ALFENTANIL

Details

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

SHOW SMILES / InChI

Structure Search

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	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019353s019lbl.pdf | https://www.drugbank.ca/drugs/DB00802

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

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15694871 \| https://www.drugbank.ca/drugs/DB00802 \| https://www.ncbi.nlm.nih.gov/pubmed/16906017 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019353s021lbl.pdf	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019353s019lbl.pdf	Primary		Approved 8429	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

C_max

Value	Dose	Co-administered	Analyte	Population
20.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7598917	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

Value	Dose	Co-administered	Analyte	Population
1241.2 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7598917	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7598917	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
59.4 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7598917	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7598917	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
8% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019353s021lbl.pdf			ALFENTANIL plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP3A5 395 CYP3A7 110

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP3A5 395	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15557344/ Page: 1.0	yes
CYP3A7 110	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15557344/ Page: 8.0	yes
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15557344/; https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/019353s023lbl.pdf Page: 1.0	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 Sources: https://pubmed.ncbi.nlm.nih.gov/15557344/; https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/019353s023lbl.pdf Page: 1.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2569	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2569
ZINC	ZINC000000601281	http://zinc15.docking.org/substances/ZINC000000601281

PubMed

Title	Date	PubMed
Pharmacokinetic aspects of treating infections in the intensive care unit: focus on drug interactions.	2001	11735605
Response surface modeling of drug interactions on cardiorespiratory control.	2001	11729897
Analgesic efficacy of tramadol 2 mg kg(-1) for paediatric day-case adenoidectomy.	2001 Apr	11573636
Tracheal intubation without muscle relaxant--a technique using sevoflurane vital capacity induction and alfentanil.	2001 Aug	11512649
A new model of electrically evoked pain and hyperalgesia in human skin: the effects of intravenous alfentanil, S(+)-ketamine, and lidocaine.	2001 Aug	11506112
Total intravenous anesthesia versus single breath technique and anesthesia maintenance with sevoflurane for bariatric operations.	2001 Aug	11501363
A pilot evaluation of alfentanil-induced miosis as a noninvasive probe for hepatic cytochrome P450 3A4 (CYP3A4) activity in humans.	2001 Dec	11753266
Absence of memory for intra-operative information during surgery with total intravenous anaesthesia.	2001 Feb	11573659
Gender differences in the pharmacokinetics of propofol in elderly patients during and after continuous infusion.	2001 Feb	11573657
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients.	2001 Jan	11575417
Comparison of five experimental pain tests to measure analgesic effects of alfentanil.	2001 Jul	11465562
Safer colonoscopy with patient-controlled analgesia and sedation with propofol and alfentanil.	2001 Jul	11427833
Comparison of the intubating laryngeal mask airway with the fiberoptic intubation in anticipated difficult airway management.	2001 Jun	11465622
Propofol alters the pharmacokinetics of alfentanil in healthy male volunteers.	2001 Jun	11465619
[The effect of encephalogram bispectral index monitoring during total intravenous anesthesia with propofol in outpatient surgery].	2001 Jun-Jul	11446941
Neural mechanisms in the cardiovascular responses to acute central hypovolaemia.	2001 May-Jun	11428384
Normalization of hypertensive responses during ambulatory surgical stress by perioperative music.	2001 May-Jun	11382277
Comparison between dexmedetomidine and propofol for sedation in the intensive care unit: patient and clinician perceptions.	2001 Nov	11878517
Pain experience during transvaginal aspiration of immature oocytes.	2001 Nov	11703205
The effects of remifentanil on epileptiform discharges during intraoperative electrocorticography in patients undergoing epilepsy surgery.	2001 Oct	11737170
Inhalation versus total intravenous anesthesia for lumbar disc herniation: comparison of hemodynamic effects, recovery characteristics, and cost.	2001 Oct	11733660
[The hereditary motor-sensory neuropathy Charcot-Marie-Tooth disease: anesthesiologic management--case report with literature review].	2001 Oct	11702326
Stability of sufentanil in human plasma samples.	2001 Oct	11591902
Reexamined: the recommended endotracheal intubating dose for nondepolarizing neuromuscular blockers of rapid onset.	2001 Oct	11574363
Postoperative analgesia in children: comparison of bupivacaine with a mixture of bupivacaine and alfentanil.	2001 Oct	11553247
Intraoperative small-dose ketamine enhances analgesia after outpatient knee arthroscopy.	2001 Sep	11524327
The in vitro effects of remifentanil, sufentanil, fentanyl, and alfentanil on isolated human right atria.	2001 Sep	11524316
[Comparative studies of patient positioning for lumbar intervertebral disk operation].	2002	12046472
A randomized study of the efficacy and recovery of remifentanil-based and alfentanil anaesthesia with desflurane or sevoflurane for gynecological surgery.	2002	11975425
Effect of sevoflurane/nitrous oxide versus propofol anaesthesia on somatosensory evoked potential monitoring of the spinal cord during surgery to correct scoliosis.	2002 Apr	12066725
Alfentanil and sufentanil in fast-track anesthesia for coronary artery bypass graft surgery.	2002 Apr	11957163
A new paradigm for the closed-loop intraoperative administration of analgesics in humans.	2002 Apr	11942720
Comparison of effects of remifentanil, alfentanil and fentanyl on cardiovascular responses to tracheal intubation in morbidly obese patients.	2002 Feb	11999595
Bispectral index variations during tracheal suction in mechanically ventilated critically ill patients: effect of an alfentanil bolus.	2002 Feb	11907667
Alfentanil-induced epileptiform activity.	2002 Feb	11903472
General anesthesia versus monitored anesthesia care with remifentanil for assisted reproductive technologies: effect on pregnancy rate.	2002 Feb	11880013
Concurrent ketamine and alfentanil administration: pharmacokinetic considerations.	2002 Jan	11881891
Concentration-effect relationships for intravenous alfentanil and ketamine infusions in human volunteers: effects on acute thresholds and capsaicin-evoked hyperpathia.	2002 Jan	11808827
Relaxation music decreases the dose of patient-controlled sedation during colonoscopy: a prospective randomized controlled trial.	2002 Jan	11756911
Effects of adding alfentanil or atracurium to lidocaine solution for intravenous regional anaesthesia.	2002 Jul	12113616
Mu-receptor agonism with alfentanil increases striatal dopamine D2 receptor binding in man.	2002 Jul	12112410
A new highly reliable instrument for the assessment of pre- and postoperative gynecological pain.	2002 Jul	12088960
Psychomotor performance after short-term anaesthesia.	2002 Jun	12094918
Postoperative nausea and vomiting after total intravenous anesthesia with propofol and remifentanil or alfentanil: how important is the opioid?	2002 Jun	12088811
Effects of remifentanil and alfentanil on the cardiovascular responses to induction of anaesthesia and tracheal intubation in the elderly.	2002 Mar	11990278
Total intravenous anesthesia for intraoperative monitoring of the motor pathways: an integral view combining clinical and experimental data.	2002 Mar	11883843
Respiratory response to skin incision during anaesthesia with infusions of propofol and alfentanil.	2002 May	12067001
Comparison of hemodynamics, recovery profile, and early postoperative pain control and costs of remifentanil versus alfentanil-based total intravenous anesthesia (TIVA).	2002 May	12031745
Co-administration of alfentanil-propofol improves laryngeal mask airway insertion compared to fentanyl-propofol.	2002 May	11983670
Mild core hypothermia and anesthetic requirement for loss of responsiveness during propofol anesthesia for craniotomy.	2002 May	11973207

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 `Sat Dec 16 16:24:08 GMT 2023` Edited by `admin` on `Sat Dec 16 16:24:08 GMT 2023`
Record UNII	1N74HM2BS7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALFENTANIL

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

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

ALFENTANYL

Common Name

English

IDS-NA-014

Code

English

ALFENTANIL [VANDF]

Common Name

English

ALFENTANIL [HSDB]

Common Name

English

AFENTANYL

Common Name

English

Alfentanil [WHO-DD]

Common Name

English

Classification Tree Code System Code

WIKIPEDIA

List_of_fentanyl_analogues