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Details

Stereochemistry ACHIRAL
Molecular Formula C21H32N6O3.ClH.H2O
Molecular Weight 470.993
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALFENTANIL HYDROCHLORIDE

SMILES

O.Cl.CCN1N=NN(CCN2CCC(COC)(CC2)N(C(=O)CC)C3=CC=CC=C3)C1=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 ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 416.5172
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

1986
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
Choice of the hypnotic and the opioid for rapid-sequence induction.
2001
Response surface modeling of drug interactions on cardiorespiratory control.
2001
Effects of fentanyl, alfentanil, remifentanil and sufentanil on loss of consciousness and bispectral index during propofol induction of anaesthesia.
2001 Apr
Tracheal intubation without muscle relaxant--a technique using sevoflurane vital capacity induction and alfentanil.
2001 Aug
Esmolol promotes electroencephalographic burst suppression during propofol/alfentanil anesthesia.
2001 Dec
[Epileptogenic drugs in anesthesia].
2001 Feb
[Hemodynamic effects of propofol induction administered with target controlled infusion pump in patients scheduled for open heart surgery].
2001 Feb 18
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients.
2001 Jan
Safer colonoscopy with patient-controlled analgesia and sedation with propofol and alfentanil.
2001 Jul
Propofol alters the pharmacokinetics of alfentanil in healthy male volunteers.
2001 Jun
[The effect of encephalogram bispectral index monitoring during total intravenous anesthesia with propofol in outpatient surgery].
2001 Jun-Jul
Selective spinal anesthesia for outpatient laparoscopy. II: epinephrine and spinal cord function.
2001 Mar
Concentration-effect relationship of intravenous alfentanil and ketamine on peripheral neurosensory thresholds, allodynia and hyperalgesia of neuropathic pain.
2001 Mar
General anaesthesia in a man with mitochondrial myopathy undergoing eye surgery.
2001 May
The effect of intravenous dexmedetomidine premedication on the dose requirement of propofol to induce loss of consciousness in patients receiving alfentanil.
2001 May
Can inflammatory pain prevent the development of acute tolerance to 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
Pain experience during transvaginal aspiration of immature oocytes.
2001 Nov
Reexamined: the recommended endotracheal intubating dose for nondepolarizing neuromuscular blockers of rapid onset.
2001 Oct
The role of drug-lipid interactions on the disposition of liposome-formulated opioid analgesics in vitro and in vivo.
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
Alfentanil and sufentanil in fast-track anesthesia for coronary artery bypass graft surgery.
2002 Apr
Analgesia for shock wave lithotripsy.
2002 Apr
Comparison of rocuronium and suxamethonium for rapid tracheal intubation in children.
2002 Feb
Pain model and fuzzy logic patient-controlled analgesia in shock-wave lithotripsy.
2002 Jan
Psychomotor performance after short-term anaesthesia.
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
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 Dec 15 15:23:41 GMT 2023
Edited
by admin
on Fri Dec 15 15:23:41 GMT 2023
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 [USAN]
Common Name English
ALFENTANIL HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
ALFENTANIL HYDROCHLORIDE [EP IMPURITY]
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
R 39,209
Code English
ALFENTANIL HYDROCHLORIDE [USP IMPURITY]
Common Name 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 Dec 15 15:23:41 GMT 2023 , Edited by admin on Fri Dec 15 15:23:41 GMT 2023
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 15:23:41 GMT 2023 , Edited by admin on Fri Dec 15 15:23:41 GMT 2023
Code System Code Type Description
CAS
70879-28-6
Created by admin on Fri Dec 15 15:23:41 GMT 2023 , Edited by admin on Fri Dec 15 15:23:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID50221107
Created by admin on Fri Dec 15 15:23:41 GMT 2023 , Edited by admin on Fri Dec 15 15:23:41 GMT 2023
PRIMARY
PUBCHEM
64762
Created by admin on Fri Dec 15 15:23:41 GMT 2023 , Edited by admin on Fri Dec 15 15:23:41 GMT 2023
PRIMARY
ChEMBL
CHEMBL634
Created by admin on Fri Dec 15 15:23:41 GMT 2023 , Edited by admin on Fri Dec 15 15:23:41 GMT 2023
PRIMARY
NCI_THESAURUS
C220
Created by admin on Fri Dec 15 15:23:41 GMT 2023 , Edited by admin on Fri Dec 15 15:23:41 GMT 2023
PRIMARY
SMS_ID
300000038460
Created by admin on Fri Dec 15 15:23:41 GMT 2023 , Edited by admin on Fri Dec 15 15:23:41 GMT 2023
PRIMARY
RXCUI
203203
Created by admin on Fri Dec 15 15:23:41 GMT 2023 , Edited by admin on Fri Dec 15 15:23:41 GMT 2023
PRIMARY RxNorm
RS_ITEM_NUM
1012906
Created by admin on Fri Dec 15 15:23:41 GMT 2023 , Edited by admin on Fri Dec 15 15:23:41 GMT 2023
PRIMARY
DRUG BANK
DBSALT001202
Created by admin on Fri Dec 15 15:23:41 GMT 2023 , Edited by admin on Fri Dec 15 15:23:41 GMT 2023
PRIMARY
FDA UNII
11S92G0TIW
Created by admin on Fri Dec 15 15:23:41 GMT 2023 , Edited by admin on Fri Dec 15 15:23:41 GMT 2023
PRIMARY
EVMPD
SUB00339MIG
Created by admin on Fri Dec 15 15:23:41 GMT 2023 , Edited by admin on Fri Dec 15 15:23:41 GMT 2023
PRIMARY
DAILYMED
11S92G0TIW
Created by admin on Fri Dec 15 15:23:41 GMT 2023 , Edited by admin on Fri Dec 15 15:23:41 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
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
ALFENTANIL HYDROCHLORIDE IS ALFENTANIL HYDROCHLORIDE HYDRATE AS PER EP MONOGRAPH
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