Alfentanil (CHEM002275)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (6)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:40 UTC
Update Date2016-11-09 01:08:43 UTC
Accession NumberCHEM002275
Identification
Common NameAlfentanil
ClassSmall Molecule
DescriptionA 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. [PubChem]
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Analgesic
  • Analgesic, Opioid
  • Anesthetic
  • Anesthetic, Intravenous
  • Drug
  • Ether
  • Metabolite
  • Narcotic
  • Opiate Agonist
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AlfentanilumChEBI
AlfentanylChEBI
N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilideChEBI
RapifenKegg
Esteve brand OF alfentanil hydrochlorideHMDB
FanaxalHMDB
ICI brand OF alfentanil hydrochlorideHMDB
Janssen brand OF alfentanil hydrochlorideHMDB
LimifenHMDB
AlfentaHMDB
Alfentanil hydrochlorideHMDB
Chemical FormulaC21H32N6O3
Average Molecular Mass416.517 g/mol
Monoisotopic Mass416.254 g/mol
CAS Registry Number71195-58-9
IUPAC NameN-{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
Traditional Namealfentanil
SMILESCCN1N=NN(CCN2CCC(COC)(CC2)N(C(=O)CC)C2=CC=CC=C2)C1=O
InChI IdentifierInChI=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
InChI KeyIDBPHNDTYPBSNI-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentAnilides
Alternative Parents
Substituents
  • Anilide
  • Piperidine
  • Azole
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Tetrazole
  • Amino acid or derivatives
  • Carboxamide group
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point140.8°C
Boiling PointNot Available
Solubility34.6 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP2.2ALOGPS
logP2.81ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)7.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area81.05 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity118.59 m³·mol⁻¹ChemAxon
Polarizability45.57 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aps-5759000000-11ce8f647981a86e2993Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0000900000-a802cc961dad7c6326a5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0395300000-498fafc6962b6fd82e9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kb-0912000000-43c2343a5fa4997ca93aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-015a-2900000000-16b845b2c742175e38cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-015a-7900000000-e9bd243460dd40507619Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-015a-2900000000-16b845b2c742175e38cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-015a-7900000000-e9bd243460dd40507619Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00kb-0912000000-43c2343a5fa4997ca93aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00kb-0912000000-b5e89d86b302adb65517Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-015a-2900000000-d76f968c16c60e097fbcSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014i-0395300000-498fafc6962b6fd82e9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-a802cc961dad7c6326a5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-015a-7900000000-7fdf62ef447e7c6e19faSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00kb-0912000000-1f6c2333f39ce390e20eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-015a-7900000000-1c558c3f776664f15eb1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9007000000-cbc10f94b61327a4ec79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9022000000-5dee7e8e9ca18ed6afa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9052000000-d1f0fa6385e6848912c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0cdr-6509300000-1d06eb64c3c9a376ea43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3109000000-3960d2bbff65d1a0ecc0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-9423000000-8194ccf6d27ec2cb2870Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-1e0b9eadc3dc511d87d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0392100000-333cd54e08c49ae75cdeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0296-1936000000-2f1acf618b9904cbaffeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009300000-f5e9f9e4f40759f2ff43Spectrum
Toxicity Profile
Route of ExposureFor intravenous injection or infusion only.
Mechanism of ToxicityOpiate 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.
MetabolismThe liver is the major site of biotransformation. 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
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the management of postoperative pain and the maintenance of general anesthesia.
Minimum Risk LevelNot Available
Health EffectsMedical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose.
SymptomsSymptoms of overexposure include characteristic rigidity of the skeletal muscles, cardiac and respiratory depression, and narrowing of the pupils.
TreatmentIntravenous administration of an opioid antagonist such as naloxone should be employed as a specific antidote to manage respiratory depression. The duration of respiratory depression following overdosage with ALFENTA may be longer than the duration of action of the opioid antagonist. Administration of an opioid antagonist should not preclude immediate establishment of a patent airway, administration of oxygen, and assisted or controlled ventilation as indicated for hypoventilation or apnea. If respiratory depression is associated with muscular rigidity, a neuromuscular blocking agent may be required to facilitate assisted or controlled ventilation. Intravenous fluids and vasoactive agents may be required to manage hemodynamic instability. (2)
Concentrations
Not Available
DrugBank IDDB00802
HMDB IDHMDB0014940
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAlfentanil
Chemspider ID46451
ChEBI ID2569
PubChem Compound ID51263
Kegg Compound IDC08005
YMDB IDNot Available
ECMDB IDNot Available
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.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11240593
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11999595
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16621415
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23446076