Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H30N2O2S |
Molecular Weight | 386.551 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC(=O)N(C1=CC=CC=C1)C2(COC)CCN(CCC3=CC=CS3)CC2
InChI
InChIKey=GGCSSNBKKAUURC-UHFFFAOYSA-N
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
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 |
DescriptionSources: http://www.drugbank.ca/drugs/DB00708Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019050s032lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00708
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL233 Sources: http://www.drugbank.ca/drugs/DB00708 |
|||
Target ID: CHEMBL4187 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16949748 |
49.0 µM [IC50] | ||
Target ID: CHEMBL2097171 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1830134 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | SUFENTA PRESERVATIVE FREE Approved UseSufentanil 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 Date1984 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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... |
30 ug single, oral Recommended |
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) Sources: Dizziness (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 |
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 |
unhealthy, adult Health Status: unhealthy Condition: Postoperative Pain Age Group: adult Sex: M+F Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/8712396/ Page: 4.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/8712396/ Page: 4.0 |
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
Title | Date | PubMed |
---|---|---|
Measurement of tracheal temperature is not a reliable index of total respiratory heat loss in mechanically ventilated patients. | 2001 |
|
Effects of fentanyl, alfentanil, remifentanil and sufentanil on loss of consciousness and bispectral index during propofol induction of anaesthesia. | 2001 Apr |
|
[Evaluation of antibacterial filters for peridural obstetrical anesthesia]. | 2001 Aug |
|
Pharmacokinetics of sufentanil in patients undergoing coronary artery bypass graft surgery. | 2001 Dec |
|
Patient-controlled epidural analgesia after abdominal surgery: ropivacaine versus bupivacaine. | 2001 Dec |
|
The continuous recording of blood pressure in patients undergoing carotid surgery under remifentanil versus sufentanil analgesia. | 2001 Dec |
|
A comparison of motor block between ropivacaine and bupivacaine for continuous labor epidural analgesia. | 2001 Feb |
|
The dose-range effects of sufentanil added to 0.125% bupivacaine on the quality of patient-controlled epidural analgesia during labor. | 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 |
|
Long-term effects of spontaneous breathing during ventilatory support in patients with acute lung injury. | 2001 Jul 1 |
|
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 |
|
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 |
|
Oesophageal Doppler monitoring overestimates cardiac output during lumbar epidural anaesthesia. | 2001 Jun |
|
Recovery after remifentanil and sufentanil for analgesia and sedation of mechanically ventilated patients after trauma or major surgery. | 2001 Jun |
|
Comparison of shockwave lithotripsy outcomes in patients receiving sufentanil or lidocaine spinal anesthesia. | 2001 Jun |
|
Either sufentanil or fentanyl, in addition to intrathecal bupivacaine, provide satisfactory early labour analgesia. | 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 |
|
Intraarticular sufentanil administration facilitates recovery after day-case knee arthroscopy. | 2001 Mar |
|
Perioperative medical management and outcome following thymectomy for myasthenia gravis. | 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 |
|
Double-blinded, single-blinded, or just blind? | 2001 Nov |
|
Combined spinal-epidural versus epidural labor analgesia. | 2001 Oct |
|
Stability of sufentanil in human plasma samples. | 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 |
|
[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 |
|
Cost containment in obstetric analgesia. | 2002 Jan |
|
Epinephrine reduces the sedative side effects of epidural sufentanil for labour analgesia. | 2002 Jan |
|
Up-and-down allocation. | 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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8607312
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
Edited
Fri Dec 15 15:17:11 GMT 2023
by
admin
on
Fri Dec 15 15:17:11 GMT 2023
|
Record UNII |
AFE2YW0IIZ
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
DEA NO. |
9740
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
||
|
NCI_THESAURUS |
C67413
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
||
|
WHO-VATC |
QN01AH03
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
||
|
LIVERTOX |
904
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
||
|
WIKIPEDIA |
List_of_fentanyl_analogues
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
||
|
WHO-ATC |
N01AH03
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
||
|
NDF-RT |
N0000175684
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
||
|
NDF-RT |
N0000175690
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
||
|
NCI_THESAURUS |
C1506
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
9316
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
6760
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
3534
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
56795
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | RxNorm | ||
|
SUFENTANIL
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
100000089189
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
41693
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
56030-54-7
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
C61956
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
m10288
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | Merck Index | ||
|
4048
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
Sufentanil
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
D017409
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
2491
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
DTXSID6023604
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
CHEMBL658
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
SUB10671MIG
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
AFE2YW0IIZ
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
SUFENTANIL
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | Sufentanil first was synthesized at Janssen Pharmaceutica in 1974. Sufentanil is marketed for use by specialist centers under different trade names, such as Sufenta and Sufentil. Sufentanil with and without lidocaine or mepivacaine is available as a transdermal patch similar to Duragesic in Europe under trade names such as Chronogesic. | ||
|
DB00708
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY | |||
|
AFE2YW0IIZ
Created by
admin on Fri Dec 15 15:17:11 GMT 2023 , Edited by admin on Fri Dec 15 15:17:11 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
TARGET -> AGONIST |
10 times more potent than Fentanyl.
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
|
||
|
SALT/SOLVATE -> PARENT |
|
||
|
SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
|
||
|
BINDER->LIGAND |
BINDING
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE INACTIVE -> PARENT |
LIVER MICROSOMES
MAJOR
|
||
|
METABOLITE -> PARENT |
|
||
|
METABOLITE INACTIVE -> PARENT |
|
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 |
|
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Biological Half-life | PHARMACOKINETIC |
|
|
|||