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 | C22H30N2O2S |
Molecular Weight | 386.551 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C6H8O7 |
Molecular Weight | 192.1235 |
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 Date4.52390388E11 |
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 |
---|---|---|
The dose-response of intrathecal sufentanil added to bupivacaine for labor analgesia. | 2000 Jun |
|
Liver and renal function after volatile induction and maintenance of anesthesia (VIMA) with sevoflurane versus TIVA with sufentanil-midazolam for CABG surgery. | 2001 |
|
Intravenous ketoprofen in thyroid and parathyroid surgery. | 2001 Apr |
|
The effects of opioids on isolated human pregnant uterine muscles. | 2001 Apr |
|
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 |
|
Subarachnoid sufentanil for early postoperative pain management in orthopedic patients: more disadvantages than benefits? | 2001 Dec |
|
The dose-range effects of sufentanil added to 0.125% bupivacaine on the quality of patient-controlled epidural analgesia during labor. | 2001 Jan |
|
The analgesic effect of sufentanil combined with ropivacaine 0.2% for labor analgesia: a comparison of three sufentanil doses. | 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 |
|
Should the angiotensin II antagonists be discontinued before surgery? | 2001 Jan |
|
[Adiuvants in the axillary brachial plexus blockade. Comparison between clonidine, sufentanil and tramadol]. | 2001 Jan-Feb |
|
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 |
|
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 |
|
Selective spinal anesthesia for outpatient laparoscopy. II: epinephrine and spinal cord function. | 2001 Mar |
|
Effects of intrathecal sufentanil on plasma oxytocin and cortisol concentrations in women during the first stage of labor. | 2001 Nov-Dec |
|
Postoperative analgesia by epidural methylprednisolone after posterolateral thoracotomy. | 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 |
|
[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 |
|
Hydromorphone for acute and chronic pain. | 2002 |
|
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 |
|
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
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Record UNII |
S9ZFX8403R
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Record Status |
Validated (UNII)
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DEA NO. |
9740
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C1506
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