ContaminantDB: Sufentanil citrate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 06:50:37 UTC

Update Date

2016-11-09 01:16:08 UTC

Accession Number

CHEM020145

Identification

Common Name

Sufentanil citrate

Class

Small Molecule

Description

Sufentanil, sold under the brand names Dsuvia and Sufenta, is a synthetic opioid analgesic drug approximately 5 to 10 times as potent as its parent drug, fentanyl, and 500 times as potent as morphine. Structurally, sufentanil differs from fentanyl through the addition of a methoxymethyl group on the piperidine ring (which is believed to reduce duration of action), and the replacement of the phenyl ring by thiophene. Sufentanil first was synthesized at Janssen Pharmaceutica in 1974.Sufentanil is marketed for use by specialist centers under different trade names, such as Sufenta and Sufentil. Sufentanil with and without lidocaine or mepivacaine is available as a transdermal patch similar to Duragesic in Europe under trade names such as Chronogesic. It is available as a sublingual tablet under the trade name Dsuvia.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Dsuvia	Kegg
Sufenta	Kegg
Sufentanil citric acid	Generator
Sufentanil	MeSH
SufentanilRatiopharm	MeSH
Sufentanil curasan	MeSH
SufentanilHameln	MeSH
Sufentanil-hameln	MeSH
Citrate, sufentanil	MeSH
Sufentanil hameln	MeSH
Sufentanil-ratiopharm	MeSH
Curasan, sufentanil	MeSH
Sulfentanil	MeSH
Sufentanil ratiopharm	MeSH
Sulfentanyl	MeSH
Janssen brand OF sufentanil citrate	MeSH
Taylor brand OF sufentanil citrate	MeSH
Curasan brand OF sufentanil citrate	MeSH
Ratiopharm brand OF sufentanil citrate	MeSH
Hameln brand OF sufentanil citrate	MeSH
2-Hydroxypropane-1,2,3-tricarboxylate
N-[4-(methoxymethyl)-1-[2-(thiophen-2-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide
2-Hydroxypropane-1,2,3-tricarboxylate; N-[4-(methoxymethyl)-1-[2-(thiophen-2-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide	Generator

Chemical Formula

C₂₈H₃₈N₂O₉S

Average Molecular Mass

578.674 g/mol

Monoisotopic Mass

578.230 g/mol

CAS Registry Number

60561-17-3

IUPAC Name

2-hydroxypropane-1,2,3-tricarboxylic acid; N-[4-(methoxymethyl)-1-[2-(thiophen-2-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide

Traditional Name

citric acid; sufentanil

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN(CCC2=CC=CS2)CC1

InChI Identifier

InChI=1S/C22H30N2O2S.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-10,17H,3,11-16,18H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

InChI Key

OJCZPLDERGDQRJ-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
Tricarboxylic acid or derivatives
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

Not Available

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	13	ChemAxon
Refractivity	111.42 m³·mol⁻¹	ChemAxon
Polarizability	44.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000090000-49a69da7e13bbb07b098	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000090000-49a69da7e13bbb07b098	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0000090000-49a69da7e13bbb07b098	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000090000-87b704a7aba107996520	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0000090000-87b704a7aba107996520	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0000090000-87b704a7aba107996520	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DBSALT000275

HMDB ID

Not Available

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

Sufentanil

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

65494

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Sufentanil citrate (CHEM020145)

Structure for CHEM020145: Sufentanil citrate