Sufentanil (CHEM002253)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:27 UTC
Update Date2016-11-09 01:08:43 UTC
Accession NumberCHEM002253
Identification
Common NameSufentanil
ClassSmall Molecule
DescriptionSufentanil is only found in individuals that have used or taken this drug. It is an opioid analgesic that is used as an adjunct in anesthesia, in balanced anesthesia, and as a primary anesthetic agent. [PubChem]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. Sufentanil's analgesic activity is, most likely, due to its conversion to morphine. Opioids open calcium-dependent inwardly rectifying potassium channels (OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Adjuvant, Anesthesia
  • Amide
  • Amine
  • Analgesic, Opioid
  • Anesthetic, Intravenous
  • Drug
  • Ether
  • Metabolite
  • Narcotic
  • Opiate Agonist
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
N-(4-(Methoxymethyl)-1-(2-(2-thienyl)ethyl)-4-piperidinyl)-N-phenylpropanamideChEBI
N-(4-(Methoxymethyl)-1-(2-(2-thienyl)ethyl)-4-piperidyl)propionanilideChEBI
SufentanilumChEBI
SufentanylChEBI
Sufentanil citrateHMDB
Hameln brand OF sufentanil citrateHMDB
SufentaHMDB
SulfentanilHMDB
Taylor brand OF sufentanil citrateHMDB
Sufentanil-hamelnHMDB
SulfentanylHMDB
Curasan brand OF sufentanil citrateHMDB
Sufentanil curasanHMDB
Citrate, sufentanilHMDB
Janssen brand OF sufentanil citrateHMDB
Sufentanil-ratiopharmHMDB
Ratiopharm brand OF sufentanil citrateHMDB
SufentanilHamelnHMDB
Sufentanil ratiopharmHMDB
Curasan, sufentanilHMDB
Sufentanil hamelnHMDB
SufentanilRatiopharmHMDB
Chemical FormulaC22H30N2O2S
Average Molecular Mass386.551 g/mol
Monoisotopic Mass386.203 g/mol
CAS Registry Number56030-54-7
IUPAC NameN-[4-(methoxymethyl)-1-[2-(thiophen-2-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide
Traditional Namesufentanil
SMILESCCC(=O)N(C1=CC=CC=C1)C1(COC)CCN(CCC2=CC=CS2)CC1
InChI IdentifierInChI=1S/C22H30N2O2S/c1-3-21(25)24(19-8-5-4-6-9-19)22(18-26-2)12-15-23(16-13-22)14-11-20-10-7-17-27-20/h4-10,17H,3,11-16,18H2,1-2H3
InChI KeyGGCSSNBKKAUURC-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
  • Aralkylamine
  • Piperidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Thiophene
  • Amino acid or derivatives
  • Carboxamide group
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Sufentanil PathwayNot AvailableNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point97°C
Boiling PointNot Available
Solubility76 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP3.4ALOGPS
logP3.61ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)8.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.78 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity111.42 m³·mol⁻¹ChemAxon
Polarizability43.85 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0019-5492000000-9d94c514876bdc8387e0Spectrum
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 , positivesplash10-000i-0009000000-0f9e477eb2153eb20409Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0096000000-73641c83c08b872641cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-06ri-1981000000-b5f4aaab095cc6fc533cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-1900000000-2fdfd1d5fa6e43fa1604Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-4900000000-bd92c052347dc0822a01Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-06ri-1981000000-b5f4aaab095cc6fc533cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-06ri-1981000000-21ca95f5c20b4e4d757bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-1900000000-9e39677aeb59104a8067Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-1900000000-2fdfd1d5fa6e43fa1604Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0096000000-73641c83c08b872641cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-0f9e477eb2153eb20409Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-06ri-1981000000-e1ff77f1523c87ecb91fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-1900000000-60ef0f8a9d7e876ae46dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-03di-4900000000-48241c15de4549023508Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-03di-4900000000-bd92c052347dc0822a01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-c5724e75fd2eba4a33acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bta-4598000000-80bef262238fe0a2f79eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0909-6691000000-402460d2376f94ba18b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1009000000-0cb97625e6c980ac5389Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-054t-1149000000-17778ea8e91b31088014Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9281000000-2236691fcff93ab6da35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0019000000-f5e780ad77af70f3877fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0598000000-624e87a85c6af29ccc41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03du-1982000000-21b1cb138ec2a44e332dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-b423e34763d99ec623ffSpectrum
Toxicity Profile
Route of ExposureEpidural; parenteral(intravenous)
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. Sufentanil's analgesic activity is, most likely, due to its conversion to morphine. Opioids open calcium-dependent inwardly rectifying potassium channels (OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.
Metabolism Half Life: 265 minutes
Toxicity ValuesLD50: 18.7 mg/kg (parenteral-intravenous, mouse)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThe main use of this medication is in operating suites and critical care where pain relief is required for a short period of time. It also offers properties of sedation and this makes it a good analgesic component of anaesthetic regimen during an operation. [Wikipedia]. Also used as an analgesic adjunct in anesthesia and as a primary anesthetic drug in procedures requiring assisted ventilation and in the relief of pain.
Minimum Risk LevelNot Available
Health Effectsmay cause respiratory arrest. [Wikipedia] Medical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose.
SymptomsRespiratory depression. [Wikipedia]
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00708
HMDB IDHMDB0014846
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSufentanil
Chemspider ID38043
ChEBI ID9316
PubChem Compound ID41693
Kegg Compound IDC08022
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=10628901
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10945855
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11137863
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11504823
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15475572
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15828831
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=16621415
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=17118343
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=9580589