

87. Mfcd00077861

88. [3h]prostin E2

89. Bms-279654 & Pge2

90. Dinoprostone Beta-cyclodextrin Clathrate

91. Dinoprostone [usan:usp:inn:ban:jan]

92. (5z,11alpha,13e,15s)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic

93. Dinoprostone [inn]

94. Dinoprostone [jan]

95. Dinoprostone [usan]

96. (+/-)-prostaglandin E2

97. Prostaglandin E2 (pge2)

98. Dinoprostone [vandf]

99. Schembl25533

100. Bspbio_001490

101. Dinoprostone [mart.]

102. Dinoprostone [usp-rs]

103. Dinoprostone [who-dd]

104. Prostaglandin E2 [mi]

105. Gtpl1883

106. Gtpl1916

107. Dtxsid4022947

108. [3h]-pge2

109. Bdbm35847

110. Dtxsid00859353

111. Dinoprostone [orange Book]

112. Hms1361k12

113. Hms1791k12

114. Hms1989k12

115. Hms2089d17

116. Hms3268j12

117. Hms3402k12

118. Hms3413c20

119. Hms3648f07

120. Hms3677c20

121. Dinoprostone [ep Monograph]

122. Dinoprostone [usp Impurity]

123. (z)-7-((1r,2r,3r)-3-hydroxy-2-((s,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic Acid

124. Amy30102

125. Ex-a1773

126. Zinc3830713

127. Dinoprostone [usp Monograph]

128. Tox21_111196

129. Lmfa03010003

130. Nsc165560

131. Nsc196514

132. S3003

133. (5z,11.alpha.,13e,15s)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic Acid

134. Akos015920228

135. Tox21_111196_1

136. Ac-6098

137. Ccg-208092

138. Ccg-208256

139. Cs-6932

140. Db00917

141. Idi1_033960

142. Prosta-5,13-dien-1-oic Acid, (5z,11-alpha,13e,15s)-11,15-dihydroxy-9-oxo-

143. Smp2_000056

144. Ncgc00092361-01

145. Ncgc00092361-02

146. Ncgc00092361-03

147. Ncgc00092361-04

148. As-71847

149. Dinoprostone 100 Microg/ml In Acetonitrile

150. Hy-101952

151. Alprostadil Impurity G [ep Impurity]

152. B7005

153. P1884

154. C00584

155. D00079

156. Prostaglandin E2, >=93% (hplc), Synthetic

157. 363p246

158. A823207

159. Q416554

160. Sr-01000946417

161. J-502620

162. Sr-01000946417-1

163. Sr-05000001459-1

164. Sr-05000001459-3

165. Sr-05000001459-4

166. Brd-k26521938-001-04-9

167. 05d31bd5-818b-4a92-8cfc-bec19926a5b3

168. 2-amino-1-benzo[1,3]dioxol-5-yl-ethanonehydrochloride

169. Dinoprostone, European Pharmacopoeia (ep) Reference Standard

170. (5z,13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoic Acid

171. (5z,13e,15s)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoate

172. Dinoprostone, United States Pharmacopeia (usp) Reference Standard

173. (5z,11?,13e,15s)-11,15-dihydroxy-9-oxo-prosta-5,13-dien-1oic Acid

174. (5z,11i+/-,13e,15s)-11,15-dihydroxy-9-oxoprosta-5,13-dienoic Acid

175. (5z,13e)-(15s)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoic Acid

176. (5z,13e,15s)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoic Acid

177. 5z,11alpha,13e,15s)-11,15-dihydroxy-9-oxo-rosta-5,13-dien-1-oic Acid

178. Prostaglandin E2, Synthetic, Powder, Bioreagent, Suitable For Cell Culture

179. (5z,11alpha,12alpha,13e,15s)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic Acid

180. (5z,11alpha,13e,15s)-11,15-dihydroxy-9-o Xo-prosta-5,13-dien-1oic Acid

181. Prostaglandin E2, Gamma-irradiated, Powder, Bioxtra, Suitable For Cell Culture

182. (5z)-7-[(1r,2r,3r)-3-hydroxy-2-[(1e,3s)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic Acid

183. 22230-04-2

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 352.5 g/mol
Molecular Formula C20H32O5
XLogP32.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count12
Exact Mass352.22497412 g/mol
Monoisotopic Mass352.22497412 g/mol
Topological Polar Surface Area94.8 Ų
Heavy Atom Count25
Formal Charge0
Complexity469
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameCervidil
Drug LabelDinoprostone vaginal insert is a thin, flat, polymeric slab which is rectangular in shape with rounded corners contained within the pouch of an off-white knitted polyester retrieval system. Each slab is buff colored, semitransparent and contains 10 m...
Active IngredientDinoprostone
Dosage FormInsert, extended release
RouteVaginal
Strength10mg
Market StatusPrescription
CompanyFerring Controlled

2 of 6  
Drug NamePrepidil
PubMed HealthDinoprostone (Vaginal)
Drug ClassesEndocrine-Metabolic Agent, Uterine Stimulant
Drug LabelPREPIDIL Gel contains dinoprostone as the naturally occurring form of prostaglandin E2 (PGE2) and is designated chemically as (5Z, 11a, 13E, 15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-oic acid. The molecular formula is C20H32O5 and the molecular w...
Active IngredientDinoprostone
Dosage FormGel
RouteEndocervical
Strength0.5mg/3gm
Market StatusPrescription
CompanyPharmacia And Upjohn

3 of 6  
Drug NameProstin e2
PubMed HealthDinoprostone (Vaginal)
Drug ClassesEndocrine-Metabolic Agent, Uterine Stimulant
Drug LabelPROSTIN E2 Vaginal Suppository, an oxytocic, contains dinoprostone as the naturally occurring prostaglandin E2 (PGE2).Its chemical name is (5Z,11,13E,15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-oic acid and the structural formula is represented b...
Active IngredientDinoprostone
Dosage FormSuppository
RouteVaginal
Strength20mg
Market StatusPrescription
CompanyPharmacia And Upjohn

4 of 6  
Drug NameCervidil
Drug LabelDinoprostone vaginal insert is a thin, flat, polymeric slab which is rectangular in shape with rounded corners contained within the pouch of an off-white knitted polyester retrieval system. Each slab is buff colored, semitransparent and contains 10 m...
Active IngredientDinoprostone
Dosage FormInsert, extended release
RouteVaginal
Strength10mg
Market StatusPrescription
CompanyFerring Controlled

5 of 6  
Drug NamePrepidil
PubMed HealthDinoprostone (Vaginal)
Drug ClassesEndocrine-Metabolic Agent, Uterine Stimulant
Drug LabelPREPIDIL Gel contains dinoprostone as the naturally occurring form of prostaglandin E2 (PGE2) and is designated chemically as (5Z, 11a, 13E, 15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-oic acid. The molecular formula is C20H32O5 and the molecular w...
Active IngredientDinoprostone
Dosage FormGel
RouteEndocervical
Strength0.5mg/3gm
Market StatusPrescription
CompanyPharmacia And Upjohn

6 of 6  
Drug NameProstin e2
PubMed HealthDinoprostone (Vaginal)
Drug ClassesEndocrine-Metabolic Agent, Uterine Stimulant
Drug LabelPROSTIN E2 Vaginal Suppository, an oxytocic, contains dinoprostone as the naturally occurring prostaglandin E2 (PGE2).Its chemical name is (5Z,11,13E,15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-oic acid and the structural formula is represented b...
Active IngredientDinoprostone
Dosage FormSuppository
RouteVaginal
Strength20mg
Market StatusPrescription
CompanyPharmacia And Upjohn

4.2 Drug Indication

For the termination of pregnancy during the second trimester (from the 12th through the 20th gestational week as calculated from the first day of the last normal menstrual period), as well as for evacuation of the uterine contents in the management of missed abortion or intrauterine fetal death up to 28 weeks of gestational age as calculated from the first day of the last normal menstrual period. Also used in the management of nonmetastatic gestational trophoblastic disease (benign hydatidiform mole). Other indications include improving the cervical inducibility (cervical "ripening") in pregnant women at or near term with a medical or obstetrical need for labor induction, and the management of postpartum hemorrhage.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Dinoprostone is equivalent to prostaglandin E2 (PGE2). It stimulates labor and delivery by stimulating the uterine, and thus terminates pregnancy. Dinoprostone is also capable of stimulating the smooth muscle of the gastrointestinal tract of man. This activity may be responsible for the vomiting and/or diarrhea that is not uncommon when dinoprostone is used to terminate pregnancy.


5.2 MeSH Pharmacological Classification

Oxytocics

Drugs that stimulate contraction of the myometrium. They are used to induce LABOR, OBSTETRIC at term, to prevent or control postpartum or postabortion hemorrhage, and to assess fetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (ABORTIFACIENTS). Oxytocics used clinically include the neurohypophyseal hormone OXYTOCIN and certain prostaglandins and ergot alkaloids. (From AMA Drug Evaluations, 1994, p1157) (See all compounds classified as Oxytocics.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
DINOPROSTONE
5.3.2 FDA UNII
K7Q1JQR04M
5.3.3 Pharmacological Classes
Prostaglandins [CS]; Prostaglandin Analog [EPC]
5.4 ATC Code

G02AD02

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


G - Genito urinary system and sex hormones

G02 - Other gynecologicals

G02A - Uterotonics

G02AD - Prostaglandins

G02AD02 - Dinoprostone


5.5 Absorption, Distribution and Excretion

Absorption

Absorbed at a rate of 0.3 mg per hour over 12 hours while the vaginal system is in place.


Route of Elimination

The major route of elimination of the products of PGE2 metabolism is the kidneys.


5.6 Metabolism/Metabolites

Rapid metabolism of dinoprostone occurs primarily in the local tissues; any systemic absorption of the medication is cleared mainly in the maternal lungs and, secondarily, at sites such as the liver and kidneys.


5.7 Biological Half-Life

Less than 5 minutes.


5.8 Mechanism of Action

Dinoprostone administered intravaginally stimulates the myometrium of the gravid uterus to contract in a manner that is similar to the contractions seen in the term uterus during labor, resulting in the evacuation of the products of conception from the uterus. It is believed that dinoprostone exerts its uterine effects via direct myometrial stimulation, but the exact mechanism of action is unkown. Other suggested mechanisms include the regulation of cellular membrane calcium transport and of intracellular concentrations of cyclic 3',5'-adenosine monophosphate. Dinoprostone also appears to produce local cervical effects including softening, effacement, and dilation. The exact mechanism of action for this effect is also unknown, but it has been suggested that this effect may be associated with collagen degradation caused by secretion of the enzyme collagenase as a partial response to locally administered dinoprostone.


API Reference Price

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11-May-2021
20-Aug-2024
GMS
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Average Price (USD/GMS)

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DOSAGE - SUPPOSITORY;VAGINAL - 20MG

USFDA APPLICATION NUMBER - 17810

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DOSAGE - INSERT, EXTENDED RELEASE;VAGINAL - 1...DOSAGE - INSERT, EXTENDED RELEASE;VAGINAL - 10MG

USFDA APPLICATION NUMBER - 20411

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