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    Carboprost Tromethamine

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    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

    2D Structure

    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 Weight 489.6 g/mol
    Molecular Formula C25H47NO8
    Hydrogen Bond Donor Count8
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count15
    Exact Mass489.33016746 g/mol
    Monoisotopic Mass489.33016746 g/mol
    Topological Polar Surface Area185 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity527
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count2
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameHemabate
    PubMed HealthCarboprost Tromethamine (Injection)
    Drug ClassesEndocrine-Metabolic Agent
    Drug LabelHEMABATE 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 IngredientCarboprost tromethamine
    Dosage FormInjectable
    RouteInjection
    Strengtheq 0.25mg base/ml
    Market StatusPrescription
    CompanyPharmacia And Upjohn

    2 of 2  
    Drug NameHemabate
    PubMed HealthCarboprost Tromethamine (Injection)
    Drug ClassesEndocrine-Metabolic Agent
    Drug LabelHEMABATE 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 IngredientCarboprost tromethamine
    Dosage FormInjectable
    RouteInjection
    Strengtheq 0.25mg base/ml
    Market StatusPrescription
    CompanyPharmacia 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]