Sufentanil

Identification

Summary

Sufentanil is an opioid used to induce and maintain anesthesia, to act as an analgesic in labor and delivery, and to treat severe, acute pain.

Brand Names

Dsuvia, Sufenta

Generic Name

Sufentanil

DrugBank Accession Number

DB00708

Background

Sufentanil is an opioid analgesic that is used as an adjunct in anesthesia, in balanced anesthesia, and as a primary anesthetic agent. It is administered by the intravenous, epidural and sublingual routes.

Also known as Dsuvia, the sublingual form is used for the management of acute pain in adults that is severe to warrant the use of an opioid analgesic in certified medically supervised healthcare settings, including hospitals, surgical centers, and emergency departments ¹⁰. Consideration may be made in the future for the use of the sublingual form in the US military in cases where analgesia is required immediately ¹¹.

The sublingual form, manufactured by AcelRx Pharmaceuticals, Inc. (AcelRx), was approved on November 2, 2018 ¹⁰. This route of administration is intended to be a simple, effective, non-invasive analgesic option to enable healthcare professionals to rapidly manage acute pain without difficult intravenous or epidural administration ¹⁰, ⁴.

Type

Small Molecule

Groups

Approved, Investigational

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Sufentanil (DB00708)

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Weight

Average: 386.551
Monoisotopic: 386.202798904

Chemical Formula

C₂₂H₃₀N₂O₂S

Synonyms

• N-(4-(Methoxymethyl)-1-(2-(2-thienyl)ethyl)-4-piperidinyl)-N-phenylpropanamide
• N-(4-(Methoxymethyl)-1-(2-(2-thienyl)ethyl)-4-piperidyl)propionanilide
• Sufentanil
• Sufentanilo
• Sufentanilum
• Sufentanyl

External IDs

• IDS-NS-001
• R 30,730
• R 30730
• R 33800
• R-30730

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Pharmacology

Indication

The indications for this drug are as follows:

1. As an analgesic adjunct in the maintenance of balanced general anesthesia in patients who are intubated and ventilated.

2. As a primary anesthetic agent for the induction and maintenance of anesthesia with 100% oxygen in patients undergoing major surgical procedures, in patients who are intubated and ventilated, such as cardiovascular surgery or neurosurgical procedures in the sitting position, to provide favorable myocardial and cerebral oxygen balance or when extended postoperative ventilation is anticipated.

3. For epidural administration as an analgesic combined with low dose (usually 12.5 mg per administration) bupivacaine usually during labor and vaginal delivery

4. The sublingual form is indicated for the management of acute pain in adults that is severe to warrant the use of an opioid analgesic in certified medically supervised healthcare settings, including hospitals, surgical centers, and emergency departments.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Acute pain		••••••••••••		••••••••••• ••••••••• •••••• ••••• ••• •••••••• •••••••
Treatment of	Acute severe pain		••••••••••••

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Associated Therapies

• General Anesthesia
• Induction and Maintenance of General Anesthesia
• Lumbar epidural anesthesia therapy
• Short opioid analgesia requirement

Contraindications & Blackbox Warnings

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Pharmacodynamics

Effect on the Central Nervous System (CNS)

In clinical settings, sufentanil exerts its principal pharmacologic effects on the central nervous system. Its primary therapeutic actions are analgesia and sedation. Sufentanil may increase pain tolerance and decrease the perception of pain. This drug depresses the respiratory centers, depresses the cough reflex, and constricts the pupils ¹³, ⁹. When used in balanced general anesthesia, sufentanil has been reported to be as much as 10 times as potent as fentanyl. When administered intravenously as a primary anesthetic agent with 100% oxygen, sufentanil is approximately 5 to 7 times as potent as fentanyl ^Label. High doses of intravenous sufentanil have been shown to cause muscle rigidity, likely as a result of an effect on the substantia nigra and the striate nucleus in the brain. Sleep-inducing (hypnotic) activity can be demonstrated by EEG alterations ^Label.

Effects on the Respiratory System

Sufentanil may cause respiratory depression ^Label.

Effects on the Cardiovascular System

Sufentanil causes peripheral vasodilation which may result in orthostatic hypotension or syncope. Bradycardia may also occur ¹³. Clinical signs or symptoms of histamine release and/or peripheral vasodilation may include pruritus, flushing, red eyes and sweating and/or orthostatic hypotension ^Label.

Effects on the Gastrointestinal Tract

Sufentanil causes a reduction in motility associated with an increase in smooth muscle tone in both the antrum of the stomach and duodenum. Digestion of food in the small intestine may be delayed and propulsive contractions are decreased. Propulsive peristaltic waves in the colon are decreased, while tone may be increased and lead to spasm, resulting in constipation. Other opioid-induced effects may include a reduction in biliary and pancreatic secretions, spasm of the sphincter of Oddi, as well as temporary elevations in serum amylase ^Label.

Mechanism of action

Sufentanil is a synthetic, potent opioid with highly selective binding to μ-opioid receptors ¹³. These receptors are widely distributed in the human brain, spinal cord, and other tissues ⁸, ⁹.

In general, opioids decrease cAMP (affecting neural signaling pathways), decrease neurotransmitter release, and cause membrane hyperpolarization, all of which contribute to the relief of painful symptoms ⁹.

Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic neural transmission via G-proteins that activate effector proteins. Binding of the opiate receptor leads to 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. The release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine, and noradrenaline is then inhibited ⁹.

Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist), also preventing neurotransmitter release ⁹.

Sufentanil and other opioids open calcium-dependent inwardly rectifying potassium channels, resulting in hyperpolarization and reduced neuronal excitability ⁸, ⁹.

Target	Actions	Organism
AMu-type opioid receptor	agonist	Humans
UDelta-type opioid receptor	agonist	Humans
UKappa-type opioid receptor	Not Available	Humans

Absorption

Bioavailability of a single sublingual tablet was 52%, decreasing to 35% with repeat dosing ⁵.

After epidural administration of incremental doses totaling 5 to 40 mcg sufentanil during labor and delivery, maternal and neonatal sufentanil plasma concentrations were at or near the 0.05 to 0.1 ng/mL limit of detection, and were slightly higher in mothers than in their infants ^Label.

Volume of distribution

Sufentanil has a distribution time of 1.4 minutes and redistribution time of 17.1 minutes ^Label. The central volume of distribution after intravenous application of sufentanil is approximately 14 L and the volume of distribution at steady state is approximately 350 L ¹³.

Protein binding

Plasma protein binding of sufentanil, related to the alpha acid glycoprotein concentration, was approximately 93% in healthy males, 91% in mothers and 79% in neonates ^Label.

Metabolism

The liver and small intestine are the major sites of biotransformation ^Label. Sufentanil is rapidly metabolized to a number of inactive metabolites, with oxidative N- and O-dealkylation being the major routes of elimination ¹³.

Route of elimination

Approximately 80% of the administered dose is excreted within 24 hours and only 2% of the dose is eliminated as unchanged drug ^Label.

Half-life

The elimination half-life is 164 minutes in adults when administered intravenously (IV). The elimination half-life of sufentanil is shorter (e.g. 97 +/- 42 minutes) in infants and children, and longer in neonates (e.g. 434 +/- 160 minutes) compared to that of adolescents and adults ^Label.

After a single administration of a 15 microgram sufentanil sublingual tablet, mean terminal phase half-lives in the range of 6-10 hours have been observed. After multiple administrations, a longer average terminal half-life of up to 18 hours was measured, owing to the higher plasma concentrations of sufentanil achieved after repeated dosing and due to the possibility to quantify these concentrations over a longer time period ¹³.

Clearance

The total plasma clearance after single intravenous administration is about 917 l/min ¹³.

The clearance of sufentanil in healthy neonates is approximately one-half that in adults and children. The clearance rate of sufentanil can be further reduced by up to a third in neonates with cardiovascular disease ^Label.

Adverse Effects

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Toxicity

LD₅₀: 18.7 mg/kg (IV in mice) ^MSDS

A Note on Respiratory Depression

Major, life-threatening, or fatal respiratory depression has been reported with the use of opioids, even in cases where it is used as recommended. Respiratory depression may lead to respiratory arrest and death if not diagnosed and treated appropriately. This drug should be administered only by persons specifically trained in the use of anesthetic drugs and the management of the respiratory effects of potent opioids, including respiration and cardiac resuscitation of patients in the age group being treated. This training must include the establishment and maintenance of a patent airway and assisted ventilation ^Label.

Carcinogenesis Long-term studies in animals to evaluate the carcinogenic potential of sufentanil have not been conducted ^Label.

Mutagenesis Sufentanil was not found to be genotoxic in the in vitro bacterial reverse mutation assay (Ames assay) or in the in vivo rat bone marrow micronucleous assay ^Label.

Reproductive Toxicity

Sufentanil caused embryolethality in rats and rabbits treated for 10-30 days during pregnancy with 2.5 times the maximum human dose by intravenous administration. The embryolethal effect was thought to be secondary to the toxicity for the mother animal model. No negative effects were noted in another study in rats that were treated with 20 times the maximum human dose in the period of organogenesis. The preclinical effects were only seen following administrations of levels significantly above the maximum human dose, which is therefore of minimal relevance for clinical use ¹³.

Pregnancy

May cause fetal harm ^Label

The Use in Lactation

Infants exposed to this drug through breast milk should be monitored for excess sedation and respiratory depression ^Label.

Pathways

Pathway	Category
Sufentanil Action Pathway	Drug action

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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1,2-Benzodiazepine	The risk or severity of adverse effects can be increased when Sufentanil is combined with 1,2-Benzodiazepine.
Abaloparatide	The risk or severity of adverse effects can be increased when Sufentanil is combined with Abaloparatide.
Abametapir	The serum concentration of Sufentanil can be increased when it is combined with Abametapir.
Acebutolol	Sufentanil may decrease the antihypertensive activities of Acebutolol.
Aceclofenac	The risk or severity of hypertension can be increased when Sufentanil is combined with Aceclofenac.

Food Interactions

• Avoid alcohol. Ingesting alcohol may potentiate the CNS depressant effects of sufentanil.
• Avoid grapefruit products. Sufentanil is a CYP3A4 substrate; therefore, concomitant ingestion of CYP3A4 inhibitors like grapefruit products may increase serum levels of sufentanil and potentiate CNS depression.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Sufentanil citrate	S9ZFX8403R	60561-17-3	OJCZPLDERGDQRJ-UHFFFAOYSA-N

International/Other Brands

Chronogesic (DURECT) / Disufen (Angenerico) / Fastfen (Cristália) / Sufenta Forte (Janssen) / Sufenta mite (Janssen) / Sufentil (Claris Lifesciences Ltd.) / Zuftil (Pisa)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Dsuvia	Tablet	30 ug/1	Sublingual	AcelRx Pharmaceuticals, Inc.	2018-11-02	Not applicable
Dzuveo	Tablet	30 ?g	Sublingual	Laboratoire Aguettant	2020-12-16	Not applicable
Dzuveo	Tablet	30 ?g	Sublingual	Laboratoire Aguettant	2020-12-16	Not applicable
Sufenta	Solution	50 ug/1mL	Intravenous	Taylor Pharmaceuticals	2008-07-02	Not applicable
Sufenta Inj 50mcg/ml	Liquid	50 mcg / mL	Intravenous	Janssen Pharmaceutica, Division Of Janssen Ortho Inc.	1985-12-31	1996-09-10

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Sufentanil Citrate	Injection	0.05 mg/1mL	Epidural; Intravenous	West-Ward Pharmaceuticals Corp.	1995-12-15	Not applicable
Sufentanil Citrate	Injection	0.05 mg/1mL	Epidural; Intravenous	Baxter Laboratories	2002-12-02	2014-03-31
Sufentanil Citrate	Injection	0.05 mg/1mL	Epidural; Intravenous	West-Ward Pharmaceuticals Corp.	1995-12-15	Not applicable
Sufentanil Citrate	Injection, solution	50 ug/1mL	Epidural; Intravenous	Hospira, Inc.	2005-07-26	Not applicable
Sufentanil Citrate	Injection	0.05 mg/1mL	Epidural; Intravenous	West-Ward Pharmaceuticals Corp.	1995-12-15	Not applicable

Categories

ATC Codes

N01AH03 — Sufentanil

• N01AH — Opioid anesthetics
• N01A — ANESTHETICS, GENERAL
• N01 — ANESTHETICS
• N — NERVOUS SYSTEM

Drug Categories

• Adjuvants, Anesthesia
• Agents that produce hypertension
• Analgesics
• Anesthetics
• Anesthetics, General
• Anesthetics, Intravenous
• Bradycardia-Causing Agents
• Central Nervous System Agents
• Central Nervous System Depressants
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 Substrates
• Fentanyl and fentanyl analogues
• High-risk opioids
• Hypotensive Agents
• Narcotics
• Nervous System
• Neuraxial Anesthetics
• Opiate Agonists
• Opioid Agonist
• Opioid Anesthetics
• Opioids
• Opioids, Anilidopiperidine
• Peripheral Nervous System Agents
• Phenylpiperidine opioids
• Piperidines
• Sensory System Agents
• Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome

Chemical TaxonomyProvided by Classyfire

Description

This compound 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

Aralkylamines / Piperidines / Thiophenes / Tertiary carboxylic acid amides / Heteroaromatic compounds / Trialkylamines / Amino acids and derivatives / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds

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Substituents

Amine / Amino acid or derivatives / Anilide / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Dialkyl ether / Ether / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Piperidine / Tertiary aliphatic amine / Tertiary amine / Tertiary carboxylic acid amide / Thiophene

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Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

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

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

AFE2YW0IIZ

CAS number

56030-54-7

InChI Key

GGCSSNBKKAUURC-UHFFFAOYSA-N

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

IUPAC Name

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

SMILES

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

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.

US20060149071

General References

1. Authors unspecified: Drug and Device News. P T. 2017 Dec;42(12):726-763. [Article]
2. Miner JR, Rafique Z, Minkowitz HS, DiDonato KP, Palmer PP: Sufentanil sublingual tablet 30mcg for moderate-to-severe acute pain in the ED. Am J Emerg Med. 2018 Jun;36(6):954-961. doi: 10.1016/j.ajem.2017.10.058. Epub 2017 Oct 31. [Article]
3. Willsie SK, Evashenk MA, Hamel LG, Hwang SS, Chiang YK, Palmer PP: Pharmacokinetic properties of single- and repeated-dose sufentanil sublingual tablets in healthy volunteers. Clin Ther. 2015 Jan 1;37(1):145-55. doi: 10.1016/j.clinthera.2014.11.001. Epub 2014 Dec 24. [Article]
4. Ringold FG, Minkowitz HS, Gan TJ, Aqua KA, Chiang YK, Evashenk MA, Palmer PP: Sufentanil sublingual tablet system for the management of postoperative pain following open abdominal surgery: a randomized, placebo-controlled study. Reg Anesth Pain Med. 2015 Jan-Feb;40(1):22-30. doi: 10.1097/AAP.0000000000000152. [Article]
5. Fisher DM, Chang P, Wada DR, Dahan A, Palmer PP: Pharmacokinetic Properties of a Sufentanil Sublingual Tablet Intended to Treat Acute Pain. Anesthesiology. 2018 May;128(5):943-952. doi: 10.1097/ALN.0000000000002145. [Article]
6. Vardanyan RS, Hruby VJ: Fentanyl-related compounds and derivatives: current status and future prospects for pharmaceutical applications. Future Med Chem. 2014 Mar;6(4):385-412. doi: 10.4155/fmc.13.215. [Article]
7. Pergolizzi JV Jr, LeQuang JA, Berger GK, Raffa RB: The Basic Pharmacology of Opioids Informs the Opioid Discourse about Misuse and Abuse: A Review. Pain Ther. 2017 Jun;6(1):1-16. doi: 10.1007/s40122-017-0068-3. Epub 2017 Mar 24. [Article]
8. Sobczak M, Salaga M, Storr MA, Fichna J: Physiology, signaling, and pharmacology of opioid receptors and their ligands in the gastrointestinal tract: current concepts and future perspectives. J Gastroenterol. 2014 Jan;49(1):24-45. doi: 10.1007/s00535-013-0753-x. Epub 2013 Feb 9. [Article]
9. Pathan H, Williams J: Basic opioid pharmacology: an update. Br J Pain. 2012 Feb;6(1):11-6. doi: 10.1177/2049463712438493. [Article]
10. FDA approves Dsuvia [Link]
11. Noting Military Potential, FDA Approves Powerful Painkiller Dsuvia [Link]
12. FDA Approved Drug Products: DSUVIA® (sufentanil) sublingual tablet, CII [Link]
13. Sufentanil EMA label [File]
14. Sufentanil [File]

External Links

Human Metabolome Database

HMDB0014846

KEGG Drug

D05938

KEGG Compound

C08022

PubChem Compound

41693

PubChem Substance

46504737

ChemSpider

38043

BindingDB

94503

RxNav

56795

ChEBI

9316

ChEMBL

CHEMBL658

ZINC

ZINC000000538386

Therapeutic Targets Database

DAP000357

PharmGKB

PA451527

Guide to Pharmacology

GtP Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Sufentanil

FDA label

Download (176 KB)

MSDS

Download (47.6 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Prevention	Analgesia / Dexmedetomidine / Elderly / Long-term Outcomes / Orthopedic Surgery / Postoperative Delirium (POD)	1
4	Active Not Recruiting	Prevention	Chronic Postoperative Pain / Dexmedetomidine / Esketamine / Postoperative Analgesia / Scoliosis Correction	1
4	Active Not Recruiting	Treatment	Driving Performance After Minor Ambulatory Surgery / Minor Surgical Procedures With Monitored Anesthesia Care	1
4	Active Not Recruiting	Treatment	Opioids Use / Postoperative pain / Spine Fusion	1
4	Completed	Basic Science	Anesthesia therapy	1

Pharmacoeconomics

Manufacturers

• Akorn inc
• Baxter healthcare corp anesthesia and critical care
• Hospira inc
• Watson laboratories inc

Packagers

• Akorn Inc.
• Baxter International Inc.
• Generamedix Inc.
• Hospira Inc.
• Mallinckrodt Inc.
• Taylor Pharmaceuticals

Dosage Forms

Form	Route	Strength
Injection, solution	Intravenous; Parenteral	50 MICROGRAMMI/ML
Tablet	Sublingual	30 ug/1
Tablet	Sublingual	30 ?g
Tablet	Sublingual	30 MICROGRAMMI
Injection	Epidural; Intravenous	0.005 MG/ML
Solution	Intravenous	50 ug/1mL
Injection, solution	Intravenous	50 μg/ml
Liquid	Epidural; Intravenous	50 mcg / mL
Liquid	Intravenous	50 mcg / mL
Injection	Epidural; Intravenous	0.05 mg/1mL
Injection	Epidural; Intravenous	50 ug/1mL
Injection, solution	Epidural; Intravenous	50 ug/1mL
Solution	Epidural; Intravenous	50 mcg / mL
Injection, solution
Injection, solution	Parenteral	250 mcg/ml
Injection, solution	Parenteral	50 mcg/ml
Injection, solution	Parenteral	50 MICROGRAMMI/ML
Injection, solution		5 MICROGRAMMI/ML
Injection, solution		50 MICROGRAMMI/ML
Injection, solution	Parenteral	5 Mikrogramm/ml
Injection, solution	Parenteral	50 Mikrogramm/ml
Injection, solution	Parenteral	0.05 MG/ML
Injection, solution	Parenteral
Tablet	Oral; Sublingual	15 MCG
Tablet	Sublingual	15 μg
Solution	Parenteral	0.250 mg

Prices

Unit description	Cost	Unit
Sufentanil citrate powder	18927.0USD	g
Sufenta 50 mcg/ml ampul	5.38USD	ml
Sufentanil 50 mcg/ml ampul	3.92USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US8778393	No	2014-07-15	2027-01-05
US8778394	No	2014-07-15	2027-01-05
US8535714	No	2013-09-17	2027-01-05
US9320710	No	2016-04-26	2027-01-05
US8202535	No	2012-06-19	2030-10-22
US8226978	No	2012-07-24	2027-01-05
US8865743	No	2014-10-21	2030-10-22
US8865211	No	2014-10-21	2027-01-05
US8574189	No	2013-11-05	2030-03-16
US8231900	No	2012-07-31	2027-01-05
US8252328	No	2012-08-28	2027-01-05
US9744129	No	2017-08-29	2027-01-05
US8945592	No	2015-02-03	2031-07-29
US8252329	No	2012-08-28	2027-01-05
US10245228	No	2019-04-02	2027-01-05
US10342762	No	2019-07-09	2027-01-05
US10507180	No	2019-12-17	2027-01-05
US10896751	No	2021-01-19	2030-03-16
US11672738	No	2018-02-02	2038-02-02
US11676691	No	2010-03-16	2030-03-16

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	136.3	MSDS
water solubility	Soluble	MSDS
logP	3.95	https://pubchem.ncbi.nlm.nih.gov/compound/sufentanil#section=Solubility
logS	-3.71	https://pubchem.ncbi.nlm.nih.gov/compound/sufentanil#section=Solubility

Predicted Properties

Property	Value	Source
Water Solubility	0.012 mg/mL	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	43.99 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

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9875
Blood Brain Barrier	+	0.9886
Caco-2 permeable	+	0.5201
P-glycoprotein substrate	Substrate	0.6673
P-glycoprotein inhibitor I	Inhibitor	0.8275
P-glycoprotein inhibitor II	Inhibitor	0.8387
Renal organic cation transporter	Non-inhibitor	0.5594
CYP450 2C9 substrate	Non-substrate	0.7923
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.713
CYP450 1A2 substrate	Non-inhibitor	0.8954
CYP450 2C9 inhibitor	Non-inhibitor	0.7839
CYP450 2D6 inhibitor	Non-inhibitor	0.8416
CYP450 2C19 inhibitor	Non-inhibitor	0.5438
CYP450 3A4 inhibitor	Inhibitor	0.6293
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.6401
Ames test	Non AMES toxic	0.7695
Carcinogenicity	Non-carcinogens	0.8861
Biodegradation	Not ready biodegradable	0.9724
Rat acute toxicity	3.0968 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9793
hERG inhibition (predictor II)	Inhibitor	0.772

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0019-5492000000-9d94c514876bdc8387e0
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-000i-0009000000-0f9e477eb2153eb20409
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-000i-0096000000-73641c83c08b872641cd
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-06ri-1981000000-b5f4aaab095cc6fc533c
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-03di-1900000000-2fdfd1d5fa6e43fa1604
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-03di-4900000000-bd92c052347dc0822a01
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000i-1019000000-b9cf6bcc6255b89a03c9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000i-0009000000-c2784bae4e1e98992e4b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000j-4494000000-76b0f999a66427fe5fb0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-9301000000-a81e0c3b62988178d35d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-03du-3590000000-9d259a2c6d87decec8f5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00kf-9330000000-b9676a5c54c970156337
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	201.426923	predicted	DarkChem Lite v0.1.0
[M-H]-	186.93564	predicted	DeepCCS 1.0 (2019)
[M+H]+	201.535823	predicted	DarkChem Lite v0.1.0
[M+H]+	189.35591	predicted	DeepCCS 1.0 (2019)
[M+Na]+	202.362923	predicted	DarkChem Lite v0.1.0
[M+Na]+	196.51707	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Mu-type opioid receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Agonist

General Function

Voltage-gated calcium channel activity

Specific Function

Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...

Gene Name

OPRM1

Uniprot ID

P35372

Uniprot Name

Mu-type opioid receptor

Molecular Weight

44778.855 Da

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. [Article]
2. Levron JC: [Pharmacokinetics and pharmacodynamics of morphinomimetics in the central nervous system]. Agressologie. 1991;32(6-7):318-20. [Article]
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. [Article]
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. [Article]
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. [Article]
6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	50	N/A	N/A	A27621

Details

Binding Properties2. Delta-type opioid receptor

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Agonist

General Function

Opioid receptor activity

Specific Function

G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...

Gene Name

OPRD1

Uniprot ID

P41143

Uniprot Name

Delta-type opioid receptor

Molecular Weight

40368.235 Da

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. [Article]
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. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	75	N/A	N/A	A27621

Details

Binding Properties3. Kappa-type opioid receptor

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

General Function

Opioid receptor activity

Specific Function

G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...

Gene Name

OPRK1

Uniprot ID

P41145

Uniprot Name

Kappa-type opioid receptor

Molecular Weight

42644.665 Da

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. [Article]
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. [Article]

×

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55