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Technical details about Alprostadil [USAN:USP:INN:BAN:JAN], learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
Also known as: Prostaglandin e1, 745-65-3, Pge1, Edex, Caverject, Muse
Molecular Formula
C20H34O5
Molecular Weight
354.5  g/mol
InChI Key
GMVPRGQOIOIIMI-DWKJAMRDSA-N
FDA UNII
F5TD010360

A potent vasodilator agent that increases peripheral blood flow.
Alprostadil is a Prostaglandin Analog and Prostaglandin E1 Agonist. The mechanism of action of alprostadil is as a Prostaglandin Receptor Agonist. The physiologic effect of alprostadil is by means of Genitourinary Arterial Vasodilation and Venous Vasodilation.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid
2.1.2 InChI
InChI=1S/C20H34O5/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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1
2.1.3 InChI Key
GMVPRGQOIOIIMI-DWKJAMRDSA-N
2.1.4 Canonical SMILES
CCCCCC(C=CC1C(CC(=O)C1CCCCCCC(=O)O)O)O
2.1.5 Isomeric SMILES
CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)O)O)O
2.2 Other Identifiers
2.2.1 UNII
F5TD010360
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Caverject

2. Edex

3. Lipo Pge1

4. Lipo-pge1

5. Minprog

6. Muse

7. Pge1

8. Pge1alpha

9. Prostaglandin E1

10. Prostaglandin E1alpha

11. Prostavasin

12. Prostin Vr

13. Prostine Vr

14. Sugiran

15. Vasaprostan

16. Viridal

2.3.2 Depositor-Supplied Synonyms

1. Prostaglandin E1

2. 745-65-3

3. Pge1

4. Edex

5. Caverject

6. Muse

7. Prostin Vr

8. Befar

9. Alprostadilum

10. Topiglan

11. Femprox

12. Alprox-td

13. L-prostaglandin E1

14. Liprostin

15. Prostandin

16. Vitaros

17. Prostin Vr Pediatric

18. Prink

19. Pge-1

20. Prostavasin

21. (11alpha,13e,15s)-11,15-dihydroxy-9-oxoprost-13-en-1-oic Acid

22. 7-((1r,2r,3r)-3-hydroxy-2-((s,e)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)heptanoic Acid

23. Alprostadil(caverject)

24. (-)-prostaglandin E1

25. (13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoate

26. 11alpha,15alpha-dihydroxy-9-oxo-13-trans-prostenoic Acid

27. Chembl495

28. U-10136

29. 7-[(1r,2r,3r)-3-hydroxy-2-[(e,3s)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic Acid

30. Vasaprostan

31. Chebi:15544

32. 9-oxo-11r,15s-dihydroxy-13e-prostaenoic Acid

33. Ono-1608

34. U-10,136

35. F5td010360

36. Nsc-165559

37. Minprog

38. Sugiran

39. Viridal

40. (13e,15s)-11alpha,15-dihydroxy-9-oxoprost-13-en-1-oic Acid

41. (1r,2r,3r)-3-hydroxy-2-((e)-(3s)-3-hydroxy-1-octenyl)-5-oxocyclopentaneheptanoic Acid

42. Lipoprost

43. Promostan

44. Prostivas

45. Alista

46. Femlife

47. Prostaglandine1

48. Rayva

49. Caverject Impulse

50. Pge1alpha

51. 7-((1r,2r,3r)-3-hydroxy-2-((s,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)heptanoic Acid

52. 7-[(1r,3r)-3-hydroxy-2-[(1e,3s)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic Acid

53. Smr000112594

54. Befar (tn)

55. Prink (tn)

56. Edex (tn)

57. Muse (tn)

58. (-)-protaglandin E1

59. U 10136

60. L-pge1

61. Sr-01000597593

62. Mr-256

63. Alprostadilum [inn-latin]

64. Prostin Vr Pediatric (tn)

65. Alprostadil Prostoglandin E1

66. Bml1-f06

67. Unii-f5td010360

68. Alprostadil(usan)

69. Hei-507

70. Ncgc00016535-01

71. Cas-745-65-3

72. Ono 1608

73. Einecs 212-017-2

74. (13e)-(15s)-11-alpha,15-dihydroxy-9-oxoprost-13-enoate

75. Mfcd00077860

76. Nsc 165559

77. Alprostadil [usan:usp:inn:ban:jan]

78. 11,15-dihydroxy-9-oxoprost-13-en-1-oic Acid

79. Pge1;prostaglandin E1

80. Ai3-62116

81. Prestwick2_001018

82. Prestwick3_001018

83. Alprostadil [inn]

84. Alprostadil [jan]

85. Dsstox_cid_2578

86. Alprostadil [usan]

87. Alprostadil [vandf]

88. Pge1 (prostaglandin E1)

89. Alprostadil [mart.]

90. Dsstox_rid_76640

91. Dsstox_gsid_22578

92. Schembl33317

93. Alprostadil [usp-rs]

94. Alprostadil [who-dd]

95. Bspbio_001175

96. Bspbio_001488

97. Mls000758964

98. Mls001424250

99. Bidd:gt0747

100. Prostaglandin E1 [mi]

101. Bpbio1_001293

102. Gtpl1882

103. Alprostadil (jp17/usp/inn)

104. Dtxsid9022578

105. Alprostadil [orange Book]

106. Pge1, Prostaglandin E1, Powder

107. Alprostadil [usp Impurity]

108. Hms1361k10

109. Hms1571k17

110. Hms1791k10

111. Hms1989k10

112. Hms2052l11

113. Hms2090l08

114. Hms2098k17

115. Hms3268i09

116. Hms3402k10

117. Hms3414n09

118. Hms3648o17

119. Hms3678n07

120. Hms3715k17

121. Alprostadil [usp Monograph]

122. Amy30076

123. Bcp01740

124. Ex-a1411

125. Hy-b0131

126. Zinc3813088

127. Tox21_110482

128. 3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic Acid

129. 3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentaneheptanoic Acid

130. Bdbm50101853

131. L-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentaneheptanoic Acid

132. Lmfa03010134

133. S1508

134. Akos015961103

135. Prost-13-en-1-oic Acid, 11,15-dihydroxy-9-oxo-, (11.alpha.,13e,15s)-

136. Prost-13-en-1-oic Acid, 11,15-dihydroxy-9-oxo-, (11alpha,13e,15s)-

137. Ac-6095

138. Bcp9000277

139. Ccg-101188

140. Cs-1905

141. Db00770

142. Nc00438

143. Idi1_033958

144. Prostaglandin E1, >=99.0% (tlc)

145. Smp2_000271

146. Ncgc00025234-02

147. Ncgc00025234-03

148. Ncgc00025234-04

149. Ncgc00025234-05

150. As-16360

151. Prostaglandin E1, Pge1, 745-65-3

152. Alprostadil 100 Microg/ml In Acetonitrile

153. 11,15-dihydroxy-9-oxoprost-13-en-1-oate

154. Ab00514004

155. B2154

156. P1917

157. Alprostadil, Meets Usp Testing Specifications

158. C04741

159. C76381

160. D00180

161. Prostaglandin E1, >=98% (hplc), Synthetic

162. Ab00514004-06

163. Ab00514004-08

164. Ab00514004_09

165. 11,15-dihydroxy-9-oxoprost-13-en-1-oic Acidl

166. 745p653

167. A838163

168. Q579348

169. Sr-01000946253

170. Sr-01000597593-1

171. Sr-01000597593-5

172. Sr-01000597593-6

173. Sr-01000946253-1

174. W-104416

175. Brd-k52459643-001-06-0

176. Brd-k52459643-001-10-2

177. Brd-k52459643-001-17-7

178. (13e)-(15s)-11,15-dihydroxy-9-oxoprost-13-enoate

179. (13e)-(15s)-11,15-dihydroxy-9-oxoprost-13-enoic Acid

180. Alprostadil, European Pharmacopoeia (ep) Reference Standard

181. (13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoic Acid

182. (11?,13e,15s)-11,15-dihydroxy-9-oxo-prost-13-en-1-oic Acid

183. (13e)-(15s)-11-alpha,15-dihydroxy-9-oxoprost-13-enoic Acid

184. 11,15-dihydroxy-9-oxoprost-13-en-1-oic Acid (acd/name 4.0)

185. 3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate

186. Alprostadil, United States Pharmacopeia (usp) Reference Standard

187. (+)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate

188. (+)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic Acid

189. (-)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate

190. (-)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic Acid

191. (11alpha,12alpha,13e,15s)-11,15-dihydroxy-9-oxoprost-13-en-1-oic Acid

192. Cyclopentaneheptanoic Acid, 3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-, L-

193. Prost-13-en-1-oic Acid, 11,15-dihydroxy-9-oxo-, (11a,13e,15s)-

194. Prostaglandin E1, Synthetic, Powder, Bioreagent, Suitable For Cell Culture

195. Cyclopentaneheptanoic Acid, 3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-, (-)-

196. Prostaglandin E1, Powder, Gamma-irradiated, Bioxtra, Suitable For Cell Culture

197. Xpg

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 354.5 g/mol
Molecular Formula C20H34O5
XLogP33.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count13
Exact Mass354.24062418 g/mol
Monoisotopic Mass354.24062418 g/mol
Topological Polar Surface Area94.8 Ų
Heavy Atom Count25
Formal Charge0
Complexity432
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 12  
Drug NameCaverject
PubMed HealthAlprostadil
Drug ClassesEndocrine-Metabolic Agent, Erectile Dysfunction Agent, Prostaglandin
Drug LabelCAVERJECT contains alprostadil as the naturally occurring form of prostaglandin E1 (PGE1) and is designated chemically as (11,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-oic acid. The molecular weight is 354.49.Alprostadil is a white to off-white c...
Active IngredientAlprostadil
Dosage FormInjectable
RouteInjection
Strength0.005mg/vial; 0.02mg/vial; 0.04mg/vial; 0.01mg/vial
Market StatusPrescription
CompanyPharmacia And Upjohn

2 of 12  
Drug NameCaverject impulse
Drug LabelCAVERJECT contains alprostadil as the naturally occurring form of prostaglandin E1 (PGE1) and is designated chemically as (11,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-oic acid. The molecular weight is 354.49.Alprostadil is a white to off-white c...
Active IngredientAlprostadil
Dosage FormInjectable
RouteInjection
Strength0.02mg/vial; 0.01mg/vial
Market StatusPrescription
CompanyPharmacia And Upjohn

3 of 12  
Drug NameEdex
PubMed HealthAlprostadil
Drug ClassesEndocrine-Metabolic Agent, Erectile Dysfunction Agent, Prostaglandin
Drug Labeledex (alprostadil for injection) is a sterile, pyrogen-free powder containing alprostadil in an alfadex (-cyclodextrin) inclusion complex. Alprostadil is an endogenous substance known as prostaglandin E1 (PGE1). edex is supplied in single-dose,...
Active IngredientAlprostadil
Dosage FormInjectable
RouteInjection
Strength0.02mg/vial; 0.04mg/vial; 0.01mg/vial
Market StatusPrescription
CompanyAuxilium Pharms

4 of 12  
Drug NameMuse
PubMed HealthAlprostadil
Drug ClassesEndocrine-Metabolic Agent, Erectile Dysfunction Agent, Prostaglandin
Drug LabelMUSE (alprostadil) is a single-use, medicated transurethral system for the delivery of alprostadil to the male urethra. Alprostadil is suspended in polyethylene glycol 1450 (as excipient) and is formed into a medicated pellet (micro-suppository mea...
Active IngredientAlprostadil
Dosage FormSuppository
RouteUrethral
Strength0.5mg; 1mg; 0.25mg; 0.125mg
Market StatusPrescription
CompanyMeda Pharms

5 of 12  
Drug NameProstin vr pediatric
PubMed HealthAlprostadil
Drug ClassesEndocrine-Metabolic Agent, Erectile Dysfunction Agent, Prostaglandin
Drug LabelPROSTIN VR PEDIATRIC Sterile Solution for intravascular infusion contains 500 micrograms alprostadil, more commonly known as prostaglandin E1, in 1.0 mL dehydrated alcohol.The chemical name for alprostadil is (11,13E,15S)-11,15 dihydroxy-9-oxo-pros...
Active IngredientAlprostadil
Dosage FormInjectable
RouteInjection
Strength0.5mg/ml
Market StatusPrescription
CompanyPharmacia And Upjohn

6 of 12  
Drug NameAlprostadil
PubMed HealthAlprostadil
Drug ClassesEndocrine-Metabolic Agent, Erectile Dysfunction Agent, Prostaglandin
Drug LabelAlprostadil injection, USP for intravascular infusion contains 500 micrograms alprostadil, more commonly known as prostaglandin E1, in 1 mL dehydrated alcohol. The chemical name for alprostadil is (1R,2R,3R)3-Hydroxy-2-[(E)-(3S)-3-hydroxy-1-octenyl]-...
Active IngredientAlprostadil
Dosage FormInjectable
RouteInjection
Strength0.5mg/ml
Market StatusPrescription
CompanyTeva Pharms Usa; Eurohlth Intl

7 of 12  
Drug NameCaverject
PubMed HealthAlprostadil
Drug ClassesEndocrine-Metabolic Agent, Erectile Dysfunction Agent, Prostaglandin
Drug LabelCAVERJECT contains alprostadil as the naturally occurring form of prostaglandin E1 (PGE1) and is designated chemically as (11,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-oic acid. The molecular weight is 354.49.Alprostadil is a white to off-white c...
Active IngredientAlprostadil
Dosage FormInjectable
RouteInjection
Strength0.005mg/vial; 0.02mg/vial; 0.04mg/vial; 0.01mg/vial
Market StatusPrescription
CompanyPharmacia And Upjohn

8 of 12  
Drug NameCaverject impulse
Drug LabelCAVERJECT contains alprostadil as the naturally occurring form of prostaglandin E1 (PGE1) and is designated chemically as (11,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-oic acid. The molecular weight is 354.49.Alprostadil is a white to off-white c...
Active IngredientAlprostadil
Dosage FormInjectable
RouteInjection
Strength0.02mg/vial; 0.01mg/vial
Market StatusPrescription
CompanyPharmacia And Upjohn

9 of 12  
Drug NameEdex
PubMed HealthAlprostadil
Drug ClassesEndocrine-Metabolic Agent, Erectile Dysfunction Agent, Prostaglandin
Drug Labeledex (alprostadil for injection) is a sterile, pyrogen-free powder containing alprostadil in an alfadex (-cyclodextrin) inclusion complex. Alprostadil is an endogenous substance known as prostaglandin E1 (PGE1). edex is supplied in single-dose,...
Active IngredientAlprostadil
Dosage FormInjectable
RouteInjection
Strength0.02mg/vial; 0.04mg/vial; 0.01mg/vial
Market StatusPrescription
CompanyAuxilium Pharms

10 of 12  
Drug NameMuse
PubMed HealthAlprostadil
Drug ClassesEndocrine-Metabolic Agent, Erectile Dysfunction Agent, Prostaglandin
Drug LabelMUSE (alprostadil) is a single-use, medicated transurethral system for the delivery of alprostadil to the male urethra. Alprostadil is suspended in polyethylene glycol 1450 (as excipient) and is formed into a medicated pellet (micro-suppository mea...
Active IngredientAlprostadil
Dosage FormSuppository
RouteUrethral
Strength0.5mg; 1mg; 0.25mg; 0.125mg
Market StatusPrescription
CompanyMeda Pharms

11 of 12  
Drug NameProstin vr pediatric
PubMed HealthAlprostadil
Drug ClassesEndocrine-Metabolic Agent, Erectile Dysfunction Agent, Prostaglandin
Drug LabelPROSTIN VR PEDIATRIC Sterile Solution for intravascular infusion contains 500 micrograms alprostadil, more commonly known as prostaglandin E1, in 1.0 mL dehydrated alcohol.The chemical name for alprostadil is (11,13E,15S)-11,15 dihydroxy-9-oxo-pros...
Active IngredientAlprostadil
Dosage FormInjectable
RouteInjection
Strength0.5mg/ml
Market StatusPrescription
CompanyPharmacia And Upjohn

12 of 12  
Drug NameAlprostadil
PubMed HealthAlprostadil
Drug ClassesEndocrine-Metabolic Agent, Erectile Dysfunction Agent, Prostaglandin
Drug LabelAlprostadil injection, USP for intravascular infusion contains 500 micrograms alprostadil, more commonly known as prostaglandin E1, in 1 mL dehydrated alcohol. The chemical name for alprostadil is (1R,2R,3R)3-Hydroxy-2-[(E)-(3S)-3-hydroxy-1-octenyl]-...
Active IngredientAlprostadil
Dosage FormInjectable
RouteInjection
Strength0.5mg/ml
Market StatusPrescription
CompanyTeva Pharms Usa; Eurohlth Intl

4.2 Drug Indication

For palliative, not definitive, therapy to temporarily maintain the patency of the ductus arteriosus until corrective or palliative surgery can be performed in neonates who have congenital heart defects and who depend upon the patent ductus for survival. Also for the treatment of erectile dysfunction due to neurogenic, vasculogenic, psychogenic, or mixed etiology.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Alprostadil (prostaglandin E1) is produced endogenously to relax vascular smooth muscle and cause vasodilation. In adult males, the vasodilatory effects of alprostadil on the cavernosal arteries and the trabecular smooth muscle of the corpora cavernosa result in rapid arteriolar inflow and expansion of the lacunar spaces within the corpora. As the expanded corporal sinusoids are compressed against the tunica albuginea, venous outflow through the subtunical vessels is impeded and penile rigidity develops. This is referred to as the corporal veno-occlusive mechanism. In infants, the vasodilatory effects of alprostadil increase pulmonary or systemic blood flow.


5.2 MeSH Pharmacological Classification

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)


Urological Agents

Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS. (See all compounds classified as Urological Agents.)


Platelet Aggregation Inhibitors

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
ALPROSTADIL
5.3.2 FDA UNII
F5TD010360
5.3.3 Pharmacological Classes
Prostaglandin Analog [EPC]; Prostaglandin E1 Agonist [EPC]; Prostaglandin Receptor Agonists [MoA]; Prostaglandins [CS]; Venous Vasodilation [PE]; Genitourinary Arterial Vasodilation [PE]
5.4 ATC Code

C - Cardiovascular system

C01 - Cardiac therapy

C01E - Other cardiac preparations

C01EA - Prostaglandins

C01EA01 - Alprostadil


G - Genito urinary system and sex hormones

G04 - Urologicals

G04B - Urologicals

G04BE - Drugs used in erectile dysfunction

G04BE01 - Alprostadil


5.5 Absorption, Distribution and Excretion

Absorption

The absolute bioavailability of alprostadil has not been determined.


Route of Elimination

Alprostadil must be infused continuously because it is very rapidly metabolized. As much as 80% of the circulating alprostadil may be metabolized in one pass through the lungs, primarily by - and -oxidation. The metabolites are excreted primarily by the kidney, and excretion is essentially complete within 24 hours after administration.


5.6 Metabolism/Metabolites

Alprostadil must be infused continuously because it is very rapidly metabolized. As much as 80% of the circulating alprostadil may be metabolized in one pass through the lungs, primarily by beta- and omega-oxidation.


5.7 Biological Half-Life

5 to 10 minutes (after a single dose), in healthy adults and neonates.


5.8 Mechanism of Action

Alprostadil causes vasodilation by means of a direct effect on vascular and ductus arteriosus (DA) smooth muscle, preventing or reversing the functional closure of the DA that occurs shortly after birth. This is because, as a form of prostaglandinE1 (PGE1) it has multiple effects on blood flow. This results in increased pulmonary or systemic blood flow in infants. In cyanotic congenital heart disease, alprostadil's actions result in an increased oxygen supply to the tissues. In infants with interrupted aortic arch or very severe aortic coarctation, alprostadil maintains distal aortic perfusion by permitting blood flow through the DA from the pulmonary artery to the aorta. In infants with aortic coarctation, alprostadil reduces aortic obstruction either by relaxing ductus tissue in the aortic wall or by increasing effective aortic diameter by dilating the DA. In infants with these aortic arch anomalies, systemic blood flow to the lower body is increased, improving tissue oxygen supply and renal perfusion. When administered by intracavernosal injection or as an intraurethral suppository, alprostadil acts locally to relax the trabecular smooth muscle of the corpora cavernosa and the cavernosal arteries. Swelling, elongation, and rigidity of the penis result when arterial blood rapidly flows into the corpus cavernosum to expand the lacunar spaces. The entrapped blood reduces the venous blood outflow as sinusoids compress against the tunica albuginea.


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