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Details

Stereochemistry ACHIRAL
Molecular Formula C22H30N2O2S.ClH
Molecular Weight 423.012
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SUFENTANIL HYDROCHLORIDE

SMILES

Cl.CCC(=O)N(C1=CC=CC=C1)C2(COC)CCN(CCC3=CC=CS3)CC2

InChI

InChIKey=WZGGBYJHSKVKGO-UHFFFAOYSA-N
InChI=1S/C22H30N2O2S.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C22H30N2O2S
Molecular Weight 386.551
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019050s032lbl.pdf

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. 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. Sufentanil is used as an analgesic adjunct in anesthesia and as a primary anesthetic drug in procedures requiring assisted ventilation and in the relief of pain.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
SUFENTA PRESERVATIVE FREE

Approved Use

Sufentanil Citrate Injection is indicated for intravenous administration in adults and pediatric patients: as an analgesic adjunct in the maintenance of balanced general anesthesia in patients who are intubated and ventilated. 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. Sufentanil Citrate Injection is indicated for epidural administration as an analgesic combined with low dose (usually 12.5 mg per administration) bupivacaine during labor and vaginal delivery.

Launch Date

4.52390388E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
63.1 pg/mL
30 μg single, sublingual
dose: 30 μg
route of administration: Sublingual
experiment type: SINGLE
co-administered:
SUFENTANIL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
278 pg × h/mL
30 μg single, sublingual
dose: 30 μg
route of administration: Sublingual
experiment type: SINGLE
co-administered:
SUFENTANIL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
13.4 h
30 μg single, sublingual
dose: 30 μg
route of administration: Sublingual
experiment type: SINGLE
co-administered:
SUFENTANIL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
7%
30 μg single, sublingual
dose: 30 μg
route of administration: Sublingual
experiment type: SINGLE
co-administered:
SUFENTANIL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.4 mg/kg single, intranasal
MTD
Dose: 0.4 mg/kg
Route: intranasal
Route: single
Dose: 0.4 mg/kg
Co-administed with::
MIDAZOLAM(5 mg)
Sources:
unknown, 18 - 65 years
n = 30
Health Status: unknown
Condition: gastroscopy
Age Group: 18 - 65 years
Sex: unknown
Population Size: 30
Sources:
Other AEs: Nausea, Hypotension...
Other AEs:
Nausea
Hypotension
Sources:
30 ug single, oral
Recommended
Dose: 30 ug
Route: oral
Route: single
Dose: 30 ug
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: Postoperative Pain
Age Group: adult
Sex: M+F
Sources:
Disc. AE: Pruritus, Dizziness...
AEs leading to
discontinuation/dose reduction:
Pruritus (1 patient)
Dizziness (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hypotension
0.4 mg/kg single, intranasal
MTD
Dose: 0.4 mg/kg
Route: intranasal
Route: single
Dose: 0.4 mg/kg
Co-administed with::
MIDAZOLAM(5 mg)
Sources:
unknown, 18 - 65 years
n = 30
Health Status: unknown
Condition: gastroscopy
Age Group: 18 - 65 years
Sex: unknown
Population Size: 30
Sources:
Nausea
0.4 mg/kg single, intranasal
MTD
Dose: 0.4 mg/kg
Route: intranasal
Route: single
Dose: 0.4 mg/kg
Co-administed with::
MIDAZOLAM(5 mg)
Sources:
unknown, 18 - 65 years
n = 30
Health Status: unknown
Condition: gastroscopy
Age Group: 18 - 65 years
Sex: unknown
Population Size: 30
Sources:
Dizziness 1 patient
Disc. AE
30 ug single, oral
Recommended
Dose: 30 ug
Route: oral
Route: single
Dose: 30 ug
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: Postoperative Pain
Age Group: adult
Sex: M+F
Sources:
Pruritus 1 patient
Disc. AE
30 ug single, oral
Recommended
Dose: 30 ug
Route: oral
Route: single
Dose: 30 ug
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: Postoperative Pain
Age Group: adult
Sex: M+F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
yes
yes (co-administration study)
Comment: Co-administration of a single dose of sufentanil sublingual tablet 15 mcg with a strong CYP3A4 inhibitor, ketoconazole, results in 77% and 19% greater AUCinf and Cmax values of sufentanil, respectively, compared to its administration alone
Page: 19.0
PubMed

PubMed

TitleDatePubMed
[Hyperoxia-induced liberation of big-endothelin into jugular venous blood of electric neurosurgical patients].
2001
Right vs left side thoracoscopic sympathectomy: effects of CO2 insufflation on haemodynamics.
2001
Small-dose selective spinal anaesthesia for short-duration outpatient gynaecological laparoscopy: recovery characteristics compared with propofol anaesthesia.
2001 Apr
Effects of fentanyl, alfentanil, remifentanil and sufentanil on loss of consciousness and bispectral index during propofol induction of anaesthesia.
2001 Apr
[Ropivacaine 0.2% versus bupivacaine 0.125% plus sufentanil for continuous peridural analgesia following extended abdominal operations].
2001 Apr
Rational use of opioids.
2001 Apr
Changes in the expression of G protein-coupled receptor kinases and beta-arrestin 2 in rat brain during opioid tolerance and supersensitivity.
2001 Apr
Sedative and analgesic practice in the intensive care unit: the results of a European survey.
2001 Aug
Subarachnoid sufentanil for early postoperative pain management in orthopedic patients: more disadvantages than benefits?
2001 Dec
Comparison of continuous epidural infusion of ropivacaine and sufentanil with intravenous patient-controlled analgesia after total hip replacement.
2001 Dec
[Low concentration Ropivacaine in labor epidural analgesia. A prospective study on obstetric and neonatal outcome].
2001 Dec
A comparison of motor block between ropivacaine and bupivacaine for continuous labor epidural analgesia.
2001 Feb
Intrathecal sufentanil and morphine for post-thoracotomy pain relief.
2001 Feb
[Prophylaxis of nausea and vomiting after thyroid surgery: comparison of oral and intravenous dolasetron with intravenous droperidol and placebo].
2001 Jul
A comparison of five solutions of local anaesthetics and/or sufentanil for continuous, postoperative epidural analgesia after major urological surgery.
2001 Jul
Long-term effects of spontaneous breathing during ventilatory support in patients with acute lung injury.
2001 Jul 1
The effect of distance from injection site to the brainstem using spinal sufentanil.
2001 Jul-Aug
Lipid soluble opioids do move in cerebrospinal fluid.
2001 Jul-Aug
Xenon anaesthesia for laparoscopic cholecystectomy in a patient with Eisenmenger's syndrome.
2001 Jun
Comparison of shockwave lithotripsy outcomes in patients receiving sufentanil or lidocaine spinal anesthesia.
2001 Jun
Minimum local analgesic dose of plain ropivacaine vs. ropivacaine combined with sufentanil during epidural analgesia for labour.
2001 Jun
Comparison of fentanyl and sufentanil in combination with bupivacaine for patient-controlled epidural analgesia during labor.
2001 Mar
Selective spinal anesthesia for outpatient laparoscopy. II: epinephrine and spinal cord function.
2001 Mar
[Recovery of neuromuscular block after continuous infusion of cisatracurium in patients with renal dysfunction].
2001 May
Minimum analgesic dose of epidural sufentanil for first-stage labor analgesia: a comparison between spontaneous and prostaglandin-induced labors in nulliparous women.
2001 May
[Obstetric analgesia in patients with Klippel-Trenaunay syndrome].
2001 Nov
Double-blinded, single-blinded, or just blind?
2001 Nov
Effects of intrathecal sufentanil on plasma oxytocin and cortisol concentrations in women during the first stage of labor.
2001 Nov-Dec
Vibration sense testing with a 128-Hz tuning fork as a tool to determine recovery from epidural neuraxial block.
2001 Nov-Dec
Obstetric anesthesia and analgesia: options for pain relief during childbirth.
2001 Oct
Combined spinal-epidural versus epidural labor analgesia.
2001 Oct
Stability of sufentanil in human plasma samples.
2001 Oct
Effect of nitrous oxide on the bispectral index and the 95% spectral edge frequency of the electroencephalogram during surgery.
2001 Oct
The role of drug-lipid interactions on the disposition of liposome-formulated opioid analgesics in vitro and in vivo.
2001 Oct
A high rate of epidural analgesia with bupivacaine-sufentanil is consistent with a low rate of caesarean section and instrumental deliveries.
2001 Oct
Effect of epidural analgesia on the fetal heart rate.
2001 Oct
Sufentanil: an overview of its use for acute pain management.
2001 Sep
[Sufentanil vs morphine combined with ropivacaine for thoracic epidural analgesia in major abdominal surgery].
2001 Sep
The effect of preoperative epidural morphine on postoperative analgesia in children.
2001 Sep
A comparison of sevoflurane, target-controlled infusion propofol, and propofol/isoflurane anesthesia in patients undergoing carotid surgery: a quality of anesthesia and recovery profile.
2001 Sep
The in vitro effects of remifentanil, sufentanil, fentanyl, and alfentanil on isolated human right atria.
2001 Sep
Hydromorphone for acute and chronic pain.
2002
Alfentanil and sufentanil in fast-track anesthesia for coronary artery bypass graft surgery.
2002 Apr
Small-dose selective spinal anesthesia for short-duration outpatient laparoscopy: recovery characteristics compared with desflurane anesthesia.
2002 Feb
Cost containment in obstetric analgesia.
2002 Jan
Epinephrine reduces the sedative side effects of epidural sufentanil for labour analgesia.
2002 Jan
A systematic review of adjuncts for intravenous regional anesthesia for surgical procedures.
2002 Jan
Epidural administration of low-dose morphine combined with clonidine for postoperative analgesia after lumbar disc surgery.
2002 Jan
Dosing of intrathecal sufentanil.
2002 Jan-Feb
Ropivacaine 2 mg/mL vs. bupivacaine 1.25 mg/mL with sufentanil using patient-controlled epidural analgesia in labour.
2002 Mar
Patents

Sample Use Guides

ANALGESIC DOSAGES Incremental or Infusion: 1 to 2 mcg/kg (expected duration of anesthesia 1 to 2 hours). Incremental or Infusion: 2 to 8 mcg/kg (expected duration of anesthesia 2 to 8 hours). ANESTHETIC DOSAGES Incremental or Infusion: 8 to 30 mcg/kg (anesthetic doses). At this anesthetic dosage range Sufentanil is generally administered as a slow injection, as an infusion, or as an injection followed by an infusion.
Route of Administration: Intravenous
In Vitro Use Guide
At a concentration of 0.1 umol/l sufentanil a significant reduction of the spontaneous sinus rate, prolongation of atrioventricular, intraventricular and His' bundle conduction could be observed.in isolated guinea-pig hearts.
Substance Class Chemical
Created
by admin
on Thu Jul 06 23:46:55 UTC 2023
Edited
by admin
on Thu Jul 06 23:46:55 UTC 2023
Record UNII
MX47GT2KWL
Record Status Validated (UNII)
Record Version
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Name Type Language
SUFENTANIL HYDROCHLORIDE
Common Name English
PROPANAMIDE, N-(4-(METHOXYMETHYL)-1-(2-(2-THIENYL)ETHYL)-4-PIPERIDINYL)-N-PHENYL-, HYDROCHLORIDE (1:1)
Systematic Name English
PROPANAMIDE, N-(4-(METHOXYMETHYL)-1-(2-(2-THIENYL)ETHYL)-4-PIPERIDINYL)-N-PHENYL-, MONOHYDROCHLORIDE
Systematic Name English
Sufentanil hydrochloride [WHO-DD]
Common Name English
Code System Code Type Description
CAS
164790-60-7
Created by admin on Thu Jul 06 23:46:56 UTC 2023 , Edited by admin on Thu Jul 06 23:46:56 UTC 2023
PRIMARY
PUBCHEM
18463211
Created by admin on Thu Jul 06 23:46:56 UTC 2023 , Edited by admin on Thu Jul 06 23:46:56 UTC 2023
PRIMARY
FDA UNII
MX47GT2KWL
Created by admin on Thu Jul 06 23:46:56 UTC 2023 , Edited by admin on Thu Jul 06 23:46:56 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY