(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

• ChemBase编号: 237
• 分子式: C20H25N3O2
• 平均质量: 339.4314
• 单一同位素质量: 339.19467706
• SMILES: O=C(N[C@@H](CC)CO)[C@H]1CN([C@H]2C(=C1)c1c3c(C2)c[nH]c3ccc1)C
• Canonical SMILES: CC[C@H](NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CO
• 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
• InChIKey: UNBRKDKAWYKMIV-QWQRMKEZSA-N

名称和登记号

名称

• IUPAC标准名: (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
• IUPAC传统名: methylergonovine
• 商标名: Basofortina; Metenarin; Methergen; Methergin; Methergine; Norforms; Partergin; Ryegonovin; Spametrin-M
• 别名: Methylergometrine; Methylergonovin; Methylergometrin; Methylergobrevin; Methylergobasine; Methylergobasin; methylergonovine maleate; Methylergonovine

登记号

• CAS号: 113-42-8
• PubChem SID: 160963700; 46507746
• PubChem CID: 8226

理论计算性质

JChem

• Acid pKa: 14.997192
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): -0.80055475
• LogD (pH = 7.4): 0.95344526
• Log P: 1.5932183
• 摩尔折射率: 99.5759 cm^3
• 极化性: 39.292522 Å^3
• 极化表面积: 68.36 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.74
• LOG S: -3.22
• 溶解度: 2.04e-01 g/l

分子性质

理化性质

• 溶解度: 25 mg/mL
• 疏水性(logP): 1.2

详细说明

DrugBank - DB00353

• Drug Groups: approved
• Description: A homolog of ergonovine containing one more CH2 group. (Merck Index, 11th ed)
• Indication: For the prevention and control of excessive bleeding following vaginal childbirth
• Pharmacology: Methylergonovine 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.
• Toxicity: Signs and symptoms of overexposure: hypertension, seizures, headache, hypotension, nausea, and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, with extensive first-pass metabolism.
• Absorption: Absorption is rapid after oral (60% bioavailability) and intramuscular (78% bioavailability) administration.
• Half Life: 3.39 hours
• 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.
• Distribution: * 56.1 ± 0 L
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com