(4R,7R)-N-[(2S)-1-hydroxypropan-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: 1122
• 分子式: C19H23N3O2
• 平均质量: 325.40482
• 单一同位素质量: 325.17902699
• SMILES: O=C(N[C@H](CO)C)[C@H]1CN([C@H]2C(=C1)c1c3c(C2)c[nH]c3ccc1)C
• Canonical SMILES: OC[C@@H](NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)C
• InChI: InChI=1S/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11-,13+,17+/m0/s1
• InChIKey: WVVSZNPYNCNODU-XTQGRXLLSA-N

名称和登记号

名称

• IUPAC标准名: (4R,7R)-N-[(2S)-1-hydroxypropan-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: ergonovine
• 商标名: Ergotrate
• 别名: Ergotrate maleate; Ergometrine; Ergobasine; Ergonovine

登记号

• CAS号: 60-79-7
• PubChem SID: 46506922; 160964585
• PubChem CID: 443884

理论计算性质

JChem

• Acid pKa: 14.998553
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): -1.3230772
• LogD (pH = 7.4): 0.43092284
• Log P: 1.070696
• 摩尔折射率: 95.0519 cm^3
• 极化性: 37.447586 Å^3
• 极化表面积: 68.36 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.53
• LOG S: -3.01
• 溶解度: 3.21e-01 g/l

分子性质

理化性质

• 溶解度: 2.68 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]
• 疏水性(logP): 0.9

详细说明

DrugBank - DB01253

• Drug Groups: approved
• Description: An ergot alkaloid with uterine and vascular smooth muscle contractile properties. [PubChem]
• Indication: Used to treat postpartum haemorrhage and postabortion haemorrhage in patients with uterine atony.
• Pharmacology: Ergonovine belongs to the group of medicines known as ergot alkaloids. These medicines are usually given to stop excessive bleeding that sometimes occurs after abortion or a baby is delivered. They work by causing the muscle of the uterus to contract.
• Toxicity: The principal symptoms of overdose are convulsions and gangrene. Other symptoms include bradycardia, confusion, diarrhoea, dizziness, dyspnoea, drowsiness, fast and/or weak pulse, miosis, hypercoagulability, loss of consciousness, nausea and vomiting, numbness and coldness of the extremities, pain in the chest, peripheral vasoconstriction, respiratory depression, rise or fall in blood pressure, severe cramping of the uterus, tachycardia, tingling, and unusual thirst.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Absorption is rapid and complete after oral or intramuscular administration.
• Half Life: t_{1/2 α}=10 minutes; t_{1/2 β}=2 hours
• Elimination: Thought to be eliminated by non-renal mechanisms (i.e. hepatic metabolism, excretion in feces)
• External Links: Wikipedia; Drugs.com