ContaminantDB: Sufentanil

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:27 UTC

Update Date

2026-05-14 16:46:42 UTC

Accession Number

CHEM002253

Identification

Common Name

Sufentanil

Class

Small Molecule

Description

Sufentanil 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
N-(4-(Methoxymethyl)-1-(2-(2-thienyl)ethyl)-4-piperidinyl)-N-phenylpropanamide	ChEBI
N-(4-(Methoxymethyl)-1-(2-(2-thienyl)ethyl)-4-piperidyl)propionanilide	ChEBI
Sufentanilum	ChEBI
Sufentanyl	ChEBI
Sufentanil citrate	HMDB
Hameln brand OF sufentanil citrate	HMDB
Sufenta	HMDB
Sulfentanil	HMDB
Taylor brand OF sufentanil citrate	HMDB
Sufentanil-hameln	HMDB
Sulfentanyl	HMDB
Curasan brand OF sufentanil citrate	HMDB
Sufentanil curasan	HMDB
Citrate, sufentanil	HMDB
Janssen brand OF sufentanil citrate	HMDB
Sufentanil-ratiopharm	HMDB
Ratiopharm brand OF sufentanil citrate	HMDB
SufentanilHameln	HMDB
Sufentanil ratiopharm	HMDB
Curasan, sufentanil	HMDB
Sufentanil hameln	HMDB
SufentanilRatiopharm	HMDB

Chemical Formula

C₂₂H₃₀N₂O₂S

Average Molecular Mass

386.551 g/mol

Monoisotopic Mass

386.203 g/mol

CAS Registry Number

56030-54-7

IUPAC Name

N-[4-(methoxymethyl)-1-[2-(thiophen-2-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide

Traditional Name

sufentanil

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 Key

GGCSSNBKKAUURC-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Anilides

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:9316 )
thiophenes (CHEBI:9316 )
ether (CHEBI:9316 )
anilide (CHEBI:9316 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Sufentanil Pathway	Not Available	Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	97°C
Boiling Point	Not Available
Solubility	76 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	3.4	ALOGPS
logP	3.61	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	8.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	32.78 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	111.42 m³·mol⁻¹	ChemAxon
Polarizability	43.85 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0019-5492000000-9d94c514876bdc8387e0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0009000000-0f9e477eb2153eb20409	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0096000000-73641c83c08b872641cd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-06ri-1981000000-b5f4aaab095cc6fc533c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-1900000000-2fdfd1d5fa6e43fa1604	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-4900000000-bd92c052347dc0822a01	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-06ri-1981000000-b5f4aaab095cc6fc533c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-06ri-1981000000-21ca95f5c20b4e4d757b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03di-1900000000-9e39677aeb59104a8067	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03di-1900000000-2fdfd1d5fa6e43fa1604	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0096000000-73641c83c08b872641cd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-0f9e477eb2153eb20409	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-06ri-1981000000-e1ff77f1523c87ecb91f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03di-1900000000-60ef0f8a9d7e876ae46d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-03di-4900000000-48241c15de4549023508	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-03di-4900000000-bd92c052347dc0822a01	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-c5724e75fd2eba4a33ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bta-4598000000-80bef262238fe0a2f79e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0909-6691000000-402460d2376f94ba18b6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1009000000-0cb97625e6c980ac5389	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-054t-1149000000-17778ea8e91b31088014	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aor-9281000000-2236691fcff93ab6da35	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0019000000-f5e780ad77af70f3877f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0598000000-624e87a85c6af29ccc41	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03du-1982000000-21b1cb138ec2a44e332d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-b423e34763d99ec623ff	Spectrum

Toxicity Profile

Route of Exposure

Epidural; parenteral(intravenous)

Mechanism of Toxicity

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.

Metabolism

Half Life: 265 minutes

Toxicity Values

LD50: 18.7 mg/kg (parenteral-intravenous, mouse)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

The 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 Level

Not Available

Health Effects

may 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.

Symptoms

Respiratory depression. [Wikipedia]

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00708

HMDB ID

HMDB0014846

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not 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.

MSDS

Link

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

Sufentanil (CHEM002253)

Structure for CHEM002253: Sufentanil