Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H32N6O3.ClH.H2O |
Molecular Weight | 470.993 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.Cl.CCN1N=NN(CCN2CCC(COC)(CC2)N(C(=O)CC)C3=CC=CC=C3)C1=O
InChI
InChIKey=YYESXRRYBUERKF-UHFFFAOYSA-N
InChI=1S/C21H32N6O3.ClH.H2O/c1-4-19(28)27(18-9-7-6-8-10-18)21(17-30-3)11-13-24(14-12-21)15-16-26-20(29)25(5-2)22-23-26;;/h6-10H,4-5,11-17H2,1-3H3;1H;1H2
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C21H32N6O3 |
Molecular Weight | 416.5172 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Alfentanil is an opioid analgesic with a rapid onset of action. Alfentanil 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, alfentanil exerts its principal pharmacologic effects on the central nervous system. Its primary actions of therapeutic value are analgesia and sedation. Alfentanil 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. Alfentanil depresses the respiratory centers, depresses the cough reflex, and constricts the pupils. Alfentanil, marketed under the trade name Alfenta, Rapifen in Australia is indicated for the management of postoperative pain and the maintenance of general anesthesia.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ALFENTA Approved UseAlfentanil HCl injection is indicated: as an analgesic adjunct given in incremental doses in the maintenance of anesthesia with barbiturate/nitrous oxide/oxygen. as an analgesic administered by continuous infusion with nitrous oxide/oxygen in the maintenance of general anesthesia. as a primary anesthetic agent for the induction of anesthesia in patients undergoing general surgery in which endotracheal intubation and mechanical ventilation are required. as the analgesic component for monitored anesthesia care (MAC). Launch Date5.36198414E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7598917 |
0.54 mg single, nasal dose: 0.54 mg route of administration: Nasal experiment type: SINGLE co-administered: |
ALFENTANIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1241.2 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7598917 |
0.54 mg single, nasal dose: 0.54 mg route of administration: Nasal experiment type: SINGLE co-administered: |
ALFENTANIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1985.7 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7598917 |
0.54 mg single, intravenous dose: 0.54 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ALFENTANIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
59.4 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7598917 |
0.54 mg single, nasal dose: 0.54 mg route of administration: Nasal experiment type: SINGLE co-administered: |
ALFENTANIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
60.1 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7598917 |
0.54 mg single, intravenous dose: 0.54 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ALFENTANIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8% |
ALFENTANIL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15557344/ Page: 1.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15557344/ Page: 8.0 |
yes | |||
yes | likely (co-administration study) Comment: Concomitant use of Alfentanil HCl Injection with a CYP3A4 inhibitor, such as macrolide antibiotics (e.g., erythromycin), azole-antifungal agents (e.g., ketoconazole), and protease inhibitors (e.g., ritonavir), may increase plasma concentrations of Alfentanil HCl Injection; discontinuation of a CYP3A4 inducer, such as rifampin, carbamazepine, and phenytoin, in Alfentanil HCl Injection-treated patients may increase alfentanil plasma concentrations and prolong opioid adverse reactions Page: 1.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Response surface modeling of drug interactions on cardiorespiratory control. | 2001 |
|
Tracheal intubation without muscle relaxant--a technique using sevoflurane vital capacity induction and alfentanil. | 2001 Aug |
|
Esmolol promotes electroencephalographic burst suppression during propofol/alfentanil anesthesia. | 2001 Dec |
|
Alfentanil-induced epileptiform activity: a simultaneous surface and depth electroencephalographic study in complex partial epilepsy. | 2001 Feb |
|
Timing of pre-emptive tenoxicam is important for postoperative analgesia. | 2001 Feb |
|
Assessment of depth of anesthesia and postoperative respiratory recovery after remifentanil- versus alfentanil-based total intravenous anesthesia in patients undergoing ear-nose-throat surgery. | 2001 Feb |
|
Remifentanil and controlled hypotension; comparison with nitroprusside or esmolol during tympanoplasty. | 2001 Jan |
|
Effect of dexmedetomidine, an alpha2-adrenoceptor agonist, on human pupillary reflexes during general anaesthesia. | 2001 Jan |
|
Safer colonoscopy with patient-controlled analgesia and sedation with propofol and alfentanil. | 2001 Jul |
|
Preoperative diclofenac is a useful adjunct to spinal anesthesia for day-case varicose vein repair. | 2001 Jul-Aug |
|
[Factors influencing early extubation after open heart surgery]. | 2001 Jun 10 |
|
The effects of chronic morphine on behavior reinforced by several opioids or by cocaine in rhesus monkeys. | 2001 May 1 |
|
Pain experience during transvaginal aspiration of immature oocytes. | 2001 Nov |
|
The effects of remifentanil on epileptiform discharges during intraoperative electrocorticography in patients undergoing epilepsy surgery. | 2001 Oct |
|
The concentration-effect relationship of the respiratory depressant effects of alfentanil and fentanyl. | 2001 Oct |
|
Postoperative analgesia in children: comparison of bupivacaine with a mixture of bupivacaine and alfentanil. | 2001 Oct |
|
Intraoperative small-dose ketamine enhances analgesia after outpatient knee arthroscopy. | 2001 Sep |
|
The in vitro effects of remifentanil, sufentanil, fentanyl, and alfentanil on isolated human right atria. | 2001 Sep |
|
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 |
|
A new paradigm for the closed-loop intraoperative administration of analgesics in humans. | 2002 Apr |
|
Analgesia for shock wave lithotripsy. | 2002 Apr |
|
Comparison of effects of remifentanil, alfentanil and fentanyl on cardiovascular responses to tracheal intubation in morbidly obese patients. | 2002 Feb |
|
Comparison of rocuronium and suxamethonium for rapid tracheal intubation in children. | 2002 Feb |
|
Concurrent ketamine and alfentanil administration: pharmacokinetic considerations. | 2002 Jan |
|
Postoperative nausea and vomiting after total intravenous anesthesia with propofol and remifentanil or alfentanil: how important is the opioid? | 2002 Jun |
|
Prolonged neuromuscular block after rocuronium in postpartum patients. | 2002 Mar |
|
Relative reinforcing effects of three opioids with different durations of action. | 2002 May |
Sample Use Guides
Spontaneously Breathing/Assisted Ventilation Induction of Analgesia: 8 to 20 mcg/kg
Maintenance of Analgesia: 3 to 5 mcg/kg q 5 to 20 min or 0.5 to 1 mcg/kg/min
Total dose: 8 to 40 mcg/kg
Assisted or Controlled Ventilation
- Assisted or Controlled Ventilation Incremental Injection
(To attenuate response to laryngoscopy and intubation) Induction of Analgesia: 20 to 50 mcg/kg
Maintenance of Analgesia: 5 to 15 mcg/kg q 5 to 20 min
Total dose: Up to 75 mcg/kg
Assisted or Controlled Ventilation
- Continuous Infusion
(To provide attenuation of response to intubation and incision) Induction of Analgesia: 50 to 75 mcg/kg
Maintenance of Analgesia: 0.5 to 3 mcg/kg/min (Average rate 1 to 1.5 mcg/kg/min) Infusion rates are variable and should be titrated to the desired clinical effect. See Infusion Dosage Guidelines Below
Total dose: Dependent on duration of procedure
Anesthetic Induction Induction of Anesthesia: 130 to 245 mcg/kg Administer slowly (over 3 minutes).
Maintenance of Anesthesia: 0.5 to 1.5 mcg/kg/min or general anesthetic.
Infusion rates are variable and should be titrated to the desired clinical effect. See Infusion Dosage Guidelines Below
Total dose: Dependent on duration of procedure
At these doses truncal rigidity should be expected and a muscle relaxant should be utilized.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17279089
Alfentanil (10 uM ) significantly increased contraction of TNF-alpha and IL-1beta treated cells via a small increase in the Ca(2+) transient and a larger increase in myofilament Ca(2+) sensitivity, effects that were not blocked by 10 uM naloxone, a broad spectrum opioid receptor antagonist.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 16:58:49 UTC 2022
by
admin
on
Fri Dec 16 16:58:49 UTC 2022
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Record UNII |
11S92G0TIW
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C1506
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NCI_THESAURUS |
C67413
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70879-28-6
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DTXSID50221107
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64762
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CHEMBL634
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C220
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203203
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1012906
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DBSALT001202
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11S92G0TIW
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SUB00339MIG
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11S92G0TIW
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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