Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H32N6O3.ClH.H2O |
Molecular Weight | 470.9942 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC(=O)N(c1ccccc1)C2(CCN(CC2)CCn3c(=O)n(CC)nn3)COC.Cl.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 | 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 | 416.518 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | ClH |
Molecular Weight | 36.4609 |
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 |
---|---|---|
Fatal cardiac ischaemia associated with prolonged desflurane anaesthesia and administration of exogenous catecholamines. | 1998 Dec |
|
Alfentanil decreases myoclonus caused by etomidate. | 1999 Jun |
|
Analgesic efficacy of tramadol 2 mg kg(-1) for paediatric day-case adenoidectomy. | 2001 Apr |
|
Tracheal intubation without muscle relaxant--a technique using sevoflurane vital capacity induction and alfentanil. | 2001 Aug |
|
A new model of electrically evoked pain and hyperalgesia in human skin: the effects of intravenous alfentanil, S(+)-ketamine, and lidocaine. | 2001 Aug |
|
Influence of pneumoperitoneum and patient positioning on respiratory system compliance. | 2001 Aug |
|
A mixture of alfentanil and morphine for rapid postoperative loading with opioid: theoretical basis and initial clinical investigation. | 2001 Aug |
|
Timing of pre-emptive tenoxicam is important for postoperative analgesia. | 2001 Feb |
|
Target-controlled alfentanil analgesia for dressing change following extensive reconstructive surgery for trauma. | 2001 Jan |
|
Effect of dexmedetomidine, an alpha2-adrenoceptor agonist, on human pupillary reflexes during general anaesthesia. | 2001 Jan |
|
Preoperative diclofenac is a useful adjunct to spinal anesthesia for day-case varicose vein repair. | 2001 Jul-Aug |
|
Response surface modeling of alfentanil-sevoflurane interaction on cardiorespiratory control and bispectral index. | 2001 Jun |
|
Comparison of the intubating laryngeal mask airway with the fiberoptic intubation in anticipated difficult airway management. | 2001 Jun |
|
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 |
|
The effects of chronic morphine on behavior reinforced by several opioids or by cocaine in rhesus monkeys. | 2001 May 1 |
|
Neural mechanisms in the cardiovascular responses to acute central hypovolaemia. | 2001 May-Jun |
|
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 |
|
The role of drug-lipid interactions on the disposition of liposome-formulated opioid analgesics in vitro and in vivo. | 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 |
|
[Comparative studies of patient positioning for lumbar intervertebral disk operation]. | 2002 |
|
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 |
|
Concentration-effect relationships for intravenous alfentanil and ketamine infusions in human volunteers: effects on acute thresholds and capsaicin-evoked hyperpathia. | 2002 Jan |
|
Mu-receptor agonism with alfentanil increases striatal dopamine D2 receptor binding in man. | 2002 Jul |
|
Effects of remifentanil and alfentanil on the cardiovascular responses to induction of anaesthesia and tracheal intubation in the elderly. | 2002 Mar |
|
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
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 Jun 25 20:59:54 UTC 2021
by
admin
on
Fri Jun 25 20:59:54 UTC 2021
|
Record UNII |
11S92G0TIW
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C1506
Created by
admin on Fri Jun 25 20:59:54 UTC 2021 , Edited by admin on Fri Jun 25 20:59:54 UTC 2021
|
||
|
NCI_THESAURUS |
C67413
Created by
admin on Fri Jun 25 20:59:54 UTC 2021 , Edited by admin on Fri Jun 25 20:59:54 UTC 2021
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
70879-28-6
Created by
admin on Fri Jun 25 20:59:54 UTC 2021 , Edited by admin on Fri Jun 25 20:59:54 UTC 2021
|
PRIMARY | |||
|
70879-28-6
Created by
admin on Fri Jun 25 20:59:54 UTC 2021 , Edited by admin on Fri Jun 25 20:59:54 UTC 2021
|
PRIMARY | |||
|
64762
Created by
admin on Fri Jun 25 20:59:54 UTC 2021 , Edited by admin on Fri Jun 25 20:59:54 UTC 2021
|
PRIMARY | |||
|
CHEMBL634
Created by
admin on Fri Jun 25 20:59:54 UTC 2021 , Edited by admin on Fri Jun 25 20:59:54 UTC 2021
|
PRIMARY | |||
|
C220
Created by
admin on Fri Jun 25 20:59:54 UTC 2021 , Edited by admin on Fri Jun 25 20:59:54 UTC 2021
|
PRIMARY | |||
|
203203
Created by
admin on Fri Jun 25 20:59:54 UTC 2021 , Edited by admin on Fri Jun 25 20:59:54 UTC 2021
|
PRIMARY | RxNorm | ||
|
1012906
Created by
admin on Fri Jun 25 20:59:54 UTC 2021 , Edited by admin on Fri Jun 25 20:59:54 UTC 2021
|
PRIMARY | USP-RS | ||
|
DBSALT001202
Created by
admin on Fri Jun 25 20:59:54 UTC 2021 , Edited by admin on Fri Jun 25 20:59:54 UTC 2021
|
PRIMARY | |||
|
11S92G0TIW
Created by
admin on Fri Jun 25 20:59:54 UTC 2021 , Edited by admin on Fri Jun 25 20:59:54 UTC 2021
|
PRIMARY | |||
|
SUB00339MIG
Created by
admin on Fri Jun 25 20:59:54 UTC 2021 , Edited by admin on Fri Jun 25 20:59:54 UTC 2021
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |