ALFENTANIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H32N6O3
Molecular Weight	416.518
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(=O)N(c1ccccc1)C2(CCN(CC2)CCn3c(=O)n(CC)nn3)COC

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	416.518
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 202 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 2451

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 579 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019353s019lbl.pdf	Primary		Approved 7968	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

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 1469

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP3A5 346 CYP3A7 104

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP3A5 346	substrate 2751 Sources: https://pubmed.ncbi.nlm.nih.gov/15557344/ Page: 1.0	yes
CYP3A7 104	substrate 2751 Sources: https://pubmed.ncbi.nlm.nih.gov/15557344/ Page: 8.0	yes
CYP3A4 1469	substrate 2751 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
Clinical interpretation of pharmacokinetic and pharmacodynamic propofol-opioid interactions.	2001	11799580
Choice of the hypnotic and the opioid for rapid-sequence induction.	2001	11766250
Pharmacokinetic aspects of treating infections in the intensive care unit: focus on drug interactions.	2001	11735605
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
Relative sensitivity to alfentanil and reliability of current perception threshold vs von Frey tactile stimulation and thermal sensory testing.	2001 Dec	11800047
Comparison of alfentanil and morphine in the prehospital treatment of patients with acute ischaemic-type chest pain.	2001 Dec	11785593
A pilot evaluation of alfentanil-induced miosis as a noninvasive probe for hepatic cytochrome P450 3A4 (CYP3A4) activity in humans.	2001 Dec	11753266
Response surface modeling of alfentanil-sevoflurane interaction on cardiorespiratory control and bispectral index.	2001 Jun	11465624
Comparison of the intubating laryngeal mask airway with the fiberoptic intubation in anticipated difficult airway management.	2001 Jun	11465622
[Factors influencing early extubation after open heart surgery].	2001 Jun 10	11433920
The effect of intravenous dexmedetomidine premedication on the dose requirement of propofol to induce loss of consciousness in patients receiving alfentanil.	2001 May	11350323
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	11309015
Neural mechanisms in the cardiovascular responses to acute central hypovolaemia.	2001 May-Jun	11428384
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
Stability of sufentanil in human plasma samples.	2001 Oct	11591902
The role of drug-lipid interactions on the disposition of liposome-formulated opioid analgesics in vitro and in vivo.	2001 Oct	11574359
Experience with an anesthesiologist interventional model for endoscopy in a pediatric hospital.	2001 Sep	11593128
Intraoperative small-dose ketamine enhances analgesia after outpatient knee arthroscopy.	2001 Sep	11524327
[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
Interaction of morphine, fentanyl, sufentanil, alfentanil, and loperamide with the efflux drug transporter P-glycoprotein.	2002 Apr	11964599
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
Analgesia for shock wave lithotripsy.	2002 Apr	11912374
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
[Sedation analgesia in interventional radiology].	2002 Feb	11898084
Pharmacological treatment of postoperative shivering: a quantitative systematic review of randomized controlled trials.	2002 Feb	11812718
Pain model and fuzzy logic patient-controlled analgesia in shock-wave lithotripsy.	2002 Jan	11954700
Concentration-effect relationships for intravenous alfentanil and ketamine infusions in human volunteers: effects on acute thresholds and capsaicin-evoked hyperpathia.	2002 Jan	11808827
Bispectral Index (BIS) may not predict awareness reaction to intubation in surgical patients.	2002 Jan	11773816
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
Improved long-lasting postoperative analgesia, recovery function and patient satisfaction after inguinal hernia repair with inguinal field block compared with general anesthesia.	2002 Jul	12059890
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
Target-controlled versus manually-controlled infusion of propofol for direct laryngoscopy and bronchoscopy.	2002 May	11973192
Relative reinforcing effects of three opioids with different durations of action.	2002 May	11961075

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 Jun 26 11:18:49 UTC 2021` Edited by `admin` on `Sat Jun 26 11:18:49 UTC 2021`
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

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

WIKIPEDIA

List_of_fentanyl_analogues