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

Details

Stereochemistry ACHIRAL
Molecular Formula C21H32N6O3.ClH
Molecular Weight 452.9789
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALFENTANIL HYDROCHLORIDE ANHYDROUS

SMILES

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

InChI

InChIKey=AQORHZJDCHLLJN-UHFFFAOYSA-N
InChI=1S/C21H32N6O3.ClH/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

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

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.

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
Comparison of the effects of intravenous alfentanil and esmolol on the cardiovascular response to double-lumen endobronchial intubation.
2001 Apr
Total intravenous anesthesia versus single breath technique and anesthesia maintenance with sevoflurane for bariatric operations.
2001 Aug
A pilot evaluation of alfentanil-induced miosis as a noninvasive probe for hepatic cytochrome P450 3A4 (CYP3A4) activity in humans.
2001 Dec
Alfentanil-induced epileptiform activity: a simultaneous surface and depth electroencephalographic study in complex partial epilepsy.
2001 Feb
Effect of dexmedetomidine, an alpha2-adrenoceptor agonist, on human pupillary reflexes during general anaesthesia.
2001 Jan
Safer colonoscopy with patient-controlled analgesia and sedation with propofol and alfentanil.
2001 Jul
Response surface modeling of alfentanil-sevoflurane interaction on cardiorespiratory control and bispectral index.
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
The effects of remifentanil on epileptiform discharges during intraoperative electrocorticography in patients undergoing epilepsy surgery.
2001 Oct
Stability of sufentanil in human plasma samples.
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
Comparison of effects of remifentanil, alfentanil and fentanyl on cardiovascular responses to tracheal intubation in morbidly obese patients.
2002 Feb
General anesthesia versus monitored anesthesia care with remifentanil for assisted reproductive technologies: effect on pregnancy rate.
2002 Feb
Concurrent ketamine and alfentanil administration: pharmacokinetic considerations.
2002 Jan
Effects of propofol and nitrous oxide on middle cerebral artery flow velocity and cerebral autoregulation.
2002 Jan
Bispectral Index (BIS) may not predict awareness reaction to intubation in surgical patients.
2002 Jan
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
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
Co-administration of alfentanil-propofol improves laryngeal mask airway insertion compared to fentanyl-propofol.
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 16:13:44 UTC 2021
Edited
by admin
on Sat Jun 26 16:13:44 UTC 2021
Record UNII
333JTI7A2M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALFENTANIL HYDROCHLORIDE ANHYDROUS
Common Name English
ALFENTANIL HYDROCHLORIDE [WHO-DD]
Common Name English
N-(1-(2-(4-ETHYL-5-OXO-2-TETRAZOLIN-1-YL)-ETHYL)-4-(METHOXYMETHYL)-4-PIPERIDYL)PROPIONANILIDE MONOHYDROCHLORIDE
Systematic Name English
ANHYDROUS ALFENTANIL HYDROCHLORIDE
MART.  
Common Name English
PROPANAMIDE, N-(1-(2-(4-ETHYL-4,5-DIHYDRO-5-OXO-1H-TETRAZOL-1-YL)ETHYL)-4-(METHOXYMETHYL)-4-PIPERIDINYL)-N-PHENYL, MONOHYDROCHLORIDE
Common Name English
ANHYDROUS ALFENTANIL HYDROCHLORIDE [MART.]
Common Name English
ALFENTANIL HYDROCHLORIDE [MI]
Common Name English
Code System Code Type Description
EPA CompTox
69049-06-5
Created by admin on Sat Jun 26 16:13:44 UTC 2021 , Edited by admin on Sat Jun 26 16:13:44 UTC 2021
PRIMARY
PUBCHEM
64761
Created by admin on Sat Jun 26 16:13:44 UTC 2021 , Edited by admin on Sat Jun 26 16:13:44 UTC 2021
PRIMARY
EVMPD
SUB70532
Created by admin on Sat Jun 26 16:13:44 UTC 2021 , Edited by admin on Sat Jun 26 16:13:44 UTC 2021
PRIMARY
ECHA (EC/EINECS)
273-846-3
Created by admin on Sat Jun 26 16:13:44 UTC 2021 , Edited by admin on Sat Jun 26 16:13:44 UTC 2021
PRIMARY
MERCK INDEX
M1499
Created by admin on Sat Jun 26 16:13:44 UTC 2021 , Edited by admin on Sat Jun 26 16:13:44 UTC 2021
PRIMARY Merck Index
CAS
69049-06-5
Created by admin on Sat Jun 26 16:13:44 UTC 2021 , Edited by admin on Sat Jun 26 16:13:44 UTC 2021
PRIMARY
FDA UNII
333JTI7A2M
Created by admin on Sat Jun 26 16:13:44 UTC 2021 , Edited by admin on Sat Jun 26 16:13:44 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY