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Chemistry

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Also known as: 59122-46-2, Cytotec, Isprelor, Sc-29333, Misoprostolum [inn-latin], Misodel
Molecular Formula
C22H38O5
Molecular Weight
382.5  g/mol
InChI Key
OJLOPKGSLYJEMD-URPKTTJQSA-N
FDA UNII
0E43V0BB57

Misoprostol
A synthetic analog of natural prostaglandin E1. It produces a dose-related inhibition of gastric acid and pepsin secretion, and enhances mucosal resistance to injury. It is an effective anti-ulcer agent and also has oxytocic properties.
Misoprostol is a Prostaglandin E1 Analog.
1 2D Structure

Misoprostol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoate
2.1.2 InChI
InChI=1S/C22H38O5/c1-4-5-14-22(2,26)15-10-12-18-17(19(23)16-20(18)24)11-8-6-7-9-13-21(25)27-3/h10,12,17-18,20,24,26H,4-9,11,13-16H2,1-3H3/b12-10+/t17-,18-,20-,22?/m1/s1
2.1.3 InChI Key
OJLOPKGSLYJEMD-URPKTTJQSA-N
2.1.4 Canonical SMILES
CCCCC(C)(CC=CC1C(CC(=O)C1CCCCCCC(=O)OC)O)O
2.1.5 Isomeric SMILES
CCCCC(C)(C/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)OC)O)O
2.2 Other Identifiers
2.2.1 UNII
0E43V0BB57
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Apo Misoprostol

2. Apo-misoprostol

3. Cytotec

4. Glefos

5. Misoprostol, (11alpha,13e)-isomer

6. Misoprostol, (11alpha,13e,16r)-isomer

7. Misoprostol, (11alpha,13z)-(+-)-isomer

8. Misoprostol, (11alpha.13e,16s)-isomer

9. Misoprostol, (11beta,13e)-(+-)-isomer

10. Misoprostol, (11beta,13e,16r)-isomer

11. Misoprostol, (11beta,13e,16s)-isomer

12. Novo Misoprostol

13. Novo-misoprostol

14. Sc 29333

15. Sc 30249

16. Sc-29333

17. Sc-30249

18. Sc29333

19. Sc30249

2.3.2 Depositor-Supplied Synonyms

1. 59122-46-2

2. Cytotec

3. Isprelor

4. Sc-29333

5. Misoprostolum [inn-latin]

6. Misodel

7. Sc 29333

8. Ccris 6859

9. Hsdb 3573

10. Methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(e)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoate

11. Brn 4155643

12. 103601-27-0

13. 0e43v0bb57

14. Prost-13-en-1-oic Acid, 11,16-dihydroxy-16-methyl-9-oxo-, Methyl Ester,(11a,13e)-

15. Ncgc00162445-02

16. Misoprostolum

17. Misoprost

18. Misotol

19. Misogon

20. Misopess

21. Misotac

22. Gymiso

23. Methyl (11alpha,13e)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate

24. 7-[(1r,2r,3r)-3-hydroxy-2-[(e)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoic Acid Methyl Ester

25. Cytotec (tn)

26. Misoprostol (methyl Ester)

27. Sr-01000695425

28. Unii-0e43v0bb57

29. Xp-16j

30. Mvi 200

31. Methyl 7-((1r,2r,3r)-3-hydroxy-2-((e)-4-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl)heptanoate

32. 11

33. A-misoprostol

34. Cas_59122-46-2

35. Misoprostol [usan:usp:inn:ban:jan]

36. Misoprostol [mi]

37. Dsstox_cid_897

38. Misoprostol [inn]

39. Misoprostol [jan]

40. Methyl (+-)-11-alpha,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate

41. Misoprostol [hsdb]

42. Misoprostol [usan]

43. Chembl606

44. Misoprostol [vandf]

45. Schembl7787

46. (11-alpha,13e)-(+-)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oic Acid Methyl Ester

47. Dsstox_rid_75852

48. Misoprostol [mart.]

49. Dsstox_gsid_20897

50. Misoprostol [usp-rs]

51. Misoprostol [who-dd]

52. Mls000028863

53. Misoprostol (jan/usp/inn)

54. Misoprostol, 1% In Cellulose

55. Gtpl1936

56. Dtxsid7020897

57. Bdbm85606

58. Chebi:94387

59. Misoprostol, >=99% (hplc)

60. Misoprostol [orange Book]

61. Regid_for_cid_5282381

62. Hms2090l10

63. Hms3648f03

64. Hms3715k08

65. Misoprostol [ep Monograph]

66. Misoprostol [usp Monograph]

67. Ex-a1774

68. Hy-b0610

69. Tox21_112010

70. Arthrotec Component Misoprostol

71. Akos015899652

72. Ccg-221093

73. Db00929

74. Prost-13-en-1-oic Acid, 11,16-dihydroxy-16-methyl-9-oxo-, Methyl Ester, (11alpha,13e)-

75. Smp1_000193

76. Misoprostol Component Of Arthrotec

77. Ncgc00162445-01

78. Ncgc00162445-03

79. (+-)-methyl (1r,2r,3r)-3-hydroxy-2-((e)-(4rs)-4-hydroxy-4-methyl-1-octenyl)-5-oxocyclopentaneheptanoate

80. 62015-39-8

81. As-83017

82. Smr000058558

83. Cas-59122-46-2

84. D00419

85. Ab00513745-05

86. 122m462

87. A832173

88. Q416025

89. Q-201409

90. Sr-01000695425-2

91. Sr-01000695425-4

92. Brd-a50310035-001-01-6

93. Misoprostol, European Pharmacopoeia (ep) Reference Standard

94. Misoprostol, United States Pharmacopeia (usp) Reference Standard

95. (+/-) Methyl 11alpha, 16-dihydroxy-16-methyl-9-oxoprost-13e-en-1-oate

96. (+/-) Methyl 11alpha,16-dihydroxy-16-methyl-9-oxoprost-13e-en-1-oate

97. (+/-) Methyl-11alpha,16-dihydroxy-16-methyl-9-oxoprost-13e-en-1-oate

98. (+/-) Methyl-11alpha,16-dihydroxy-16-methyl-9-oxoprost13e-en-1-oate

99. (+/-)-(11a,13e)-11,16-dihydroxy-16-methyl-9-oxo-prost-13-en-1-oic Acid Methyl Ester

100. (11alpha,13e)-11,16-dihydroxy-16-methyl-9-oxoprosta-13-ene-1-oic Acid Methyl Ester

101. 9-oxo-11alpha,16-dihydroxy-16-methyl-prost-13e-en-1-oic Acid, Methyl Ester

102. Misoprostol For System Suitability, European Pharmacopoeia (ep) Reference Standard

103. (+/-)-methyl (1r,2r,3r)-3-hydroxy-2-((e)-(4rs)-4-hydroxy-4-methyl-1-octenyl)-5-oxocyclopentaneheptanoate

104. Methyl 7-[(1r,2r,3r)-2-[(e)-4-methyl-4-oxidanyl-oct-1-enyl]-3-oxidanyl-5-oxidanylidene-cyclopentyl]heptanoate

105. Methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(1e)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate

106. Prost-13-en-1-oic Acid, 11,16-dihydroxy-16-methyl-9-oxo-, Methyl Ester, (11.alpha.,13e)-(+/-)-

107. Prost-13-en-1-oic Acid, 11,16-dihydroxy-16-methyl-9-oxo-, Methyl Ester, (11alpha,13e)-(+-)-

108. Rel-methyl 7-((1r,2r,3r)-3-hydroxy-2-((e)-4-hydroxy-4-methyloct-1-en-1-yl)-5-oxocyclopentyl)heptanoate

2.4 Create Date
2005-10-11
3 Chemical and Physical Properties
Molecular Weight 382.5 g/mol
Molecular Formula C22H38O5
XLogP33.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count14
Exact Mass382.27192431 g/mol
Monoisotopic Mass382.27192431 g/mol
Topological Polar Surface Area83.8 Ų
Heavy Atom Count27
Formal Charge0
Complexity487
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameCytotec
PubMed HealthMisoprostol (By mouth)
Drug ClassesAntiulcer, Protectant, Endocrine-Metabolic Agent
Drug LabelMisoprostol oral tablets contain either 100 mcg or 200 mcg of misoprostol, a synthetic prostaglandin E1 analog.Misoprostol contains approximately equal amounts of the two diastereomers presented below with their enantiomers indicated by ():Misopros...
Active IngredientMisoprostol
Dosage FormTablet
RouteOral
Strength0.2mg; 0.1mg
Market StatusPrescription
CompanyGd Searle

2 of 4  
Drug NameMisoprostol
PubMed HealthMisoprostol (By mouth)
Drug ClassesAntiulcer, Protectant, Endocrine-Metabolic Agent
Drug LabelMisoprostol oral tablets contain either 100 mcg or 200 mcg of misoprostol, a synthetic prostaglandin E1 analog.Misoprostol contains approximately equal amounts of the two diastereomers presented below with their enantiomers indicated by ():Misopros...
Active IngredientMisoprostol
Dosage FormTablet
RouteOral
Strength0.1mg; 0.2mg
Market StatusPrescription
CompanyNovel Labs; Ivax Sub Teva Pharms

3 of 4  
Drug NameCytotec
PubMed HealthMisoprostol (By mouth)
Drug ClassesAntiulcer, Protectant, Endocrine-Metabolic Agent
Drug LabelMisoprostol oral tablets contain either 100 mcg or 200 mcg of misoprostol, a synthetic prostaglandin E1 analog.Misoprostol contains approximately equal amounts of the two diastereomers presented below with their enantiomers indicated by ():Misopros...
Active IngredientMisoprostol
Dosage FormTablet
RouteOral
Strength0.2mg; 0.1mg
Market StatusPrescription
CompanyGd Searle

4 of 4  
Drug NameMisoprostol
PubMed HealthMisoprostol (By mouth)
Drug ClassesAntiulcer, Protectant, Endocrine-Metabolic Agent
Drug LabelMisoprostol oral tablets contain either 100 mcg or 200 mcg of misoprostol, a synthetic prostaglandin E1 analog.Misoprostol contains approximately equal amounts of the two diastereomers presented below with their enantiomers indicated by ():Misopros...
Active IngredientMisoprostol
Dosage FormTablet
RouteOral
Strength0.1mg; 0.2mg
Market StatusPrescription
CompanyNovel Labs; Ivax Sub Teva Pharms

4.2 Therapeutic Uses

Abortifacient Agents, Nonsteroidal; Anti-Ulcer Agents; Oxytocics

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


Misoprostol is indicated for the prevention of gastric ulcer associated with the use of nonsteroidal anti-inflammatory drugs (NSAIDs), including aspirin, in patients at high risk of complications from gastric ulcer, such as the elderly, and in patients with concomitant disease or patients at high risk of developing gastric ulceration, such as those with a history of ulcer. /Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 2085


Misoprostol is indicated in the short-term treatment of duodenal ulcer. /NOT included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 2085


The efficacy and tolerability of mifepristone in combo with misoprostol for termination of early pregnancy (up to 49 days of amenorrhea) are established.

PMID:8574255 Aub'eny E et al; Int J Fertil Menopausal Stud 40 (Suppl 2): 85-91 (1995)


For more Therapeutic Uses (Complete) data for MISOPROSTOL (8 total), please visit the HSDB record page.


4.3 Drug Warning

Misoprostol is contraindicated during pregnancy. Studies in humans have shown that misoprostol causes an increase in the frequency and intensity of uterine contractions. Misoprostol administration has also been associated with a higher incidence of uterine bleeding and expulsion of uterine contents. Miscarriages caused by misoprostol are likely to be incomplete, resulting in very serious medical complications, sometimes requiring hospitalization and surgery, and possibly causing infertility.

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 2086


Patients of childbearing potential may use misoprostol if nonsteroidal anti-inflammatory drug (NSAID) therapy is required and patient is at high risk of complications from gastric ulcers associated with the use of NSAIDs, or is at high risk of developing gastric ulceration. Such patients must comply with effective contraceptive measures, must have had a negative serum pregnancy test within 2 weeks prior to initiation of therapy and must start misoprostol therapy only on the second or third day of the next normal menstrual period.

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 2086


It is unlikely that misoprostol is distributed into breast milk since it is rapidly metabolized throughout the body. however, it is not known if the active metabolite, misoprostol acid, is distributed into breast milk. Therefore, administration of misoprostol to nursing women is not recommended because of the potential distribution of misoprostol acid, which could cause significant diarrhea in the nursing infant.

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 2086


Misoprostol generally is well tolerated. The frequency of adverse effects does not appear to be affected by patient age in adults. The most frequent adverse effects associated with misoprostol therapy involve the GI tract (e.g., diarrhea, nausea, abdominal pain).

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 2169


For more Drug Warnings (Complete) data for MISOPROSTOL (8 total), please visit the HSDB record page.


4.4 Drug Indication

Misoprostol is indicated as a tablet to reduce the risk of NSAID induced gastric ulcers but not duodenal ulcers in high risk patients. Misoprostol is also formulated in combination with diclofenac to treat symptoms of osteoarthritis or rheumatoid arthritis in patients with a high risk of developing gastric ulcers. Misoprostol is used off label for the management of miscarriages, prevention of post partum hemorrhage, and is also used alone or in combination with mifepristone in other countries for first trimester abortions.


FDA Label


Induction of labour


Induction of labour


5 Pharmacology and Biochemistry
5.1 Pharmacology

Misoprostol is a prostaglandin E1 analog used to reduce the risk of NSAID induced gastric ulcers by reducing secretion of gastric acid from parietal cells. Misoprostol is also used to manage miscarriages and used alone or in combination with mifepristone for first trimester abortions. An oral dose of misoprostol has an 8 minute onset of action and a duration of action of approximately 2 hours, a sublingual dose has an 11 minute onset of action and a duration of action of approximately 3 hours, a vaginal dose has a 20 minute onset of action and a duration of action of approximately 4 hours, and a rectal dose has a 100 minute onset of action and a duration of action of approximately 4 hours.


5.2 MeSH Pharmacological Classification

Oxytocics

Drugs that stimulate contraction of the myometrium. They are