2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one

• ChemBase编号: 1091
• 分子式: C13H16ClNO
• 平均质量: 237.72524
• 单一同位素质量: 237.09204182
• SMILES: Clc1c(C2(NC)CCCCC2=O)cccc1
• Canonical SMILES: CNC1(CCCCC1=O)c1ccccc1Cl
• InChI: InChI=1S/C13H16ClNO/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14/h2-3,6-7,15H,4-5,8-9H2,1H3
• InChIKey: YQEZLKZALYSWHR-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one
• IUPAC传统名: (+-)-ketamine; ketamine
• 商标名: CLSTA 20; Esketamine; Ketaject; Ketalar; Ketalar base; Ketanest; Ketolar
• 别名: (-)-Ketamine; (S)-(-)-Ketamine; (S)-Ketamine; CI 581 base; Ketamine HCL; Ketamine Base; l-Ketamine; Ketamine

登记号

• CAS号: 6740-88-1
• PubChem SID: 160964554; 46508295
• PubChem CID: 3821
• CHEBI ID: 6121
• ATC码: N01AX03
• CHEMBL: 742
• Chemspider ID: 3689
• DrugBank ID: DB01221
• KEGG ID: D08098
• 美国药典/FDA物质标识码: 690G0D6V8H
• 维基百科标题: Ketamine

理论计算性质

JChem

• Acid pKa: 18.783304
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 1.4100732
• LogD (pH = 7.4): 3.0185769
• Log P: 3.3473027
• 摩尔折射率: 65.5538 cm^3
• 极化性: 25.949158 Å^3
• 极化表面积: 29.1 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: 2.69
• LOG S: -3.71
• 溶解度: 4.64e-02 g/l

分子性质

理化性质

• 熔点: 262°C (503.6°F)
• 疏水性(logP): 2.9

药理学性质

• 给药途径: IV, IM, Insufflated, oral, topical
• 依赖倾向: Medium
• 排泄: renal (>90%)
• 半衰期: 2.5–3 hours.
• 代谢: Hepatic, primarily by CYP3A4
• 法定药品分级: CD (UK); S8 (Australia); Schedule I (Canada); Schedule III (US)
• 妊娠期药物分类: B

详细说明

DrugBank - DB01221

• Drug Groups: approved
• Description: A cyclohexanone derivative used for induction of anesthesia. Its mechanism of action is not well understood, but ketamine can block NMDA receptors (receptors, N-methyl-D-aspartate) and may interact with sigma receptors. [PubChem]
• Indication: For use as the sole anesthetic agent for diagnostic and surgical procedures that do not require skeletal muscle relaxation.
• Pharmacology: Ketamine is a rapid-acting general anesthetic producing an anesthetic state characterized by profound analgesia, normal pharyngeal-laryngeal reflexes, normal or slightly enhanced skeletal muscle tone, cardiovascular and respiratory stimulation, and occasionally a transient and minimal respiratory depression. Ketamine is indicated as the sole anesthetic agent for diagnostic and surgical procedures that do not require skeletal muscle relaxation. The anesthetic state produced by Ketamine has been termed “dissociative anesthesia” in that it appears to selectively interrupt association pathways of the brain before producing somesthetic sensory blockade. It may selectively depress the thalamoneocortical system before significantly obtunding the more ancient cerebral centers and pathways (reticularactivating and limbic systems).
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Rapidly absorbed following parenteral administration.
• Half Life: 2.5-3 hours.
• References: Harrison NL, Simmonds MA: Quantitative studies on some antagonists of N-methyl D-aspartate in slices of rat cerebral cortex. Br J Pharmacol. 1985 Feb;84(2):381-91. [Pubmed] ; Bergman SA: Ketamine: review of its pharmacology and its use in pediatric anesthesia. Anesth Prog. 1999 Winter;46(1):10-20. [Pubmed] ; Bonanno FG: Ketamine in war/tropical surgery (a final tribute to the racemic mixture). Injury. 2002 May;33(4):323-7. [Pubmed] ; Lankenau SE, Sanders B, Bloom JJ, Hathazi D, Alarcon E, Tortu S, Clatts MC: First injection of ketamine among young injection drug users (IDUs) in three U.S. cities. Drug Alcohol Depend. 2007 Mar 16;87(2-3):183-93. Epub 2006 Sep 18. [Pubmed] ; Reboso Morales JA, Gonzalez Miranda F: [Ketamine] Rev Esp Anestesiol Reanim. 1999 Mar;46(3):111-22. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Harrison NL, Simmonds MA: Quantitative studies on some antagonists of N-methyl D-aspartate in slices of rat cerebral cortex. Br J Pharmacol. 1985 Feb;84(2):381-91. Pubmed
• Bergman SA: Ketamine: review of its pharmacology and its use in pediatric anesthesia. Anesth Prog. 1999 Winter;46(1):10-20. Pubmed
• Bonanno FG: Ketamine in war/tropical surgery (a final tribute to the racemic mixture). Injury. 2002 May;33(4):323-7. Pubmed
• Lankenau SE, Sanders B, Bloom JJ, Hathazi D, Alarcon E, Tortu S, Clatts MC: First injection of ketamine among young injection drug users (IDUs) in three U.S. cities. Drug Alcohol Depend. 2007 Mar 16;87(2-3):183-93. Epub 2006 Sep 18. Pubmed
• Reboso Morales JA, Gonzalez Miranda F: [Ketamine] Rev Esp Anestesiol Reanim. 1999 Mar;46(3):111-22. Pubmed