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

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

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
Alfentanil decreases myoclonus caused by etomidate.
1999 Jun
Analgesic efficacy of tramadol 2 mg kg(-1) for paediatric day-case adenoidectomy.
2001 Apr
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
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
Timing of pre-emptive tenoxicam is important for postoperative analgesia.
2001 Feb
Target-controlled alfentanil analgesia for dressing change following extensive reconstructive surgery for trauma.
2001 Jan
Effect of dexmedetomidine, an alpha2-adrenoceptor agonist, on human pupillary reflexes during general anaesthesia.
2001 Jan
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
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
Neural mechanisms in the cardiovascular responses to acute central hypovolaemia.
2001 May-Jun
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
The role of drug-lipid interactions on the disposition of liposome-formulated opioid analgesics in vitro and in vivo.
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
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
Alfentanil-induced epileptiform activity.
2002 Feb
[Sedation analgesia in interventional radiology].
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
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
Mu-receptor agonism with alfentanil increases striatal dopamine D2 receptor binding in man.
2002 Jul
Effects of remifentanil and alfentanil on the cardiovascular responses to induction of anaesthesia and tracheal intubation in the elderly.
2002 Mar
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 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
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY