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
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)
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 |
---|---|---|
Combined spinal epidural for labour analgesia--duration, efficacy and side effects of adding sufentanil or fentanyl to bupivacaine intrathecally vs plain bupivacaine. | 1999 Oct |
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The dose-response of intrathecal sufentanil added to bupivacaine for labor analgesia. | 2000 Jun |
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Mental status change and aphasia after labor analgesia with intrathecal sufentanil/bupivacaine. | 2000 May |
|
[Hyperoxia-induced liberation of big-endothelin into jugular venous blood of electric neurosurgical patients]. | 2001 |
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Right vs left side thoracoscopic sympathectomy: effects of CO2 insufflation on haemodynamics. | 2001 |
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Rational use of opioids. | 2001 Apr |
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Intravenous ketoprofen in thyroid and parathyroid surgery. | 2001 Apr |
|
Oral transmucosal fentanyl and sufentanil for incident pain. | 2001 Aug |
|
Dose of prophylactic intravenous ephedrine during spinal anesthesia for cesarean section. | 2001 Aug |
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Effects of sufentanil and NMDA antagonists on a C-fibre reflex in the rat. | 2001 Aug |
|
More epidural than intravenous sufentanil is required to provide comparable postoperative pain relief. | 2001 Aug |
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Subarachnoid sufentanil for early postoperative pain management in orthopedic patients: more disadvantages than benefits? | 2001 Dec |
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Neostigmine combined with bupivacaine, clonidine, and sufentanil for spinal labor analgesia. | 2001 Dec |
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The continuous recording of blood pressure in patients undergoing carotid surgery under remifentanil versus sufentanil analgesia. | 2001 Dec |
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[Low concentration Ropivacaine in labor epidural analgesia. A prospective study on obstetric and neonatal outcome]. | 2001 Dec |
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Subarachnoid sufentanil for early postoperative pain management in orthopedic patients: a placebo-controlled, double-blind study using spinal microcatheters. | 2001 Feb |
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Extended femoral nerve sheath block after total hip arthroplasty: continuous versus patient-controlled techniques. | 2001 Feb |
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Continuous intrathecal sufentanil for postoperative analgesia. | 2001 Jan |
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Should the angiotensin II antagonists be discontinued before surgery? | 2001 Jan |
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[Prophylaxis of nausea and vomiting after thyroid surgery: comparison of oral and intravenous dolasetron with intravenous droperidol and placebo]. | 2001 Jul |
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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 |
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Recovery after remifentanil and sufentanil for analgesia and sedation of mechanically ventilated patients after trauma or major surgery. | 2001 Jun |
|
Double-blinded, single-blinded, or just blind? | 2001 Nov |
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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 |
|
Stability of sufentanil in human plasma samples. | 2001 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 |
|
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 |
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.
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Classification Tree | Code System | Code | ||
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DEA NO. |
9740
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NCI_THESAURUS |
C1506
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NCI_THESAURUS |
C67413
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1623648
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65494
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W-113
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m10288
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C47731
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CHEMBL658
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S9ZFX8403R
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SUB04616MIG
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DBSALT000275
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58964
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PRIMARY | RxNorm |
ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD