(1R,9R,10R)-17-(prop-2-en-1-yl)-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-trien-4-ol

• ChemBase编号: 387
• 分子式: C19H25NO
• 平均质量: 283.4079
• 单一同位素质量: 283.19361443
• SMILES: [C@@]123[C@H]([C@H](N(CC2)CC=C)Cc2c1cc(cc2)O)CCCC3
• Canonical SMILES: C=CCN1CC[C@@]23[C@H]([C@H]1Cc1c3cc(cc1)O)CCCC2
• InChI: InChI=1S/C19H25NO/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19/h2,6-7,13,16,18,21H,1,3-5,8-12H2/t16-,18+,19+/m0/s1
• InChIKey: OZYUPQUCAUTOBP-QXAKKESOSA-N

名称和登记号

名称

• IUPAC标准名: (1R,9R,10R)-17-(prop-2-en-1-yl)-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-trien-4-ol; (1R,9R,10R)-17-(prop-2-en-1-yl)-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2,4,6-trien-4-ol
• IUPAC传统名: levallorphan
• 商标名: Levallofano [Dcit]; Levallorphane [INN-French]; Levallorphanum [INN-Latin]; Levalorfano [INN-Spanish]; Lorfan; Naloxiphan
• 别名: Levallorphan

登记号

• CAS号: 152-02-3
• PubChem SID: 46505682; 160963850
• PubChem CID: 5359371
• CHEMBL: 1254682
• Chemspider ID: 4514267
• DrugBank ID: DB00504
• 美国药典/FDA物质标识码: 353613BU4U
• 维基百科标题: Levallorphan

理论计算性质

JChem

• Acid pKa: 10.3627615
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 0.6962585
• LogD (pH = 7.4): 1.9874055
• Log P: 3.7553673
• 摩尔折射率: 87.2436 cm^3
• 极化性: 33.84198 Å^3
• 极化表面积: 23.47 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.91
• LOG S: -4.05
• 溶解度: 2.52e-02 g/l

分子性质

理化性质

• 溶解度: 633 mg/L
• 疏水性(logP): 3.9

药理学性质

• 给药途径: Oral
• 法定药品分级: Rx-only

详细说明

DrugBank - DB00504

• Drug Groups: approved
• Description: An opioid antagonist with properties similar to those of naloxone; in addition it also possesses some agonist properties. It should be used cautiously; levallorphan reverses severe opioid-induced respiratory depression but may exacerbate respiratory depression such as that induced by alcohol or other non-opioid central depressants. (From Martindale, The Extra Pharmacopoeia, 30th ed, p683)
• Indication: For the complete or partial reversal of narcotic depression, including respiratory depression, induced by opioids.
• Pharmacology: Levallorphan, an opioid antagonist similar to naloxone, is used to treat drug overdoses. Levallorphan differs from naloxone in that it also possesses some agonist properties. It is an analogue of levelorphanol that counteracts the actions of narcotic analgesics such as morphine. It is used especially in the treatment of respiratory depression due to narcotic overdoses. Levallorphan prevents or reverses the effects of opioids including respiratory depression, sedation and hypotension. Also, it can reverse the psychotomimetic and dysphoric effects of agonist-antagonists such as pentazocine.
• Toxicity: Oral, rat LD₅₀: 109±4 mg/kg
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Rapidly absorbed.
• Half Life: 1 hour