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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

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
Response surface modeling of drug interactions on cardiorespiratory control.
2001
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
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
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
Safer colonoscopy with patient-controlled analgesia and sedation with propofol and alfentanil.
2001 Jul
Preoperative diclofenac is a useful adjunct to spinal anesthesia for day-case varicose vein repair.
2001 Jul-Aug
[Factors influencing early extubation after open heart surgery].
2001 Jun 10
The effects of chronic morphine on behavior reinforced by several opioids or by cocaine in rhesus monkeys.
2001 May 1
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
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
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
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
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
Comparison of rocuronium and suxamethonium for rapid tracheal intubation in children.
2002 Feb
Concurrent ketamine and alfentanil administration: pharmacokinetic considerations.
2002 Jan
Postoperative nausea and vomiting after total intravenous anesthesia with propofol and remifentanil or alfentanil: how important is the opioid?
2002 Jun
Prolonged neuromuscular block after rocuronium in postpartum patients.
2002 Mar
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 16 16:58:49 UTC 2022
Edited
by admin
on Fri Dec 16 16:58:49 UTC 2022
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 16 16:58:49 UTC 2022 , Edited by admin on Fri Dec 16 16:58:49 UTC 2022
NCI_THESAURUS C67413
Created by admin on Fri Dec 16 16:58:49 UTC 2022 , Edited by admin on Fri Dec 16 16:58:49 UTC 2022
Code System Code Type Description
CAS
70879-28-6
Created by admin on Fri Dec 16 16:58:49 UTC 2022 , Edited by admin on Fri Dec 16 16:58:49 UTC 2022
PRIMARY
EPA CompTox
DTXSID50221107
Created by admin on Fri Dec 16 16:58:49 UTC 2022 , Edited by admin on Fri Dec 16 16:58:49 UTC 2022
PRIMARY
PUBCHEM
64762
Created by admin on Fri Dec 16 16:58:49 UTC 2022 , Edited by admin on Fri Dec 16 16:58:49 UTC 2022
PRIMARY
ChEMBL
CHEMBL634
Created by admin on Fri Dec 16 16:58:49 UTC 2022 , Edited by admin on Fri Dec 16 16:58:49 UTC 2022
PRIMARY
NCI_THESAURUS
C220
Created by admin on Fri Dec 16 16:58:49 UTC 2022 , Edited by admin on Fri Dec 16 16:58:49 UTC 2022
PRIMARY
RXCUI
203203
Created by admin on Fri Dec 16 16:58:49 UTC 2022 , Edited by admin on Fri Dec 16 16:58:49 UTC 2022
PRIMARY RxNorm
RS_ITEM_NUM
1012906
Created by admin on Fri Dec 16 16:58:49 UTC 2022 , Edited by admin on Fri Dec 16 16:58:49 UTC 2022
PRIMARY
DRUG BANK
DBSALT001202
Created by admin on Fri Dec 16 16:58:49 UTC 2022 , Edited by admin on Fri Dec 16 16:58:49 UTC 2022
PRIMARY
FDA UNII
11S92G0TIW
Created by admin on Fri Dec 16 16:58:49 UTC 2022 , Edited by admin on Fri Dec 16 16:58:49 UTC 2022
PRIMARY
EVMPD
SUB00339MIG
Created by admin on Fri Dec 16 16:58:49 UTC 2022 , Edited by admin on Fri Dec 16 16:58:49 UTC 2022
PRIMARY
DAILYMED
11S92G0TIW
Created by admin on Fri Dec 16 16:58:49 UTC 2022 , Edited by admin on Fri Dec 16 16:58:49 UTC 2022
PRIMARY
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