REMIFENTANIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H28N2O5
Molecular Weight	376.4467
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(=O)N(C1=CC=CC=C1)C2(CCN(CCC(=O)OC)CC2)C(=O)OC

InChI

InChIKey=ZTVQQQVZCWLTDF-UHFFFAOYSA-N

InChI=1S/C20H28N2O5/c1-4-17(23)22(16-8-6-5-7-9-16)20(19(25)27-3)11-14-21(15-12-20)13-10-18(24)26-2/h5-9H,4,10-15H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C20H28N2O5
Molecular Weight	376.4467
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/2004/20630se5-005_ultiva_lbl.pdf | https://www.drugbank.ca/drugs/DB00899 | https://www.ncbi.nlm.nih.gov/pubmed/16526829

Remifentanil (marketed by Abbott as Ultiva) is a potent ultra short-acting synthetic opioid analgesic drug. It is given to patients during surgery to relieve pain and as an adjunct to an anaesthetic. ULTIVA is a µ-opioid agonist with rapid onset and peak effect, and short duration of action. The µ-opioid activity of ULTIVA is antagonized by opioid antagonists such as naloxone. ULTIVA is indicated for IV administration: 1. As an analgesic agent for use during the induction and maintenance of general anesthesia for inpatient and outpatient procedures. 2. For continuation as an analgesic into the immediate postoperative period in adult patients under the direct supervision of an anesthesia practitioner in a postoperative anesthesia care unit or intensive care setting. 3. As an analgesic component of monitored anesthesia care in adult patients.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/20630se5-005_ultiva_lbl.pdf	Agonist 2662

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 608 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/20630se5-005_ultiva_lbl.pdf	Primary		Approved 8360	ULTIVA Approved Use ULTIVA is indicated for IV administration: 1.As an analgesic agent for use during the induction and maintenance of general anesthesia for inpatient and outpatient procedures. 2.For continuation as an analgesic into the immediate postoperative period in adult patients under the direct supervision of an anesthesia practitioner in a postoperative anesthesia care unit or intensive care setting. 3.As an analgesic component of monitored anesthesia care in adult patients. Launch Date 8.371296E11

C_max

Value	Dose	Co-administered	Analyte	Population
194 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14766712	6 μg/kg/h 1 times / day other, intravenous dose: 6 μg/kg/h route of administration: Intravenous experiment type: OTHER co-administered:		REMIFENTANIL ACID blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
14 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14766712	6 μg/kg/h 1 times / day other, intravenous dose: 6 μg/kg/h route of administration: Intravenous experiment type: OTHER co-administered:		REMIFENTANIL blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
8080 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14766712	6 μg/kg/h 1 times / day other, intravenous dose: 6 μg/kg/h route of administration: Intravenous experiment type: OTHER co-administered:		REMIFENTANIL ACID blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
745 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14766712	6 μg/kg/h 1 times / day other, intravenous dose: 6 μg/kg/h route of administration: Intravenous experiment type: OTHER co-administered:		REMIFENTANIL blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.48 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14766712	6 μg/kg/h 1 times / day other, intravenous dose: 6 μg/kg/h route of administration: Intravenous experiment type: OTHER co-administered:		REMIFENTANIL ACID blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
11.4 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14766712	6 μg/kg/h 1 times / day other, intravenous dose: 6 μg/kg/h route of administration: Intravenous experiment type: OTHER co-administered:		REMIFENTANIL blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
30% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020630s020lbl.pdf	0.5 μg/kg/min 1 times / day other, intravenous dose: 0.5 μg/kg/min route of administration: Intravenous experiment type: OTHER co-administered:		REMIFENTANIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8802	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8802
ZINC	ZINC000000538283	http://zinc15.docking.org/substances/ZINC000000538283

PubMed

Title	Date	PubMed
[Total intravenous anesthesia (TIVA) and balanced anesthesia with short-acting anesthetics for ENT surgery in children].	1999	10220941
Remifentanil, propofol or both for conscious sedation during eye surgery under regional anaesthesia.	1999 Nov	10713867
Bradycardia after administration of remifentanil.	2000 Mar	10793617
Anesthesia for magnetic resonance guided neurosurgery: initial experience with a new open magnetic resonance imaging system.	2001 Apr	11294459
Remifentanil.	2001 Aug	11571418
Target-controlled infusion or manually controlled infusion of propofol in high-risk patients with severely reduced left ventricular function.	2001 Aug	11505347
Small doses of remifentanil or sufentanil for blunting cardiovascular changes induced by tracheal intubation: a double-blind comparison.	2001 Feb	11270019
Influence of hemorrhagic shock on remifentanil: a pharmacokinetic and pharmacodynamic analysis.	2001 Feb	11176098
Sevoflurane--nitrous oxide anaesthesia supplemented with remifentanil: effect on recovery and cognitive function.	2001 Feb	11167470
The effect of remifentanil on the heat pain threshold in volunteers.	2001 Feb	11159234
Use of remifentanil in a patient with peripartum cardiomyopathy requiring Caesarean section.	2001 Jan	11575392
Remifentanil versus meperidine for monitored anesthesia care: a comparison study in older patients undergoing ambulatory colonoscopy.	2001 Jan	11133605
Opioid chronopharmacology.	2001 Jul	11531909
Esmolol is not an alternative to remifentanil for fast-track outpatient gynecologic laparoscopic surgery.	2001 Jul	11429376
Monitored anesthesia care using remifentanil and propofol for awake craniotomy.	2001 Jul	11426102
Sevoflurane with remifentanil allows rapid tracheal intubation without neuromuscular blocking agents.	2001 Jul-Aug	11495870
Recovery after remifentanil and sufentanil for analgesia and sedation of mechanically ventilated patients after trauma or major surgery.	2001 Jun	11573581
Safety and efficacy of remifentanil infusion in craniosynostosis repair in infants.	2001 Jun	11455235
Remifentanil- and fentanyl-based anesthesia for intraoperative monitoring of somatosensory evoked potentials.	2001 Jun	11375835
Recovery from propofol anaesthesia supplemented with remifentanil.	2001 Mar	11573525
[Alterations in left ventricular-arterial coupling and mechanical efficiency produced by remifentanil during cardiac anesthesia].	2001 Mar	11337645
Intravenous anaesthesia with remifentanil in a preterm infant.	2001 Mar	11240891
[Esterase-metabolized remifentanil hydrochloride opioid (Ultiva-TM), a new step towards the solution of the problem of regulation of analgetic components of general anesthesia].	2001 Mar-Apr	11494899
[Anesthesia in extreme obesity].	2001 May	11413802
Dose-dependent regional cerebral blood flow changes during remifentanil infusion in humans: a positron emission tomography study.	2001 May	11388521
A patient with hypertrophic obstructive cardiomyopathy presenting for total knee replacement.	2001 May	11385898
Propofol and remifentanil pharmacodynamic interaction during orthopedic surgical procedures as measured by effects on bispectral index.	2001 May	11377158
Effect of age on recovery from remifentanil anaesthesia.	2001 Oct	11669432
Threshold-level repetitive transcranial electrical stimulation for intraoperative monitoring of central motor conduction.	2001 Oct	11599831
Does functional ability in the postoperative period differ between remifentanil- and fentanyl-based anesthesia?	2001 Sep	11578882

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Anesthesia Induction of Anesthesia: Continuous IV infusion: 0.5 to 1 mcg/kg/min. If endotracheal intubation is to occur in less than 8 minutes, an initial dose of 1 mcg/kg may be administered over 30 to 60 seconds. Maintenance of Anesthesia: With Nitrous Oxide, 0.4 mg/kg/min by continuous IV infusion. Infusion dose range: 0.1 to 2 mcg/kg/min. Supplemental IV bolus: 1 mcg/kg every 2 to 5 minutes.

Route of Administration: Intravenous

In Vitro Use Guide

Remifentanil (10(-8) - 10(-4) mol/ L) caused a concentration-dependent vasorelaxation in the human being artery rings.

Substance Class	Chemical Created by `admin` on `Thu Jul 06 22:37:49 UTC 2023` Edited by `admin` on `Thu Jul 06 22:37:49 UTC 2023`
Record UNII	P10582JYYK
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

REMIFENTANIL

Official Name

English

GI 87084X

Code

English

RAMIFENTANYL

Common Name

English

Remifentanil [WHO-DD]

Common Name

English

REMIFENTANIL [MI]

Common Name

English

ULTIVA-

Common Name

English

remifentanil [INN]

Common Name

English

REMIFENTANYL

Common Name

English

REMIFENTANIL [VANDF]

Common Name

English

IDS-NR-005

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C67413