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Carbetocin Acetate

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Chemistry

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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

Carbetocin Acetate

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 Formula	C₄₅H₆₉N₁₁O₁₂S
Molecular Weight	988.2 g/mol
XLogP3	-1.1
Hydrogen Bond Donor Count	10
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	18
Exact Mass	987.48478785 g/mol
Monoisotopic Mass	987.48478785 g/mol
Topological Polar Surface Area	388 Å²
Heavy Atom Count	69
Formal Charge	0
Complexity	1850
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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