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 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 |
---|---|---|---|---|
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 |
---|---|---|
Fatal cardiac ischaemia associated with prolonged desflurane anaesthesia and administration of exogenous catecholamines. | 1998 Dec |
|
Choice of the hypnotic and the opioid for rapid-sequence induction. | 2001 |
|
Response surface modeling of drug interactions on cardiorespiratory control. | 2001 |
|
Effects of fentanyl, alfentanil, remifentanil and sufentanil on loss of consciousness and bispectral index during propofol induction of anaesthesia. | 2001 Apr |
|
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 |
|
[Epileptogenic drugs in anesthesia]. | 2001 Feb |
|
[Hemodynamic effects of propofol induction administered with target controlled infusion pump in patients scheduled for open heart surgery]. | 2001 Feb 18 |
|
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients. | 2001 Jan |
|
Safer colonoscopy with patient-controlled analgesia and sedation with propofol and alfentanil. | 2001 Jul |
|
Propofol alters the pharmacokinetics of alfentanil in healthy male volunteers. | 2001 Jun |
|
[The effect of encephalogram bispectral index monitoring during total intravenous anesthesia with propofol in outpatient surgery]. | 2001 Jun-Jul |
|
Selective spinal anesthesia for outpatient laparoscopy. II: epinephrine and spinal cord function. | 2001 Mar |
|
Concentration-effect relationship of intravenous alfentanil and ketamine on peripheral neurosensory thresholds, allodynia and hyperalgesia of neuropathic pain. | 2001 Mar |
|
General anaesthesia in a man with mitochondrial myopathy undergoing eye surgery. | 2001 May |
|
The effect of intravenous dexmedetomidine premedication on the dose requirement of propofol to induce loss of consciousness in patients receiving alfentanil. | 2001 May |
|
Can inflammatory pain prevent the development of acute tolerance to alfentanil? | 2001 May |
|
Does discontinuation of desflurane at the time of neostigmine administration speed recovery from cisatracurium block compared to that with a propofol-based technique? | 2001 May |
|
Pain experience during transvaginal aspiration of immature oocytes. | 2001 Nov |
|
Reexamined: the recommended endotracheal intubating dose for nondepolarizing neuromuscular blockers of rapid onset. | 2001 Oct |
|
The role of drug-lipid interactions on the disposition of liposome-formulated opioid analgesics in vitro and in vivo. | 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 |
|
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 |
|
Alfentanil and sufentanil in fast-track anesthesia for coronary artery bypass graft surgery. | 2002 Apr |
|
Analgesia for shock wave lithotripsy. | 2002 Apr |
|
Comparison of rocuronium and suxamethonium for rapid tracheal intubation in children. | 2002 Feb |
|
Pain model and fuzzy logic patient-controlled analgesia in shock-wave lithotripsy. | 2002 Jan |
|
Psychomotor performance after short-term anaesthesia. | 2002 Jun |
|
Effects of remifentanil and alfentanil on the cardiovascular responses to induction of anaesthesia and tracheal intubation in the elderly. | 2002 Mar |
|
Prolonged neuromuscular block after rocuronium in postpartum patients. | 2002 Mar |
|
Respiratory response to skin incision during anaesthesia with infusions of propofol and alfentanil. | 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 15 15:23:41 GMT 2023
by
admin
on
Fri Dec 15 15:23:41 GMT 2023
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Record UNII |
11S92G0TIW
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Record Status |
Validated (UNII)
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Record Version |
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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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300000038460
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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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Related Record | Type | Details | ||
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ANHYDROUS->SOLVATE | |||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
ALFENTANIL HYDROCHLORIDE IS ALFENTANIL HYDROCHLORIDE HYDRATE AS PER EP MONOGRAPH
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |