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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Sufentanil
- Accession Number
- DB00708 (APRD00671, DB05563)
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Description
An opioid analgesic that is used as an adjunct in anesthesia, in balanced anesthesia, and as a primary anesthetic agent. [PubChem]
- Structure
Structure for Sufentanil (DB00708)
- 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 30730 / R 33800
- Product Ingredients
Ingredient UNII CAS InChI Key Sufentanil Citrate S9ZFX8403R 60561-17-3 OJCZPLDERGDQRJ-UHFFFAOYSA-N - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Sufenta Solution 50 ug/1mL Intravenous Taylor Pharmaceuticals 2008-07-02 Not applicable US 
Sufenta Inj 50mcg/ml Liquid 50 mcg Intravenous Janssen Pharmaceutica, Division Of Janssen Ortho Inc. 1985-12-31 1996-09-10 Canada 
Sufenta Inj 50mcg/ml Liquid 50 mcg Epidural; Intravenous Janssen Pharmaceuticals 1985-12-31 2007-11-26 Canada Sufentanil Citrate Injection 50 ug/1mL Epidural; Intravenous Akorn 2010-12-01 Not applicable US Sufentanil Citrate Injection, solution 50 ug/1mL Epidural; Intravenous Hospira, Inc. 2006-10-06 2006-10-06 US Sufentanil Citrate Injection USP Solution 50 mcg Epidural; Intravenous Sandoz Canada Incorporated 2001-08-01 Not applicable Canada Sufentanil Citrate Injection, USP Solution 50 mcg Epidural; Intravenous Sterimax Inc 2016-10-18 Not applicable Canada Zalviso Tablet 15 μg Sublingual Grunenthal Gmb H 2015-09-18 Not applicable EU 
Zalviso Tablet 15 μg Sublingual Grunenthal Gmb H 2015-09-18 Not applicable EU Zalviso Tablet 15 μg Sublingual Grunenthal Gmb H 2015-09-18 Not applicable EU - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Sufentanil Citrate Injection 0.05 mg/1mL Epidural; Intravenous West-Ward Pharmaceuticals Corp. 1995-12-15 Not applicable US Sufentanil Citrate Injection 0.05 mg/1mL Epidural; Intravenous Baxter Laboratories 2002-12-02 2014-03-31 US Sufentanil Citrate Injection 0.05 mg/1mL Epidural; Intravenous West-Ward Pharmaceuticals Corp. 1995-12-15 Not applicable US Sufentanil Citrate Injection 0.05 mg/1mL Epidural; Intravenous West-Ward Pharmaceuticals Corp. 1995-12-15 Not applicable US Sufentanil Citrate Injection, solution 50 ug/1mL Epidural; Intravenous Hospira, Inc. 2005-07-26 Not applicable US - International/Other Brands
- Chronogesic (DURECT) / Disufen (Angenerico) / Fastfen (Cristália) / Sufenta (Janssen) / Sufenta Forte (Janssen) / Sufenta mite (Janssen) / Sufentil (Claris Lifesciences Ltd.) / Zuftil (Pisa)
- Categories
- Adjuvants, Anesthesia
- 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
- Fentanyl
- Hypotensive Agents
- Narcotics
- Nervous System
- Opiate Agonists
- Opioid Agonist
- Opioid Anesthetics
- Opioids
- Opioids, Anilidopiperidine
- Peripheral Nervous System Agents
- Piperidines
- Sensory System Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- UNII
- AFE2YW0IIZ
- CAS number
- 56030-54-7
- Weight
- Average: 386.551
Monoisotopic: 386.202798904 - Chemical Formula
- C22H30N2O2S
- 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
Pharmacology
- Indication
Used as an analgesic adjunct in anesthesia and as a primary anesthetic drug in procedures requiring assisted ventilation and in the relief of pain.
- Associated Therapies
- Pharmacodynamics
Sufentanil is a synthetic opioid analgesic. Sufentanil interacts predominately with the opioid mu-receptor. These mu-binding sites are discretely distributed in the human brain, spinal cord, and other tissues. In clinical settings, sufentanil exerts its principal pharmacologic effects on the central nervous system. Its primary actions of therapeutic value are analgesia and sedation. Sufentanil may increase the patient's tolerance for pain and decrease the perception of suffering, although the presence of the pain itself may still be recognized. In addition to analgesia, alterations in mood, euphoria and dysphoria, and drowsiness commonly occur. Sufentanil depresses the respiratory centers, depresses the cough reflex, and constricts the pupils.
- Mechanism of action
Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates 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. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Sufentanil's analgesic activity is, most likely, due to its conversion to morphine. Opioids open calcium-dependent inwardly rectifying potassium channels (OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.
Target Actions Organism AMu-type opioid receptor agonistHuman UDelta-type opioid receptor agonistHuman UKappa-type opioid receptor otherHuman - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half life
265 minutes
- Clearance
- Not Available
- Toxicity
LD50: 18.7 mg/kg (IV in mice)
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Sufentanil Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction (2-benzhydryloxyethyl)diethyl-methylammonium iodide The risk or severity of adverse effects can be increased when (2-benzhydryloxyethyl)diethyl-methylammonium iodide is combined with Sufentanil. (R)-warfarin The metabolism of (R)-warfarin can be decreased when combined with Sufentanil. (S)-Warfarin The metabolism of (S)-Warfarin can be decreased when combined with Sufentanil. 16-Bromoepiandrosterone The metabolism of 16-Bromoepiandrosterone can be decreased when combined with Sufentanil. 2,5-Dimethoxy-4-ethylamphetamine The risk or severity of serotonin syndrome can be increased when Sufentanil is combined with 2,5-Dimethoxy-4-ethylamphetamine. 2,5-Dimethoxy-4-ethylthioamphetamine The risk or severity of serotonin syndrome can be increased when Sufentanil is combined with 2,5-Dimethoxy-4-ethylthioamphetamine. 3,4-Methylenedioxyamphetamine The risk or severity of serotonin syndrome can be increased when Sufentanil is combined with 3,4-Methylenedioxyamphetamine. 3,5-diiodothyropropionic acid The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Sufentanil. 4-Bromo-2,5-dimethoxyamphetamine The risk or severity of serotonin syndrome can be increased when Sufentanil is combined with 4-Bromo-2,5-dimethoxyamphetamine. 4-hydroxycoumarin The metabolism of 4-hydroxycoumarin can be decreased when combined with Sufentanil. - Food Interactions
- Not Available
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
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014846
- KEGG Drug
- D05938
- KEGG Compound
- C08022
- PubChem Compound
- 41693
- PubChem Substance
- 46504737
- ChemSpider
- 38043
- BindingDB
- 94503
- ChEBI
- 9316
- ChEMBL
- CHEMBL658
- Therapeutic Targets Database
- DAP000357
- PharmGKB
- PA451527
- IUPHAR
- 3534
- Guide to Pharmacology
- GtP Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Sufentanil
- ATC Codes
- N01AH03 — Sufentanil
- AHFS Codes
- 28:08.08 — Opiate Agonists
- MSDS
- Download (47.6 KB)
Clinical Trials
- Clinical Trials
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 Solution Intravenous 50 ug/1mL Liquid Epidural; Intravenous 50 mcg Liquid Intravenous 50 mcg 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 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
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 97 °C PhysProp water solubility 76 mg/L (at 25 °C) ROY,SD & FLYNN,GL (1988) logP 3.95 SANGSTER (1993) logS -3.71 ADME Research, USCD - 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- 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
- Anilide / Aralkylamine / Piperidine / Tertiary carboxylic acid amide / Heteroaromatic compound / Thiophene / Amino acid or derivatives / Carboxamide group / Tertiary amine / Tertiary aliphatic amine show 15 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- piperidines, thiophenes, ether, anilide (CHEBI:9316)
Targets
- Kind
- Protein
- Organism
- Human
- 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
- 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]
- Levron JC: [Pharmacokinetics and pharmacodynamics of morphinomimetics in the central nervous system]. Agressologie. 1991;32(6-7):318-20. [PubMed:1688220]
- 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]
- 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]
- 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]
- 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
- Human
- 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
- 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]
- 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
- Human
- Pharmacological action
- Unknown
- Actions
- Other
- 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
- 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]
- 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
- Human
- 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
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Drug created on June 13, 2005 07:24 / Updated on October 16, 2018 08:30