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Identification
Name Remifentanil
Accession Number DB00899 (APRD01216)
Type small molecule
Groups approved
Description

Remifentanil (marketed by Abbott as Ultiva) is a potent ultra 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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Remifentanyl
Brand names
  • Ultiva (Abbott Laboratories)
Brand name mixtures Not Available
Categories
  • Hypnotics and Sedatives
  • Anesthetics, Intravenous
  • Analgesics, Opioid
CAS number 132875-61-7
Weight Average: 376.4467
Monoisotopic: 376.199822016
Chemical Formula C20H28N2O5
InChI Key InChIKey=ZTVQQQVZCWLTDF-UHFFFAOYSA-N
InChI
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
Plain Text
IUPAC Name
methyl 1-(3-methoxy-3-oxopropyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate
SMILES
CCC(=O)N(C1=CC=CC=C1)C1(CCN(CCC(=O)OC)CC1)C(=O)OC
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Acetanilides
Substructures
  • Carboxylic Acids and Derivatives
  • Acetates
  • Amino Ketones
  • Ethers
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Acetanilides
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Anilines
  • Piperidines
Pharmacology
Indication For use during the induction and maintenance of general anesthesia.
Pharmacodynamics Remifentanil is an opioid agonist with rapid onset and peak effect and ultra-short duration of action. The opioid activity of remifentanil is antagonized by opioid antagonists such as naloxone. The analgesic effects of remifentanil are rapid in onset and offset. Its effects and side effects are dose dependent and similar to other opioids. Remifentanil in humans has a rapid blood-brain equilibration half-time of 1 ± 1 minutes (mean ± SD) and a rapid onset of action.
Mechanism of action Remifentanil is a µ-opioid agonist with rapid onset and peak effect, and short duration of action. The µ-opioid activity of remifentanil is antagonized by opioid antagonists such as naloxone.
Absorption Not Available
Volume of distribution
  • 350 mL/kg
  • 452 ± 144 mL/kg [neonates]
  • 223 ± 30.6 mL/kg [adolescents]
Protein binding 70% (bound to plasma proteins)
Metabolism

By hydrolysis of the propanoic acid-methyl ester linkage by nonspecific blood and tissue esterases.
Route of elimination Remifentanil is an esterase-metabolized opioid. The carboxylic acid metabolite is essentially inactive (1/4600 as potent as remifentanil in dogs) and is excreted by the kidneys with an elimination half-life of approximately 90 minutes.
Half life 1-20 minutes
Clearance
  • 40 mL/min/kg [young, healthy adults]
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00416 Remifentanil Pathway SMP00416
Pharmacoeconomics
Manufacturers
  • Bioniche teoranta
Packagers
Dosage forms
Form Route Strength
Powder, for solution Intravenous
Prices
Unit description Cost Unit
Ultiva 5 mg vial 118.15 USD vial
Ultiva 2 mg vial 57.2 USD vial
Ultiva 1 mg vial 30.19 USD vial
Patents
Country Patent Number Approved Expires
United States 5866591 1998-03-10 2018-03-10
United States 5019583 1993-07-12 2010-07-12
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP 1.4 PhysProp
Predicted Properties
Property Value Source
water solubility 5.91e-01 g/l ALOGPS
logP 1.75 ALOGPS
logP 1.52 ChemAxon Molconvert
logS -2.80 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 76.15 ChemAxon Molconvert
rotatable bond count 9 ChemAxon Molconvert
refractivity 100.56 ChemAxon Molconvert
polarizability 40.82 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C08021 Link_out
PubChem Compound 60815 Link_out
PubChem Substance 46504538 Link_out
ChemSpider 54803 Link_out
BindingDB 50012491 Link_out
Therapeutic Targets Database DAP000264 Link_out
PharmGKB PA451232 Link_out
Drug Product Database 2230410 Link_out
RxList http://www.rxlist.com/cgi/generic2/ultiva.htm Link_out
Drugs.com http://www.drugs.com/cdi/remifentanil.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Remifentanil Link_out
ATC Codes
  • N01AH06
AHFS Codes
  • 28:08.08
PDB Entries Not Available
FDA label show (380.3 KB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Mu-type opioid receptor

Pharmacological action: yes
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin

Organism class: human
UniProt ID: P35372 Link_out
Gene: OPRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  2. Scott LJ, Perry CM: Spotlight on remifentanil for general anaesthesia. CNS Drugs. 2005;19(12):1069-74. Pubmed
  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
  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
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  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
  7. Patel SS, Spencer CM: Remifentanil. Drugs. 1996 Sep;52(3):417-27; discussion 428. Pubmed

2. Delta-type opioid receptor

Pharmacological action: unknown
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins

Organism class: human
UniProt ID: P41143 Link_out
Gene: OPRD1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2008 Sep 24. Pubmed
  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
  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
  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
  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
  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

3. Kappa-type opioid receptor

Pharmacological action: unknown
Actions: agonist

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

Organism class: human
UniProt ID: P41145 Link_out
Gene: OPRK1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2009 Oct 29. Pubmed
  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. Epub 2008 Mar 5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on January 13, 2011 08:35

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.