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Details

Stereochemistry ACHIRAL
Molecular Formula C22H30N2O2S.C6H8O7
Molecular Weight 578.674
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SUFENTANIL CITRATE

SMILES

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

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 C6H8O7
Molecular Weight 192.1235
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
Optimal dose of intrathecal clonidine added to sufentanil plus bupivacaine for labour analgesia.
2000 Sep
Clinical interpretation of pharmacokinetic and pharmacodynamic propofol-opioid interactions.
2001
[Hyperoxia-induced liberation of big-endothelin into jugular venous blood of electric neurosurgical patients].
2001
[Evaluation of antibacterial filters for peridural obstetrical anesthesia].
2001 Aug
Dose of prophylactic intravenous ephedrine during spinal anesthesia for cesarean section.
2001 Aug
Sedative and analgesic practice in the intensive care unit: the results of a European survey.
2001 Aug
The effect of intrathecal analgesia on the success of external cephalic version.
2001 Aug
Subarachnoid sufentanil for early postoperative pain management in orthopedic patients: more disadvantages than benefits?
2001 Dec
Neostigmine combined with bupivacaine, clonidine, and sufentanil for spinal labor analgesia.
2001 Dec
[Low concentration Ropivacaine in labor epidural analgesia. A prospective study on obstetric and neonatal outcome].
2001 Dec
Intrathecal sufentanil and morphine for post-thoracotomy pain relief.
2001 Feb
Small doses of remifentanil or sufentanil for blunting cardiovascular changes induced by tracheal intubation: a double-blind comparison.
2001 Feb
Continuous intrathecal sufentanil for postoperative analgesia.
2001 Jan
The analgesic effect of sufentanil combined with ropivacaine 0.2% for labor analgesia: a comparison of three sufentanil doses.
2001 Jan
Should the angiotensin II antagonists be discontinued before surgery?
2001 Jan
[Prophylaxis of nausea and vomiting after thyroid surgery: comparison of oral and intravenous dolasetron with intravenous droperidol and placebo].
2001 Jul
Low dose intrathecal ropivacaine with or without sufentanil provides effective analgesia and does not impair motor strength during labour: a pilot study.
2001 Jul-Aug
Lipid soluble opioids do move in cerebrospinal fluid.
2001 Jul-Aug
Comparative study of liquid-liquid extraction and solid-phase extraction methods for the separation of sufentanil from plasma before gas chromatographic-mass spectrometric analysis.
2001 Mar
Life-threatening pneumothorax of the ventilated lung during thoracoscopic pleurectomy.
2001 May
Combined spinal-epidural versus epidural labor analgesia.
2001 Oct
Stability of sufentanil in human plasma samples.
2001 Oct
Effect of epidural analgesia on the fetal heart rate.
2001 Oct
[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
Intrathecal labor analgesia with bupivacaine and sufentanil: the effect of adding 2.25 microg epinephrine.
2001 Sep-Oct
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
Small-dose selective spinal anesthesia for short-duration outpatient laparoscopy: recovery characteristics compared with desflurane anesthesia.
2002 Feb
Sufentanil potentiates the inhibitory effect of epinephrine on intestinal motility.
2002 Jan
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 Wed Jul 05 22:54:01 UTC 2023
Edited
by admin
on Wed Jul 05 22:54:01 UTC 2023
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
Sufentanil citrate [WHO-DD]
Common 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
Classification Tree Code System Code
DEA NO. 9740
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
NCI_THESAURUS C1506
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
NCI_THESAURUS C67413
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
Code System Code Type Description
RS_ITEM_NUM
1623648
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
PRIMARY
PUBCHEM
65494
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
PRIMARY
CAS
60561-17-3
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
PRIMARY
USAN
W-113
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
PRIMARY
ECHA (EC/EINECS)
262-295-4
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
PRIMARY
EPA CompTox
DTXSID5048928
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
PRIMARY
MERCK INDEX
M10288
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C47731
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
PRIMARY
ChEMBL
CHEMBL658
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
PRIMARY
FDA UNII
S9ZFX8403R
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
PRIMARY
DAILYMED
S9ZFX8403R
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
PRIMARY
SMS_ID
100000091108
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
PRIMARY
EVMPD
SUB04616MIG
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
PRIMARY
DRUG BANK
DBSALT000275
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
PRIMARY
RXCUI
58964
Created by admin on Wed Jul 05 22:54:01 UTC 2023 , Edited by admin on Wed Jul 05 22:54:01 UTC 2023
PRIMARY RxNorm
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ACTIVE MOIETY