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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:45 UTC
HMDB IDHMDB0014846
Secondary Accession Numbers
  • HMDB14846
Metabolite Identification
Common NameSufentanil
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.
Structure
Data?1582753227
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 Weight386.551
Monoisotopic Molecular Weight386.202798904
IUPAC NameN-[4-(methoxymethyl)-1-[2-(thiophen-2-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide
Traditional Namesufentanil
CAS Registry Number56030-54-7
SMILES
CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN(CCC2=CC=CS2)CC1
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point97 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 g/LNot Available
LogP2.8Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM191.330932474
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+189.31831661259
DarkChem[M-H]-185.99131661259
DeepCCS[M+H]+189.35630932474
DeepCCS[M-H]-186.93630932474
DeepCCS[M-2H]-221.29130932474
DeepCCS[M+Na]+196.51730932474
AllCCS[M+H]+193.532859911
AllCCS[M+H-H2O]+191.032859911
AllCCS[M+NH4]+195.832859911
AllCCS[M+Na]+196.532859911
AllCCS[M-H]-190.232859911
AllCCS[M+Na-2H]-190.932859911
AllCCS[M+HCOO]-191.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SufentanilCCC(=O)N(C1=CC=CC=C1)C1(COC)CCN(CCC2=CC=CS2)CC14061.9Standard polar33892256
SufentanilCCC(=O)N(C1=CC=CC=C1)C1(COC)CCN(CCC2=CC=CS2)CC12898.5Standard non polar33892256
SufentanilCCC(=O)N(C1=CC=CC=C1)C1(COC)CCN(CCC2=CC=CS2)CC12847.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sufentanil GC-MS (Non-derivatized) - 70eV, Positivesplash10-0019-5492000000-9d94c514876bdc8387e02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sufentanil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sufentanil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Sufentanil LC-ESI-QTOF , positive-QTOFsplash10-000i-0009000000-0f9e477eb2153eb204092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sufentanil LC-ESI-QTOF , positive-QTOFsplash10-000i-0096000000-73641c83c08b872641cd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sufentanil LC-ESI-QTOF , positive-QTOFsplash10-06ri-1981000000-b5f4aaab095cc6fc533c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sufentanil LC-ESI-QTOF , positive-QTOFsplash10-03di-1900000000-2fdfd1d5fa6e43fa16042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sufentanil LC-ESI-QTOF , positive-QTOFsplash10-03di-4900000000-bd92c052347dc0822a012017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sufentanil 30V, Positive-QTOFsplash10-06ri-1981000000-b5f4aaab095cc6fc533c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sufentanil 30V, Positive-QTOFsplash10-06ri-1981000000-21ca95f5c20b4e4d757b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sufentanil 40V, Positive-QTOFsplash10-03di-1900000000-9e39677aeb59104a80672021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sufentanil 40V, Positive-QTOFsplash10-03di-1900000000-2fdfd1d5fa6e43fa16042021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sufentanil 20V, Positive-QTOFsplash10-000i-0096000000-73641c83c08b872641cd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sufentanil 10V, Positive-QTOFsplash10-000i-0009000000-0f9e477eb2153eb204092021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sufentanil 30V, Positive-QTOFsplash10-06ri-1981000000-e1ff77f1523c87ecb91f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sufentanil 40V, Positive-QTOFsplash10-03di-1900000000-60ef0f8a9d7e876ae46d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sufentanil 50V, Positive-QTOFsplash10-03di-4900000000-48241c15de45490235082021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sufentanil 50V, Positive-QTOFsplash10-03di-4900000000-bd92c052347dc0822a012021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sufentanil 10V, Positive-QTOFsplash10-000i-0009000000-c5724e75fd2eba4a33ac2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sufentanil 20V, Positive-QTOFsplash10-0bta-4598000000-80bef262238fe0a2f79e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sufentanil 40V, Positive-QTOFsplash10-0909-6691000000-402460d2376f94ba18b62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sufentanil 10V, Negative-QTOFsplash10-000i-1009000000-0cb97625e6c980ac53892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sufentanil 20V, Negative-QTOFsplash10-054t-1149000000-17778ea8e91b310880142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sufentanil 40V, Negative-QTOFsplash10-0aor-9281000000-2236691fcff93ab6da352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sufentanil 10V, Positive-QTOFsplash10-000i-0019000000-f5e780ad77af70f3877f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sufentanil 20V, Positive-QTOFsplash10-000i-0598000000-624e87a85c6af29ccc412021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sufentanil 40V, Positive-QTOFsplash10-03du-1982000000-21b1cb138ec2a44e332d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sufentanil 10V, Negative-QTOFsplash10-000i-0009000000-b423e34763d99ec623ff2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00708 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00708 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00708
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID38043
KEGG Compound IDC08022
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSufentanil
METLIN IDNot Available
PubChem Compound41693
PDB IDNot Available
ChEBI ID9316
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins
Gene Name:
OPRD1
Uniprot ID:
P41143
Molecular weight:
40412.3
References
  1. Freye E, Latasch L, Portoghese PS: The delta receptor is involved in sufentanil-induced respiratory depression--opioid subreceptors mediate different effects. Eur J Anaesthesiol. 1992 Nov;9(6):457-62. [PubMed:1330549 ]
  2. Zhu J, Xue JC, Law PY, Claude PA, Luo LY, Yin J, Chen C, Liu-Chen LY: The region in the mu opioid receptor conferring selectivity for sufentanil over the delta receptor is different from that over the kappa receptor. FEBS Lett. 1996 Apr 15;384(2):198-202. [PubMed:8612823 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
Gene Name:
OPRM1
Uniprot ID:
P35372
Molecular weight:
44778.9
References
  1. Hurle MA: Changes in the expression of G protein-coupled receptor kinases and beta-arrestin 2 in rat brain during opioid tolerance and supersensitivity. J Neurochem. 2001 Apr;77(2):486-92. [PubMed:11299311 ]
  2. Levron JC: [Pharmacokinetics and pharmacodynamics of morphinomimetics in the central nervous system]. Agressologie. 1991;32(6-7):318-20. [PubMed:1688220 ]
  3. Ilien B, Galzi JL, Mejean A, Goeldner M, Hirth C: A mu-opioid receptor-filter assay. Rapid estimation of binding affinity of ligands and reversibility of long-lasting ligand-receptor complexes. Biochem Pharmacol. 1988 Oct 15;37(20):3843-51. [PubMed:2847746 ]
  4. Colpaert FC, Leysen JE, Michiels M, van den Hoogen RH: Epidural and intravenous sufentanil in the rat: analgesia, opiate receptor binding, and drug concentrations in plasma and brain. Anesthesiology. 1986 Jul;65(1):41-9. [PubMed:3014923 ]
  5. Leysen JE, Gommeren W: In vitro binding properties of 3H-sufentanil, a superior ligand for the mu-opiate receptor. Arch Int Pharmacodyn Ther. 1982 Dec;260(2):287-9. [PubMed:6131653 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
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
Gene Name:
OPRK1
Uniprot ID:
P41145
Molecular weight:
42644.7
References
  1. Zhu J, Xue JC, Law PY, Claude PA, Luo LY, Yin J, Chen C, Liu-Chen LY: The region in the mu opioid receptor conferring selectivity for sufentanil over the delta receptor is different from that over the kappa receptor. FEBS Lett. 1996 Apr 15;384(2):198-202. [PubMed:8612823 ]
  2. Chang HM, Berde CB, Holz GG 4th, Steward GF, Kream RM: Sufentanil, morphine, met-enkephalin, and kappa-agonist (U-50,488H) inhibit substance P release from primary sensory neurons: a model for presynaptic spinal opioid actions. Anesthesiology. 1989 Apr;70(4):672-7. [PubMed:2467589 ]