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Chemistry

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Also known as: Methylergometrine, Methylergobasin, Methylergometrin, Methylergobasine, Methylergobrevin, Methylergonovin

Molecular Formula

C₂₀H₂₅N₃O₂

Molecular Weight

339.4 g/mol

InChI Key

UNBRKDKAWYKMIV-QWQRMKEZSA-N

FDA UNII

W53L6FE61V

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

Methylergonovine is an Ergot Derivative.

1 2D Structure

Methylergonovine

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

2.1.2 InChI

InChI=1S/C20H25N3O2/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/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25)/t13-,14+,18-/m1/s1

2.1.3 InChI Key

UNBRKDKAWYKMIV-QWQRMKEZSA-N

2.1.4 Canonical SMILES

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

2.1.5 Isomeric SMILES

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

2.2 Other Identifiers

2.2.1 UNII

W53L6FE61V

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 Maleate

2.3.2 Depositor-Supplied Synonyms

1. Methylergometrine

2. Methylergobasin

3. Methylergometrin

4. Methylergobasine

5. Methylergobrevin

6. Methylergonovin

7. 113-42-8

8. Methylergometrine Maleate

9. Ergotyl

10. Methergine

11. Methergen

12. Partergin

13. Basofortina

14. Methylergometrine (inn)

15. Ergometrine, Methyl-

16. W53l6fe61v

17. Chembl1201356

18. Me 277

19. D-lysergic Acid-(+)-butanolamide-(2)

20. (6ar,9r)-n-[(2s)-1-hydroxybutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxamide

21. Ncgc00017258-04

22. Metilergometrina

23. Metilergometrinio

24. Dsstox_cid_3283

25. Methylergometrinum

26. Metilergometrina [dcit]

27. Dsstox_rid_76957

28. Lysergic Acid Butanolamide

29. Dsstox_gsid_23283

30. Methylergometrine [inn]

31. Methylergometrine [inn:ban]

32. Lysergamide, N-((s)-1-(hydroxymethyl)propyl)-

33. Methylergometrinum [inn-latin]

34. Metilergometrinio [inn-spanish]

35. (8beta)-n-[(2s)-1-hydroxybutan-2-yl]-6-methyl-9,10-didehydroergoline-8-carboxamide

36. Ergotyl (tn)

37. D-lysergic Acid-dl-hydroxybutylamide-2

38. Hsdb 3364

39. N-(alpha-(hydroxymethyl)propyl)-d-lysergamide

40. Einecs 204-027-0

41. Unii-w53l6fe61v

42. Cas-113-42-8

43. H8d

44. 9,10-didehydro-n-(1-(hydroxymethyl)propyl)-6-methylergoline-8-carboxamide

45. 9,10-didehydro-n-(alpha-(hydroxymethyl)propyl)-6-methyl-ergoline-8-beta-carboxamide

46. Ergoline-8-carboxamide, 9,10-didehydro-n-(1-(hydroxymethyl)propyl)-6-methyl-, (8beta(s))-

47. Spectrum_000263

48. Prestwick3_000374

49. Spectrum2_000613

50. Spectrum3_000502

51. Spectrum5_001879

52. Biomol-nt_000154

53. Lopac0_000794

54. Schembl78176

55. Bspbio_000527

56. Bspbio_002023

57. Gtpl150

58. Kbioss_000743

59. Methylergonovine [mi]

60. Divk1c_000357

61. Spbio_000546

62. D-lysergic Acid 1-butanolamide

63. Bpbio1_000442

64. Bpbio1_000581

65. Methylergometrine [hsdb]

66. Methylergonovine [vandf]

67. Chebi:92607

68. Kbio1_000357

69. Kbio2_000743

70. Kbio2_003311

71. Kbio2_005879

72. Kbio3_001523

73. Dtxsid00904978

74. Ninds_000357

75. Methylergometrine [who-dd]

76. Tox21_110809

77. Bdbm50330860

78. Zinc95619105

79. Tox21_110809_1

80. Ccg-204878

81. Db00353

82. Sdccgsbi-0050771.p005

83. (8beta)-n-[(1s)-1-(hydroxymethyl)propyl]-6-methyl-9,10-didehydroergoline-8-carboxamide

84. Ergoline-8-beta-carboxamide, 9,10-didehydro-n-((s)-1-(hydroxymethyl)propyl)-6-methyl-

85. Idi1_000357

86. Ncgc00017258-03

87. Ncgc00017258-05

88. Ncgc00017258-06

89. Ncgc00017258-08

90. Ncgc00017258-12

91. Ncgc00024646-02

92. Ncgc00024646-03

93. Sbi-0050771.p004

94. Ab00514664

95. D08207

96. Ab00053497_03

97. Q424477

98. Brd-k34685430-001-01-1

99. Brd-k34685430-050-04-2

100. Brd-k34685430-050-06-7

101. (4r,7r)-n-[(2s)-1-hydroxybutan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

102. (8.beta.)-n-((1s)-1-(hydroxymethyl)propyl)-6-methyl-9,10-didehydroergoline-8-carboxamide

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₅N₃O₂
Molecular Weight	339.4 g/mol
XLogP3	2.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Exact Mass	339.19467705 g/mol
Monoisotopic Mass	339.19467705 g/mol
Topological Polar Surface Area	68.4 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	549
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
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 Information

1 of 2
Drug Name	Methergine
PubMed Health	Methylergonovine (Injection)
Drug Classes	Uterine Stimulant
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 2
Drug Name	Methergine
PubMed Health	Methylergonovine (Injection)
Drug Classes	Uterine Stimulant
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

4.2 Therapeutic Uses

Oxytocics

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)

For routine management after delivery of the placenta; postpartum atony and hemorrhage; subinvolution. Under full obstetric supervision, it may be given in the second stage of labor following delivery of the anterior shoulder. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for METHERGINE - methylergonovine maleate tablet, coated (February 2010). Available from, as of March 6, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=b91d1729-2e8e-4398-9a0d-02763bcfe284

Methylergonovine is a first-line agent for the treatment of postpartum hemorrhage; methylergonovine usually is given after oxytocin. Administration of parenteral ergot alkaloids during the third stage of labor decreases mean blood loss and the incidence of postpartum blood loss of 500 mL or more. /NOT included in US product label/

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 3307

Ergonovine and methylergonovine should not be used for the induction or augmentation of labor.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 3307

For more Therapeutic Uses (Complete) data for METHYLERGONOVINE (6 total), please visit the HSDB record page.

4.3 Drug Warning

/Contraindications of methylergonovine therapy include:/ hypertension; toxemia; pregnancy; and hypersensitivity.

Use of Methergine is contraindicated during pregnancy because of its uterotonic effects.

This drug should not be administered iv routinely because of the possibility of inducing sudden hypertensive and cerebrovascular accidents. If iv administration is considered essential as a lifesaving measure, methylergonovine should be given slowly over a period of no less than 60 seconds with careful monitoring of blood pressure. Intra-arterial or periarterial injection should be strictly avoided.

Caution should be exercised in the presence of sepsis, obliterative vascular disease, hepatic or renal involvement. Also use with caution during the second stage of labor. The necessity for manual removal of a retained placenta should occur only rarely with proper technique and adequate allowance of time for its spontaneous separation.

For more Drug Warnings (Complete) data for METHYLERGONOVINE (13 total), please visit the HSDB record page.

4.4 Drug Indication

For the prevention and control of excessive bleeding following vaginal childbirth

5 Pharmacology and Biochemistry

5.1 Pharmacology

Methylergometrine is a semisynthetic ergot alkaloid and a derivative of ergonovine and is used for the prevention and control of postpartum and post-abortion hemorrhage. In general, the effects of all the ergot alkaloids appear to results from their actions as partial agonists or antagonists at adrenergic, dopaminergic, and tryptaminergic receptors. The spectrum of effects depends on the agent, dosage, species, tissue, and experimental or physiological conditions. All of the alkaloids of ergot significantly increase the motor activity of the uterus. After small doses contractions are increased in force or frequency, or both, but are followed by a normal degree of relaxation. As the dose is increased, contractions become more forceful and prolonged, resting tonus is markedly increased, and sustained contracture can result.

5.2 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.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

METHYLERGONOVINE

5.3.2 FDA UNII

W53L6FE61V

5.3.3 Pharmacological Classes

Ergot Derivative [EPC]; Ergolines [CS]

5.4 ATC Code

G - Genito urinary system and sex hormones

G02 - Other gynecologicals

G02A - Uterotonics

G02AB - Ergot alkaloids

G02AB01 - Methylergometrine

5.5 Absorption, Distribution and Excretion

Absorption

Absorption is rapid after oral (60% bioavailability) and intramuscular (78% bioavailability) administration.

Route of Elimination

Ergot alkaloids are mostly eliminated by hepatic metabolism and excretion, and the decrease in bioavailability following oral administration is probably a result of first-pass metabolism in the liver.

Volume of Distribution

56.1 0 L

A delayed gastrointestinal absorption (Tmax about 3 hours) of methylergonovine tablets might be observed in postpartum women during continuous treatment with this oxytocic agent.

Pharmacokinetic studies following an iv injection have shown that methylergonovine is rapidly distributed from plasma to peripheral tissues within 2-3 minutes or less. The bioavailability after oral administration was reported to be about 60% with no accumulation after repeated doses. During delivery, with intramuscular injection, bioavailability increased to 78%. Ergot alkaloids are mostly eliminated by hepatic metabolism and excretion, and the decrease in bioavailability following oral administration is probably a result of first-pass metabolism in the liver.

Bioavailability studies conducted in fasting healthy female volunteers have shown that oral absorption of a 0.2 mg methylergonovine tablet was fairly rapid with a mean peak plasma concentration of 3243 +/- 1308 pg/mL observed at 1.12 +/- 0.82 hours.

For a 0.2 mg intramuscular injection, a mean peak plasma concentration of 5918 +/- 1952 pg/mL was observed at 0.41 +/- 0.21 hours. The extent of absorption of the tablet, based upon methylergonovine plasma concentrations, was found to be equivalent to that of the i.m. solution given orally, and the extent of oral absorption of the i.m. solution was proportional to the dose following administration of 0.1, 0.2, and 0.4 mg.

For more Absorption, Distribution and Excretion (Complete) data for METHYLERGONOVINE (15 total), please visit the HSDB record page.

5.6 Metabolism/Metabolites

Hepatic, with extensive first-pass metabolism.

Drug Facts and Comparisons 2012. Wolters Kluwer Health St. Louis, MO 2012, p. 452

5.7 Biological Half-Life

3.39 hours

The plasma level decline was biphasic with a mean elimination half-life of 3.39 hours (range 1.5 to 12.7 hours).

Plasma concentrations of methylergonovine appear to decline in a biphasic manner. Following IV administration of methylergonovine to adults with normal renal function, the half-life of the drug in the initial phase (t1/2 alpha?) reportedly ranges from about 1-5 minutes and the half-life in the terminal phase (t1/2 beta) ranges from about 0.5-2 hours.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 3308

5.8 Mechanism of Action

Methylergometrine acts directly on the smooth muscle of the uterus and increases the tone, rate, and amplitude of rhythmic contractions through binding and the resultant antagonism of the dopamine D1 receptor. Thus, it induces a rapid and sustained tetanic uterotonic effect which shortens the third stage of labor and reduces blood loss.

Methylergonovine acts directly on the smooth muscle of the uterus and increases the tone, rate, and amplitude of rhythmic contractions. Thus, it induces a rapid and sustained tetanic uterotonic effect which shortens the third stage of labor and reduces blood loss.

Ergonovine maleate and methylergonovine maleate are pharmacologically similar. Both drugs directly stimulate contractions of uterine and vascular smooth muscle. Following administration of usual therapeutic doses of ergonovine or methylergonovine, intense contractions of the uterus are produced and are usually followed by periods of relaxation. Larger doses of the drugs, however, produce sustained, forceful contractions followed by only short or no periods of relaxation. The drugs increase the amplitude and frequency of uterine contractions and uterine tone which in turn impede uterine blood flow. Ergonovine and methylergonovine also increase contractions of the cervix.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 3308

Ergonovine and methylergonovine produce vasoconstriction, mainly of capacitance vessels; increased central venous pressure, elevated blood pressure, and, rarely, peripheral ischemia and gangrene may result. Methylergonovine reportedly may interfere with prolactin secretion, but this effect has not been definitely established.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 3308

Ergot alkaloids are antagonists of actions of 5-hydroxytryptamine and of certain metabolic actions of catecholamines. /Ergot alkaloids/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 876

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