Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H32N6O3.ClH |
| Molecular Weight | 452.978 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCN1N=NN(CCN2CCC(COC)(CC2)N(C(=O)CC)C3=CC=CC=C3)C1=O
InChI
InChIKey=AQORHZJDCHLLJN-UHFFFAOYSA-N
InChI=1S/C21H32N6O3.ClH/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
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.
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 Date1986 |
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 |
|---|---|---|---|---|
Page: 1.0 |
yes | |||
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 |
|---|---|---|
| Clinical interpretation of pharmacokinetic and pharmacodynamic propofol-opioid interactions. | 2001 |
|
| Choice of the hypnotic and the opioid for rapid-sequence induction. | 2001 |
|
| Pharmacokinetic aspects of treating infections in the intensive care unit: focus on drug interactions. | 2001 |
|
| Response surface modeling of drug interactions on cardiorespiratory control. | 2001 |
|
| Relative sensitivity to alfentanil and reliability of current perception threshold vs von Frey tactile stimulation and thermal sensory testing. | 2001 Dec |
|
| Comparison of alfentanil and morphine in the prehospital treatment of patients with acute ischaemic-type chest pain. | 2001 Dec |
|
| A pilot evaluation of alfentanil-induced miosis as a noninvasive probe for hepatic cytochrome P450 3A4 (CYP3A4) activity in humans. | 2001 Dec |
|
| Esmolol promotes electroencephalographic burst suppression during propofol/alfentanil anesthesia. | 2001 Dec |
|
| Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients. | 2001 Jan |
|
| 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 |
|
| Inhalation versus total intravenous anesthesia for lumbar disc herniation: comparison of hemodynamic effects, recovery characteristics, and cost. | 2001 Oct |
|
| [The hereditary motor-sensory neuropathy Charcot-Marie-Tooth disease: anesthesiologic management--case report with literature review]. | 2001 Oct |
|
| Stability of sufentanil in human plasma samples. | 2001 Oct |
|
| Reexamined: the recommended endotracheal intubating dose for nondepolarizing neuromuscular blockers of rapid onset. | 2001 Oct |
|
| The concentration-effect relationship of the respiratory depressant effects of alfentanil and fentanyl. | 2001 Oct |
|
| The role of drug-lipid interactions on the disposition of liposome-formulated opioid analgesics in vitro and in vivo. | 2001 Oct |
|
| Experience with an anesthesiologist interventional model for endoscopy in a pediatric hospital. | 2001 Sep |
|
| [Comparative studies of patient positioning for lumbar intervertebral disk operation]. | 2002 |
|
| A randomized study of the efficacy and recovery of remifentanil-based and alfentanil anaesthesia with desflurane or sevoflurane for gynecological surgery. | 2002 |
|
| Effect of sevoflurane/nitrous oxide versus propofol anaesthesia on somatosensory evoked potential monitoring of the spinal cord during surgery to correct scoliosis. | 2002 Apr |
|
| 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 |
|
| Bispectral index variations during tracheal suction in mechanically ventilated critically ill patients: effect of an alfentanil bolus. | 2002 Feb |
|
| Alfentanil-induced epileptiform activity. | 2002 Feb |
|
| [Sedation analgesia in interventional radiology]. | 2002 Feb |
|
| General anesthesia versus monitored anesthesia care with remifentanil for assisted reproductive technologies: effect on pregnancy rate. | 2002 Feb |
|
| Pharmacological treatment of postoperative shivering: a quantitative systematic review of randomized controlled trials. | 2002 Feb |
|
| Pain model and fuzzy logic patient-controlled analgesia in shock-wave lithotripsy. | 2002 Jan |
|
| Effects of propofol and nitrous oxide on middle cerebral artery flow velocity and cerebral autoregulation. | 2002 Jan |
|
| Concentration-effect relationships for intravenous alfentanil and ketamine infusions in human volunteers: effects on acute thresholds and capsaicin-evoked hyperpathia. | 2002 Jan |
|
| Bispectral Index (BIS) may not predict awareness reaction to intubation in surgical patients. | 2002 Jan |
|
| Relaxation music decreases the dose of patient-controlled sedation during colonoscopy: a prospective randomized controlled trial. | 2002 Jan |
|
| Effects of adding alfentanil or atracurium to lidocaine solution for intravenous regional anaesthesia. | 2002 Jul |
|
| Mu-receptor agonism with alfentanil increases striatal dopamine D2 receptor binding in man. | 2002 Jul |
|
| A new highly reliable instrument for the assessment of pre- and postoperative gynecological pain. | 2002 Jul |
|
| Improved long-lasting postoperative analgesia, recovery function and patient satisfaction after inguinal hernia repair with inguinal field block compared with general anesthesia. | 2002 Jul |
|
| Psychomotor performance after short-term anaesthesia. | 2002 Jun |
|
| Postoperative nausea and vomiting after total intravenous anesthesia with propofol and remifentanil or alfentanil: how important is the opioid? | 2002 Jun |
|
| Effects of remifentanil and alfentanil on the cardiovascular responses to induction of anaesthesia and tracheal intubation in the elderly. | 2002 Mar |
|
| Implicit memory for words played during isoflurane- or propofol-based anesthesia: the lexical decision task. | 2002 Mar |
|
| Respiratory response to skin incision during anaesthesia with infusions of propofol and alfentanil. | 2002 May |
|
| Comparison of hemodynamics, recovery profile, and early postoperative pain control and costs of remifentanil versus alfentanil-based total intravenous anesthesia (TIVA). | 2002 May |
|
| Co-administration of alfentanil-propofol improves laryngeal mask airway insertion compared to fentanyl-propofol. | 2002 May |
|
| Mild core hypothermia and anesthetic requirement for loss of responsiveness during propofol anesthesia for craniotomy. | 2002 May |
|
| Target-controlled versus manually-controlled infusion of propofol for direct laryngoscopy and bronchoscopy. | 2002 May |
|
| 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
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.
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ACTIVE MOIETY
SUBSTANCE RECORD
