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Chemistry

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Also known as: Prostaglandin f2alpha, 551-11-1, Pgf2alpha, Prostaglandin f2a, Amoglandin, Enzaprost

Molecular Formula

C₂₀H₃₄O₅

Molecular Weight

354.5 g/mol

InChI Key

PXGPLTODNUVGFL-YNNPMVKQSA-N

FDA UNII

B7IN85G1HY

A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.

1 2D Structure

Dinoprost

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic 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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1

2.1.3 InChI Key

PXGPLTODNUVGFL-YNNPMVKQSA-N

2.1.4 Canonical SMILES

CCCCCC(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O

2.1.5 Isomeric SMILES

CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

B7IN85G1HY

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 9alpha,11beta Pgf2

2. 9alpha,11beta-pgf2

3. Alpha, Pgf2

4. Enzaprost F

5. Estrofan

6. F2 Alpha, Prostaglandin

7. F2alpha, Prostaglandin

8. Pgf2

9. Pgf2 Alpha

10. Pgf2alpha

11. Prostaglandin F2

12. Prostaglandin F2 Alpha

13. Prostaglandin F2alpha

2.3.2 Depositor-Supplied Synonyms

1. Prostaglandin F2alpha

2. 551-11-1

3. Pgf2alpha

4. Prostaglandin F2a

5. Amoglandin

6. Enzaprost

7. Enzaprost F

8. Panacelan

9. L-pgf2-alpha

10. Prostaglandin F2 Alpha

11. Prostaglandin F2-alpha

12. Protamodin

13. L-prostaglandin F2-alpha

14. Cyclosin

15. Dinoprostum

16. Dinoprosta

17. Prostin F2alpha

18. Prosmon

19. Prostaglandin F2.alpha.

20. U-14583

21. Pgf2a

22. Prostarmon F

23. U 14583

24. Chembl815

25. B7in85g1hy

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

27. (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((s,e)-3-hydroxyoct-1-en-1-yl)cyclopentyl)hept-5-enoic Acid

28. Chebi:15553

29. U-14,583

30. Ncgc00160385-01

31. 7-(3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-5-heptenoic Acid

32. Prostin F2-alpha

33. Pgf-2alpha

34. Pgf2 Alpha

35. Pgf2-alpha

36. 9s,11r,15s-trihydroxy-5z,13e-prostadienoic Acid

37. (+)-prostaglandin F2a

38. 9alpha,11alpha-pgf2

39. Pgf2

40. Prostin F 2 Alpha

41. Pgf2.alpha.

42. Prostaglandin F(sub 2a)

43. Dinoprostum [inn-latin]

44. (5z,13e,15s)-9alpha,11alpha,15-trihydroxyprosta-5,13-dien-1-oic Acid

45. 7-[3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic Acid

46. Dinoprosta [inn-spanish]

47. (5z,9alpha,11alpha,13e,15s)-9,11,15-trihydroxyprosta-5,13-dien-1-oic Acid

48. Ccris 4253

49. Hsdb 3315

50. Dinoprost [usan:inn:ban:jan]

51. (+-)-pgf2alpha

52. 9a,11a-pgf2

53. Sr-01000721847

54. (e,z)-(1r,2r,3r,5s)-7-(3,5-dihydroxy-2-((3s)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic Acid

55. (+-)-pgf2-alpha

56. Dl-prostaglandin F2-alpha

57. Pgf2-alpha Racemic Mixt.

58. Unii-b7in85g1hy

59. (+)-prostaglandin F2alpha

60. Prostaglandin F2alpha, Dl-

61. Brn 2225571

62. 9,11,15-trihydroxyprosta-5,13-dien-1-oic Acid

63. Prosmon (tn)

64. Prosta-5,13-dien-1-oic Acid, 9,11,15-trihydroxy-, (5z,9alpha,11alpha,13e,15s)-

65. 15-epi Pgf2alpha

66. Prostaglandin F2-alpha, Racemic Mixt.

67. Brn 4153898

68. Dinoprost [inn]

69. Dinoprost [jan]

70. Dinoprost [hsdb]

71. Dinoprost [usan]

72. Dsstox_cid_2946

73. Dinoprost [mart.]

74. (5z,9alpha,11alpha,13e,15s)-9,11,15-trihydroxyprosta-3,13-dien-1-oic Acid

75. 5-heptenoic Acid, 7-(3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-, L-

76. Dinoprost [who-dd]

77. Dsstox_rid_76800

78. Dsstox_gsid_22946

79. Schembl24292

80. Bspbio_001494

81. 23518-25-4

82. 5-heptenoic Acid, 7-(3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-, (1r-(1alpha(z),2beta(s*,e),3alpha,5alpha))-

83. Bml1-f08

84. Gtpl1884

85. Dinoprost (jp17/usan/inn)

86. 15(r)-prostaglandin F2 Alpha

87. 9,11,15-trihydroxy-(5z,9a,11a,13e,15s)-prosta-5,13-dien-1-oic Acid

88. Dtxsid9022946

89. Ex-a4115a

90. Hms1361k16

91. Hms1791k16

92. Hms1989k16

93. Hms2089f11

94. Hms3402k16

95. Hms3648n11

96. Amy30098

97. Zinc3830709

98. Tox21_111777

99. Bdbm50035622

100. Lmfa03010002

101. Mfcd00135231

102. Pdsp2_000079

103. Prostaglandin F2.alpha. [mi]

104. Ccg-208257

105. Cs-4232

106. Db12789

107. 5-heptenoic Acid, 7-(3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-, (+-)-

108. 5-heptenoic Acid, 7-(3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-, Dl-

109. Idi1_033964

110. Ncgc00160385-02

111. Ncgc00160385-04

112. Ncgc00160385-05

113. Ncgc00160385-06

114. As-56892

115. Cas-551-11-1

116. Hy-12956

117. P1885

118. 62p015

119. C00639

120. D00081

121. A830494

122. Q421375

123. Sr-01000946457

124. Sr-01000721847-2

125. Sr-01000721847-4

126. Sr-01000946457-1

127. (5z,13e)-(15s)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate

128. (5z,9alpha,11alpha,13e,15s)-9,11,15-trihydroxyprosta-5,13-dienoate

129. (5z,9alpha,11alpha,13e,15s)-9,11,15-trihydroxyprosta-5,13-dienoic Acid

130. Prosta-10,13-dien-1-oic Acid, 9,11,15-trihydroxy-, (5z,9.alpha.,11.alpha.,13e,15s)

131. (5z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(1e,3s)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic Acid

132. (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((s,e)-3-hydroxyoct-1-enyl)-cyclopentyl)-hept-5-enoic Acid

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

134. (z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-{(e)-(3s)-3-hydroxy-1-octenyl}-cyclopentyl]-5-heptenoic Acid

135. 13535-33-6

136. Prosta-5,13-dien-1-oic Acid, 9,11,15-trihydroxy-, (5z,9-alpha,11-alpha,13e,15s)-(+-)-

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₃₄O₅
Molecular Weight	354.5 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	12
Exact Mass	354.24062418 g/mol
Monoisotopic Mass	354.24062418 g/mol
Topological Polar Surface Area	98 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	432
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Abortifacient Agents, Nonsteroidal; Oxytocics

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

...SOME PHYSICIANS PREFER TO DEFER ABORTION UNTIL AFTER 16TH WK, WHEN INTRA-AMNIOTIC ROUTE CAN BE EMPLOYED MORE SAFELY. /DINOPROST TROMETHAMINE/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 625

EXTRA-AMNIOTIC TECHNIQUE, WHICH IS STILL INVESTIGATIONAL, REQUIRES TRANSVAGINAL INTRAUTERINE EXTRAOVULAR PLACEMENT OF INDWELLING CATHETER. ... RESERVED FOR TERMINATION OF PREGNANCIES BETWEEN 13TH & 15TH WK... /DINOPROST TROMETHAMINE/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 625

DOSAGE THAT ACHIEVES EFFECTIVE CONCN WITHIN MYOMETRIUM IS LOWEST WITH INTRAUTERINE ADMIN. INTRA-AMNIOTIC INSTILLATION IS ACCOMPLISHED WITH LONG SPINAL NEEDLE INSERTED TRANSABDOMINALLY INTO AMNIOTIC SAC. /DINOPROST TROMETHAMINE/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 625

For more Therapeutic Uses (Complete) data for PROSTAGLANDIN F2ALPHA (15 total), please visit the HSDB record page.

4.2 Drug Warning

ASTHMATIC INDIVIDUALS ARE PARTICULARLY SENSITIVE, & PGF2ALPHA HAS CAUSED INTENSE BRONCHOSPASM.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 644

SOME INVESTIGATORS HAVE INDICATED THAT PROSTAGLANDINS MAY SHOW NARROWER DOSE-RESPONSE RANGE FOR PRODN OF PHYSIOLOGICAL CONTRACTIONS & OCCURRENCE OF UTERINE HYPERTONUS, POTENTIAL HAZARD THAT MAY BE AVOIDED BY VERY CAUTIOUS STEPWISE INCREMENTS IN RATE OF INFUSION. /PROSTAGLANDINS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 871

FOR ABORTION IN 2ND TRIMESTER...RESULTS IN...FREQUENT BUT TOLERABLE SIDE EFFECTS. HOWEVER, FOR VERY EARLY ABORTION (MENSES DELAYED UP TO SEVERAL WK), RATE OF SUCCESS REPORTED IS LOW & SERIOUS SIDE EFFECTS HAVE RESULTED FROM DOSES REQUIRED. /PROSTAGLANDINS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 871

...CONTRAINDICATED IN ACUTE PELVIC INFLAMMATION. IT SHOULD BE USED CAUTIOUSLY IN PT WITH HISTORY OF HYPERTENSION, ASTHMA, GLAUCOMA, EPILEPSY, OR CARDIOVASCULAR DISEASE.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 878

For more Drug Warnings (Complete) data for PROSTAGLANDIN F2ALPHA (11 total), please visit the HSDB record page.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Abortifacient Agents, Nonsteroidal

Non-steroidal chemical compounds with abortifacient activity. (See all compounds classified as Abortifacient Agents, Nonsteroidal.)

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.)

5.2 ATC Code

G - Genito urinary system and sex hormones

G02 - Other gynecologicals

G02A - Uterotonics

G02AD - Prostaglandins

G02AD01 - Dinoprost

5.3 Absorption, Distribution and Excretion

AMONG COMPD OCCURRING IN SEMEN THAT ARE OF CURRENT RESEARCH INTEREST ARE PROSTAGLANDINS (25 MG/ML). /PROSTAGLANDINS/

Casarett, L.J., and J. Doull. Toxicology: The Basic Science of Poisons. New York: MacMillan Publishing Co., 1975., p. 263

APART FROM GENERALLY SLOW & SPECIES-DEPENDENT ISOMERIZATION, PGS E & F ARE RATHER STABLE IN BLOOD, BUT THEY ARE RAPIDLY DEGRADED & INACTIVATED BY TISSUE-BOUND ENZYMES; SOME 80-90% OR MORE IS DESTROYED DURING SINGLE PASSAGE THROUGH LIVER OR LUNGS. /PROSTAGLANDINS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 641

DEG OF BINDING OF PROSTAGLANDINS TO PLASMA PROTEINS APPEARS TO HAVE LITTLE INFLUENCE ON THEIR RATES OF METABOLISM & ELIMINATION. ... CLEARANCE RATES OF (3)H DID NOT CHANGE WHETHER PROSTAGLANDINS WERE ADMIN IN FREE FORM OR BOUND TO RAT PLASMA ALBUMIN. /PROSTAGLANDINS/

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 165

5.4 Metabolism/Metabolites

...PROSTAGLANDINS ARE RAPIDLY METABOLIZED... /PROSTAGLANDINS/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 626

5.5 Mechanism of Action

...THERE IS NO SINGLE PROSTAGLANDIN RECEPTOR. ... IT IS POSSIBLE TO DEMONSTRATE CALCIUM DEPENDENCE OF DIVERSE RESPONSES TO PROSTAGLANDINS & TO OBSERVE ALTERED CALCIUM FLUXES. ...PROSTAGLANDINS MAY EITHER STIMULATE OR INHIBIT ACCUM OF CYCLIC AMP. /PROSTAGLANDINS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 645

RESPONSES TO PROSTAGLANDIN F2ALPHA SHOW SPECIES VARIATION, BUT VASODILATATION HAS BEEN OBSERVED FOLLOWING INJECTION INTO HUMAN BRACHIAL ARTERY OF PGF2ALPHA... SUPERFICIAL VEINS OF HAND ARE CONTRACTED BY PFG2ALPHA...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 642

PROMPT SUBSIDENCE OF PROGESTERONE OUTPUT & REGRESSION OF CORPUS LUTEUM FOLLOWS PARENTERAL INJECTION OF PROSTAGLANDIN F2ALPHA... THIS EFFECT INTERRUPTS EARLY PREGNANCY, WHICH IS DEPENDENT ON LUTEAL RATHER THAN PLACENTAL PROGESTERONE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 645

OXYTOCIN & PROSTAGLANDINS AFFECT UTERINE SMOOTH MUSCLES BY DIFFERENT MECHANISMS, & THEIR EFFECTS ARE ADDITIVE. POSSIBLE ADVANTAGES OF THEIR COMBINED USE ARE BEING EXPLORED. /PROSTAGLANDINS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 871

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