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Remifentanil

July 24, 2017
Common Name

Remifentanil Description

Remifentanil (marketed by Abbott as Ultiva) is a potent litra short-acting synthetic opioid analgesic drug. It is given to patients during surgery to relieve pain and as an adjunct to an anaesthetic. Remifentanil is a specific mu-type-opioid receptor agonist. Hence, it causes a reduction in sympathetic nervous system tone, respiratory depression and analgesia. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source UltivaKegg RemifentanylHMDB Remifentanil monohydrochlorideMeSH Remifentanil hydrochlorideMeSH 3-(4-Methoxycarbonyl-4-((1-oxopropyl)phenylamino)-1-piperidine)propanoic acid methyl esterMeSH

Chemical Formlia

C20H28N2O5 Average Molecliar Weight

376.4467 Monoisotopic Molecliar Weight

376.199822016 IUPAC Name

methyl 1-(3-methoxy-3-oxopropyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate Traditional Name

remifentanil CAS Registry Number

132875-61-7 SMILES

CCC(=O)N(C1=CC=CC=C1)C1(CCN(CCC(=O)OC)CC1)C(=O)OC

InChI Identifier

InChI=1S/C20H28N2O5/c1-4-17(23)22(16-8-6-5-7-9-16)20(19(25)27-3)11-14-21(15-12-20)13-10-18(24)26-2/h5-9H,4,10-15H2,1-3H3

InChI Key

ZTVQQQVZCWLTDF-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Alpha amino acids and derivatives Alternative Parents

  • Piperidinecarboxylic acids
  • Anilides
  • Dicarboxylic acids and derivatives
  • Tertiary carboxylic acid amides
  • Methyl esters
  • Trialkylamines
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Alpha-amino acid or derivatives
  • Piperidinecarboxylic acid
  • Anilide
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Piperidine
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Methyl ester
  • Carboxamide group
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • monocarboxylic acid amide (CHEBI:8802 )
  • alpha-amino acid ester (CHEBI:8802 )
  • anilide (CHEBI:8802 )
  • piperidinecarboxylate ester (CHEBI:8802 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Analgesics, Opioid
  • Anesthetics, Intravenous
  • Hypnotics and Sedatives

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility5.91e-01 g/LNot Available LogP1.4Not Available

    Predicted Properties

    Property Value Source Water Solubility0.59 mg/mLALOGPS logP1.75ALOGPS logP1.52ChemAxon logS-2.8ALOGPS pKa (Strongest Basic)7.51ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area76.15 Å2ChemAxon Rotatable Bond Count9ChemAxon Refractivity100.56 m3·mol-1ChemAxon Polarizability40.82 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-004i-0009000000-b9035e2706d5ac9b57a7View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-02di-0397000000-c610a2d0adc44d55166bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-03di-0930000000-436dbd271b442dcde5bfView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-03e9-4900000000-79234a6e65fb22f3b487View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-01q9-9700000000-5ce11ade40e1a80e4958View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Remifentanil PathwaySMP00416Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00899

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00899

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00899 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

    54803 KEGG Compound ID

    C08021 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Remifentanil NuGOwiki Link

    HMDB15036 Metagene Link

    HMDB15036 METLIN ID

    Not Available PubChem Compound

    60815 PDB ID

    Not Available ChEBI ID

    8802

    Product: Nexturastat A

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins
    Gene Name:
    OPRD1
    Uniprot ID:
    P41143
    Molecular weight:
    40412.3
    References
    1. Stucke AG, Zuperku EJ, Sanchez A, Tonkovic-Capin M, Tonkovic-Capin V, Mustapic S, Stuth EA: Opioid receptors on bulbospinal respiratory neurons are not activated during neuronal depression by clinically relevant opioid concentrations. J Neurophysiol. 2008 Nov;100(5):2878-88. doi: 10.1152/jn.90620.2008. Epub 2008 Sep 24. [PubMed:18815346 ]
    2. Rodrigues AR, Castro MS, Francischi JN, Perez AC, Duarte ID: Participation of ATP-sensitive K+ channels in the peripheral antinociceptive effect of fentanyl in rats. Braz J Med Biol Res. 2005 Jan;38(1):91-7. Epub 2005 Jan 18. [PubMed:15665994 ]
    3. Poonawala T, Levay-Young BK, Hebbel RP, Gupta K: Opioids heal ischemic wounds in the rat. Wound Repair Regen. 2005 Mar-Apr;13(2):165-74. [PubMed:15828941 ]
    4. Sahin AS, Duman A, Atalik EK, Ogun CO, Sahin TK, Erol A, Ozergin U: The mechanisms of the direct vascular effects of fentanyl on isolated human saphenous veins in vitro. J Cardiothorac Vasc Anesth. 2005 Apr;19(2):197-200. [PubMed:15868528 ]
    5. Darwish M, Tempero K, Kirby M, Thompson J: Pharmacokinetics and dose proportionality of fentanyl effervescent buccal tablets in healthy volunteers. Clin Pharmacokinet. 2005;44(12):1279-86. [PubMed:16372825 ]
    6. Darwish M, Kirby M, Robertson P Jr, Tracewell W, Jiang JG: Pharmacokinetic properties of fentanyl effervescent buccal tablets: a phase I, open-label, crossover study of single-dose 100, 200, 400, and 800 microg in healthy adult volunteers. Clin Ther. 2006 May;28(5):707-14. [PubMed:16861092 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
    Gene Name:
    OPRM1
    Uniprot ID:
    P35372
    Molecular weight:
    44778.9
    References
    1. Scott LJ, Perry CM: Remifentanil: a review of its use during the induction and maintenance of general anaesthesia. Drugs. 2005;65(13):1793-823. [PubMed:16114980 ]
    2. Scott LJ, Perry CM: Spotlight on remifentanil for general anaesthesia. CNS Drugs. 2005;19(12):1069-74. [PubMed:16332149 ]
    3. Warner DS, Hindman BJ, Todd MM, Sawin PD, Kirchner J, Roland CL, Jamerson BD: Intracranial pressure and hemodynamic effects of remifentanil versus alfentanil in patients undergoing supratentorial craniotomy. Anesth Analg. 1996 Aug;83(2):348-53. [PubMed:8694317 ]
    4. Guy J, Hindman BJ, Baker KZ, Borel CO, Maktabi M, Ostapkovich N, Kirchner J, Todd MM, Fogarty-Mack P, Yancy V, Sokoll MD, McAllister A, Roland C, Young WL, Warner DS: Comparison of remifentanil and fentanyl in patients undergoing craniotomy for supratentorial space-occupying lesions. Anesthesiology. 1997 Mar;86(3):514-24. [PubMed:9066316 ]
    5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    6. Hoke JF, Cunningham F, James MK, Muir KT, Hoffman WE: Comparative pharmacokinetics and pharmacodynamics of remifentanil, its principle metabolite (GR90291) and alfentanil in dogs. J Pharmacol Exp Ther. 1997 Apr;281(1):226-32. [PubMed:9103501 ]
    7. Patel SS, Spencer CM: Remifentanil. Drugs. 1996 Sep;52(3):417-27; discussion 428. [PubMed:8875131 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions
    Gene Name:
    OPRK1
    Uniprot ID:
    P41145
    Molecular weight:
    42644.7
    References
    1. Wong GT, Li R, Jiang LL, Irwin MG: Remifentanil post-conditioning attenuates cardiac ischemia-reperfusion injury via kappa or delta opioid receptor activation. Acta Anaesthesiol Scand. 2010 Apr;54(4):510-8. doi: 10.1111/j.1399-6576.2009.02145.x. Epub 2009 Oct 29. [PubMed:19878098 ]
    2. Pascoe JE, Williams KL, Mukhopadhyay P, Rice KC, Woods JH, Ko MC: Effects of mu, kappa, and delta opioid receptor agonists on the function of hypothalamic-pituitary-adrenal axis in monkeys. Psychoneuroendocrinology. 2008 May;33(4):478-86. doi: 10.1016/j.psyneuen.2008.01.006. Epub 2008 Mar 5. [PubMed:18325678 ]

    PMID: 24039875

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