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 2662

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 608 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019353s019lbl.pdf	Primary		Approved 8360	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 1709

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP3A5 391 CYP3A7 110

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP3A5 391	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15557344/ Page: 1.0	yes
CYP3A7 110	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15557344/ Page: 8.0	yes
CYP3A4 1709	substrate 3326 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
Response surface modeling of drug interactions on cardiorespiratory control.	2001	11729897
Comparison of the effects of intravenous alfentanil and esmolol on the cardiovascular response to double-lumen endobronchial intubation.	2001 Apr	11284817
Influence of pneumoperitoneum and patient positioning on respiratory system compliance.	2001 Aug	11498317
Absence of memory for intra-operative information during surgery with total intravenous anaesthesia.	2001 Feb	11573659
[Epileptogenic drugs in anesthesia].	2001 Feb	11270238
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients.	2001 Jan	11575417
Target-controlled alfentanil analgesia for dressing change following extensive reconstructive surgery for trauma.	2001 Jan	11302113
Remifentanil and controlled hypotension; comparison with nitroprusside or esmolol during tympanoplasty.	2001 Jan	11212044
Myopexy (Faden) results in more postoperative vomiting after strabismus surgery in children.	2001 Jan	11152035
Preoperative diclofenac is a useful adjunct to spinal anesthesia for day-case varicose vein repair.	2001 Jul-Aug	11495873
Propofol alters the pharmacokinetics of alfentanil in healthy male volunteers.	2001 Jun	11465619
[Factors influencing early extubation after open heart surgery].	2001 Jun 10	11433920
[The effect of encephalogram bispectral index monitoring during total intravenous anesthesia with propofol in outpatient surgery].	2001 Jun-Jul	11446941
Selective spinal anesthesia for outpatient laparoscopy. II: epinephrine and spinal cord function.	2001 Mar	11305827
Induction with propofol target-concentration infusion vs. 8% sevoflurane inhalation and alfentanil in hypertensive patients.	2001 Mar	11251433
General anaesthesia in a man with mitochondrial myopathy undergoing eye surgery.	2001 May	11350477
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
The role of drug-lipid interactions on the disposition of liposome-formulated opioid analgesics in vitro and in vivo.	2001 Oct	11574359
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
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
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
[Sedation analgesia in interventional radiology].	2002 Feb	11898084
Effects of propofol and nitrous oxide on middle cerebral artery flow velocity and cerebral autoregulation.	2002 Jan	11843738
Concentration-effect relationships for intravenous alfentanil and ketamine infusions in human volunteers: effects on acute thresholds and capsaicin-evoked hyperpathia.	2002 Jan	11808827
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
Postoperative nausea and vomiting after total intravenous anesthesia with propofol and remifentanil or alfentanil: how important is the opioid?	2002 Jun	12088811
Effects of low-dose alfentanil administration on central respiratory drive and respiratory pattern in spontaneously breathing ASA 1 patients.	2002 Jun	12010267
Implicit memory for words played during isoflurane- or propofol-based anesthesia: the lexical decision task.	2002 Mar	11873032
Respiratory response to skin incision during anaesthesia with infusions of propofol and alfentanil.	2002 May	12067001
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 `Thu Jul 06 21:53:41 UTC 2023` Edited by `admin` on `Thu Jul 06 21:53:41 UTC 2023`
Record UNII	1N74HM2BS7
Record Status	`Validated (UNII)`
Record Version

Download

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