U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C21H32N6O3
Molecular Weight 416.518
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALFENTANIL

SMILES

CCC(=O)N(c1ccccc1)C2(CCN(CC2)CCn3c(=O)n(CC)nn3)COC

InChI

InChIKey=IDBPHNDTYPBSNI-UHFFFAOYSA-N
InChI=1S/C21H32N6O3/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

HIDE SMILES / InChI

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

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ALFENTA

Approved Use

Alfentanil 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 Date

536198400000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
20.1 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
1241.2 ng × min/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
59.4 min
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
8%
ALFENTANIL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
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
PubMed

PubMed

TitleDatePubMed
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
Effects of fentanyl, alfentanil, remifentanil and sufentanil on loss of consciousness and bispectral index during propofol induction of anaesthesia.
2001 Apr
Total intravenous anesthesia versus single breath technique and anesthesia maintenance with sevoflurane for bariatric operations.
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
Relative sensitivity to alfentanil and reliability of current perception threshold vs von Frey tactile stimulation and thermal sensory testing.
2001 Dec
A pilot evaluation of alfentanil-induced miosis as a noninvasive probe for hepatic cytochrome P450 3A4 (CYP3A4) activity in humans.
2001 Dec
Gender differences in the pharmacokinetics of propofol in elderly patients during and after continuous infusion.
2001 Feb
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients.
2001 Jan
Comparison of five experimental pain tests to measure analgesic effects of alfentanil.
2001 Jul
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
Patient-controlled analgesia during SWL treatments.
2001 Jun
Influence of pneumoperitoneum and patient positioning on preload and splanchnic blood volume in laparoscopic surgery of the lower abdomen.
2001 Jun
[The effect of encephalogram bispectral index monitoring during total intravenous anesthesia with propofol in outpatient surgery].
2001 Jun-Jul
Comparison between dexmedetomidine and propofol for sedation in the intensive care unit: patient and clinician perceptions.
2001 Nov
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 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
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
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
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
[Sedation analgesia in interventional radiology].
2002 Feb
Pharmacological treatment of postoperative shivering: a quantitative systematic review of randomized controlled trials.
2002 Feb
Concurrent ketamine and alfentanil administration: pharmacokinetic considerations.
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
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
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
Patents

Sample Use Guides

Spontaneously Breathing/Assisted Ventilation Induction of Analgesia: 8 to 20 mcg/kg
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:18:49 UTC 2021
Edited
by admin
on Sat Jun 26 11:18:49 UTC 2021
Record UNII
1N74HM2BS7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALFENTANIL
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
PROPANAMIDE, N-(1-(2-(4-ETHYL-4,5-DIHYDRO-5-OXO-1H-TETRAZOL-1-YL)ETHYL)-4-(METHOXYMETHYL)-4-PIPERIDINYL)-N-PHENYL-
Systematic Name English
ALFENTANIL [MI]
Common Name English
R-39209-
Code English
N-(1-(2-(4-ETHYL-4,5-DIHYDRO-5-OXO-1H-TETRAZOL-1-YL)ETHYL)-4-(METHOXYMETHYL) -4-PIPERIDINYL)-N-PHENYLPROPANAMIDE
Systematic Name English
ALFENTANIL [INN]
Common Name English
RAPIFEN
Common Name English
ALFENTANIL [WHO-DD]
Common Name English
ALFENTANYL
Common Name English
IDS-NA-014
Code English
ALFENTANIL [VANDF]
Common Name English
ALFENTANIL [HSDB]
Common Name English
AFENTANYL
Common Name English
Classification Tree Code System Code
WIKIPEDIA List_of_fentanyl_analogues
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
FDA ORPHAN DRUG 206405
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
NDF-RT N0000175690
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
NCI_THESAURUS C1506
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
FDA ORPHAN DRUG 206505
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
WHO-VATC QN01AH02
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
WHO-ATC N01AH02
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
DEA NO. 9737
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
NCI_THESAURUS C67413
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
NDF-RT N0000175684
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
Code System Code Type Description
PUBCHEM
51263
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY
RXCUI
480
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY RxNorm
LACTMED
Alfentanil
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY
DRUG BANK
DB00802
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY
WEB RESOURCE
ALFENTANIL
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY
ChEMBL
CHEMBL634
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY
IUPHAR
7108
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY
NCI_THESAURUS
C61626
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY
WIKIPEDIA
ALFENTANIL
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY While alfentanil tends to cause fewer cardiovascular complications than other similar drugs such as fentanyl and remifentanil, it tends to give stronger respiratory depression and so requires careful monitoring of breathing and vital signs. Almost exclusively used by anesthesia providers during portions of a case where quick, fast acting (though not long lasting) pain control is needed (i.e. during a nerve block, head pinning etc..) Alfentanil is administered by the parenteral (injected) route for fast onset of effects and precise control of dosage. Alfentanil is a restricted drug which is classified as Schedule II in the USA, according to the U.S. DEA website. Alfentanil was discovered at Janssen Pharmaceutica in 1976.
DRUG CENTRAL
114
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY
EVMPD
SUB05317MIG
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY
MERCK INDEX
M1499
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY Merck Index
CAS
71195-58-9
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY
EPA CompTox
71195-58-9
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY
MESH
D015760
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY
FDA UNII
1N74HM2BS7
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY
HSDB
6789
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY
INN
4818
Created by admin on Sat Jun 26 11:18:50 UTC 2021 , Edited by admin on Sat Jun 26 11:18:50 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
METABOLIC ENZYME -> SUBSTRATE
Alfentanil is relatively distinctive among CYP3A substrates, in that the metabolic capacity (in vitro intrinsic clearance) of CYP3A5 equaled or exceeded that of CYP3A4.
METABOLIC ENZYME -> SUBSTRATE
IN VITRO
METABOLIC ENZYME -> SUBSTRATE
IN VITRO
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
BINDER->LIGAND
BINDING
EXCRETED UNCHANGED
FECAL; URINE
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
Related Record Type Details
METABOLITE INACTIVE -> PARENT
Alfentanil is relatively distinctive among CYP3A substrates, in that the metabolic capacity (in vitro intrinsic clearance) of CYP3A5 equaled or exceeded that of CYP3A4.
METABOLITE INACTIVE -> PARENT
MAJOR
URINE
METABOLITE INACTIVE -> PARENT
MAJOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC