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

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

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

• Pain, Acute
• Acute, severe Pain

Associated Therapies

• Anesthetic induction and maintenance
• Adjunct to general anesthesia therapy
• Lumbar epidural anesthesia therapy
• Short opioid analgesia requirement

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.

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 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

Learn about our commercial Adverse Effects data.

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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

Pathway	Category
Sufentanil Action Pathway	Drug 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.

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• Withdrawn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

Drug	Interaction
Unlock Additional Data
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.
Acemetacin	The risk or severity of hypertension can be increased when Sufentanil is combined with Acemetacin.
Acetazolamide	The risk or severity of adverse effects can be increased when Sufentanil is combined with Acetazolamide.
Acetophenazine	The risk or severity of hypotension and CNS depression can be increased when Acetophenazine is combined with Sufentanil.
Acetylsalicylic acid	The risk or severity of hypertension can be increased when Sufentanil is combined with Acetylsalicylic acid.
Aclidinium	The risk or severity of adverse effects can be increased when Sufentanil is combined with Aclidinium.
Agomelatine	The risk or severity of adverse effects can be increased when Sufentanil is combined with Agomelatine.
Alclofenac	The 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
A rating for the strength of the evidence supporting each drug interaction.
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Action
Action
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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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

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
Unlock Additional Data
Dsuvia	Tablet	30 ug/1	Sublingual	AcelRx Pharmaceuticals, Inc	2018-11-02	Not applicable
Sufenta	Solution	50 ug/1mL	Intravenous	Taylor Pharmaceuticals	2008-07-02	Not applicable
Sufenta Inj 50mcg/ml	Liquid		Intravenous	Janssen Pharmaceutica, Division Of Janssen Ortho Inc.	1985-12-31	1996-09-10
Sufenta Inj 50mcg/ml	Liquid		Epidural; Intravenous	Janssen Pharmaceuticals	1985-12-31	2007-11-26
Sufentanil Citrate	Injection, solution	50 ug/1mL	Epidural; Intravenous	Hospira, Inc.	2006-10-06	2006-10-06
Sufentanil Citrate	Injection	50 ug/1mL	Epidural; Intravenous	Akorn, Inc.	2010-12-01	Not applicable
Sufentanil Citrate Injection	Solution		Epidural; Intravenous	Teligent Ou	Not applicable	Not applicable
Sufentanil Citrate Injection USP	Solution		Epidural; Intravenous	Sandoz Canada Incorporated	2001-08-01	Not applicable
Sufentanil Citrate Injection USP	Solution		Epidural; Intravenous	Sterimax Inc	2016-10-18	Not applicable
Zalviso	Tablet	15 μg	Sublingual	Grunenthal Gmb H	2015-09-18	Not applicable

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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Unlock Additional Data
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
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

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

• 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

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]

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

AHFS Codes

• 28:08.08 — Opiate Agonists

FDA label

Download (176 KB)

MSDS

Download (47.6 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Prevention	Analgesia / Dexmedetomidine / Elderly / Long-term Outcome / Orthopedic Procedures / Postoperative Delirium	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	Trigeminal Neuralgia (TN)	1
4	Completed	Not Available	Aortic Aneurysms	1
4	Completed	Basic Science	Anaesthesia therapy	1
4	Completed	Other	Bronchoscopy / Fentanyl / Narcotrend / Remifentanil / Sedation, Conscious / Sufentanil	1
4	Completed	Prevention	Aortic Valve Stenosis / Ischemic Heart Disease	1
4	Completed	Supportive Care	Pain	1
4	Completed	Supportive Care	Post Operative Nausea and Vomiting (PONV) / Postoperative pain	1
4	Completed	Supportive Care	Postoperative; Dysfunction Following Cardiac Surgery	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
Tablet	Sublingual	30 ug/1
Solution	Intravenous	50 ug/1mL
Liquid	Epidural; Intravenous
Liquid	Intravenous
Injection	Epidural; Intravenous	0.05 mg/1mL
Injection	Epidural; Intravenous	50 ug/1mL
Injection, solution	Epidural; Intravenous	50 ug/1mL
Solution	Epidural; Intravenous
Tablet	Sublingual	15 μg

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
Unlock Additional Data
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

Additional Data Available

Filed On
Filed On
The date on which a patent was filed with the relevant government.
Learn more

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	43.85 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

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	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
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

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