Identification

Name
Sufentanil
Accession Number
DB00708
Description

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
Thumb
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

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.

Label

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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 12, 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 12. 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 12. 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.

TargetActionsOrganism
AMu-type opioid receptor
agonist
Humans
UDelta-type opioid receptor
agonist
Humans
UKappa-type opioid receptorNot AvailableHumans
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 12.

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 12.

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 12.

Clearance

The total plasma clearance after single intravenous administration is about 917 l/min 12.

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 12.

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.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Sufentanil Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbametapirThe serum concentration of Sufentanil can be increased when it is combined with Abametapir.
AcebutololSufentanil may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Sufentanil is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Sufentanil is combined with Acemetacin.
AcetazolamideThe risk or severity of adverse effects can be increased when Sufentanil is combined with Acetazolamide.
AcetophenazineThe risk or severity of hypotension and CNS depression can be increased when Acetophenazine is combined with Sufentanil.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Sufentanil is combined with Acetylsalicylic acid.
AclidiniumThe risk or severity of adverse effects can be increased when Sufentanil is combined with Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Sufentanil is combined with Agomelatine.
AlclofenacThe risk or severity of hypertension can be increased when Sufentanil is combined with Alclofenac.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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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

Product Ingredients
IngredientUNIICASInChI Key
Sufentanil citrateS9ZFX8403R60561-17-3OJCZPLDERGDQRJ-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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DsuviaTablet30 ug/1SublingualAcelRx Pharmaceuticals, Inc2018-11-02Not applicableUs
SufentaSolution50 ug/1mLIntravenousTaylor Pharmaceuticals2008-07-02Not applicableUs
Sufenta Inj 50mcg/mlLiquidIntravenousJanssen Pharmaceutica, Division Of Janssen Ortho Inc.1985-12-311996-09-10Canada
Sufenta Inj 50mcg/mlLiquidEpidural; IntravenousJanssen Pharmaceuticals1985-12-312007-11-26Canada
Sufentanil CitrateInjection, solution50 ug/1mLEpidural; IntravenousHospira, Inc.2006-10-062006-10-06Us
Sufentanil CitrateInjection50 ug/1mLEpidural; IntravenousAkorn, Inc.2010-12-01Not applicableUs
Sufentanil Citrate InjectionSolutionEpidural; IntravenousTeligent OuNot applicableNot applicableCanada
Sufentanil Citrate Injection USPSolutionEpidural; IntravenousSandoz Canada Incorporated2001-08-01Not applicableCanada
Sufentanil Citrate Injection USPSolutionEpidural; IntravenousSterimax Inc2016-10-18Not applicableCanada
ZalvisoTablet15 μgSublingualGrunenthal Gmb H2015-09-18Not applicableEu
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Sufentanil CitrateInjection0.05 mg/1mLEpidural; IntravenousWest-Ward Pharmaceuticals Corp.1995-12-15Not applicableUs
Sufentanil CitrateInjection, solution50 ug/1mLEpidural; IntravenousHospira, Inc.2005-07-26Not applicableUs
Sufentanil CitrateInjection0.05 mg/1mLEpidural; IntravenousWest-Ward Pharmaceuticals Corp.1995-12-15Not applicableUs
Sufentanil CitrateInjection0.05 mg/1mLEpidural; IntravenousBaxter Laboratories2002-12-022014-03-31Us
Sufentanil CitrateInjection0.05 mg/1mLEpidural; IntravenousWest-Ward Pharmaceuticals Corp.1995-12-15Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
N01AH03 — Sufentanil
Drug Categories
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
show 3 more
Substituents
Amine / Amino acid or derivatives / Anilide / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Dialkyl ether
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
piperidines, thiophenes, ether, anilide (CHEBI:9316)

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. [PubMed:29234209]
  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. [PubMed:29122372]
  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. [PubMed:25544247]
  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. [PubMed:25318408]
  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. [PubMed:29498947]
  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. [PubMed:24635521]
  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. [PubMed:28341939]
  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. [PubMed:23397116]
  9. Pathan H, Williams J: Basic opioid pharmacology: an update. Br J Pain. 2012 Feb;6(1):11-6. doi: 10.1177/2049463712438493. [PubMed:26516461]
  10. FDA approves Dsuvia [Link]
  11. Noting Military Potential, FDA Approves Powerful Painkiller Dsuvia [Link]
  12. Sufentanil EMA label [File]
  13. Sufentanil [File]
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
AHFS Codes
  • 28:08.08 — Opiate Agonists
FDA label
Download (176 KB)
MSDS
Download (47.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionAnalgesia / Dexmedetomidine / Elderly / Long-term Outcome / Orthopedic Procedures / Postoperative Delirium1
4Active Not RecruitingTreatmentDriving Performance After Minor Ambulatory Surgery / Minor Surgical Procedures With Monitored Anesthesia Care1
4Active Not RecruitingTreatmentTrigeminal Neuralgia (TN)1
4CompletedNot AvailableAortic Aneurysms1
4CompletedBasic ScienceAnaesthesia therapy1
4CompletedOtherBronchoscopy / Fentanyl / Narcotrend / Remifentanil / Sedation, Conscious / Sufentanil1
4CompletedPreventionAortic Valve Stenosis / Ischemic Heart Disease1
4CompletedSupportive CarePain1
4CompletedSupportive CarePost Operative Nausea and Vomiting (PONV) / Postoperative pain1
4CompletedSupportive CarePostoperative; Dysfunction Following Cardiac Surgery1

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
FormRouteStrength
TabletSublingual30 ug/1
SolutionIntravenous50 ug/1mL
LiquidEpidural; Intravenous
LiquidIntravenous
InjectionEpidural; Intravenous0.05 mg/1mL
InjectionEpidural; Intravenous50 ug/1mL
Injection, solutionEpidural; Intravenous50 ug/1mL
SolutionEpidural; Intravenous
TabletSublingual15 μg
Prices
Unit descriptionCostUnit
Sufentanil citrate powder18927.0USD g
Sufenta 50 mcg/ml ampul5.38USD ml
Sufentanil 50 mcg/ml ampul3.92USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8778393No2014-07-152027-01-05Us
US8778394No2014-07-152027-01-05Us
US8535714No2013-09-172027-01-05Us
US9320710No2016-04-262027-01-05Us
US8202535No2012-06-192030-10-22Us
US8226978No2012-07-242027-01-05Us
US8865743No2014-10-212030-10-22Us
US8865211No2014-10-212027-01-05Us
US8574189No2013-11-052030-03-16Us
US8231900No2012-07-312027-01-05Us
US8252328No2012-08-282027-01-05Us
US9744129No2017-08-292027-01-05Us
US8945592No2015-02-032031-07-29Us
US8252329No2012-08-282027-01-05Us
US10245228No2019-04-022027-01-05Us
US10342762No2019-07-092027-01-05Us
US10507180No2019-12-172027-01-05Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)136.3MSDS
water solubilitySolubleMSDS
logP3.95https://pubchem.ncbi.nlm.nih.gov/compound/sufentanil#section=Solubility
logS-3.71https://pubchem.ncbi.nlm.nih.gov/compound/sufentanil#section=Solubility
Predicted Properties
PropertyValueSource
Water Solubility0.012 mg/mLALOGPS
logP3.4ALOGPS
logP3.61ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)8.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.78 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity111.42 m3·mol-1ChemAxon
Polarizability43.85 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9875
Blood Brain Barrier+0.9886
Caco-2 permeable+0.5201
P-glycoprotein substrateSubstrate0.6673
P-glycoprotein inhibitor IInhibitor0.8275
P-glycoprotein inhibitor IIInhibitor0.8387
Renal organic cation transporterNon-inhibitor0.5594
CYP450 2C9 substrateNon-substrate0.7923
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.713
CYP450 1A2 substrateNon-inhibitor0.8954
CYP450 2C9 inhibitorNon-inhibitor0.7839
CYP450 2D6 inhibitorNon-inhibitor0.8416
CYP450 2C19 inhibitorNon-inhibitor0.5438
CYP450 3A4 inhibitorInhibitor0.6293
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6401
Ames testNon AMES toxic0.7695
CarcinogenicityNon-carcinogens0.8861
BiodegradationNot ready biodegradable0.9724
Rat acute toxicity3.0968 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9793
hERG inhibition (predictor II)Inhibitor0.772
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0009000000-0f9e477eb2153eb20409
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0096000000-73641c83c08b872641cd
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-06ri-1981000000-b5f4aaab095cc6fc533c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-1900000000-2fdfd1d5fa6e43fa1604
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-4900000000-bd92c052347dc0822a01

Targets

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. [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]
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. [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]
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. [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]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase 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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. 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. [PubMed:29498947]
  2. Sufentanil EMA label [File]

Drug created on June 13, 2005 07:24 / Updated on August 05, 2020 23:35

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