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Details

Stereochemistry ACHIRAL
Molecular Formula C21H32N6O3
Molecular Weight 416.5172
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALFENTANIL

SMILES

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

InChI

InChIKey=IDBPHNDTYPBSNI-UHFFFAOYSA-N
InChI=1S/C21H32N6O3/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

HIDE SMILES / InChI

Molecular Formula C21H32N6O3
Molecular Weight 416.5172
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ALFENTA
PubMed

PubMed

TitleDatePubMed
Alfentanil decreases myoclonus caused by etomidate.
1999 Jun
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
Analgesic efficacy of tramadol 2 mg kg(-1) for paediatric day-case adenoidectomy.
2001 Apr
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
A new model of electrically evoked pain and hyperalgesia in human skin: the effects of intravenous alfentanil, S(+)-ketamine, and lidocaine.
2001 Aug
A mixture of alfentanil and morphine for rapid postoperative loading with opioid: theoretical basis and initial clinical investigation.
2001 Aug
Relative sensitivity to alfentanil and reliability of current perception threshold vs von Frey tactile stimulation and thermal sensory testing.
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
[Epileptogenic drugs in anesthesia].
2001 Feb
Timing of pre-emptive tenoxicam is important for postoperative analgesia.
2001 Feb
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients.
2001 Jan
Effect of dexmedetomidine, an alpha2-adrenoceptor agonist, on human pupillary reflexes during general anaesthesia.
2001 Jan
Comparison of five experimental pain tests to measure analgesic effects of alfentanil.
2001 Jul
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
Patient-controlled analgesia during SWL treatments.
2001 Jun
Influence of pneumoperitoneum and patient positioning on preload and splanchnic blood volume in laparoscopic surgery of the lower abdomen.
2001 Jun
Selective spinal anesthesia for outpatient laparoscopy. II: epinephrine and spinal cord function.
2001 Mar
Auditory information processing during adequate propofol anesthesia monitored by electroencephalogram bispectral index.
2001 May
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 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
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
Intraoperative small-dose ketamine enhances analgesia after outpatient knee arthroscopy.
2001 Sep
[Sedation analgesia in interventional radiology].
2002 Feb
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
Relaxation music decreases the dose of patient-controlled sedation during colonoscopy: a prospective randomized controlled trial.
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
Psychomotor performance after short-term anaesthesia.
2002 Jun
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
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
Target-controlled versus manually-controlled infusion of propofol for direct laryngoscopy and bronchoscopy.
2002 May
Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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 Tue Oct 22 00:24:02 UTC 2019
Edited
by admin
on Tue Oct 22 00:24:02 UTC 2019
Record UNII
1N74HM2BS7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALFENTANIL
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
PROPANAMIDE, N-(1-(2-(4-ETHYL-4,5-DIHYDRO-5-OXO-1H-TETRAZOL-1-YL)ETHYL)-4-(METHOXYMETHYL)-4-PIPERIDINYL)-N-PHENYL-
Systematic Name English
ALFENTANIL [MI]
Common Name English
R-39209-
Code English
ALFENTA
Brand Name English
N-(1-(2-(4-ETHYL-4,5-DIHYDRO-5-OXO-1H-TETRAZOL-1-YL)ETHYL)-4-(METHOXYMETHYL) -4-PIPERIDINYL)-N-PHENYLPROPANAMIDE
Systematic Name English
ALFENTANIL [INN]
Common Name English
RAPIFEN
Common Name English
ALFENTANIL [WHO-DD]
Common Name English
ALFENTANYL
Common Name English
IDS-NA-014
Code English
ALFENTANIL [VANDF]
Common Name English
ALFENTANIL [HSDB]
Common Name English
AFENTANYL
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 206405
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
NDF-RT N0000175690
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
NCI_THESAURUS C1506
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
FDA ORPHAN DRUG 206505
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
WHO-VATC QN01AH02
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
WHO-ATC N01AH02
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
DEA NO. 9737
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
NCI_THESAURUS C67413
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
NDF-RT N0000175684
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
Code System Code Type Description
PUBCHEM
51263
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
PRIMARY
RXCUI
480
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
PRIMARY RxNorm
LactMed
71195-58-9
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
PRIMARY
DRUG BANK
DB00802
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
PRIMARY
WEB RESOURCE
ALFENTANIL
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
PRIMARY
ChEMBL
CHEMBL634
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
PRIMARY
IUPHAR
7108
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
PRIMARY
NCI_THESAURUS
C61626
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
PRIMARY
WIKIPEDIA
ALFENTANIL
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
PRIMARY While alfentanil tends to cause fewer cardiovascular complications than other similar drugs such as fentanyl and remifentanil, it tends to give stronger respiratory depression and so requires careful monitoring of breathing and vital signs. Almost exclusively used by anesthesia providers during portions of a case where quick, fast acting (though not long lasting) pain control is needed (i.e. during a nerve block, head pinning etc..) Alfentanil is administered by the parenteral (injected) route for fast onset of effects and precise control of dosage. Alfentanil is a restricted drug which is classified as Schedule II in the USA, according to the U.S. DEA website. Alfentanil was discovered at Janssen Pharmaceutica in 1976.
EVMPD
SUB05317MIG
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
PRIMARY
MERCK INDEX
M1499
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
PRIMARY Merck Index
CAS
71195-58-9
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
PRIMARY
EPA CompTox
71195-58-9
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
PRIMARY
MESH
D015760
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
PRIMARY
HSDB
71195-58-9
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
PRIMARY
INN
4818
Created by admin on Tue Oct 22 00:24:02 UTC 2019 , Edited by admin on Tue Oct 22 00:24:02 UTC 2019
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
Alfentanil is relatively distinctive among CYP3A substrates, in that the metabolic capacity (in vitro intrinsic clearance) of CYP3A5 equaled or exceeded that of CYP3A4.
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
Related Record Type Details
METABOLITE INACTIVE -> PARENT
Alfentanil is relatively distinctive among CYP3A substrates, in that the metabolic capacity (in vitro intrinsic clearance) of CYP3A5 equaled or exceeded that of CYP3A4.
METABOLITE INACTIVE -> PARENT
MAJOR
URINE
METABOLITE INACTIVE -> PARENT
MAJOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC