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

Details

Stereochemistry ACHIRAL
Molecular Formula C21H32N6O3
Molecular Weight 416.5172
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALFENTANIL

SMILES

CCN1N=NN(CCN2CCC(COC)(CC2)N(C(=O)CC)C3=CC=CC=C3)C1=O

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
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
Fatal cardiac ischaemia associated with prolonged desflurane anaesthesia and administration of exogenous catecholamines.
1998 Dec
Clinical interpretation of pharmacokinetic and pharmacodynamic propofol-opioid interactions.
2001
Pharmacokinetic aspects of treating infections in the intensive care unit: focus on drug interactions.
2001
Analgesic efficacy of tramadol 2 mg kg(-1) for paediatric day-case adenoidectomy.
2001 Apr
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
Comparison of alfentanil and morphine in the prehospital treatment of patients with acute ischaemic-type chest pain.
2001 Dec
Absence of memory for intra-operative information during surgery with total intravenous anaesthesia.
2001 Feb
Myopexy (Faden) results in more postoperative vomiting after strabismus surgery in children.
2001 Jan
General anaesthesia in a man with mitochondrial myopathy undergoing eye surgery.
2001 May
Can inflammatory pain prevent the development of acute tolerance to alfentanil?
2001 May
Auditory information processing during adequate propofol anesthesia monitored by electroencephalogram bispectral index.
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
Normalization of hypertensive responses during ambulatory surgical stress by perioperative music.
2001 May-Jun
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
Inhalation versus total intravenous anesthesia for lumbar disc herniation: comparison of hemodynamic effects, recovery characteristics, and cost.
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
Alfentanil and sufentanil in fast-track anesthesia for coronary artery bypass graft surgery.
2002 Apr
Pharmacological treatment of postoperative shivering: a quantitative systematic review of randomized controlled trials.
2002 Feb
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
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
Improved long-lasting postoperative analgesia, recovery function and patient satisfaction after inguinal hernia repair with inguinal field block compared with general anesthesia.
2002 Jul
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
Prolonged neuromuscular block after rocuronium in postpartum patients.
2002 Mar
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
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.
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
ALFENTANYL
Common Name English
IDS-NA-014
Code English
ALFENTANIL [VANDF]
Common Name English
ALFENTANIL [HSDB]
Common Name English
AFENTANYL
Common Name English
Alfentanil [WHO-DD]
Common Name English
Classification Tree Code System Code
WIKIPEDIA List_of_fentanyl_analogues
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
FDA ORPHAN DRUG 206405
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
NDF-RT N0000175690
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
NCI_THESAURUS C1506
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
FDA ORPHAN DRUG 206505
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
WHO-VATC QN01AH02
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
WHO-ATC N01AH02
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
DEA NO. 9737
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
NCI_THESAURUS C67413
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
NDF-RT N0000175684
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
Code System Code Type Description
PUBCHEM
51263
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
PRIMARY
RXCUI
480
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PRIMARY RxNorm
LACTMED
Alfentanil
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
PRIMARY
DRUG BANK
DB00802
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
PRIMARY
WEB RESOURCE
ALFENTANIL
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
PRIMARY
ChEMBL
CHEMBL634
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
PRIMARY
IUPHAR
7108
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
PRIMARY
NCI_THESAURUS
C61626
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
PRIMARY
WIKIPEDIA
ALFENTANIL
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
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 Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
PRIMARY
EVMPD
SUB05317MIG
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PRIMARY
DAILYMED
1N74HM2BS7
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PRIMARY
SMS_ID
100000085240
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PRIMARY
MERCK INDEX
M1499
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PRIMARY Merck Index
CAS
71195-58-9
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PRIMARY
EPA CompTox
DTXSID9022570
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
PRIMARY
CHEBI
2569
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
PRIMARY
MESH
D015760
Created by admin on Thu Jul 06 21:53:43 UTC 2023 , Edited by admin on Thu Jul 06 21:53:43 UTC 2023
PRIMARY
FDA UNII
1N74HM2BS7
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PRIMARY
HSDB
6789
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PRIMARY
INN
4818
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PRIMARY