disodium 2,6-bis(propan-2-yl)phenoxymethyl phosphate

• ChemBase编号: 4453
• 分子式: C13H19Na2O5P
• 平均质量: 332.240261
• 单一同位素质量: 332.0765489
• SMILES: CC(C)c1c(c(ccc1)C(C)C)OCOP(=O)([O-])[O-].[Na+].[Na+]
• Canonical SMILES: CC(c1cccc(c1OCOP(=O)([O-])[O-])C(C)C)C.[Na+].[Na+]
• InChI: InChI=1S/C13H21O5P.2Na/c1-9(2)11-6-5-7-12(10(3)4)13(11)17-8-18-19(14,15)16;;/h5-7,9-10H,8H2,1-4H3,(H2,14,15,16);;/q;2*+1/p-2
• InChIKey: LWYLQNWMSGFCOZ-UHFFFAOYSA-L

名称和登记号

名称

• IUPAC标准名: disodium 2,6-bis(propan-2-yl)phenoxymethyl phosphate
• IUPAC传统名: dipotassium 2,6-diisopropylphenoxymethyl phosphate
• 商标名: Lusedra
• 别名: Fospropofol

登记号

• CAS号: 258516-87-9
• PubChem SID: 99443268; 160967885
• PubChem CID: 3038497

理论计算性质

JChem

• Acid pKa: 1.4372194
• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 1.192822
• LogD (pH = 7.4): 0.28466505
• Log P: 3.6020257
• 摩尔折射率: 70.6341 cm^3
• 极化性: 28.436102 Å^3
• 极化表面积: 81.65 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.31
• LOG S: -2.29
• 溶解度: 1.71e+00 g/l

详细说明

DrugBank - DB06716

• Drug Groups: approved
• Description: Fospropofol is a prodrug and gets converted into Propofol in the liver. Fospropofol is, therefore, a short acting hypnotic/sedative/anesthetic agent. It has uses in general anesthesia, procedure sedation, and veterinary medicine.
• Indication: Used for induction and/or maintenance of anaesthesia and for management of refractory status epilepticus.
• Pharmacology: Fospropofol is a prodrug of propofol, a sedative hypnotic drug. Unlike propofol, fospropofol is water soluble and can be administered in an aqueous solution. Fospropofol is metabolized to propofol by phosphatases into propofol, fomaldehyde and phosphate. Propofol is a sedative-hypnotic agent for use in the induction and maintenance of anesthesia or sedation. Intravenous injection of a therapeutic dose of propofol produces hypnosis rapidly with minimal excitation, usually within 40 seconds from the start of an injection (the time for one arm-brain circulation).
• Toxicity: Overdosage may increase pharmacologic and adverse effects or cause death.
• Biotransformation: Hepatically metabolized mainly by glucuronidation at the C1-hydroxyl. Hydroxylation of the benzene ring to 4-hydroxypropofol may also occur via CYP2B6 and 2C9 with subsequent conjugation to sulfuric and/or glucuronic acid. Hydroxypropofol has approximately 1/3 of hypnotic activity of propofol.
• Absorption: Rapid - time to onset of unconsciousness is 15-30 seconds, due to rapid distribution from plasma to the CNS. Distribution is so rapid that peak plasma concentrations cannot be readily measured. Duration of action is 5-10 minutes.
• Elimination: It is chiefly eliminated by hepatic conjugation to inactive metabolites which are excreted by the kidney.
• References: Garnock-Jones KP, Scott LJ: Fospropofol. Drugs. 2010 Mar 5;70(4):469-77. doi: 10.2165/11204450-000000000-00000. [Pubmed] ; Schywalsky M, Ihmsen H, Tzabazis A, Fechner J, Burak E, Vornov J, Schwilden H: Pharmacokinetics and pharmacodynamics of the new propofol prodrug GPI 15715 in rats. Eur J Anaesthesiol. 2003 Mar;20(3):182-90. [Pubmed]
• External Links: Wikipedia

参考文献

• Garnock-Jones KP, Scott LJ: Fospropofol. Drugs. 2010 Mar 5;70(4):469-77. doi: 10.2165/11204450-000000000-00000. Pubmed
• Schywalsky M, Ihmsen H, Tzabazis A, Fechner J, Burak E, Vornov J, Schwilden H: Pharmacokinetics and pharmacodynamics of the new propofol prodrug GPI 15715 in rats. Eur J Anaesthesiol. 2003 Mar;20(3):182-90. Pubmed