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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:04 UTC
HMDB IDHMDB0015661
Secondary Accession Numbers
  • HMDB15661
Metabolite Identification
Common NameFospropofol
DescriptionFospropofol, also known as lusedra or aquavan, belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety. After in-vivo conversion of fospropofol into propofol by endothelial alkaline phosphatase, propofol crosses the blood-brain barrier, binds to GABA-A receptors and acts as an agonist. Fospropofol is a drug which is used for monitored anaesthesia care sedation in patients undergoing diagnostic procedures like bronchoscopy and colonscopy or minor surgical procedures like arthroscopy and bunionectomy. . Fospropofol is an extremely weak basic (essentially neutral) compound (based on its pKa). Unlike propofol, fospropofol is water soluble and can be administered in an aqueous solution. It is a prodrug and gets converted into Propofol in the liver. Overdosage may lead to cardiorespiratory depression, formic acid toxicity (methanol toxicity-like effects), and/or phosphate-induced hypocalemia. The metabolite, formaldehyde, is quickly oxidized into formic acid by glutathione dependent and independent dehydrogenases and erythrocytes.
Structure
Data?1582753321
Synonyms
ValueSource
LusedraHMDB
Fospropofol disodiumHMDB
Methanol, (2,6-bis(1-methylethyl)phenoxy)-, dihydrogen phosphate, disodium saltHMDB
AquavanHMDB
{[2,6-bis(propan-2-yl)phenoxy]methoxy}phosphonateGenerator
FospropofolMeSH
Chemical FormulaC13H21O5P
Average Molecular Weight288.2766
Monoisotopic Molecular Weight288.112660294
IUPAC Name{[2,6-bis(propan-2-yl)phenoxy]methoxy}phosphonic acid
Traditional Namefospropofol
CAS Registry Number258516-87-9
SMILES
CC(C)C1=CC=CC(C(C)C)=C1OCOP(O)(O)=O
InChI Identifier
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)
InChI KeyQVNNONOFASOXQV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassCumenes
Direct ParentCumenes
Alternative Parents
Substituents
  • Phenylpropane
  • Cumene
  • Phenoxy compound
  • Phenol ether
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.71 g/LALOGPS
logP2.23ALOGPS
logP3.6ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)1.44ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity72.88 m³·mol⁻¹ChemAxon
Polarizability29.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+164.98231661259
DarkChem[M-H]-163.91931661259
DeepCCS[M+H]+157.00930932474
DeepCCS[M-H]-154.65130932474
DeepCCS[M-2H]-187.53730932474
DeepCCS[M+Na]+163.47630932474
AllCCS[M+H]+165.432859911
AllCCS[M+H-H2O]+162.032859911
AllCCS[M+NH4]+168.532859911
AllCCS[M+Na]+169.432859911
AllCCS[M-H]-166.432859911
AllCCS[M+Na-2H]-166.932859911
AllCCS[M+HCOO]-167.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FospropofolCC(C)C1=CC=CC(C(C)C)=C1OCOP(O)(O)=O2714.2Standard polar33892256
FospropofolCC(C)C1=CC=CC(C(C)C)=C1OCOP(O)(O)=O1938.7Standard non polar33892256
FospropofolCC(C)C1=CC=CC(C(C)C)=C1OCOP(O)(O)=O2080.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fospropofol,1TMS,isomer #1CC(C)C1=CC=CC(C(C)C)=C1OCOP(=O)(O)O[Si](C)(C)C1987.4Semi standard non polar33892256
Fospropofol,1TMS,isomer #1CC(C)C1=CC=CC(C(C)C)=C1OCOP(=O)(O)O[Si](C)(C)C1937.2Standard non polar33892256
Fospropofol,1TMS,isomer #1CC(C)C1=CC=CC(C(C)C)=C1OCOP(=O)(O)O[Si](C)(C)C2773.9Standard polar33892256
Fospropofol,2TMS,isomer #1CC(C)C1=CC=CC(C(C)C)=C1OCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2017.6Semi standard non polar33892256
Fospropofol,2TMS,isomer #1CC(C)C1=CC=CC(C(C)C)=C1OCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2032.5Standard non polar33892256
Fospropofol,2TMS,isomer #1CC(C)C1=CC=CC(C(C)C)=C1OCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2441.8Standard polar33892256
Fospropofol,1TBDMS,isomer #1CC(C)C1=CC=CC(C(C)C)=C1OCOP(=O)(O)O[Si](C)(C)C(C)(C)C2242.4Semi standard non polar33892256
Fospropofol,1TBDMS,isomer #1CC(C)C1=CC=CC(C(C)C)=C1OCOP(=O)(O)O[Si](C)(C)C(C)(C)C2135.1Standard non polar33892256
Fospropofol,1TBDMS,isomer #1CC(C)C1=CC=CC(C(C)C)=C1OCOP(=O)(O)O[Si](C)(C)C(C)(C)C2889.6Standard polar33892256
Fospropofol,2TBDMS,isomer #1CC(C)C1=CC=CC(C(C)C)=C1OCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2474.6Semi standard non polar33892256
Fospropofol,2TBDMS,isomer #1CC(C)C1=CC=CC(C(C)C)=C1OCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2383.3Standard non polar33892256
Fospropofol,2TBDMS,isomer #1CC(C)C1=CC=CC(C(C)C)=C1OCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2682.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fospropofol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9610000000-96197934c8dd427d84bc2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fospropofol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fospropofol 10V, Positive-QTOFsplash10-0002-9460000000-77d9f6f35e06e586586b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fospropofol 20V, Positive-QTOFsplash10-01ot-9830000000-6a695cd3d402804870122017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fospropofol 40V, Positive-QTOFsplash10-01qa-9800000000-2ead84a2c2e8273497282017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fospropofol 10V, Negative-QTOFsplash10-000i-6190000000-ccb0ef8d15b189274cd52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fospropofol 20V, Negative-QTOFsplash10-004i-9000000000-a05f7f83bcc46e8926042017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fospropofol 40V, Negative-QTOFsplash10-004i-9000000000-f43f690bddd2f24c47c62017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fospropofol 10V, Positive-QTOFsplash10-000i-2390000000-7c86240b3a58e75ab5a22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fospropofol 20V, Positive-QTOFsplash10-002r-1930000000-b89742e8a68fc5b76c462021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fospropofol 40V, Positive-QTOFsplash10-000x-9810000000-29bec296079fdf66a1c72021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fospropofol 10V, Negative-QTOFsplash10-000i-2090000000-079d943d19c33bea53982021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fospropofol 20V, Negative-QTOFsplash10-004i-9000000000-2dd173dfe9a30642b89d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fospropofol 40V, Negative-QTOFsplash10-004i-9000000000-5f4b7c7826ff5a7f13022021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06716 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06716 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06716
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFospropofol
METLIN IDNot Available
PubChem Compound3038498
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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:12650488 ]
  2. Garnock-Jones KP, Scott LJ: Fospropofol. Drugs. 2010 Mar 5;70(4):469-77. doi: 10.2165/11204450-000000000-00000. [PubMed:20205488 ]
  3. Bengalorkar GM, Bhuvana K, Sarala N, Kumar T: Fospropofol: clinical pharmacology. J Anaesthesiol Clin Pharmacol. 2011 Jan;27(1):79-83. [PubMed:21804712 ]
  4. Patwardhan A, Edelmayer R, Annabi E, Price T, Malan P, Dussor G: Receptor specificity defines algogenic properties of propofol and fospropofol. Anesth Analg. 2012 Oct;115(4):837-40. Epub 2012 May 14. [PubMed:22584560 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Lejus C, Fautrel A, Malledant Y, Guillouzo A: Inhibition of cytochrome P450 2E1 by propofol in human and porcine liver microsomes. Biochem Pharmacol. 2002 Oct 1;64(7):1151-6. [PubMed:12234619 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Guitton J, Buronfosse T, Desage M, Flinois JP, Perdrix JP, Brazier JL, Beaune P: Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95. [PubMed:9771309 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Guitton J, Buronfosse T, Desage M, Flinois JP, Perdrix JP, Brazier JL, Beaune P: Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95. [PubMed:9771309 ]
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
References
  1. Lejus C, Fautrel A, Malledant Y, Guillouzo A: Inhibition of cytochrome P450 2E1 by propofol in human and porcine liver microsomes. Biochem Pharmacol. 2002 Oct 1;64(7):1151-6. [PubMed:12234619 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular weight:
55710.075
References
  1. Guitton J, Buronfosse T, Desage M, Flinois JP, Perdrix JP, Brazier JL, Beaune P: Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95. [PubMed:9771309 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
References
  1. Mo SL, Liu YH, Duan W, Wei MQ, Kanwar JR, Zhou SF: Substrate specificity, regulation, and polymorphism of human cytochrome P450 2B6. Curr Drug Metab. 2009 Sep;10(7):730-53. [PubMed:19702527 ]
  2. Oda Y, Hamaoka N, Hiroi T, Imaoka S, Hase I, Tanaka K, Funae Y, Ishizaki T, Asada A: Involvement of human liver cytochrome P4502B6 in the metabolism of propofol. Br J Clin Pharmacol. 2001 Mar;51(3):281-5. [PubMed:11298076 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Guitton J, Buronfosse T, Desage M, Flinois JP, Perdrix JP, Brazier JL, Beaune P: Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95. [PubMed:9771309 ]
  2. Lejus C, Fautrel A, Malledant Y, Guillouzo A: Inhibition of cytochrome P450 2E1 by propofol in human and porcine liver microsomes. Biochem Pharmacol. 2002 Oct 1;64(7):1151-6. [PubMed:12234619 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. Guitton J, Buronfosse T, Desage M, Flinois JP, Perdrix JP, Brazier JL, Beaune P: Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95. [PubMed:9771309 ]
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular weight:
56517.005
References
  1. Guitton J, Buronfosse T, Desage M, Flinois JP, Perdrix JP, Brazier JL, Beaune P: Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95. [PubMed:9771309 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRB2
Uniprot ID:
P47870
Molecular weight:
59149.9
References
  1. Franks NP: Molecular targets underlying general anaesthesia. Br J Pharmacol. 2006 Jan;147 Suppl 1:S72-81. [PubMed:16402123 ]

Only showing the first 10 proteins. There are 13 proteins in total.