132875-61-7

Usage

Uses

Used in Anesthesia:
Remifentanil is used as an analgesic for induction and maintenance of surgical anesthesia. Its rapid onset and short duration of action make it a favorable choice for various surgical procedures.
Used in Pain Management:
Remifentanil is used as an analgesic for managing acute and severe pain in patients, particularly in intensive care settings. Its quick recovery and minimal impact on renal or liver function make it a suitable option for patients with compromised organ function.
Used in Research:
Remifentanil is used as a research tool for studying the effects of opioids on the central nervous system and pain perception. Its unique pharmacokinetic properties allow for precise control of drug exposure and the study of opioid receptor interactions.

World Health Organization (WHO)

Remifentanil is defined as an opioid narcotic with an addictionforming and addiction-sustaining liability similar to morphine.

Pharmacology

Remifentanil is a MOP agonist with a similar potency to fentanyl and approximately 20 times more than alfentanil. It has a rapid blood–brain equilibration time of just over 1min, with a short context-sensitive half-life of 3–5min, which is unaffected by duration of infusion. This makes it ideally suited for infusion during anaesthesia and in critical care. It may be titrated rapidly to achieve the desired effect. Remifentanil is available as a lyophilised white crystalline powder containing glycine; it should not be administered via the epidural or intrathecal routes. There may be increased opioid sensitivity in hepatic disease, resulting in a lower dosage requirement. Other situations requiring a reduction in dose include haemorrhage and shock and when administering in elderly patients. The high clearance and low VD imply that the offset of effect is caused by metabolism rather than redistribution. Hypothermia, such as may occur in cardiac surgery, may reduce clearance by up to 20%. There is some evidence to suggest that acute opioid tolerance and hyperalgesia may occur, particularly after remifentanil infusions. If high doses are used without neuromuscular blockade, muscle rigidity may be a problem, though this is less likely if using a concentration of 100 μgml-1 or less and an infusion rate of 0.2–0.5μgkg-1 min-1. Bradycardia has also been reported.

Clinical Use

Analgesic Induction of anaesthesia

Drug interactions

Potentially hazardous interactions with other drugs Anti-arrhythmics: delayed absorption of mexiletine. Antidepressants: possible CNS excitation or depression (hypertension or hypotension) in patients also receiving MAOIs (including moclobemide) - avoid; possibly increased sedative effects with tricyclics. Antihistamines: sedative effects possibly increased with sedating antihistamines. Antipsychotics: enhanced sedative and hypotensive effect. Antivirals: concentration possibly increased by ritonavir (risk of toxicity) - avoid. Dopaminergics: avoid with selegiline. Nalmefene: avoid concomitant use. Sodium oxybate: enhanced effect of sodium oxybate - avoid.

Metabolism

Remifentanil is an esterase metabolised opioid that is susceptible to metabolism by non-specific blood and tissue esterases. The metabolism of remifentanil results in the formation of an essentially inactive carboxylic acid metabolite (1/4600th as potent as remifentanil). About 95% of a dose of remifentanil is excreted in the urine as the metabolite.

Upstream product

• 72996-78-2 methyl 4-[N-(1-oxopropyl)-N-phenylamino]-4-piperidinecarboxylate 
• 292638-85-8 acrylic acid methyl ester 
• 938184-95-3 methyl 3-(4-N-aminophenyl-4-carbomethoxy-piperidino)propionate 
• 79-03-8 propionyl chloride 
• 67-56-1 methanol 
• 1233201-81-4 C₂₅H₃₅N₃O₄ 
• 61085-87-8 methyl 4-[N-(1-oxopropyl)-N-phenylamino]-4-piperidinecarboxylate hydrochloride 
• 1031691-16-3 methyl-3-(4-N-aminophenyl-4-carboxcylic acid-piperidino)proppionate 
• 498-94-2 isonipecotic acid 
• 404-24-0 2,2,2-trifluoro-N-phenylacetamide 
• 62-53-3 aniline 
• 132539-07-2 remifnetanil hydrochloride 

Downstream Products

• 132539-07-2 remifnetanil hydrochloride 

Related news

Clinical InformationSedation using dexmedetomidine and REMIFENTANIL (cas 132875-61-7) with local anesthesia for intraoperative speech monitoring: a case reportSedação com dexmedetomidina e REMIFENTANIL (cas 132875-61-7) em anestesia local para monitoração intraoperatória da fala: um relato de caso09/04/2019

Background and objectiveSome surgical procedures such as laryngoplasty require patients to remain conscious during the intraoperative phase in order to enable speech monitoring. Dexmedetomidine and remifentanil were used in this study, since they promote appropriate patient collaboration with fa...detailed

REMIFENTANIL (cas 132875-61-7) attenuates lipopolysaccharide-induced oxidative injury by downregulating PKCβ2 activation and inhibiting autophagy in H9C2 cardiomyocytes09/02/2019

AimLipopolysaccharide (LPS)-induced myocardial injury is a leading cause of death in patients with sepsis, which is associated with excessive activation of PKCβ (especially PKCβ2) and autophagy. Remifentanil, a μ-opioid receptor agonist, is well demonstrated to have beneficial effects during ...detailed

Research paperOptimized PID control of propofol and REMIFENTANIL (cas 132875-61-7) coadministration for general anesthesia08/30/2019

A closed-loop control system for the control of the depth of hypnosis in anesthesia by using propofol-remifentanil coadministration and the Bispectral Index as feedback signal is proposed. A PID controller is employed together with a fixed ratio between propofol and remifentanil infusions. The r...detailed

Original ArticleSerious adverse events attributed to REMIFENTANIL (cas 132875-61-7) patient-controlled analgesia during labour in The Netherlands08/27/2019

BackgroundDuring labour, remifentanil patient-controlled analgesia is used as an alternative to neuraxial analgesia. Remifentanil is associated with hypoventilation and respiratory depression but the frequency of serious maternal and neonatal adverse events is unknown. The aim of this study was ...detailed

Relevant academic research and scientific papers

Synthetic method of anesthetic analgesic drug

The invention discloses a synthetic method of an anesthetic analgesic drug. According to the synthetic method, 4-piperidinecarboxylic acid is used as a raw material and subjected to alkylation, bromination, methylation, acylation and the like to prepare the anesthetic analgesic drug. The method avoids the usage of highly toxic cyanide, so the safety and controllability of operation are improved; the method avoids an elimination reaction in reaction process, thereby accelerating reaction speed and shortening reaction time; and the method reduces reaction temperature, shortens the reaction time,and is more suitable for industrial production.

METHOD FOR PRODUCING N-PHENYL-N-(4-PIPERIDINYL) AMIDE SALTS

The invention relates to a method for producing N-phenyl-N-(4-piperidinyl)amide salts, particularly pharmaceutically tolerable addition salts of the compound Remifentanil, in that a compound of the formula (III) is reacted with an acrylic acid alkyl ester of the formula CH2═CH—C(O)—OR: where independently of each other R denotes low-molecular alkyl, preferably (C1-4)alkyl, preferably methyl or ethyl, R1 denotes low-molecular alkyl, preferably (C1-4)alkyl, preferably methyl or ethyl; and HX denotes an inorganic or organic acid, wherein the components are optionally reacted in the presence of a catalyst, preferably at a higher temperature, thereby obtaining the salt of the compound of formula (I).

Ugi reaction for the synthesis of 4-aminopiperidine-4-carboxylic acid derivatives. Application to the synthesis of carfentanil and remifentanil

A two-step sequence involving an Ugi four-component reaction was developed for the preparation of 4-aminopiperidine-4-carboxylic acid derivatives. This strategy has led to the successful preparation of two drugs carfentanil and remifentanil in shorter times and better yields than previously described methods.

Alternate Process for Remifentanil Preparation

An alternate process for synthesizing opiate or opioid analgesics and anesthetics, and intermediates thereof is provided. In particular, a process of synthesizing synthetic opiate or opioid compounds such as, for example, remifentanil, carfentanil, sufentanil, fentanyl, and alfentanil are disclosed.

PROCESS FOR SYNTHESIZING REMIFENTANIL

A process for synthesizing remifentanil or carfentanil, as well as intermediates for use in the preparation of synthetic opiate or opioid compounds. The process comprising reacting a 4-amino 4-carbamyl piperidine with a base in a closed reaction chamber at elevated temperature and pressure to form to intermediate which may be esterified with an alcohol, alkylated, and acylated to produce a synthetic opiate or opioid compound.

Process for preparing remifentanil, intermediates thereof, use of said intermediates and processes for their preparation

A process for preparing remifentanil by conversion of the nitrile group of a cyanopiperidinyl propanoate derivative to an ester group. Advantageously, with this process the number of steps for preparing remifentanil from commercial products is significantly reduced, compared to the processes known in the art.

CRYSTALLINE FORM OF REMIFENTANIL HYDROCHLORIDE

The present invention relates to a crystalline polymorphic form of remifentanil hydrochloride. The invention also describes methods of preparing a polymorphic form of remifentanil hydrochloride.

Combination of selected opioids with muscarine antagonists for treating urinary incontinence

Active compound combinations of compounds of group A, particularly opioids, and compounds of group B, particularly anti-muscarine agents and other substances suitable for treatment of an increased urge to urinate or urinary incontinence. Related pharmaceutical formulations and methods of treatment of an increased urge to urinate or urinary incontinence are also provided.

Design, Synthesis, and Pharmacological Evaluation of Ultrashort- to Long-Acting Opioid Analgetics

In an effort to discover a potent ultrashort-acting μ opioid analgetic that is capable of metabolizing to an inactive species independent of hepatic function, several classes of 4-anilidopiperidine analgetics were synthesized and evaluated.One series of compounds displayed potent μ opioid agonist activity with a high degree of analgesic efficacy and an ultrashort to long duration of action.These analgetics, 4-(methoxycarbonyl)-4--1-piperidinepropanoic acid alkyl esters, were evaluated in vitro in the guinea pig ileum for μ opioid activity, in vivo in the rat tail withdrawal assay for analgesic efficacy and duration of action, and in vitro in human whole blood for their ability to be metabolized in blood.Compounds in this series were all shown to be potent μ agonists in vitro, but depending upon the alkyl ester substitution the potency and duration of action in vivo varied substantially.The discrepancies between the in vitro and in vivo activities and variations in duration of action are probably due to different rates of ester hydrolysis by blood esterase(s).The SAR with respect to analgesic activity and duration of action as a function of the various esters synthesized id discussed.It was also demonstrated that the duration of action for the ultrashort-acting analgetic, 8, does not change upon prolonged infusion or administration of multiple bolus injections.