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    Remifentanil molecular structure

    Remifentanil Stats & Data

    Ultiva
    NPS DataHub
    MW376.45
    FormulaC20H28N2O5
    CAS132875-61-7
    IUPACmethyl 1-(3-methoxy-3-oxopropyl)-4-(phenyl-propanoylamino)piperidine-4-carboxylate
    SMILESCOC(=O)CCN1CCC(CC1)(C(=O)OC)N(C(=O)CC)c1ccccc1
    InChIKeyZTVQQQVZCWLTDF-UHFFFAOYSA-N
    Chemical Class Opioid
    Psychoactive Class Depressant
    Half-Life Elimination half-life ~1–20 minutes; context-sensitive half-time ~3–4 minutes.

    Pharmacology

    DrugBank
    Half-life 1-20 minutes Protein binding 70% (bound to plasma proteins) State Solid Clearance * 40 mL/min/kg young, healthy adults

    Description

    Remifentanil (marketed by Abbott as Ultiva) is a potent ultra short-acting synthetic opioid given to patients during surgery for pain relief and adjunctive to an anaesthetic. Remifentanil is a specific mu-type-opioid receptor agonist which means it reduces sympathetic nervous system tone, and causes respiratory depression and analgesia.

    Mechanism of Action

    Remifentanil is a µ-opioid agonist with rapid onset and peak effect, and short duration of action. The µ-opioid activity of remifentanil is antagonized by opioid antagonists such as naloxone.

    Pharmacodynamics

    Remifentanil is an opioid agonist with rapid onset and peak effect and ultra-short duration of action. The opioid activity of remifentanil is antagonized by opioid antagonists such as naloxone. The analgesic effects of remifentanil are rapid in onset and offset. Its effects and side effects are dose dependent and similar to other opioids. Remifentanil in humans has a rapid blood-brain equilibration half-time of 1 ± 1 minutes (mean ± SD) and a rapid onset of action.

    Metabolism

    By hydrolysis of the propanoic acid-methyl ester linkage by nonspecific blood and tissue esterases.

    Indication

    For use during the induction and maintenance of general anesthesia.

    Elimination

    Remifentanil is an esterase-metabolized opioid. The carboxylic acid metabolite is essentially inactive (1/4600 as potent as remifentanil in dogs) and is excreted by the kidneys with an elimination half-life of approximately 90 minutes.

    Volume of Distribution

    * 350 mL/kg * 452 ± 144 mL/kg neonates * 223 ± 30.6 mL/kg adolescents

    Effect Profile

    Curated
    Opioid 7.6

    Strong euphoria and pain relief with moderate itching/nausea, low sedation

    Euphoria / Warmth×3
    10
    Analgesia×2
    8
    Sedation / Relaxation×1
    3
    Itching / Nausea×1
    6

    Tolerance & Pharmacokinetics

    drugs.wiki
    Half-Life
    Elimination half-life ~1–20 minutes; context-sensitive half-time ~3–4 minutes.
    Addiction Potential
    Very high; profound µ-agonist reinforcement with rapid tolerance and severe withdrawal if abrupt discontinuation after prolonged infusion.

    Tolerance Decay

    Full tolerance 6h Half tolerance 2d Baseline ~7d

    Clinically, meaningful tolerance to remifentanil’s analgesia can develop within hours of infusion; tolerance decays over days to weeks after cessation. Values are approximate and based on clinical observations of acute tolerance rather than long-term dependence.

    Cross-Tolerances

    other µ-opioid agonists
    80% ●●○

    Harm Reduction

    drugs.wiki

    Standard anaesthetic practice uses continuous infusions of 0.05–0.25 µg kg⁻¹ min⁻¹; analgesia ceases within ~5 min of pump stoppage due to ester hydrolysis. Context-sensitive half-life is ~3–4 min regardless of infusion length. Bolus dosing outside monitored settings is strongly discouraged because apnoea or chest wall rigidity can occur before the syringe is empty. Chest/truncal rigidity with potent opioids is more likely with rapid IV pushes; slow administration and airway support are essential in clinical settings. Metabolism is by nonspecific blood/tissue esterases to an inactive acid; CYP inhibitors are not expected to prolong effect. Remifentanil can produce acute tolerance and opioid-induced hyperalgesia, especially after higher doses or abrupt cessation of infusions; expect rebound pain/craving within minutes once stopped. In overdose, prioritize airway/ventilation; give naloxone in small, titrated IV boluses (e.g., 0.04 mg) to restore breathing while minimizing severe withdrawal, and be prepared for re-sedation if longer-acting opioids or other depressants are present. Non-medical IV use carries high risks of hypoxia, infection, and BBVs; if people use regardless, sterile technique, low-dead-space syringes, never using alone, and access to naloxone/overdose response training reduce but do not eliminate risk.

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