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

• ChemBase ID: 4453
• Molecular Formular: C13H19Na2O5P
• Molecular Mass: 332.240261
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium 2,6-bis(propan-2-yl)phenoxymethyl phosphate
• IUPAC Traditional name: dipotassium 2,6-diisopropylphenoxymethyl phosphate
• Brand Name: Lusedra
• Synonyms: Fospropofol

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.4372194
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.192822
• LogD (pH = 7.4): 0.28466505
• Log P: 3.6020257
• Molar Refractivity: 70.6341 cm^3
• Polarizability: 28.436102 Å^3
• Polar Surface Area: 81.65 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.31
• LOG S: -2.29
• Solubility (Water): 1.71e+00 g/l

DETAILS

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

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