Fospropofol

Fospropofol
Clinical data
AHFS/Drugs.com	Monograph
License data	US FDA: Fospropofol;
Pregnancy; category	B;
Dependence; liability	unknown
Routes of; administration	Intravenous
ATC code	N01 ;
Legal status
Legal status	US: Schedule IV;
Pharmacokinetic data
Protein binding	98%
Metabolism	Hepatic glucuronidation
Elimination half-life	0.81 hours
Excretion	Renal
Identifiers
	IUPAC name disodium [2,6-di(propan-2-yl)phenoxy]methyl phosphate;
CAS Number	258516-89-1 ; 258516-87-9 (disodium salt);
PubChem CID	3038498;
DrugBank	DB06716 ;
ChemSpider	2302062 ;
UNII	LZ257RZP7K;
KEGG	D04257 ;
ChEMBL	ChEMBL1201766 ;
CompTox Dashboard (EPA)	DTXSID50870295 ;
Chemical and physical data
Formula	C13H21O5P
Molar mass	288.280 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)c1cccc(c1OCOP(=O)(O)O)C(C)C;
	InChI InChI=1S/C13H21O5P/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) ; Key:QVNNONOFASOXQV-UHFFFAOYSA-N ;
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Fospropofol (INN^[3]), often used as the disodium salt (trade name Lusedra^[4]) is an intravenous sedative-hypnotic agent. It is currently approved for use in sedation of adult patients undergoing diagnostic or therapeutic procedures such as endoscopy.

Clinical applications

Several water-soluble derivatives and prodrugs of the widely used intravenous anesthetic agent propofol have been developed, of which fospropofol has been found to be the most suitable for clinical development thus far.^[5]^[6] Purported advantages of this water-soluble chemical compound include less pain at the site of intravenous administration, less potential for hyperlipidemia with long-term administration, and less chance for bacteremia.^{[citation needed]} Often, fospropofol is administered in conjunction with an opioid such as fentanyl.^{[citation needed]}

Clinical pharmacology

Mechanism of action

Fospropofol is a prodrug of propofol; as an organophosphate it is metabolized by alkaline phosphatases to phosphate and formaldehyde and the active metabolite, propofol.

Pharmacodynamics

Pharmacokinetics

Initial trial results on fospropofol pharmacokinetics were retracted by the investigators. As of 2011, new results were not available.^[7]

Controlled substance

Fospropofol is classified as a Schedule IV controlled substance in the United States' Controlled Substances Act.^[8]

References

^ ^a ^b "LUSEDRA (fospropofol disodium) Injection" (PDF). Woodcliff Lake, New Jersey: Eisai Inc. October 2009. Archived from the original (PDF) on 22 November 2010. Retrieved 2 August 2010.
^ "Fospropofol disodium". PubChem Compound. Bethesda, Maryland: U.S. National Library of Medicine. Retrieved 9 February 2017.
^ "Recommended INNs 2006, pt 56" (PDF). World Health Organization. Retrieved 20 April 2016.
^ "FDA Approves Fospropofol and Follows ASAs Labeling Recommendation". American Society of Anesthesiologists. 2008-12-15. Archived from the original on 2011-05-26. Retrieved 2011-03-30.
^ Cooke A, Anderson A, Buchanan K, Byford A, Gemmell D, Hamilton N, et al. (April 2001). "Water-soluble propofol analogues with intravenous anaesthetic activity". Bioorganic & Medicinal Chemistry Letters. 11 (7): 927–930. doi:10.1016/S0960-894X(01)00088-9. PMID 11294393.
^ Bennett DJ, Anderson A, Buchanan K, Byford A, Cooke A, Gemmell DK, et al. (June 2003). "Novel water soluble 2,6-dimethoxyphenyl ester derivatives with intravenous anaesthetic activity". Bioorganic & Medicinal Chemistry Letters. 13 (12): 1971–1975. doi:10.1016/S0960-894X(03)00346-9. PMID 12781176.
^ Mahajan B, Kaushal S, Mahajan R (January 2012). "Fospropofol: pharmacokinetics?". Journal of Anaesthesiology Clinical Pharmacology. 28 (1): 134–135. doi:10.4103/0970-9185.92472. PMC 3275955. PMID 22345970.
^ "Schedule of Controlled Substances; Placement of Fospropofol into Schedule IV^{[permanent dead link]}," 74 Federal Register 192 (October 6, 2009), pp. 51234–51236.

[Eisai2009-1] "LUSEDRA (fospropofol disodium) Injection" (PDF). Woodcliff Lake, New Jersey: Eisai Inc. October 2009. Archived from the original (PDF) on 22 November 2010. Retrieved 2 August 2010.

[PubChem-2] "Fospropofol disodium". PubChem Compound. Bethesda, Maryland: U.S. National Library of Medicine. Retrieved 9 February 2017.

[3] "Recommended INNs 2006, pt 56" (PDF). World Health Organization. Retrieved 20 April 2016.

[4] "FDA Approves Fospropofol and Follows ASAs Labeling Recommendation". American Society of Anesthesiologists. 2008-12-15. Archived from the original on 2011-05-26. Retrieved 2011-03-30.

[5] Cooke A, Anderson A, Buchanan K, Byford A, Gemmell D, Hamilton N, et al. (April 2001). "Water-soluble propofol analogues with intravenous anaesthetic activity". Bioorganic & Medicinal Chemistry Letters. 11 (7): 927–930. doi:10.1016/S0960-894X(01)00088-9. PMID 11294393.

[6] Bennett DJ, Anderson A, Buchanan K, Byford A, Cooke A, Gemmell DK, et al. (June 2003). "Novel water soluble 2,6-dimethoxyphenyl ester derivatives with intravenous anaesthetic activity". Bioorganic & Medicinal Chemistry Letters. 13 (12): 1971–1975. doi:10.1016/S0960-894X(03)00346-9. PMID 12781176.

[7] Mahajan B, Kaushal S, Mahajan R (January 2012). "Fospropofol: pharmacokinetics?". Journal of Anaesthesiology Clinical Pharmacology. 28 (1): 134–135. doi:10.4103/0970-9185.92472. PMC 3275955. PMID 22345970.

[8] "Schedule of Controlled Substances; Placement of Fospropofol into Schedule IV^{[permanent dead link]}," 74 Federal Register 192 (October 6, 2009), pp. 51234–51236.

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