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    Carbetocin Acetate

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: 37025-55-1, Pabal, Carbetocino, Carbetocinum, Chebi:59204, Lv-101
    Molecular Formula
    C45H69N11O12S
    Molecular Weight
    988.2  g/mol
    InChI Key
    NSTRIRCPWQHTIA-DTRKZRJBSA-N
    FDA UNII
    88TWF8015Y
    Carbetocin is a long-acting synthetic agonist analogue of human oxytocin, with antihemorrhagic and uterotonic activities. Upon administration, carbetocin targets, binds to and activates peripheral oxytocin receptors that are present on the smooth musculature of the uterus. This causes uterus contractions and prevents excessive bleeding after childbirth, particularly following Cesarean section, and may be used to decrease blood loss during hysteroscopic myomectomy.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[(3R,6S,9S,12S,15S)-6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-[(2S)-butan-2-yl]-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentazacycloicosane-3-carbonyl]pyrrolidine-2-carboxamide
    2.1.2 InChI
    InChI=1S/C45H69N11O12S/c1-6-25(4)38-44(66)51-28(15-16-34(46)57)40(62)52-31(21-35(47)58)41(63)54-32(23-69-18-8-10-37(60)50-30(42(64)55-38)20-26-11-13-27(68-5)14-12-26)45(67)56-17-7-9-33(56)43(65)53-29(19-24(2)3)39(61)49-22-36(48)59/h11-14,24-25,28-33,38H,6-10,15-23H2,1-5H3,(H2,46,57)(H2,47,58)(H2,48,59)(H,49,61)(H,50,60)(H,51,66)(H,52,62)(H,53,65)(H,54,63)(H,55,64)/t25-,28-,29-,30-,31-,32-,33-,38-/m0/s1
    2.1.3 InChI Key
    NSTRIRCPWQHTIA-DTRKZRJBSA-N
    2.1.4 Canonical SMILES
    CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CSCCCC(=O)NC(C(=O)N1)CC2=CC=C(C=C2)OC)C(=O)N3CCCC3C(=O)NC(CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
    2.1.5 Isomeric SMILES
    CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSCCCC(=O)N[C@H](C(=O)N1)CC2=CC=C(C=C2)OC)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
    2.2 Other Identifiers
    2.2.1 UNII
    88TWF8015Y
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-deamino-1-monocarba-2-(tyr(ome))-oxytocin

    2. Dcomot

    3. Depotocin

    4. Oxytocin, 1-desamino-1-monocarba-(tyr(ome))(2)-

    5. Oxytocin, 1-desamino-1-monocarba-(tyrosine(o-methyl))(2)-

    2.3.2 Depositor-Supplied Synonyms

    1. 37025-55-1

    2. Pabal

    3. Carbetocino

    4. Carbetocinum

    5. Chebi:59204

    6. Lv-101

    7. Carbetocinum [inn-latin]

    8. Carbetocino [inn-spanish]

    9. Deamino-2-o-methyltyrosine-1-carbaoxytocin

    10. 1-butyric Acid-2-(3-(p-methoxyphenyl)-l-alanine)oxytocin

    11. 88twf8015y

    12. 1-butanoic Acid-2-(o-methyl-l-tyrosine)-1-carbaoxytocin

    13. Fe 992097

    14. Fe-992097

    15. 7-pentaoxo-1-thia-4,7,10,13,16-pentazacycloicosane-3-carbonyl]pyrrolidine-2-carboxamide

    16. C45h69n11o12s

    17. (2s)-n-[(2s)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[(3r,6s,9s,12s,15s)-6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-[(2s)-butan-2-yl]-15-[(4-methoxyphenyl)methyl]-5,8,11,14,1

    18. Carbetocin [mi]

    19. Carbetocin [inn]

    20. Carbetocin [usan]

    21. Carbetocin [mart.]

    22. Carbetocin [who-dd]

    23. Schembl39224

    24. Carbetocin [usan:inn:ban]

    25. Unii-88twf8015y

    26. Chembl3301668

    27. Gtpl11169

    28. Dtxsid90897527

    29. 1-carbaoxytocin, 1-butanoic Acid-2-(o-methyl-l-tyrosine)-

    30. (2s)-n-[(2s)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[(3r,6s,9s,12s,15s)-6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-[(2s)-butan-2-yl]-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentazacycloicosane-3-carbonyl]pyrrolidine-2-carboxamide

    31. Who 5014

    32. Einecs 253-312-6

    33. Bdbm50044677

    34. Mfcd01076600

    35. Akos015994647

    36. Zinc150338703

    37. Db01282

    38. Hs-2007

    39. Ncgc00485451-02

    40. Hy-17573

    41. 025c551

    42. A823503

    43. Carbetocin 100 Microg/ml In Acetonitrile:methanol

    44. Q5037853

    45. 1-buttersaeure-2-(3-(4-methoxyphenyl)-l-alanin)oxytocin

    46. 1-carboxytocin, 1-butanoic Acid-2-(o-methyl-l-tyrosine)-

    47. Ethyl?2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate

    48. (2s)-2-{[(2s)-1-{[(3r,6s,9s,12s,15s)-12-[(2s)-butan-2-yl]-9-(2-carbamoylethyl)-6-(carbamoylmethyl)-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentaazacycloicosan-3-yl]carbonyl}pyrrolidin-2-yl]formamido}-n-(carbamoylmethyl)-4-methylpentanamide

    49. 1-[6-(2-amino-2-oxo-ethyl)-9-(3-amino-3-oxo-propyl)-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-12-sec-butyl-1-thia-4,7,10,13,16-pentazacycloicosane-3-carbonyl]-n-[1-[(2-amino-2-oxo-ethyl)carbamoyl]-3-methyl-butyl]pyrrolidine-2-carboxamide; 2,2,2-t;carbetocin

    50. 1-{[(3r,6s,9s,12s,15s)-6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-[(2s)-butan-2-yl]-15-(4-methoxybenzyl)-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentaazacycloicosan-3-yl]carbonyl}-l-prolyl-l-leucylglycinamide

    51. Glycinamide, N-(4-mercapto-1-oxobutyl)-o-methyl-l-tyrosyl-l-isoleucyl-l-glutaminyl-l-asparaginyl-l-cysteinyl-l-prolyl-l-leucyl-, Cyclic (1->5)-thioether

    52. O-methyl-n-(4-sulfanylbutanoyl)-l-tyrosyl-l-isoleucyl-l-glutaminyl-l-asparaginyl-l-cysteinyl-l-prolyl-l-leucyl-glycinamide Cyclic (1->5)-thioether

    2.4 Create Date
    2007-08-20
    3 Chemical and Physical Properties
    Molecular Weight 988.2 g/mol
    Molecular Formula C45H69N11O12S
    XLogP3-1.1
    Hydrogen Bond Donor Count10
    Hydrogen Bond Acceptor Count13
    Rotatable Bond Count18
    Exact Mass987.48478785 g/mol
    Monoisotopic Mass987.48478785 g/mol
    Topological Polar Surface Area388 Ų
    Heavy Atom Count69
    Formal Charge0
    Complexity1850
    Isotope Atom Count0
    Defined Atom Stereocenter Count8
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Used to control postpartum hemorrhage and bleeding after giving birth.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Carbetocin is a drug used to control postpartum hemorrhage, bleeding after giving birth. It is sold under the trade name Duratocin. It is an analogue of oxytocin, and its action is similar to that of oxytocin; it causes contraction of the uterus.

    5.2 MeSH Pharmacological Classification

    Delayed-Action Preparations

    Dosage forms of a drug that act over a period of time by controlled-release processes or technology. (See all compounds classified as Delayed-Action Preparations.)

    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 ATC Code

    H - Systemic hormonal preparations, excl. sex hormones and insulins

    H01 - Pituitary and hypothalamic hormones and analogues

    H01B - Posterior pituitary lobe hormones

    H01BB - Oxytocin and analogues

    H01BB03 - Carbetocin

    5.4 Absorption, Distribution and Excretion

    Absorption

    Bioavailability is 80% following intramuscular injection.

    5.5 Biological Half-Life

    40 minutes

    5.6 Mechanism of Action

    Carbetocin binds to oxytocin receptors present on the smooth musculature of the uterus, resulting in rhythmic contractions of the uterus, increased frequency of existing contractions, and increased uterine tone. The oxytocin receptor content of the uterus is very low in the non-pregnant state, and increases during pregnancy, reaching a peak at the time of delivery.