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

5.36198414E11
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: 1.0
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
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
Total intravenous anesthesia versus single breath technique and anesthesia maintenance with sevoflurane for bariatric operations.
2001 Aug
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
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
[Factors influencing early extubation after open heart surgery].
2001 Jun 10
The effect of intravenous dexmedetomidine premedication on the dose requirement of propofol to induce loss of consciousness in patients receiving 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
Neural mechanisms in the cardiovascular responses to acute central hypovolaemia.
2001 May-Jun
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
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
Experience with an anesthesiologist interventional model for endoscopy in a pediatric hospital.
2001 Sep
Intraoperative small-dose ketamine enhances analgesia after outpatient knee arthroscopy.
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
[Sedation analgesia in interventional radiology].
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
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
Total intravenous anesthesia for intraoperative monitoring of the motor pathways: an integral view combining clinical and experimental data.
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
Patents

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.
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