1.0 2009-07-21 20:27:42 UTC 2026-05-14 16:49:39 UTC T3D2898 Fentanyl SmallMolecule Fentanyl belongs to the fentanyls, a subclass of piperidines within the organic compounds. This exogenous compound has the formula C22H28N2O and an average molecular weight of 336.47 g/mol. At room temperature, it exists as a solid. It is classified as an organoheterocyclic compound and functions as a drug (PMC12390419), analgesic (PMC10641973, PMC12327405, PMC5576180, PMC6205722, PMC8196964), and opioid analgesic (PMC10641973, PMC12327405, PMC5576180, PMC6205722, PMC8196964). Its clinical applications include use as an anesthetic (PMC10641973, PMC12327405, PMC5576180, PMC6205722, PMC8196964), intravenous anaesthetic (PMC10641973, PMC12327405, PMC5576180, PMC6205722, PMC8196964), and anaesthesia adjuvant (PMC10641973, PMC12327405, PMC5576180, PMC6205722, PMC8196964). Biologically, fentanyl acts as a mu-opioid receptor agonist (PMC10641973, PMC12327405, PMC5576180, PMC6205722, PMC8196964). Its recorded protein targets include the mu-type opioid receptor (OPRM1), delta-type opioid receptor (OPRD1), kappa-type opioid receptor (OPRK1), ATP-dependent translocase ABCB1, and voltage-gated inwardly rectifying potassium channel KCNH2. Fentanyl is used as a treatment for dyspnea (PMC10527530) and pain (PMC10527530, PMC10560398, PMC10641973, PMC12327405, PMC12390419, PMC13301566, PMC9786992), and it has therapeutic effects on anxiety, depression, and pain (PMC12002424). It is associated with bradycardia (PMC8196964). Exposure routes include buccal, epidural, intramuscular, intravenous, nasal, oral, sublingual, topical, transdermal, and transmucosal, as well as smoking (PMC12002424) and inhalation (PMC12002424, PMC12390419, PMC8196964). The compound is found in 27 recorded sources, including healthcare, pharmaceuticals and veterinary products (analgesics and anesthetics), food preservation, building and construction (tents or canopies), household cleaning and consumer products (such as bleaching agents, perfumes within detergents and soaps, and smoking requisites), and electrical and electronic equipment (such as antennas, coils, and colour television systems). Drug Synthetic Toxin Organic Compound Amine Amide Drug Adjuvant, Anesthesia Analgesic Analgesic, Opioid Narcotic Opiate Agonist Anesthetic Anesthetic, Intravenous Adjuvant Metabolite Synthetic Compound 1-Phenethyl-4-(N-phenylpropionamido)piperidine 1-Phenethyl-4-N-propionylanilinopiperidine Abstral Actiq Duragesic Durogesic Fentanest Fentanil Fentanila Fentanilo Fentanyl citrate Fentanylum Lazanda N-(1-Phenethyl-4-piperidinyl)-N-phenylpropionamide N-(1-Phenethyl-4-piperidyl)propionanilide N-(1-Phenethyl-piperidin-4-yl)-N-phenyl-propionamide N-(1-Phenethylpiperidin-4-yl)-N-phenylpropionamide N-Phenethyl-4-(N-propionylanilino)piperidine N-Phenyl-N-(1-(2-phenylethyl)-4-piperidinyl)propanamide Nasalfent Phentanyl Rapinyl Subsys C22H28N2O 336.4705 336.220163528 N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide fentanyl 437-38-7 CCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C1=CC=CC=C1 InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3 PJMPHNIQZUBGLI-UHFFFAOYSA-N Organic compounds Organoheterocyclic compounds Piperidines Fentanyls Fentanyls Amino acids and derivatives Anilides Aralkylamines Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds Phenethylamines Tertiary carboxylic acid amides Trialkylamines Amine Amino acid or derivatives Anilide Aralkylamine Aromatic heteromonocyclic compound Azacycle Benzenoid Carbonyl group Carboxamide group Carboxylic acid derivative Fentanyl Hydrocarbon derivative Monocyclic benzene moiety Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenethylamine Tertiary aliphatic amine Tertiary amine Tertiary carboxylic acid amide Aromatic heteromonocyclic compounds anilide monocarboxylic acid amide piperidines Detected and Not Quantified Exogenous Membrane Fentanyl Action Pathway SMP0000415 Fentanyl Opioid Agonist Action Pathway SMP0125203 Fentanyl Metabolism SMP0125222 Fentanyl Drug Metabolism Action Pathway SMP0143252 Solid White powder. melting_point 87.5°C solubility 200 mg/L (at 25°C) logp 4.05 logp 4.12 ALOGPS logs -4.15 ALOGPS solubility 2.40e-02 g/l ALOGPS logp 3.82 ChemAxon pka_strongest_basic 8.77 ChemAxon iupac N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide ChemAxon average_mass 336.4705 ChemAxon mono_mass 336.220163528 ChemAxon smiles CCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C1=CC=CC=C1 ChemAxon formula C22H28N2O ChemAxon inchi InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3 ChemAxon inchikey PJMPHNIQZUBGLI-UHFFFAOYSA-N ChemAxon polar_surface_area 23.55 ChemAxon refractivity 103.48 ChemAxon polarizability 40.03 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Epidural; parental (transdermal, intramuscular). 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. Fentanyl'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 hypopolarization and reduced neuronal excitability. Fentanyl is metabolized primarily via human cytochrome P450 3A4 isoenzyme system. Route of Elimination: Fentanyl is metabolized primarily via human cytochrome P450 3A4 isoenzyme system and mostly eliminated in urine. Within 72 hours of IV fentanyl administration, approximately 75% of the dose is excreted in urine, mostly as metabolites with less than 10% representing unchanged drug. Half Life: 7 hours (range 3-12) LD50: 3.1 mg/kg (rat) LD50: 0.03 mg/kg (monkeys) No indication of carcinogenicity to humans (not listed by IARC). For the treatment of cancer patients with severe pain that breaks through their regular narcotic therapy. Used as an inhalation anesthetic. (L1484) #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f721ec41368> More common symptoms are dizziness, light-headedness, or feeling faint; drowsiness; nausea or vomiting; unusual tiredness or weakness. Less common or rare ones are blurred or double vision or other vision problems; confusion; constipation; convulsions (seizures); difficult or painful urination; mental depression; shortness of breath, trouble in breathing, tightness in the chest, or wheezing; skin rash, hives, or itching; unusual excitement (L1484) For the management of hypoventilation, immediate countermeasures include removing the Fentanyl and physically or verbally stimulating the patient. These actions can be followed by administration of a specific narcotic antagonist such as naloxone. The duration of hypoventilation following an overdose may be longer than the effects of the narcotic antagonist's action (the half-life of naloxone ranges from 30 to 81 minutes). The interval between IV antagonist doses should be carefully chosen because of the possibility of re-narcotization after system removal; repeated administration of naloxone may be necessary. Reversal of the narcotic effect may result in acute onset of pain and the release of catecholamines. Always ensure a patent airway is established and maintained, administer oxygen and assist or control respiration as indicated and use an oropharyngeal airway or endotracheal tube if necessary. Adequate body temperature and fluid intake should be maintained. (L1712) DB00813 HMDB14951 3345 CHEMBL596 3228 119915 Fentanyl Fentanyl 4420811 18301803 18001263 17617282 Martindale. The Extra Pharmacopoeia, 30th ed. Drugs.com: http://www.drugs.com/cons/Fentanyl.html Drugs.com: http://www.drugs.com/cons/Tramadol.html RxList: The Internet Drug Index (2009).: http://www.rxlist.com/ BE0000770 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. Fentanyl'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. Inhibitory 0.0029 uM BindingDB 50008984 Inhibitory 0.00397 uM BindingDB 50008984 Inhibitory 0.00845 uM BindingDB 50008984 IC50 0.0013 uM BindingDB 50008984 IC50 0.0031 uM BindingDB 50008984 BE0000632 Inhibitory 0.0848 uM BindingDB 50008984 Inhibitory 0.1965 uM BindingDB 50008984 Inhibitory 0.197 uM BindingDB 50008984 Inhibitory 0.255 uM BindingDB 50008984 Inhibitory 1.13 uM BindingDB 50008984 IC50 1.58 uM BindingDB 50008984 IC50 5.893 uM BindingDB 50008984 BE0000420 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. Fentanyl'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. Inhibitory 0.1527 uM BindingDB 50008984 Inhibitory 1 uM BindingDB 50008984 BE0001032 IC50 6.5 uM BindingDB 50008984 BE0000090 IC50 1.8197 uM BindingDB 50008984