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Methylergonovine Maleate

Synopsis, Chemistry

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Also known as: Methylergometrine maleate, 57432-61-8, Methergine, Erezingen, Methylergobasine maleate, Ir84jpz1rk

Molecular Formula

C₂₄H₂₉N₃O₆

Molecular Weight

455.5 g/mol

InChI Key

NOFOWWRHEPHDCY-DAUURJMHSA-N

FDA UNII

IR84JPZ1RK

A homolog of ERGONOVINE containing one more CH2 group. (Merck Index, 11th ed)

1 2D Structure

Methylergonovine Maleate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;(Z)-but-2-enedioic acid

2.1.2 InChI

InChI=1S/C20H25N3O2.C4H4O4/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13;5-3(6)1-2-4(7)8/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25);1-2H,(H,5,6)(H,7,8)/b;2-1-/t13-,14+,18-;/m1./s1

2.1.3 InChI Key

NOFOWWRHEPHDCY-DAUURJMHSA-N

2.1.4 Canonical SMILES

CCC(CO)NC(=O)C1CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C.C(=CC(=O)O)C(=O)O

2.1.5 Isomeric SMILES

CC[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C.C(=C\C(=O)O)\C(=O)O

2.2 Other Identifiers

2.2.1 UNII

IR84JPZ1RK

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Mthergin

2. Methergin

3. Methergine

4. Methylergobasin

5. Methylergometrin

6. Methylergometrine

7. Methylergometrine Maleate

8. Methylergonovine

2.3.2 Depositor-Supplied Synonyms

1. Methylergometrine Maleate

2. 57432-61-8

3. Methergine

4. Erezingen

5. Methylergobasine Maleate

6. Ir84jpz1rk

7. Methylergometrine (maleate)

8. Nsc-757104

9. Methylergonovine Maleate [usp]

10. Methylergonovine Maleate (usp)

11. Methylergonovine Maleate Salt

12. Usaf Uctl-8

13. Maleic Acid, Methyl Ergonovine

14. Einecs 260-734-4

15. Unii-ir84jpz1rk

16. Ergonovine, Methyl-, Maleate (1:1)

17. Methyl Ergonovine Maleate Salt

18. Methergine Maleate

19. Methergine (tn)

20. 9,10-didehydro-n-((s)-1-(hydroxymethyl)propyl)-6-methylergoline-8beta-carboxamide Maleate (1:1) (salt)

21. Schembl239437

22. Spectrum1500404

23. Chebi:6874

24. Chembl1200843

25. Dtxsid1023283

26. Hms501b19

27. Methylergometrine Maleate (jp17)

28. Hms1920n11

29. Hms2091f22

30. Hms2096k09

31. Hms3262o10

32. Hms3414f15

33. Hms3678f15

34. Hms3713k09

35. Methylergonovinium Bimaleate

36. Pharmakon1600-01500404

37. Tox21_500794

38. Ccg-39168

39. Methylergonovine Maleate [mi]

40. Nsc757104

41. Akos024282479

42. Lp00794

43. Methylergometrine Maleate [jan]

44. Nsc 757104

45. Methylergonovine Maleate [vandf]

46. Methylergometrine Maleate [mart.]

47. Methylergonovine Maleate [usp-rs]

48. Ncgc00261479-01

49. 9,10-didehydro-n-[(s)-1-(hydroxymethyl)propyl]-6-methylergoline-8beta-carboxamide Maleate Salt

50. Ergoline-8-carboxamide, 9,10-didehydro-n-((1s)-1-(hydroxymethyl)propyl)-6-methyl-, (8beta)-, (2z)-2-butenedioate (1:1) (salt)

51. Ergoline-8-carboxamide, 9,10-didehydro-n-(1-(hydroxymethyl)propyl)-6-methyl-, (8beta(s))-, (z)-2-butenedioate (1:1) (salt)

52. Methylergometrine Maleate [who-dd]

53. Hy-100988

54. B6347

55. Cs-0020668

56. Eu-0100794

57. Methylergonovine Maleate [orange Book]

58. D00680

59. M 2776

60. Methylergometrine Maleate [ep Monograph]

61. Methylergonovine Maleate [usp Monograph]

62. 432m618

63. N-[alpha-(hydroxymethyl)propyl]-d-lysergamide Maleate

64. Q27280864

65. Methylergometrine Maleate, European Pharmacopoeia (ep) Reference Standard

66. [8?(s)]-9,10-didehydro-n-[1-(hydroxymethyl)propyl]-6-methylergoline-8-carboxamide Maleate

67. Methylergometrine For System Suitability, European Pharmacopoeia (ep) Reference Standard

68. Methylergonovine Maleate, United States Pharmacopeia (usp) Reference Standard

69. (8beta)-9,10-didehydro-n-[(1s)-1-(hydroxymethyl)propyl]-6-methyl-ergoline-8-carbox-amide Maleate

70. 7054-07-1

71. 9,10-didehydro-n-((s)-1-(hydroxymethyl)propyl)-6-methylergoline-8.beta.-carboxamide Maleate

72. Ergoline-8-carboxamide, 9,10-didehydro-n-(1-(hydroxymethyl)propyl)-6-methyl-, (8.beta.(s))-, (z)-2-butenedioate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₂₉N₃O₆
Molecular Weight	455.5 g/mol
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	6
Exact Mass	455.20563565 g/mol
Monoisotopic Mass	455.20563565 g/mol
Topological Polar Surface Area	143 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	668
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Methergine
Drug Label	Methergine(methylergonovine maleate) is a semi-synthetic ergot alkaloid used for the prevention and controlof postpartum hemorrhage.Methergine is available in sterile ampuls of 1 mL, containing 0.2mg methylergonovine maleate for intramuscular...
Active Ingredient	Methylergonovine maleate
Dosage Form	Tablet; Injectable
Route	Injection; Oral
Strength	0.2mg/ml; 0.2mg
Market Status	Prescription
Company	Edison Theraps

2 of 4
Drug Name	Methylergonovine maleate
PubMed Health	Methylergonovine (Injection)
Drug Classes	Uterine Stimulant
Drug Label	Methylergonovine Maleate is a semi-synthetic ergot alkaloid used for the prevention and control of postpartum hemorrhage.Methylergonovine Maleate Tablets, USP is available in tablets for oral ingestion containing 0.2 mg methylergonovine maleate....
Active Ingredient	Methylergonovine maleate
Dosage Form	Tablet; Injectable
Route	Injection; Oral
Strength	0.2mg/ml; 0.2mg
Market Status	Prescription
Company	Novel Labs; Ergoject; Luitpold

3 of 4
Drug Name	Methergine
Drug Label	Methergine(methylergonovine maleate) is a semi-synthetic ergot alkaloid used for the prevention and controlof postpartum hemorrhage.Methergine is available in sterile ampuls of 1 mL, containing 0.2mg methylergonovine maleate for intramuscular...
Active Ingredient	Methylergonovine maleate
Dosage Form	Tablet; Injectable
Route	Injection; Oral
Strength	0.2mg/ml; 0.2mg
Market Status	Prescription
Company	Edison Theraps

4 of 4
Drug Name	Methylergonovine maleate
PubMed Health	Methylergonovine (Injection)
Drug Classes	Uterine Stimulant
Drug Label	Methylergonovine Maleate is a semi-synthetic ergot alkaloid used for the prevention and control of postpartum hemorrhage.Methylergonovine Maleate Tablets, USP is available in tablets for oral ingestion containing 0.2 mg methylergonovine maleate....
Active Ingredient	Methylergonovine maleate
Dosage Form	Tablet; Injectable
Route	Injection; Oral
Strength	0.2mg/ml; 0.2mg
Market Status	Prescription
Company	Novel Labs; Ergoject; Luitpold

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

Ergot Derivative [EPC]; Ergolines [CS]