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Details

Stereochemistry ACHIRAL
Molecular Formula C21H32N6O3.ClH
Molecular Weight 452.978
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALFENTANIL HYDROCHLORIDE ANHYDROUS

SMILES

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

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 416.5172
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
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
Clinical interpretation of pharmacokinetic and pharmacodynamic propofol-opioid interactions.
2001
Choice of the hypnotic and the opioid for rapid-sequence induction.
2001
Analgesic efficacy of tramadol 2 mg kg(-1) for paediatric day-case adenoidectomy.
2001 Apr
Comparison of the effects of intravenous alfentanil and esmolol on the cardiovascular response to double-lumen endobronchial intubation.
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
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
Relative sensitivity to alfentanil and reliability of current perception threshold vs von Frey tactile stimulation and thermal sensory testing.
2001 Dec
Alfentanil-induced epileptiform activity: a simultaneous surface and depth electroencephalographic study in complex partial epilepsy.
2001 Feb
Timing of pre-emptive tenoxicam is important for postoperative analgesia.
2001 Feb
Assessment of depth of anesthesia and postoperative respiratory recovery after remifentanil- versus alfentanil-based total intravenous anesthesia in patients undergoing ear-nose-throat surgery.
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
Remifentanil and controlled hypotension; comparison with nitroprusside or esmolol during tympanoplasty.
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
Comparison of the intubating laryngeal mask airway with the fiberoptic intubation in anticipated difficult airway management.
2001 Jun
[Factors influencing early extubation after open heart surgery].
2001 Jun 10
[The effect of encephalogram bispectral index monitoring during total intravenous anesthesia with propofol in outpatient surgery].
2001 Jun-Jul
Induction with propofol target-concentration infusion vs. 8% sevoflurane inhalation and alfentanil in hypertensive patients.
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
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
[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
Postoperative analgesia in children: comparison of bupivacaine with a mixture of bupivacaine and alfentanil.
2001 Oct
Experience with an anesthesiologist interventional model for endoscopy in a pediatric hospital.
2001 Sep
A randomized study of the efficacy and recovery of remifentanil-based and alfentanil anaesthesia with desflurane or sevoflurane for gynecological surgery.
2002
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
A new paradigm for the closed-loop intraoperative administration of analgesics in humans.
2002 Apr
Alfentanil-induced epileptiform activity.
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
Concurrent ketamine and alfentanil administration: pharmacokinetic considerations.
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
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
Postoperative nausea and vomiting after total intravenous anesthesia with propofol and remifentanil or alfentanil: how important is the opioid?
2002 Jun
Total intravenous anesthesia for intraoperative monitoring of the motor pathways: an integral view combining clinical and experimental data.
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
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 Dec 15 15:48:51 UTC 2023
Edited
by admin
on Fri Dec 15 15:48:51 UTC 2023
Record UNII
333JTI7A2M
Record Status Validated (UNII)
Record Version
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Name Type Language
ALFENTANIL HYDROCHLORIDE ANHYDROUS
Common Name English
N-(1-(2-(4-ETHYL-5-OXO-2-TETRAZOLIN-1-YL)-ETHYL)-4-(METHOXYMETHYL)-4-PIPERIDYL)PROPIONANILIDE MONOHYDROCHLORIDE
Systematic Name English
Alfentanil hydrochloride [WHO-DD]
Common 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
DTXSID0048927
Created by admin on Fri Dec 15 15:48:51 UTC 2023 , Edited by admin on Fri Dec 15 15:48:51 UTC 2023
PRIMARY
PUBCHEM
64761
Created by admin on Fri Dec 15 15:48:51 UTC 2023 , Edited by admin on Fri Dec 15 15:48:51 UTC 2023
PRIMARY
EVMPD
SUB70532
Created by admin on Fri Dec 15 15:48:51 UTC 2023 , Edited by admin on Fri Dec 15 15:48:51 UTC 2023
PRIMARY
ECHA (EC/EINECS)
273-846-3
Created by admin on Fri Dec 15 15:48:51 UTC 2023 , Edited by admin on Fri Dec 15 15:48:51 UTC 2023
PRIMARY
MERCK INDEX
m1499
Created by admin on Fri Dec 15 15:48:51 UTC 2023 , Edited by admin on Fri Dec 15 15:48:51 UTC 2023
PRIMARY Merck Index
CAS
69049-06-5
Created by admin on Fri Dec 15 15:48:51 UTC 2023 , Edited by admin on Fri Dec 15 15:48:51 UTC 2023
PRIMARY
FDA UNII
333JTI7A2M
Created by admin on Fri Dec 15 15:48:51 UTC 2023 , Edited by admin on Fri Dec 15 15:48:51 UTC 2023
PRIMARY
SMS_ID
100000135405
Created by admin on Fri Dec 15 15:48:51 UTC 2023 , Edited by admin on Fri Dec 15 15:48:51 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY