Identification
- Summary
Alfentanil is an opioid agonist used to induce and maintain anesthesia, as well as an analgesic.
- Brand Names
- Alfenta
- Generic Name
- Alfentanil
- DrugBank Accession Number
- DB00802
- Background
A short-acting opioid anesthetic and analgesic derivative of fentanyl. It produces an early peak analgesic effect and fast recovery of consciousness. Alfentanil is effective as an anesthetic during surgery, for supplementation of analgesia during surgical procedures, and as an analgesic for critically ill patients.
- Type
- Small Molecule
- Groups
- Approved, Illicit
- Structure
Structure for Alfentanil (DB00802)
- Weight
- Average: 416.5172
Monoisotopic: 416.25358892 - Chemical Formula
- C21H32N6O3
- Synonyms
- Alfentanil
- Alfentanilo
- Alfentanilum
- Alfentanyl
- N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide
- External IDs
- IDS-NA-014
Pharmacology
- Indication
For the management of postoperative pain and the maintenance of general anesthesia.
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- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Alfentanil is a synthetic opioid analgesic. Alfentanil interacts predominately with the opioid mu-receptor. These mu-binding sites are discretely distributed in the human brain, spinal cord, and other tissues. In clinical settings, alfentanil exerts its principal pharmacologic effects on the central nervous system. Its primary actions of therapeutic value are analgesia and sedation. Alfentanil may increase the patient's tolerance for pain and decrease the perception of suffering, although the presence of the pain itself may still be recognized. In addition to analgesia, alterations in mood, euphoria and dysphoria, and drowsiness commonly occur. Alfentanil depresses the respiratory centers, depresses the cough reflex, and constricts the pupils.
- Mechanism of action
Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Alfentanil's analgesic activity is, most likely, due to its conversion to morphine. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.
Target Actions Organism AMu-type opioid receptor agonistHumans - Absorption
For intravenous injection or infusion only.
- Volume of distribution
- 0.4 to 1 L/kg
- Protein binding
92%
- Metabolism
The liver is the major site of biotransformation.
Hover over products below to view reaction partners
- Route of elimination
Only 1.0% of the dose is excreted as unchanged drug; urinary excretion is the major route of elimination of metabolites.
- Half-life
90-111 minutes
- Clearance
- 5 mL/kg/min
- Adverse Effects
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Symptoms of overexposure include characteristic rigidity of the skeletal muscles, cardiac and respiratory depression, and narrowing of the pupils.
- Pathways
Pathway Category Alfentanil Action Pathway Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Alfentanil is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Alfentanil can be increased when it is combined with Abametapir. Abatacept The metabolism of Alfentanil can be increased when combined with Abatacept. Acalabrutinib The metabolism of Alfentanil can be decreased when combined with Acalabrutinib. Acebutolol Alfentanil may decrease the antihypertensive activities of Acebutolol. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Alfentanil hydrochloride 11S92G0TIW 70879-28-6 YYESXRRYBUERKF-UHFFFAOYSA-N - International/Other Brands
- Rapifen (Janssen)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alfenta Injection 500 ug/1mL Intravenous Taylor Pharmaceuticals 2008-02-25 Not applicable US 
Alfenta Inj 500mcg/ml Solution 500 mcg / mL Intravenous Janssen Pharmaceuticals 1988-12-31 2008-09-05 Canada 
Alfentanil Injection 500 ug/1mL Intravenous Akorn 2013-07-19 Not applicable US Alfentanil Hydrochloride Injection 500 ug/1mL Intravenous Akorn 2010-02-01 2025-04-30 US Alfentanil Injection USP Solution 500 mcg / mL Intravenous Sandoz Canada Incorporated 2004-11-01 2019-08-01 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alfentanil Hydrochloride Injection, solution 500 ug/1mL Intravenous Hospira, Inc. 2006-02-20 2021-05-01 US
Categories
- ATC Codes
- N01AH02 — Alfentanil
- Drug Categories
- Agents that produce hypertension
- Analgesics
- Anesthetics
- Anesthetics, General
- Anesthetics, Intravenous
- Bradycardia-Causing Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Substrates
- Fentanyl and fentanyl analogues
- High-risk opioids
- Narcotics
- Nervous System
- Opiate Agonists
- Opioid Agonist
- Opioid Anesthetics
- Opioids
- Opioids, Anilidopiperidine
- P-glycoprotein inhibitors
- Peripheral Nervous System Agents
- Phenylpiperidine opioids
- Piperidines
- Sensory System Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Anilides
- Direct Parent
- Anilides
- Alternative Parents
- Piperidines / Tetrazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Trialkylamines / Amino acids and derivatives / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Organic oxides show 2 more
- Substituents
- Amine / Amino acid or derivatives / Anilide / Aromatic heteromonocyclic compound / Azacycle / Azole / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Dialkyl ether show 15 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- piperidines, monocarboxylic acid amide (CHEBI:2569)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 1N74HM2BS7
- CAS number
- 71195-58-9
- InChI Key
- IDBPHNDTYPBSNI-UHFFFAOYSA-N
- InChI
- InChI=1S/C21H32N6O3/c1-4-19(28)27(18-9-7-6-8-10-18)21(17-30-3)11-13-24(14-12-21)15-16-26-20(29)25(5-2)22-23-26/h6-10H,4-5,11-17H2,1-3H3
- IUPAC Name
- N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-1,2,3,4-tetrazol-1-yl)ethyl]-4-(methoxymethyl)piperidin-4-yl}-N-phenylpropanamide
- SMILES
- CCN1N=NN(CCN2CCC(COC)(CC2)N(C(=O)CC)C2=CC=CC=C2)C1=O
References
- Synthesis Reference
Jacob Mathew, J. Killgore, "New methods for the synthesis of alfentanil, sufentanil, and remifentanil." U.S. Patent US20060149071, issued July 06, 2006.
US20060149071- General References
- External Links
- Human Metabolome Database
- HMDB0014940
- KEGG Drug
- D07122
- KEGG Compound
- C08005
- PubChem Compound
- 51263
- PubChem Substance
- 46505618
- ChemSpider
- 46451
- BindingDB
- 83450
- 480
- ChEBI
- 2569
- ChEMBL
- CHEMBL634
- ZINC
- ZINC000000601281
- Therapeutic Targets Database
- DAP001134
- PharmGKB
- PA448084
- RxList
- RxList Drug Page
- Wikipedia
- Alfentanil
- MSDS
- Download (51.3 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Not Available Digestive System Diseases / Disorientation 1 4 Completed Prevention Anesthesia Intubation Complications 1 4 Completed Prevention Emergence Agitation 1 4 Completed Prevention Lower Esophageal Sphincter 1 4 Completed Treatment Blood Pressures / Electroconvulsive Therapy 1
Pharmacoeconomics
- Manufacturers
- Akorn inc
- Hospira inc
- Packagers
- Akorn Inc.
- Baxter International Inc.
- Hospira Inc.
- Taylor Pharmaceuticals
- Dosage Forms
Form Route Strength Injection Intravenous 500 ug/1mL Injection, solution Intravenous 500 ug/1mL Solution Intravenous 500 mcg / mL Injection, solution Injection, solution Parenteral 0.5 mg/ml Injection Intravenous Injection, solution Intravenous 0.5 mg/ml Injection Intravenous 0.5 mg/ml - Prices
Unit description Cost Unit Alfenta 500 mcg/ml ampul 5.26USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 140.8 Janssens, F.; US. Patent 4,167,574; September 11, 1979; assigned to Janssen Pharmaceutica NV. water solubility 34.6 mg/L Not Available logP 2.16 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.252 mg/mL ALOGPS logP 2.2 ALOGPS logP 2.81 Chemaxon logS -3.2 ALOGPS pKa (Strongest Basic) 7.5 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 81.05 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 118.59 m3·mol-1 Chemaxon Polarizability 45.56 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9957 Blood Brain Barrier + 0.9396 Caco-2 permeable - 0.5368 P-glycoprotein substrate Substrate 0.7156 P-glycoprotein inhibitor I Inhibitor 0.8809 P-glycoprotein inhibitor II Non-inhibitor 0.8381 Renal organic cation transporter Non-inhibitor 0.7077 CYP450 2C9 substrate Non-substrate 0.7897 CYP450 2D6 substrate Non-substrate 0.9115 CYP450 3A4 substrate Substrate 0.7407 CYP450 1A2 substrate Non-inhibitor 0.9067 CYP450 2C9 inhibitor Inhibitor 0.6051 CYP450 2D6 inhibitor Non-inhibitor 0.9003 CYP450 2C19 inhibitor Non-inhibitor 0.5591 CYP450 3A4 inhibitor Inhibitor 0.6691 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6692 Ames test AMES toxic 0.5858 Carcinogenicity Non-carcinogens 0.7729 Biodegradation Not ready biodegradable 0.9877 Rat acute toxicity 2.9997 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.6413 hERG inhibition (predictor II) Inhibitor 0.5893
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 208.5222055 predictedDarkChem Lite v0.1.0 [M-H]- 191.95323 predictedDeepCCS 1.0 (2019) [M+H]+ 208.5472055 predictedDarkChem Lite v0.1.0 [M+H]+ 194.50354 predictedDeepCCS 1.0 (2019) [M+Na]+ 209.2824055 predictedDarkChem Lite v0.1.0 [M+Na]+ 202.86462 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Voltage-gated calcium channel activity
- Specific Function
- Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
- Gene Name
- OPRM1
- Uniprot ID
- P35372
- Uniprot Name
- Mu-type opioid receptor
- Molecular Weight
- 44778.855 Da
References
- Garrido M, Gubbens-Stibbe J, Tukker E, Cox E, von Frijtag J, Kunzel D, IJzerman A, Danhof M, van der Graaf PH: Pharmacokinetic-pharmacodynamic analysis of the EEG effect of alfentanil in rats following beta-funaltrexamine-induced mu-opioid receptor "knockdown" in vivo. Pharm Res. 2000 Jun;17(6):653-9. [Article]
- Lotsch J, Geisslinger G: Are mu-opioid receptor polymorphisms important for clinical opioid therapy? Trends Mol Med. 2005 Feb;11(2):82-9. [Article]
- Oertel BG, Schmidt R, Schneider A, Geisslinger G, Lotsch J: The mu-opioid receptor gene polymorphism 118A>G depletes alfentanil-induced analgesia and protects against respiratory depression in homozygous carriers. Pharmacogenet Genomics. 2006 Sep;16(9):625-36. [Article]
- Leung A, Wallace MS, Ridgeway B, Yaksh T: Concentration-effect relationship of intravenous alfentanil and ketamine on peripheral neurosensory thresholds, allodynia and hyperalgesia of neuropathic pain. Pain. 2001 Mar;91(1-2):177-87. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase 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 react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Klees TM, Sheffels P, Dale O, Kharasch ED: Metabolism of alfentanil by cytochrome p4503a (cyp3a) enzymes. Drug Metab Dispos. 2005 Mar;33(3):303-11. Epub 2004 Nov 22. [Article]
- Kharasch ED, Jubert C, Senn T, Bowdle TA, Thummel KE: Intraindividual variability in male hepatic CYP3A4 activity assessed by alfentanil and midazolam clearance. J Clin Pharmacol. 1999 Jul;39(7):664-9. [Article]
- Klees TM, Sheffels P, Thummel KE, Kharasch ED: Pharmacogenetic determinants of human liver microsomal alfentanil metabolism and the role of cytochrome P450 3A5. Anesthesiology. 2005 Mar;102(3):550-6. [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- 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 un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Klees TM, Sheffels P, Dale O, Kharasch ED: Metabolism of alfentanil by cytochrome p4503a (cyp3a) enzymes. Drug Metab Dispos. 2005 Mar;33(3):303-11. Epub 2004 Nov 22. [Article]
- Klees TM, Sheffels P, Thummel KE, Kharasch ED: Pharmacogenetic determinants of human liver microsomal alfentanil metabolism and the role of cytochrome P450 3A5. Anesthesiology. 2005 Mar;102(3):550-6. [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- 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 un...
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57525.03 Da
References
- Flockhart Table of Drug Interactions [Link]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
- Gene Name
- ORM1
- Uniprot ID
- P02763
- Uniprot Name
- Alpha-1-acid glycoprotein 1
- Molecular Weight
- 23511.38 Da
References
- Belpaire FM, Bogaert MG: Binding of alfentanil to human alpha 1-acid glycoprotein, albumin and serum. Int J Clin Pharmacol Ther Toxicol. 1991 Mar;29(3):96-102. [Article]
- Kumar K, Crankshaw DP, Morgan DJ, Beemer GH: The effect of cardiopulmonary bypass on plasma protein binding of alfentanil. Eur J Clin Pharmacol. 1988;35(1):47-52. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Belpaire FM, Bogaert MG: Binding of alfentanil to human alpha 1-acid glycoprotein, albumin and serum. Int J Clin Pharmacol Ther Toxicol. 1991 Mar;29(3):96-102. [Article]
- Kumar K, Crankshaw DP, Morgan DJ, Beemer GH: The effect of cardiopulmonary bypass on plasma protein binding of alfentanil. Eur J Clin Pharmacol. 1988;35(1):47-52. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Wandel C, Kim R, Wood M, Wood A: Interaction of morphine, fentanyl, sufentanil, alfentanil, and loperamide with the efflux drug transporter P-glycoprotein. Anesthesiology. 2002 Apr;96(4):913-20. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55