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    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
    Methylergonovine Maleate
    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 Weight 455.5 g/mol
    Molecular Formula C24H29N3O6
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count6
    Exact Mass455.20563565 g/mol
    Monoisotopic Mass455.20563565 g/mol
    Topological Polar Surface Area143 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity668
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameMethergine
    Drug LabelMethergine(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 IngredientMethylergonovine maleate
    Dosage FormTablet; Injectable
    RouteInjection; Oral
    Strength0.2mg/ml; 0.2mg
    Market StatusPrescription
    CompanyEdison Theraps

    2 of 4  
    Drug NameMethylergonovine maleate
    PubMed HealthMethylergonovine (Injection)
    Drug ClassesUterine Stimulant
    Drug LabelMethylergonovine 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 IngredientMethylergonovine maleate
    Dosage FormTablet; Injectable
    RouteInjection; Oral
    Strength0.2mg/ml; 0.2mg
    Market StatusPrescription
    CompanyNovel Labs; Ergoject; Luitpold

    3 of 4  
    Drug NameMethergine
    Drug LabelMethergine(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 IngredientMethylergonovine maleate
    Dosage FormTablet; Injectable
    RouteInjection; Oral
    Strength0.2mg/ml; 0.2mg
    Market StatusPrescription
    CompanyEdison Theraps

    4 of 4  
    Drug NameMethylergonovine maleate
    PubMed HealthMethylergonovine (Injection)
    Drug ClassesUterine Stimulant
    Drug LabelMethylergonovine 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 IngredientMethylergonovine maleate
    Dosage FormTablet; Injectable
    RouteInjection; Oral
    Strength0.2mg/ml; 0.2mg
    Market StatusPrescription
    CompanyNovel 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]

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