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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
Structure of ALFENTANIL HYDROCHLORIDE

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

HIDE SMILES / InChI

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.

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
Response surface modeling of drug interactions on cardiorespiratory control.
2001
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
Esmolol promotes electroencephalographic burst suppression during propofol/alfentanil anesthesia.
2001 Dec
Absence of memory for intra-operative information during surgery with total intravenous anaesthesia.
2001 Feb
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 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
[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
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
[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
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
Alfentanil-induced epileptiform activity.
2002 Feb
[Sedation analgesia in interventional radiology].
2002 Feb
Comparison of rocuronium and suxamethonium for rapid tracheal intubation in children.
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
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
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 low-dose alfentanil administration on central respiratory drive and respiratory pattern in spontaneously breathing ASA 1 patients.
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
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
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
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 Fri Jun 25 20:59:54 UTC 2021
Edited
by admin
on Fri Jun 25 20:59:54 UTC 2021
Record UNII
11S92G0TIW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALFENTANIL HYDROCHLORIDE
EP   MART.   ORANGE BOOK   USAN   USP   VANDF  
USAN  
Official Name English
ALFENTANIL HYDROCHLORIDE [ORANGE BOOK]
Common Name English
R 39209
Code English
ALFENTANIL HYDROCHLORIDE [MART.]
Common Name English
ALFENTANIL HYDROCHLORIDE [VANDF]
Common Name English
R-39209
Code English
PROPANAMIDE, N-(1-(2-(4-ETHYL-4,5-DIHYDRO-5-OXO-1H-TETRAZOL-1-YL)ETHYL)-4-(METHOXYMETHYL)-4-PIPERIDINYL)-N-PHENYL-, HYDROCHLORIDE, HYDRATE (1:1:1)
Systematic Name English
ALFENTANIL HYDROCHLORIDE MONOHYDRATE
MI  
Common Name English
ALFENTANIL HYDROCHLORIDE MONOHYDRATE [MI]
Common Name English
ALFENTANIL HYDROCHLORIDE [USP]
Common Name English
ALFENTANIL HYDROCHLORIDE [USAN]
Common Name English
ALFENTANIL HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
R-39,209
Code English
N-(1-(2-(4-ETHYL-5-OXO-2-TETRAZOLIN-1-YL)-ETHYL)-4-(METHOXYMETHYL)-4-PIPERIDYL)PROPIONANILIDE MONOHYDROCHLORIDE MONOHYDRATE
Systematic 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, MONOHYDRATE
Common Name English
ALFENTANIL HYDROCHLORIDE [EP]
Common Name English
R 39,209
Code English
ALFENTA
Brand Name English
ALFENTANIL HYDROCHLORIDE [USP-RS]
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
CAS
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
EPA CompTox
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
PUBCHEM
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
ChEMBL
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
NCI_THESAURUS
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
RXCUI
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
USP_CATALOG
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
DRUG BANK
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
FDA UNII
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
EVMPD
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
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