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Fospropofol

July 24, 2017
Common Name

Fospropofol Description

Fospropofol is only found in individuals that have used or taken this drug. It 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.The action of propofol involves a positive modliation of the inhibitory function of the neurotransmitter gama-aminobutyric acid (GABA) through GABA-A receptors. Structure

MOLSDFPDBSMILESInChI

Synonyms

Value Source AquavanKegg LusedraKegg Methanol, (2,6-bis(1-methylethyl)phenoxy)-, dihydrogen phosphate, disodium saltMeSH

Chemical Formlia

C13H19Na2O5P Average Molecliar Weight

332.2403 Monoisotopic Molecliar Weight

332.07654958 IUPAC Name

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

disodium 2,6-diisopropylphenoxymethyl phosphate CAS Registry Number

258516-87-9 SMILES

[Na+].[Na+].CC(C)C1=CC=CC(C(C)C)=C1OCOP([O-])([O-])=O

InChI Identifier

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

InChI Key

LWYLQNWMSGFCOZ-UHFFFAOYSA-L Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Cumenes Alternative Parents

  • Phenylpropanes
  • Phenoxy compounds
  • Phenol ethers
  • Alkyl phosphates
  • Organooxygen compounds
  • Organic sodium salts
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Phenylpropane
  • Cumene
  • Phenoxy compound
  • Phenol ether
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic alkali metal salt
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic sodium salt
  • Organic salt
  • Organooxygen compound
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anesthetics, Intravenous
  • Hypnotics and Sedatives

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility1.71 mg/mLALOGPS logP3.31ALOGPS logP3.6ChemAxon logS-2.3ALOGPS pKa (Strongest Acidic)1.44ChemAxon pKa (Strongest Basic)-5ChemAxon Physiological Charge-2ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area81.65 Å2ChemAxon Rotatable Bond Count6ChemAxon Refractivity70.63 m3·mol-1ChemAxon Polarizability28.49 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06716

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06716

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB06716 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    2302061 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Fospropofol NuGOwiki Link

    HMDB15661 Metagene Link

    HMDB15661 METLIN ID

    Not Available PubChem Compound

    3038497 PDB ID

    Not Available ChEBI ID

    Not Available

    Product: Staurosporine

    References Synthesis Reference Not 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 ]

    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 ]
    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:
    GABRB3
    Uniprot ID:
    P28472
    Molecular weight:
    54115.0
    References
    1. Franks NP: Molecular targets underlying general anaesthesia. Br J Pharmacol. 2006 Jan;147 Suppl 1:S72-81. [PubMed:16402123 ]
    General function:
    Involved in ion channel activity
    Specific function:
    Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient
    Gene Name:
    SCN2A
    Uniprot ID:
    Q99250
    Molecular weight:
    227972.6
    References
    1. Haeseler G, Karst M, Foadi N, Gudehus S, Roeder A, Hecker H, Dengler R, Leuwer M: High-affinity blockade of voltage-operated skeletal muscle and neuronal sodium channels by halogenated propofol analogues. Br J Pharmacol. 2008 Sep;155(2):265-75. doi: 10.1038/bjp.2008.255. Epub 2008 Jun 23. [PubMed:18574460 ]
    General function:
    Involved in ion channel activity
    Specific function:
    This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. This sodium channel may be present in both denervated and innervated skeletal muscle
    Gene Name:
    SCN4A
    Uniprot ID:
    P35499
    Molecular weight:
    208059.2
    References
    1. Haeseler G, Karst M, Foadi N, Gudehus S, Roeder A, Hecker H, Dengler R, Leuwer M: High-affinity blockade of voltage-operated skeletal muscle and neuronal sodium channels by halogenated propofol analogues. Br J Pharmacol. 2008 Sep;155(2):265-75. doi: 10.1038/bjp.2008.255. Epub 2008 Jun 23. [PubMed:18574460 ]

    PMID: 25385595

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