U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H30N2O2S.C6H8O7
Molecular Weight 578.6765
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SUFENTANIL CITRATE

SMILES

CCC(=O)N(c1ccccc1)C2(CCN(CCc3cccs3)CC2)COC.C(C(=O)O)C(CC(=O)O)(C(=O)O)O

InChI

InChIKey=OJCZPLDERGDQRJ-UHFFFAOYSA-N
InChI=1S/C22H30N2O2S.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-10,17H,3,11-16,18H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

HIDE SMILES / InChI

Molecular Formula C22H30N2O2S
Molecular Weight 386.5527
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C6H8O7
Molecular Weight 192.1238
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
Clinical interpretation of pharmacokinetic and pharmacodynamic propofol-opioid interactions.
2001
Liver and renal function after volatile induction and maintenance of anesthesia (VIMA) with sevoflurane versus TIVA with sufentanil-midazolam for CABG surgery.
2001
[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
Subarachnoid sufentanil for early postoperative pain management in orthopedic patients: more disadvantages than benefits?
2001 Dec
Pharmacokinetics of sufentanil in patients undergoing coronary artery bypass graft surgery.
2001 Dec
Comparison of continuous epidural infusion of ropivacaine and sufentanil with intravenous patient-controlled analgesia after total hip replacement.
2001 Dec
Patient-controlled epidural analgesia after abdominal surgery: ropivacaine versus bupivacaine.
2001 Dec
Neostigmine combined with bupivacaine, clonidine, and sufentanil for spinal labor analgesia.
2001 Dec
The continuous recording of blood pressure in patients undergoing carotid surgery under remifentanil versus sufentanil analgesia.
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
Xenon anaesthesia for laparoscopic cholecystectomy in a patient with Eisenmenger's syndrome.
2001 Jun
Recovery after remifentanil and sufentanil for analgesia and sedation of mechanically ventilated patients after trauma or major surgery.
2001 Jun
[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
Postoperative analgesia by epidural methylprednisolone after posterolateral thoracotomy.
2001 Oct
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
Levobupivacaine combined with sufentanil and epinephrine for intrathecal labor analgesia: a comparison with racemic bupivacaine.
2001 Oct
The role of drug-lipid interactions on the disposition of liposome-formulated opioid analgesics in vitro and in vivo.
2001 Oct
A comparison of fentanyl, sufentanil, and remifentanil for fast-track cardiac anesthesia.
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
Hydromorphone for acute and chronic pain.
2002
Interaction of morphine, fentanyl, sufentanil, alfentanil, and loperamide with the efflux drug transporter P-glycoprotein.
2002 Apr
Alfentanil and sufentanil in fast-track anesthesia for coronary artery bypass graft surgery.
2002 Apr
Pharmacokinetics of a 24-hour intravenous ketoprofen infusion in children.
2002 Feb
Compatibility of ropivacaine with morphine, sufentanil, fentanyl, or clonidine.
2002 Feb
Small-dose selective spinal anesthesia for short-duration outpatient laparoscopy: recovery characteristics compared with desflurane anesthesia.
2002 Feb
Cost-effectiveness of analgesia after Caesarean section. A comparison of intrathecal morphine and epidural PCA.
2002 Jan
Sufentanil potentiates the inhibitory effect of epinephrine on intestinal motility.
2002 Jan
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
Up-and-down allocation.
2002 Mar
Total intravenous anesthesia for intraoperative monitoring of the motor pathways: an integral view combining clinical and experimental data.
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 Fri Jun 25 20:56:22 UTC 2021
Edited
by admin
on Fri Jun 25 20:56:22 UTC 2021
Record UNII
S9ZFX8403R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SUFENTANIL CITRATE
EP   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN  
Official Name English
SUFENTA
Brand Name English
SUFENTANIL CITRATE [VANDF]
Common Name English
SUFENTANIL CITRATE CII
USP-RS  
Common Name English
SUFENTANIL CITRATE [EP MONOGRAPH]
Common Name English
SUFENTANIL CITRATE [USAN]
Common Name English
SUFENTANIL CITRATE [MI]
Common Name English
R-33800
Code English
SUFENTANIL CITRATE [USP MONOGRAPH]
Common Name English
SUFENTANIL CITRATE CII [USP-RS]
Common Name English
PROPANAMIDE, N-(4-(METHOXYMETHYL)-1-(2-(THIENYL)ETHYL)-4-PIPERIDINYL)-N-PHENYL-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)
Systematic Name English
DSUVIA
Brand Name English
N-(4-(METHOXYMETHYL)-1-(2-(2-THIENYL)ETHYL)-4-PIPERIDYL)PROPIONANILIDE CITRATE (1:1)
Systematic Name English
SUFENTANIL CITRATE [ORANGE BOOK]
Common Name English
SUFENTANIL CITRATE [MART.]
Common Name English
SUFENTANIL CITRATE [WHO-DD]
Common Name English
Classification Tree Code System Code
DEA NO. 9740
Created by admin on Fri Jun 25 20:56:23 UTC 2021 , Edited by admin on Fri Jun 25 20:56:23 UTC 2021
NCI_THESAURUS C1506
Created by admin on Fri Jun 25 20:56:23 UTC 2021 , Edited by admin on Fri Jun 25 20:56:23 UTC 2021
NCI_THESAURUS C67413
Created by admin on Fri Jun 25 20:56:23 UTC 2021 , Edited by admin on Fri Jun 25 20:56:23 UTC 2021
Code System Code Type Description
USP_CATALOG
1623648
Created by admin on Fri Jun 25 20:56:23 UTC 2021 , Edited by admin on Fri Jun 25 20:56:23 UTC 2021
PRIMARY USP-RS
PUBCHEM
65494
Created by admin on Fri Jun 25 20:56:23 UTC 2021 , Edited by admin on Fri Jun 25 20:56:23 UTC 2021
PRIMARY
CAS
60561-17-3
Created by admin on Fri Jun 25 20:56:23 UTC 2021 , Edited by admin on Fri Jun 25 20:56:23 UTC 2021
PRIMARY
ECHA (EC/EINECS)
262-295-4
Created by admin on Fri Jun 25 20:56:23 UTC 2021 , Edited by admin on Fri Jun 25 20:56:23 UTC 2021
PRIMARY
EPA CompTox
60561-17-3
Created by admin on Fri Jun 25 20:56:23 UTC 2021 , Edited by admin on Fri Jun 25 20:56:23 UTC 2021
PRIMARY
MERCK INDEX
M10288
Created by admin on Fri Jun 25 20:56:23 UTC 2021 , Edited by admin on Fri Jun 25 20:56:23 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C47731
Created by admin on Fri Jun 25 20:56:23 UTC 2021 , Edited by admin on Fri Jun 25 20:56:23 UTC 2021
PRIMARY
ChEMBL
CHEMBL658
Created by admin on Fri Jun 25 20:56:23 UTC 2021 , Edited by admin on Fri Jun 25 20:56:23 UTC 2021
PRIMARY
FDA UNII
S9ZFX8403R
Created by admin on Fri Jun 25 20:56:23 UTC 2021 , Edited by admin on Fri Jun 25 20:56:23 UTC 2021
PRIMARY
EVMPD
SUB04616MIG
Created by admin on Fri Jun 25 20:56:23 UTC 2021 , Edited by admin on Fri Jun 25 20:56:23 UTC 2021
PRIMARY
DRUG BANK
DBSALT000275
Created by admin on Fri Jun 25 20:56:23 UTC 2021 , Edited by admin on Fri Jun 25 20:56:23 UTC 2021
PRIMARY
RXCUI
58964
Created by admin on Fri Jun 25 20:56:23 UTC 2021 , Edited by admin on Fri Jun 25 20:56:23 UTC 2021
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY