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Dinoprost Tromethamine

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ACTIVE PHARMA INGREDIENTS

6 API Suppliers, 1 USDMF, 2 CEP/COS, 2 NDC API, 3 VMF, 6 Listed Suppliers

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1 USDMF
2 CEP/COS
2 NDC API
3 VMF
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5 FDF Dossiers, 1 FDA Orange Book, 2 Canada, 2 Listed Dossiers

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1 FDA Orange Book
2 Canada
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1 Nanjing Well Pharmaceutical, 2 Actylis, 1 Finar

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2 Parenteral, 2 Topical, 1 Solubilizers

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2 Topical
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2 APIs

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1 Health Canada Patents

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1 Health Canada Patents

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1 EDQM , 1 USP , 1 Others

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1 EDQM
1 USP
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Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

USDMF

CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

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API REF. PRICE (USD/KG)

$ 0

MARKET PLACE

API

FDF

0INTERMEDIATES

FINISHED DOSAGE FORMULATIONS

FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

South Africa

Listed Dossiers

0 DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

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Chemistry

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Also known as: 38562-01-5, Dinolytic, Zinoprost, Prostin f2 alpha, Dinoprost trometamol, Pgf2alpha tham

Molecular Formula

C₂₄H₄₅NO₈

Molecular Weight

475.6 g/mol

InChI Key

IYGXEHDCSOYNKY-RZHHZEQLSA-N

FDA UNII

CT6BBQ5A68

Dinoprost Tromethamine is a synthetic analogue of the naturally occurring prostaglandin F2 alpha. Prostaglandin F2 alpha stimulates myometrial activity, relaxes the cervix, inhibits corpus luteal steroidogenesis, and induces luteolysis by direct action on the corpus luteum. (NCI04)

1 2D Structure

Dinoprost Tromethamine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-amino-2-(hydroxymethyl)propane-1,3-diol;(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.C4H11NO3/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;5-4(1-6,2-7)3-8/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25);6-8H,1-3,5H2/b7-4-,13-12+;/t15-,16+,17+,18-,19+;/m0./s1

2.1.3 InChI Key

IYGXEHDCSOYNKY-RZHHZEQLSA-N

2.1.4 Canonical SMILES

CCCCCC(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O.C(C(CO)(CO)N)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.C(C(CO)(CO)N)O

2.2 Other Identifiers

2.2.1 UNII

CT6BBQ5A68

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Lutalyse

2. Minprostin F2 Alpha

3. Pgf2alpha Tromethamine

4. Prostaglandin F2alpha Tromethamine

5. Prostin F2

6. Prostin F2 Alpha

2.3.2 Depositor-Supplied Synonyms

1. 38562-01-5

2. Dinolytic

3. Zinoprost

4. Prostin F2 Alpha

5. Dinoprost Trometamol

6. Pgf2alpha Tham

7. Prostalmon F

8. Pgf2-alpha Tham

9. Prostaglandin F2alpha Tham

10. Panacelan F Tromethamine Salt

11. Prostaglandin F2-alpha Tham

12. Prostaglandin F2a Tromethamine

13. Pgf2a Tham

14. Dinoprost Tromethamine Salt

15. Enzaprost F Compd. With Trisamine

16. U-14,583e

17. Prostaglandin F(sub 2a) Tromethamine

18. Dinoprost (tromethamine Salt)

19. Lutalyse

20. (e,z)-(1r,2r,3r,5s)-7-(3,5-dihydroxy-2-((3s)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic Acid Compound With 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)

21. Prostamate

22. Nsc-196515

23. Prostaglandin F2alpha Tris Salt

24. Pronalgon F

25. Ct6bbq5a68

26. U-14583e

27. Mls000028821

28. Chebi:31502

29. Dinoprost, Trometamol Salt

30. Tham Pgf2-alpha

31. Ensaprost

32. Smr000058792

33. U-14-583e

34. Lutalyse (veterinary)

35. Pgf2-alpha Tris Salt

36. Pgf2-alpha Tromethamine

37. Prostaglandin F2a Tris Salt

38. Pgf2-alpha Tromethamine Salt

39. Protaglandin F2-alpha-tham Salt

40. Prostaglandin F2-alpha Tham Salt

41. Prostaglandin F2-alpha Tromethamine

42. Tromethamine Prostaglandin F2-alpha

43. 2-amino-2-(hydroxymethyl)propane-1,3-diol (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((s,e)-3-hydroxyoct-1-en-1-yl)cyclopentyl)hept-5-enoate

44. Prostaglandin F2

45. A

46. Einecs 254-002-3

47. Prostin F2 Alpha (tn)

48. U 14585

49. Unii-ct6bbq5a68

50. Nsc 196515

51. Dinoprost Tromethamine (jan/usp)

52. Prostaglandin F2?

53. 5-heptenoic Acid, 7-(3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-, Tham

54. 7-(3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-5-heptenoic Acid, Tromethamine Salt

55. Dinoprost Tromethamine [usan:usp:jan]

56. Pgf2.alpha. Tham

57. Pgf2alpha-tham

58. Prostaglandinf2atrissalt

59. Prostaglandin F2a Tham

60. Opera_id_1888

61. 7-[3, Tromethamine Salt

62. Dinoprost Tromethamine Powder

63. 1,3-propanediol, 2-amino-2-(hydroxymethyl)-, (5z,9alpha,11alpha,13e,15s)-9,11,15-trihydroxyprosta-5,13-dien-1-oate (salt)

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

65. Prosta-5,13-dien-1-oic Acid, 9,11,15-trihydroxy-, (5z,9alpha,11alpha,13e,15s)-, Compd. With 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)

66. Schembl203377

67. Prostaglandin F2.alpha. Tham

68. Chembl1200896

69. Dtxsid1045582

70. Regid_for_cid_5282415

71. Hms2230j05

72. Ex-a4115

73. Dinoprost Tromethamine [jan]

74. Dinoprost Trometamol [mart.]

75. Dinoprost Tromethamine [usan]

76. Hy-12956a

77. Nsc196515

78. S5056

79. Dinoprost Trometamol [who-dd]

80. Dinoprost Tromethamine [vandf]

81. Akos015920234

82. Ccg-269499

83. Db01160

84. Dinoprost Tromethamine [usp-rs]

85. Pgf2 Alpha (prostaglandin F2 Alpha )

86. Prostaglandin F2alpha Tromethamine Salt

87. Prostin F2 Alpha,3-propanediol (1:1)

88. Prosta-5,13-dien-1-oic Acid, 9,11,15-trihydroxy-, (5z,9.alpha.,11.alpha.,13e,15s)-, Compd. With 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)

89. Prostaglandin F2alpha (tromethamine Salt)

90. U-14

91. Dinoprost Trometamol [ep Monograph]

92. Dinoprost Tromethamine [green Book]

93. Dinoprost Tromethamine [orange Book]

94. B7617

95. Dinoprost Tromethamine [usp Monograph]

96. D01352

97. Prostaglandin F2.alpha.,3-propanediol (1:1)

98. Prostaglandin F2.alpha. Tromethamine Salt

99. 562d015

100. 562p015

101. Sr-01000946463

102. Sr-01000946463-1

103. Prostaglandin F2.alpha. Tromethamine Salt [mi]

104. Wln: L5tj Aq B2u4vq C1u1yq5 Dq &q1xz1q1q

105. Dinolytic; Pgf2-alpha Tham; Zinoprost; Prostin F2 Alpha

106. Prostaglandin F2alpha Tris Salt, >=99%, Synthetic, Powder

107. Prostaglandin F2alpha Tris Salt, Synthetic, Cell Culture Tested

108. Prostaglandin F2alpha Tromethamine Salt;dinoprost Tromethamine

109. Dinoprost Trometamol, European Pharmacopoeia (ep) Reference Standard

110. 5-heptenoic Acid,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-, Tham

111. Dinoprost Compd. With 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)

112. Dinoprost Tromethamine, United States Pharmacopeia (usp) Reference Standard

113. 9?,11?,15s-trihydroxy-prosta-5z,13e-dien-1-oic Acid Tris(hydroxymethyl)aminomethane Salt

114. (e,2r,3r,5s)-7-[3,5-dihydroxy-2-[(3s)-(3-hydroxy-1-octenyl)]cyclopentyl]-5-heptenoic Acid Compound With 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)@component Of Prostin F2 Alpha, Injectable

115. 2-amino-2-(hydroxymethyl)propane-1,3-diol(z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((s,e)-3-hydroxyoct-1-en-1-yl)cyclopentyl)hept-5-enoate

116. Prosta-5, (5z,9.alpha.,11.alpha.,13e,15s)-9,11,15-trihydroxy- Compd. With (trimethylolamino)methane

117. Prosta-5, 9,11,15-trihydroxy-, (5z,9.alpha.,11.alpha.,13e,15s)-, Compd. With 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)

2.4 Create Date

2005-10-11

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₄₅NO₈
Molecular Weight	475.6 g/mol
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	15
Exact Mass	475.31451739 g/mol
Monoisotopic Mass	475.31451739 g/mol
Topological Polar Surface Area	185 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	486
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	2

4 Drug and Medication Information

4.1 Drug Indication

Used for aborting second-trimester pregnancy (between the twelfth to eighteenth week of gestation) and in incomplete abortion or for therapeutic abortion in cases of intrauterine fetal death and congenital abnormalities incompatible with life. Also used at low-doses for medically indicated induction of labor at term. Also injected intra-arterially for use as a vasodilator to assist in angiography.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Dinoprost tromethamine is the tromethamine (THAM) salt of the naturally occurring prostaglandin F2_alpha. Prostaglandin F2_alpha has several pharmacologic effects on the female reproductive system, including stimulation of myometrial activity, relaxation of the cervix, inhibition of steroidogenesis by corpora lutea, and can potentially lyse corpora lutea.

5.2 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.)

5.3 Absorption, Distribution and Excretion

Absorption

Slowly absorbed from the amniotic fluid into systemic circulation.

5.4 Metabolism/Metabolites

Enzymatic dehydrogenation primarily in the maternal lungs and also in the liver.

5.5 Biological Half-Life

The half-life of dinoprost in amniotic fluid is 3 to 6 hours. The plasma half-life of dinoprost after intravenous administration is reported to be less than 1 minute.

5.6 Mechanism of Action

Dinoprost tromethamine appears to act directly on the myometrium, but this has not been completely established. Dinoprost stimulates myometrial contractions (via its interaction with the prostaglandin receptors) in the gravid uterus that are similar to the contractions that occur in the term uterus during labor. These contractions are usually sufficient to cause abortion. Uterine response to prostaglandins increases gradually throughout pregnancy. Dinoprost also facilitates cervical dilatation and softening.

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