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)
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 |
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 Sources: |
unknown, 18 - 65 years Health Status: unknown Age Group: 18 - 65 years Sex: unknown Sources: |
Other AEs: Nausea, Hypotension... |
30 ug single, oral Recommended |
unhealthy, adult |
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 Sources: |
unknown, 18 - 65 years Health Status: unknown Age Group: 18 - 65 years Sex: unknown Sources: |
|
Nausea | 0.4 mg/kg single, intranasal MTD Dose: 0.4 mg/kg Route: intranasal Route: single Dose: 0.4 mg/kg Sources: |
unknown, 18 - 65 years Health Status: unknown Age Group: 18 - 65 years Sex: unknown Sources: |
|
Dizziness | 1 patient Disc. AE |
30 ug single, oral Recommended |
unhealthy, adult |
Pruritus | 1 patient Disc. AE |
30 ug single, oral Recommended |
unhealthy, adult |
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 |
---|---|---|
No reduction in the sufentanil requirement of elderly patients undergoing ventilatory support in the medical intensive care unit. | 1999 Oct |
|
Optimal dose of intrathecal clonidine added to sufentanil plus bupivacaine for labour analgesia. | 2000 Sep |
|
Liver and renal function after volatile induction and maintenance of anesthesia (VIMA) with sevoflurane versus TIVA with sufentanil-midazolam for CABG surgery. | 2001 |
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[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 |
|
Changes in the expression of G protein-coupled receptor kinases and beta-arrestin 2 in rat brain during opioid tolerance and supersensitivity. | 2001 Apr |
|
The effects of opioids on isolated human pregnant uterine muscles. | 2001 Apr |
|
Sedative and analgesic practice in the intensive care unit: the results of a European survey. | 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 |
|
The effect of intrathecal analgesia on the success of external cephalic version. | 2001 Aug |
|
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 |
|
Subarachnoid sufentanil for early postoperative pain management in orthopedic patients: a placebo-controlled, double-blind study using spinal microcatheters. | 2001 Feb |
|
Continuous intrathecal sufentanil for postoperative analgesia. | 2001 Jan |
|
A randomized, double-blinded comparison of intrathecal morphine, sufentanil and their combination versus IV morphine patient-controlled analgesia for postthoracotomy pain. | 2001 Jan |
|
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 |
|
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 |
|
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 |
|
Life-threatening pneumothorax of the ventilated lung during thoracoscopic pleurectomy. | 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 |
|
Fetal heart rate abnormalities after regional analgesia for labor pain: the effect of intrathecal opioids. | 2001 May-Jun |
|
[Obstetric analgesia in patients with Klippel-Trenaunay syndrome]. | 2001 Nov |
|
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 |
|
A high rate of epidural analgesia with bupivacaine-sufentanil is consistent with a low rate of caesarean section and instrumental deliveries. | 2001 Oct |
|
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 |
|
Cost-effectiveness of analgesia after Caesarean section. A comparison of intrathecal morphine and epidural PCA. | 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
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
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Record UNII |
S9ZFX8403R
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Validated (UNII)
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DEA NO. |
9740
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C1506
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C67413
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IMPURITY -> PARENT |
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