基本情報
- CAS
57432-61-8- 標準SMILES
CC[C@@H](CO)NC(=O)[C@@H]1C=C2c3cccc4[nH]cc(c34)C[C@H]2N(C)C1.O=C(O)/C=C\C(=O)O- InChIKey
NOFOWWRHEPHDCY-DAUURJMHSA-N- 分子式
- C24H29N3O6
- 平均分子量
- 455.5 g/mol
- 単同位体質量
- 455.20563565
概要
Methylergonovine Maleate is an ergoline alkaloid. It has a role as a geroprotector.
名称と識別子
- 優先名称
- Methergine
- IUPAC
- (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
- 現地名
- メチルエルゴメトリンマレイン酸塩
- 英語名
- Methylergonovine maleate salt
- 分子式
- C20H25N3O2.C4H4O4
- 分子量
- 455.5
名称と別名
Methylergonovine maleate57432-61-8MethergineMaleic acid, methyl ergonovineIR84JPZ1RKNSC-757104DTXSID1023283Methylergonovine maleate (USP)Methylergonovine maleate [USP]NSC186067RefChem:55614DTXCID901476300
名称をさらに表示
メチルエルゴメトリンマレイン酸塩パルタンMメテナリン9,10-ジデヒドロ-N-[(S)-1-(ヒドロキシメチル)プロピル]-6-メチルエルゴリン-8β-カルボアミド·マレイン酸マレイン酸メチルエルゴメトリンマレイン酸メチルエルゴメトリンFメチレジールデルガニンメチルエルゴメトリン·マレイン酸メテルギンメチルエルゴメトリンマレイン酸塩 (JP17)ErezinDerganinPartan MMetenarinMetherginRyegonovin
260-734-4Ergoline-8-carboxamide, 9,10-didehydro-N-((1S)-1-(hydroxymethyl)propyl)-6-methyl-,(8beta)-,(2Z)-2-butenedioate(1:1)(salt)Methylergometrine maleateMethyl Ergonovine Maleate SaltMethylergometrine (maleate)ErezingenMethylergobasine maleate(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
物性
構造計算による物性
- 極性表面積
- 143 Ų
- 水素結合供与体数
- 5
- 水素結合受容体数
- 7
- 回転可能結合数
- 6
- 重原子数
- 33
- 形式電荷
- 0
- 複雑度
- 668
実験および物理化学的性質
Human Drugs
Breast Feeding; Lactation; Milk, Human; Ergot Alkaloids; Oxytocics
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section183.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 1720 C · 1720C (dec)
- 沸点
- 561.98 °C · 561.98°C (rough estimate)
- 比重(密度)
- 1.2744 · 1.2744 (rough estimate)
- 屈折率
- 1.65 · 1.6500 (estimate)
- 貯蔵温度
- -20 °C · -20°C Freezer
- 溶解性
- 2 O: · H2O: 25 mg/mL
- 外見
- Solid
- 色
- 白い
- 水溶解度
- 25 mM · Soluble to 25 mM in water
- InChIKey
- NOFOWWRHEPHDCY-GTRJEQPHNA-N
- SMILES
- C(/C(=O)O)=C/C(=O)O.CN1C[C@H](C(=O)N[C@H](CO)CC)C=C2C3C=CC=C4NC=C(C=34)C[C@@]12[H] |&1:11,15,32,r|
化学的性質
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P260, P261, P262, P263, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P318, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
危険有害性情報
Other Safety InformationIMAP assessments - Ergoline-8-carboxamide, 9,10-didehydro-N-[1-(hydroxymethyl)propyl]-6-methyl-, [8.beta.(S)]-, (Z)-2-butenedioate (1:1) (salt): Environment tier I assessment
Hazard Classes and Categories
Acute Tox. 3 (100%)
Acute Tox. 3 (100%)
毒性情報
Treatment
Treatment for ergotism consists of vasodilators, anticoagulants and low molecular weight dextrans. If necessary, a sympathetic nerve blockade may be carried out, such as brachial plexus blockade. Temporary sedation (e.g. haloperidol) will be necessary in hallucination and diazepam is used for convulsions. There is no specific antidote. (L1921)
Health EffectsIngestion of ergoline alkaloids is known to cause the disease ergotism. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. (A2913)
Exposure RoutesIngestion (L1920). Absorption is rapid after oral (60% bioavailability) and intramuscular (78% bioavailability) administration.
化学と産業
薬理情報
Metabolism/Metabolites
Hepatic, with extensive first-pass metabolism. 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. Half Life: 3.39 hours
FDA Pharmacological Classification
METHYLERGONOVINE MALEATE
Ergolines [CS]; Ergot Derivative [EPC]
MeSH Pharmacological Classification
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)
用途と製造
Uses
Methylergometrine is a synthetic analogue of ergonovine, an alkaloid of the ergoline family that occurs in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi like other ergoline alkaloids. Methylergometrine is a blood vessel constrictor and smooth muscle agonist most commonly used to prevent or control excessive bleeding following childbirth and spontaneous or elective abortion. It also causes uterine contractions to aid in expulsion of retained products of conception after a missed abortion (miscarriage in which all or part of the fetus remains in the uterus) and to help deliver the placenta after childbirth. The drug is currently prepared via reaction of (+)-lysergic acid with L-(+)-aminobutanol, using different coupling reagents, and is available under the name Methergine as tablets or injection (IM or IV) or in liquid form to be taken orally. (L1918, L1923)
応用分野
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