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15-methylprostaglandin F2alpha-tromethamine

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Also known as: Hemabate, 58551-69-2, Carboprost trometamol, Prostinfenem, Carboprost trometanol, Carboprost (tromethamine)

Molecular Formula

C₂₅H₄₇NO₈

Molecular Weight

489.6 g/mol

InChI Key

UMMADZJLZAPZAW-XOWPVRJPSA-N

FDA UNII

U4526F86FJ

Carboprost Tromethamine is the tromethamine salt of the (15S)-15 methyl analogue of naturally occurring prostaglandin F2 alpha (PGF2 alpha) with oxytocic activity. Mimicking endogenous PGF2 alpha, carboprost activates prostaglandin F receptor, a G-protein coupled receptor, on smooth muscle cells, thereby resulting in smooth muscle contractions. When administered intramuscularly on gravid subjects, this agent induces myometrium contractions, thereby initiating luteolysis and consequently parturition. Furthermore, carboprost's action on vascular smooth muscle and gastrointestinal tract sphincters leads to raised blood pressure and induces vomiting or diarrhea, respectively.

1 2D Structure

Carboprost 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-hydroxy-3-methyloct-1-enyl]cyclopentyl]hept-5-enoic acid

2.1.2 InChI

InChI=1S/C21H36O5.C4H11NO3/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25;5-4(1-6,2-7)3-8/h5,7,12,14,16-19,22-23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25);6-8H,1-3,5H2/b7-5-,14-12+;/t16-,17-,18+,19-,21+;/m1./s1

2.1.3 InChI Key

UMMADZJLZAPZAW-XOWPVRJPSA-N

2.1.4 Canonical SMILES

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

2.1.5 Isomeric SMILES

CCCCC[C@@](C)(/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

U4526F86FJ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 15-methylprostaglandin F2alpha-tromethamine

2. Carboprost Trometamol

3. Hemabate

4. Prostin M-15

2.3.2 Depositor-Supplied Synonyms

1. Hemabate

2. 58551-69-2

3. Carboprost Trometamol

4. Prostinfenem

5. Carboprost Trometanol

6. Carboprost (tromethamine)

7. U-32921e

8. U-32,921e

9. U4526f86fj

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

11. 2-amino-2-(hydroxymethyl)propane-1,3-diol;(z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(e,3s)-3-hydroxy-3-methyloct-1-enyl]cyclopentyl]hept-5-enoic Acid

12. 15-methyl Prostaglandin F2alpha

13. Prostin / 15m

14. Unii-u4526f86fj

15. Carboprost Tromethamine [usan]

16. Hemabate (tn)

17. Prostin/15

18. Carboprost Tromethamine [usan:usp]

19. U 32921e

20. Carboprost Tromethanimine

21. 15-methyl Pgf2 Alpha

22. Prostin/15m

23. 15(s)15-methyl Pgf2-alpha Tromethamine Salt

24. Carboprost Tromethamine Salt

25. Schembl433085

26. 15(s)15-methyl Prostaglandin F2-alpha Tromethamine

27. Carboprost Tromethamine (usp)

28. Chembl1237105

29. (15s)-15-methylprostaglandin F(sub 2alpha) Tromethamine

30. Dtxsid601015618

31. Hy-a0195

32. Carboprost Trometamol [mart.]

33. Akos037435222

34. Carboprost Trometamol [who-dd]

35. Carboprost Tromethamine [usp-rs]

36. Carboprost Tromethamine Salt [mi]

37. Carboprost Trometamol [ep Monograph]

38. Carboprost Tromethamine [orange Book]

39. Cs-0017541

40. Carboprost Tromethamine [usp Monograph]

41. D00682

42. E78557

43. U32921

44. 551c692

45. J-507750

46. Q18578732

47. (15s)-15-methylprostaglandin F(sub 2.alpha.) Tromethamine

48. (5z,9?,11?,15e,15s)-9,11,15-trihydroxy-15-methylprosta-5,13-dien-1-oic Acid Tris(hydroxymethyl)aminomethane Salt

49. 2-amino-2-(hydroxymethyl)propane-1,3-diol (e)-7-((1s,3s,5r)-3,5-dihydroxy-2-((s,z)-3-hydroxy-3-methyloct-1-en-1-yl)cyclopentyl)hept- 5-enoate

50. 2-amino-2-(hydroxymethyl)propane-1,3-diol (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((s,e)-3-hydroxy-3-methyloct-1-en-1-yl)cyclopentyl)hept-5-enoate

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

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

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₄₇NO₈
Molecular Weight	489.6 g/mol
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	15
Exact Mass	489.33016746 g/mol
Monoisotopic Mass	489.33016746 g/mol
Topological Polar Surface Area	185 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	527
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 Information

1 of 2
Drug Name	Hemabate
PubMed Health	Carboprost Tromethamine (Injection)
Drug Classes	Endocrine-Metabolic Agent
Drug Label	HEMABATE Sterile Solution, an oxytocic, contains the tromethamine salt of the (15S)-15 methyl analogue of naturally occurring prostaglandin F2 in a solution suitable for intramuscular injection.Carboprost tromethamine is the established name for th...
Active Ingredient	Carboprost tromethamine
Dosage Form	Injectable
Route	Injection
Strength	eq 0.25mg base/ml
Market Status	Prescription
Company	Pharmacia And Upjohn

2 of 2
Drug Name	Hemabate
PubMed Health	Carboprost Tromethamine (Injection)
Drug Classes	Endocrine-Metabolic Agent
Drug Label	HEMABATE Sterile Solution, an oxytocic, contains the tromethamine salt of the (15S)-15 methyl analogue of naturally occurring prostaglandin F2 in a solution suitable for intramuscular injection.Carboprost tromethamine is the established name for th...
Active Ingredient	Carboprost tromethamine
Dosage Form	Injectable
Route	Injection
Strength	eq 0.25mg base/ml
Market Status	Prescription
Company	Pharmacia And Upjohn

5 Pharmacology and Biochemistry

5.1 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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Prostaglandins [CS]; Prostaglandin Analog [EPC]

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