SUFENTANIL

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Search structure


Synonyms	IDS-NS-001 R 30,730 R-30730 Sufentanil Sufentanyl
Status
Molecule Category	Free-form
ATC	N01AH03
UNII	AFE2YW0IIZ
EPA CompTox	DTXSID6023604


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	GGCSSNBKKAUURC-UHFFFAOYSA-N
Smiles	CCC(=O)N(c1ccccc1)C1(COC)CCN(CCc2cccs2)CC1
InChI	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

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H30N2O2S
Molecular Weight	386.56
AlogP	4.21
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	8.0
Polar Surface Area	32.78
Molecular species	BASE
Aromatic Rings	2.0
Heavy Atoms	27.0

Assay Description	Organism	Bioactivity	Reference
Inhibition of electrically evoked contraction in guinea pig ileum determined in vitro	Cavia porcellus	7.43 nM
Displacement of [3H]nalotrexone from rat-brain Opioid receptors	Rattus norvegicus	2.3 nM
In vitro affinity to displace [3H]naloxone from opiate receptor in freshly prepared rat brain homogenates	None	0.02 nM
Ability to displace [3H]naloxone from the Opioid receptor mu 1 isolated from the rat brain membranes.	None	0.22 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-3.06 %
Agonist activity at human mu opioid receptor expressed in CHO cell membranes after 1 hr by [35S]-GTPgammaS binding assay	Homo sapiens	1.3 nM
Agonist activity at human mu opioid receptor expressed in human U2OS cells co-transfected with beta-arrestin-2 assessed as increase in beta-arrestin-2 recruitment after 90 mins by BRET assay	Homo sapiens	1.5 nM
Displacement of [3H]DAMGO from rat brain mu opioid receptor incubated for 60 mins by microbeta scintillation counting method	Rattus norvegicus	0.4 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	12.47 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.08 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.08 %

Related Entries

Cross References

Resources	Reference
ChEBI	9316
ChEMBL	CHEMBL658
DrugBank	DB00708
DrugCentral	2491
FDA SRS	AFE2YW0IIZ
Human Metabolome Database	HMDB0014846
Guide to Pharmacology	3534
KEGG	C08022
PharmGKB	PA451527
PubChem	41693
SureChEMBL	SCHEMBL26728
ZINC	ZINC000000538386

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).