Identification

Name
Remifentanil
Accession Number
DB00899  (APRD01216)
Type
Small Molecule
Groups
Approved
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.

Structure
Thumb
Synonyms
  • Remifentanil
  • Remifentanilo
  • Remifentanyl
External IDs
GI 87084X / IDS-NR-005
Product Ingredients
IngredientUNIICASInChI Key
Remifentanil hydrochloride5V444H5WIC132539-07-2WFBMIPUMYUHANP-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Remifentanil for InjectionPowder, for solutionIntravenousTEVA Canada Limited2014-06-05Not applicableCanada
Remifentanil for InjectionPowder, for solutionIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Remifentanil for InjectionPowder, for solutionIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Remifentanil for InjectionPowder, for solutionIntravenousTEVA Canada Limited2014-06-05Not applicableCanada
Remifentanil Hydrochloride for InjectionPowder, for solutionIntravenousSterimax IncNot applicableNot applicableCanada
Remifentanil Hydrochloride for InjectionPowder, for solutionIntravenousSterimax Inc2011-09-29Not applicableCanada
Remifentanil Hydrochloride for InjectionPowder, for solutionIntravenousSterimax Inc2011-09-27Not applicableCanada
UltivaInjection, powder, lyophilized, for solution1 mg/1mLIntravenousMylan Institutional LLC1996-11-06Not applicableUs
UltivaInjection, powder, lyophilized, for solution5 mg/5mLIntravenousAbbott1996-07-172012-11-29Us
UltivaPowder, for solutionIntravenousAbbvie1997-03-172013-10-02Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Remifentanil HydrochlorideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousFresenius Kabi USA, LLC2018-01-19Not applicableUs
Remifentanil HydrochlorideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousFresenius Kabi USA, LLC2018-01-19Not applicableUs
Remifentanil HydrochlorideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousFresenius Kabi USA, LLC2018-01-19Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories
UNII
P10582JYYK
CAS number
132875-61-7
Weight
Average: 376.4467
Monoisotopic: 376.199822016
Chemical Formula
C20H28N2O5
InChI Key
ZTVQQQVZCWLTDF-UHFFFAOYSA-N
InChI
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
IUPAC Name
methyl 1-(3-methoxy-3-oxopropyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate
SMILES
CCC(=O)N(C1=CC=CC=C1)C1(CCN(CCC(=O)OC)CC1)C(=O)OC

Pharmacology

Indication

For use during the induction and maintenance of general anesthesia.

Associated Therapies
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.

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.

TargetActionsOrganism
AMu-type opioid receptor
agonist
Humans
UDelta-type opioid receptor
agonist
Humans
UKappa-type opioid receptor
agonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption
Not Available
Volume of distribution
  • 350 mL/kg
  • 452 ± 144 mL/kg [neonates]
  • 223 ± 30.6 mL/kg [adolescents]
Protein binding

70% (bound to plasma proteins)

Metabolism

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

Route of 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.

Half life

1-20 minutes

Clearance
  • 40 mL/min/kg [young, healthy adults]
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Remifentanil Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1-benzylimidazoleThe risk or severity of hypertension can be increased when Remifentanil is combined with 1-benzylimidazole.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may increase the analgesic activities of Remifentanil.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may increase the analgesic activities of Remifentanil.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may increase the analgesic activities of Remifentanil.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Remifentanil is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Remifentanil is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Remifentanil is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Remifentanil.
AbediterolThe risk or severity of hypertension can be increased when Remifentanil is combined with Abediterol.
AcebutololThe therapeutic efficacy of Acebutolol can be increased when used in combination with Remifentanil.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

Synthesis Reference

Jacob Mathew, J. Killgore, "New methods for the synthesis of alfentanil, sufentanil, and remifentanil." U.S. Patent US20060149071, issued July 06, 2006.

US20060149071
General References
Not Available
External Links
Human Metabolome Database
HMDB0015036
KEGG Drug
D08473
KEGG Compound
C08021
PubChem Compound
60815
PubChem Substance
46504538
ChemSpider
54803
BindingDB
50012491
RxNav
73032
ChEBI
8802
ChEMBL
CHEMBL1005
ZINC
ZINC000000538283
Therapeutic Targets Database
DAP000264
PharmGKB
PA451232
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Remifentanil
ATC Codes
N01AH06 — Remifentanil
AHFS Codes
  • 28:08.08 — Opiate Agonists
FDA label
Download (380 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceSleep Apnea1
0CompletedTreatmentOSAS (Obstructive Sleep Apneas Syndrome)1
0RecruitingOtherCoronary Artery Disease / Delirium1
1CompletedNot AvailablePain1
1CompletedDiagnosticDepth of Anaesthesia1
1CompletedDiagnosticOpioid; Intoxication, Perception Disturbance (Acute) / Overdose of Opiate / Pain, Acute / Respiratory Depression / Safety Issues1
1CompletedHealth Services ResearchRespiratory Depression1
1CompletedTreatmentPain / Stress1
1Unknown StatusSupportive CareOSAS (Obstructive Sleep Apneas Syndrome)1
1, 2Active Not RecruitingPreventionAnaesthesia therapy / Cesarean Section1
1, 2CompletedBasic ScienceSedative Overdose1
1, 2CompletedSupportive CarePreterm, Infant1
1, 2CompletedTreatmentHematologic Diseases / Neoplasms1
1, 2CompletedTreatmentOverdose, Drug1
1, 2CompletedTreatmentPain, Acute / Respiration stimulated / Sedation1
1, 2RecruitingHealth Services ResearchAnalgesic Adverse Reaction / Inhalant Use / Nociceptive Pain1
1, 2TerminatedSupportive CareMechanical Ventilator Care / Preterm, Infant1
2Active Not RecruitingOtherSedation, Conscious1
2CompletedPreventionPre-Eclampsia, Severe / Pregnancy1
2CompletedSupportive CareAnalgesic Adverse Reaction1
2CompletedSupportive CareIdiopathic Scoliosis1
2CompletedTreatmentAnaesthesia therapy1
2CompletedTreatmentAnaesthesia therapy / Hysterectomy / Ketamine / Morphine1
2CompletedTreatmentHyperalgesia1
2CompletedTreatmentProgressive Infantile Idiopathic Scoliosis1
2CompletedTreatmentUrological Surgery1
2CompletedTreatmentAdjunct to general anesthesia therapy1
2Not Yet RecruitingTreatmentAnalgesics, Opioid / Respiratory Insufficiency / Ventilator Weaning1
2RecruitingOtherEffect of Anesthesia in Discharge Time From Postanesthesia Care Unit / Effect of Anesthesia in Discharge Time From the Hospital / Effect of Anesthesia in Extubation Time / Effect of Anesthesia in Postoperative Adverse Events / Effect of Anesthesia in Postoperative Pain1
2RecruitingTreatmentHallux Valgus and Bunion / Sedation1
2RecruitingTreatmentHyperalgesia1
2RecruitingTreatmentPain, Acute1
2TerminatedBasic ScienceHealthy Volunteers1
2, 3RecruitingTreatmentObstetrical analgesia therapy / Obstetrical Anesthesia / Postpartum Depression1
2, 3Unknown StatusTreatmentObesity, Morbid1
3CompletedNot AvailableCognitive Ability, General1
3CompletedOtherBreast Diseases1
3CompletedOtherFeticide / Termination of Pregnancy1
3CompletedSupportive CareBradycardia / Hypotension1
3CompletedSupportive CareTumor of Ear, Nose and Throat1
3CompletedTreatmentAnaesthesia therapy1
3CompletedTreatmentAnaesthesia therapy / Craniotomy / Neurosurgery1
3CompletedTreatmentBreech Presentation / Pregnancy1
3CompletedTreatmentComplications, Pregnancy / Complications; Cesarean Section / Fetus or Neonate Affected by External Version Before Labor / Inhalation of Nitrous Oxide / Non-cephalic Presentation1
3CompletedTreatmentIntubation, Endotracheal1
3CompletedTreatmentSpinal Puncture1
3CompletedTreatmentVentilations, Mechanical1
3RecruitingSupportive CareAnaesthesia / Children / Heart Diseases / Magnetic Resonance Imaging (MRI)1
3RecruitingSupportive CareIntra-tracheal Intubation1
3RecruitingTreatmentAnaesthesia therapy / Child's Development / Neurologic toxicity1
3RecruitingTreatmentHysterectomy, Vaginal / Suburethral Slings1
3RecruitingTreatmentStroke1
3TerminatedTreatmentAnaesthesia therapy / Opioid-Related Disorders1
3TerminatedTreatmentAnalgesia1
3Unknown StatusBasic SciencePostherpetic Neuralgia1
4Active Not RecruitingPreventionAnesthesia, Intratracheal / Hernia / Intravenous Anesthesia / Pain, Acute / Pain, Chronic1
4Active Not RecruitingTreatmentAnaesthesia therapy1
4CompletedNot AvailableAnaesthesia therapy2
4CompletedNot AvailableIntubation, Endotracheal1
4CompletedNot AvailablePatients Requiring Ambulatory Surgery Under General Anesthesia1
4CompletedBasic ScienceAnaesthesia therapy1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedBasic SciencePharyngeal Dysfunction / Pharyngeal Swallowing1
4CompletedBasic ScienceSecondary Hyperalgesia1
4CompletedDiagnosticAlteration of Cognitive Function / Gastrointestinal Dysfunction1
4CompletedDiagnosticAnaesthesia therapy / Electroencephalography/ Drug Effect1
4CompletedDiagnosticAutonomic Nervous System Activity1
4CompletedOtherBronchoscopy / Fentanyl / Narcotrend / Remifentanil / Sedation, Conscious / Sufentanil1
4CompletedOtherPolyps, Nasal1
4CompletedPreventionAgitation1
4CompletedPreventionAnaesthesia therapy / Palonosetron / Ponv1
4CompletedPreventionAortic Valve Stenosis / Ischemic Heart Disease1
4CompletedPreventionCervical Disc Herniation / Cervical Spinal Stenosis / Cervical Spine Damage1
4CompletedPreventionChronic Rhinosinusitis1
4CompletedPreventionCoronary Artery Disease1
4CompletedPreventionCoughing1
4CompletedPreventionDrug Usage2
4CompletedPreventionElective Thyroidectomy1
4CompletedPreventionEndovascular Repair of Aortic Aneurysm / Endovascular Treatment of Arteriosclerosis Obliterans of Lower Extremities1
4CompletedPreventionFentanyl / Pain, Chronic / Remifentanil / Sternotomy1
4CompletedPreventionHeart Diseases / Hyperglycemia1
4CompletedPreventionHyperalgesia2
4CompletedPreventionIntravenous Anesthetic Agent Overdose1
4CompletedPreventionIntubation, Endotracheal1
4CompletedPreventionMandibular Prognathism / Mandibular Retrognathism1
4CompletedPreventionMyocardial Ischemic Reperfusion Injury1
4CompletedPreventionOSAS (Obstructive Sleep Apneas Syndrome) / Sleep Apnea Syndromes1
4CompletedPreventionOpen Craniotomy1
4CompletedPreventionPostoperative Confusion1
4CompletedPreventionPostoperative pain2
4CompletedPreventionSupratentorial Neoplasms1
4CompletedPreventionThyroidectomy1
4CompletedPreventionUpper Respiratory Tract Infection1
4CompletedScreeningAnaesthesia therapy / Neuromuscular Blockade1
4CompletedScreeningPatients Undergoing Major Abdominal Surgery / Postoperative Confusion1
4CompletedSupportive CareAnaesthesia therapy1
4CompletedSupportive CareColonoscopy1
4CompletedSupportive CareHypothermia1
4CompletedSupportive CareIntubating Conditions1
4CompletedSupportive CareIntubation; Difficult1
4CompletedSupportive CareRemifentanil Concentration for Smooth Emergence1
4CompletedSupportive CareRespiratory Distress Syndrome1
4CompletedSupportive CareTranscervical Resection of Endometrium / Transcervical Resection of Fibroids / Transcervical Resection of Polyp1
4CompletedSupportive CareUnderdosing of Unspecified General Anesthetics1
4CompletedTreatmentAdverse Effects / Pain, Labor / Satisfaction1
4CompletedTreatmentAnaesthesia therapy2
4CompletedTreatmentAnaesthesia therapy / Electroconvulsive Therapy1
4CompletedTreatmentAnesthetics Agent / Anesthetics, Intravenous / Cardiopulmonary Bypass / Pharmacology1
4CompletedTreatmentCarotid Artery Stenosis1
4CompletedTreatmentChronic Calculous Cholecystitis1
4CompletedTreatmentCoughing1
4CompletedTreatmentCoughing / High Blood Pressure (Hypertension)1
4CompletedTreatmentDeep Extubation1
4CompletedTreatmentDeep Sedation / Delayed Emergence From Anesthesia1
4CompletedTreatmentDiagnostic Colonoscopy Screening1
4CompletedTreatmentDrug Usage1
4CompletedTreatmentEfficacy and Safety of Mivacurium Chloride for Pediatric Patients1
4CompletedTreatmentEndoscopic Retrograde Cholangiopancreatography1
4CompletedTreatmentFractures, Closed / Hip Arthritis / Knee Arthropathy1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Myocardial Ischemia / Tachycardia1
4CompletedTreatmentInduction of Anaesthesia1
4CompletedTreatmentIschemic Heart Disease / Surgery, Cardiac1
4CompletedTreatmentKidney Stones1
4CompletedTreatmentLabour / Pain1
4CompletedTreatmentLung Function1
4CompletedTreatmentMuscle Relaxation1
4CompletedTreatmentOSAS (Obstructive Sleep Apneas Syndrome)1
4CompletedTreatmentOpioid Induced Pharyngeal and Esophageal Dysfunction1
4CompletedTreatmentOpioid Induced Swallowing Disorders1
4CompletedTreatmentOsteoarthritis (OA) / Pain, Chronic1
4CompletedTreatmentPain4
4CompletedTreatmentPain Relief in Labour1
4CompletedTreatmentPain, Labor1
4CompletedTreatmentFunctional disorders of the biliary tract / Pancreatic Diseases1
4CompletedTreatmentPancreatic Stone Disease1
4CompletedTreatmentPediatric Rigid Bronchoscopy1
4CompletedTreatmentRealisation of Bronchial Fibroscopy1
4CompletedTreatmentRespiration, Artificial / Respiratory Insufficiency / Sedation, Conscious1
4CompletedTreatmentSedation1
4CompletedTreatmentSupraglottic Airways for General Anesthesia1
4CompletedTreatmentSurgical Procedures, Operative1
4CompletedTreatmentTachycardia1
4CompletedTreatmentTooth Extractions1
4CompletedTreatmentTracheal Extubation1
4CompletedTreatmentUrinary Tract Problem1
4CompletedTreatmentVentricular Tachycardia (VT)1
4CompletedTreatmentAdjunct to general anesthesia therapy1
4Enrolling by InvitationSupportive CareHemodynamics Instability1
4Not Yet RecruitingBasic ScienceAdjunct to general anesthesia therapy / Hemodynamics Instability / Intravenous Anesthesia2
4Not Yet RecruitingDiagnosticDiastolic Dysfunction1
4Not Yet RecruitingPreventionAnaesthesia therapy1
4Not Yet RecruitingPreventionCoughing1
4Not Yet RecruitingPreventionIllness, Critical1
4Not Yet RecruitingPreventionIntravenous Anesthesia1
4Not Yet RecruitingScreeningCerebral Oxygen Saturation / Hypotension Drug-Induced1
4Not Yet RecruitingSupportive CareBronchoscopy1
4Not Yet RecruitingTreatmentAnaesthesia therapy / Intubation Complications / Neuromuscular Blockade1
4Not Yet RecruitingTreatmentMyoclonus1
4RecruitingNot AvailableGeneral Surgery1
4RecruitingBasic SciencePharyngeal Dysfunction / Pharyngeal Swallowing1
4RecruitingDiagnosticBispectral Index / Induction of anesthesia therapy / Target Controlled Infusion (TCI)1
4RecruitingPreventionAcute Lung Injury (ALI) / Chronic Lung Diseases / Lung Inflammation / Postoperative Complications1
4RecruitingPreventionIntra-abdominal and Intrapelvic Surgery / Intra-abdominal Surgery1
4RecruitingPreventionOpioid-Induced Disorders1
4RecruitingSupportive CareAnesthesia, Conduction / Drug Drug Interaction (DDI)1
4RecruitingSupportive CareLocal Anesthesia1
4RecruitingTreatmentAnterior Cervical Discectomy and Fusion (ACDF)1
4RecruitingTreatmentBMI >30 kg/m2 / Nausea, Postoperative / Opioids Use / Postoperative pain / Vomiting, Postoperative1
4RecruitingTreatmentBrain / Sedation1
4RecruitingTreatmentChild, Only / Pain / Remifentanil / Tonsillectomy1
4RecruitingTreatmentPain, Labor1
4RecruitingTreatmentPostoperative pain1
4RecruitingTreatmentRespiratory Distress Syndrome, Newborn1
4TerminatedBasic ScienceASA Class I/II Patients Scheduled for Surgery Under General Anesthesia1
4TerminatedDiagnosticVentricular Dysfunction / Young Healthy Adults1
4TerminatedOtherCardiac Diseases1
4TerminatedPreventionCarotid Artery Stenosis1
4TerminatedSupportive CarePain1
4TerminatedTreatmentAnaesthesia therapy1
4TerminatedTreatmentAnalgesia / Sedation1
4TerminatedTreatmentAnesthesia Recovery Period / Postoperative pain1
4TerminatedTreatmentFailed Conscious Sedation During Procedure1
4TerminatedTreatmentMinor burns / Pain1
4Unknown StatusNot AvailableComplications, Pregnancy / Hypertension, Pregnancy-Induced / Prophylaxis of preeclampsia1
4Unknown StatusNot AvailableDeviation Septum Nasal1
4Unknown StatusBasic ScienceHyperalgesia4
4Unknown StatusPreventionAgitation1
4Unknown StatusPreventionAnesthesia; Reaction1
4Unknown StatusPreventionDelirium1
4Unknown StatusPreventionPostoperative Confusion1
4Unknown StatusSupportive CareLung Cancers1
4Unknown StatusTreatmentAdrenal Suppression / Hemodynamics Instability1
4Unknown StatusTreatmentAnaesthesia therapy / Hemodynamics / Oxidative Stress1
4Unknown StatusTreatmentCognitive Ability, General / Injuries, Brain1
4Unknown StatusTreatmentGoiter, Nodular1
4Unknown StatusTreatmentHaemodynamic Rebound1
4Unknown StatusTreatmentHemodynamics / Hysteroscopy / Sedation1
4Unknown StatusTreatmentPostoperative Cognitive Dysfunction1
Not AvailableCompletedNot AvailableAnaesthesia therapy3
Not AvailableCompletedNot AvailableAnaesthesia therapy / Disorder of Oxygen Transport / Drug Drug Interaction (DDI) / Hemodynamics Instability1
Not AvailableCompletedNot AvailableAnaesthesia therapy / Effects of Dexmedetomidine / Elderly Patients / Emergence From Anesthesia / Recovery From Anesthesia1
Not AvailableCompletedNot AvailableAnalgesia1
Not AvailableCompletedNot AvailableComplication of Labor and/or Delivery1
Not AvailableCompletedNot AvailableCoronary Artery Bypass Graft Surgery Patients / Dexmedetomidine / Dysrhythmia, Cardiac / Hypokalemia / Remifentanil1
Not AvailableCompletedNot AvailableEpilepsies1
Not AvailableCompletedNot AvailableFemale Patients Undergoing Thyroidectomy1
Not AvailableCompletedNot AvailableHead and Neck Disorder / Pain1
Not AvailableCompletedNot AvailableHypotension,Controlled1
Not AvailableCompletedNot AvailableLabor; Prolonged, First Stage / Labor; Prolonged, Second Stage / Pain, Labor1
Not AvailableCompletedNot AvailableSedative Adverse Reaction1
Not AvailableCompletedNot AvailableSurgery, Cardiac1
Not AvailableCompletedNot AvailableTraumatic Brain Injury (TBI)1
Not AvailableCompletedBasic ScienceAnaesthesia therapy / Neuromuscular Blockade1
Not AvailableCompletedBasic ScienceCritical Care / Deep Sedation / Sedation, Conscious1
Not AvailableCompletedBasic ScienceLumbar Surgery1
Not AvailableCompletedBasic ScienceOverdose, Drug1
Not AvailableCompletedDiagnosticAnaesthesia therapy1
Not AvailableCompletedDiagnosticCervical Cancers / Gallbladder Inflammation / Ovarian Cancer / Ovarian Cysts / Uterine Leiomyomas1
Not AvailableCompletedDiagnosticEndoscopic Sinus Surgery1
Not AvailableCompletedDiagnosticMeasure of Nociception1
Not AvailableCompletedDiagnosticSedation During1
Not AvailableCompletedHealth Services ResearchPain1
Not AvailableCompletedOtherAnaesthesia therapy / General Surgery / Ophthalmic1
Not AvailableCompletedOtherLaryngospasm1
Not AvailableCompletedOtherObese1
Not AvailableCompletedOtherOsteoarthritis (OA) / Short Stature1
Not AvailableCompletedPreventionAVM / ICH / Neoplasms, Brain1
Not AvailableCompletedPreventionAnaesthesia therapy / Coughing2
Not AvailableCompletedPreventionAnaesthesia therapy / Coughing / Extubation1
Not AvailableCompletedPreventionAnaesthesia therapy / Pain1
Not AvailableCompletedPreventionAdjunct to general anesthesia therapy / Cesarean Delivery / Pregnancy1
Not AvailableCompletedPreventionCoughing1
Not AvailableCompletedPreventionEmergence Agitation1
Not AvailableCompletedPreventionGeneral Surgery With Endotracheal Intubation1
Not AvailableCompletedPreventionGeneral Surgery / Prostate Cancer1
Not AvailableCompletedPreventionHealthy Volunteers2
Not AvailableCompletedPreventionHemodynamic Responses During Tracheal Intubation1
Not AvailableCompletedPreventionHip Arthroplasty1
Not AvailableCompletedPreventionHypophysectomy1
Not AvailableCompletedPreventionIntraoperative Awareness1
Not AvailableCompletedPreventionIntubation, Intratracheal1
Not AvailableCompletedPreventionKidney Donation/Transplantation1
Not AvailableCompletedPreventionPain2
Not AvailableCompletedPreventionPatients Undergoing Thyroidectomy1
Not AvailableCompletedPreventionPeripheral Obliterative Arteriopathy1
Not AvailableCompletedPreventionPost Operative Nausea and Vomiting (PONV)1
Not AvailableCompletedPreventionPost Operative Sore Throat1
Not AvailableCompletedPreventionPostoperative pain1
Not AvailableCompletedPreventionRespiratory Complications2
Not AvailableCompletedPreventionStress Response1
Not AvailableCompletedPreventionStroke, Ischemic1
Not AvailableCompletedPreventionThyroidectomy1
Not AvailableCompletedPreventionVitrectomy Operation Under General Anesthesia1
Not AvailableCompletedPreventionVocal Cord; Injury, Superficial1
Not AvailableCompletedScreeningGeneral Surgery / Pain1
Not AvailableCompletedSupportive CareC.Delivery; Surgery (Previous), Gynecological / Delayed Emergence From Anesthesia / Inappropriate Device Stimulation of Tissue1
Not AvailableCompletedSupportive CareCataracts / Corneal Inflammation / Pterygium / Retina Detachment / Vitreous Hemorrhage1
Not AvailableCompletedSupportive CareHyperalgesia / Ibuprofen / Postoperative pain / Remifentanil1
Not AvailableCompletedSupportive CarePain1
Not AvailableCompletedSupportive CarePatients Undergoing Laparoscopic Gastrectomy1
Not AvailableCompletedSupportive CarePostoperative pain1
Not AvailableCompletedSupportive CareStrabismus1
Not AvailableCompletedTreatmentAdult Intracranial Tumor / Adult Solid Tumor1
Not AvailableCompletedTreatmentAdverse Effect of Other General Anesthetics1
Not AvailableCompletedTreatmentAdverse Reaction to Drug / Analgesic Adverse Reaction / Arteriovenous Fistulas / Chronic Kidney Disease (CKD) / Midazolam Adverse Reaction / Patients Satisfaction / Sedative Adverse Reaction1
Not AvailableCompletedTreatmentAnaesthesia therapy1
Not AvailableCompletedTreatmentAnaesthesia therapy / Neuromuscular Blockade1
Not AvailableCompletedTreatmentAnaesthesia therapy / Pain1
Not AvailableCompletedTreatmentAnesthetics Agent / Propofol / Remifentanil1
Not AvailableCompletedTreatmentAnxiety Preoperative / Midazolam Premedication / Premedication1
Not AvailableCompletedTreatmentColonoscopy1
Not AvailableCompletedTreatmentDrug Usage1
Not AvailableCompletedTreatmentDysrhythmia, Cardiac1
Not AvailableCompletedTreatmentEarly Gastric Cancer Patients Who Were Scheduled for Endoscopic Submucosal Dissection1
Not AvailableCompletedTreatmentEmergence Delirium1
Not AvailableCompletedTreatmentFractures, Compression1
Not AvailableCompletedTreatmentIschemic Heart Disease1
Not AvailableCompletedTreatmentMicrovascular Breast Flap in Plastic Surgery1
Not AvailableCompletedTreatmentNeoplasms, Brain1
Not AvailableCompletedTreatmentOptic Nerve Sheath Diameter / Robot Assisted Laparoscopic Radical Prostatectomy1
Not AvailableCompletedTreatmentOsteoarthritis (OA)2
Not AvailableCompletedTreatmentPain2
Not AvailableCompletedTreatmentPain, Chronic1
Not AvailableCompletedTreatmentPostoperative Cognitive Functions1
Not AvailableCompletedTreatmentPostoperative Complications1
Not AvailableCompletedTreatmentPostoperative pain1
Not AvailableCompletedTreatmentPregnancy Termination1
Not AvailableCompletedTreatmentScheduled Laparoscopic Surgery1
Not AvailableCompletedTreatmentShort Duration Analgesia / Skull Pin Insertion1
Not AvailableCompletedTreatmentSurgical Blood Loss1
Not AvailableCompletedTreatmentTracheal Intubation1
Not AvailableEnrolling by InvitationTreatmentChest Wall Disorders1
Not AvailableNot Yet RecruitingBasic ScienceAcute Nociceptive Pain / Allodynia / Hyperalgesia / Opioid-Induced Hyperalgesia1
Not AvailableNot Yet RecruitingOtherSKNA According to Different Anesthetics1
Not AvailableNot Yet RecruitingPreventionAnaesthesia therapy1
Not AvailableNot Yet RecruitingPreventionEndoscopic Sinus Surgery2
Not AvailableNot Yet RecruitingPreventionFunctional Endoscopic Sinus Surgery (FESS)1
Not AvailableNot Yet RecruitingPreventionRobotic-assisted Laparoscopic Radical Prostatectomy1
Not AvailableNot Yet RecruitingSupportive CareCardiovascular Heart Disease1
Not AvailableNot Yet RecruitingTreatmentBronchoscopy / Sedation2
Not AvailableRecruitingNot AvailableAnaesthesia therapy1
Not AvailableRecruitingNot AvailableGeneral Anesthetics Toxicity / Lymphocyte Destruction / Metastatic Colorectal Cancer (MCRC) / Molecular Mechanism of Pharmacological Action / Survival Rate1
Not AvailableRecruitingNot AvailableIntravenous Anesthesia1
Not AvailableRecruitingNot AvailableOocyte Retrieval / Sedation, Conscious / Ventilatory Depression1
Not AvailableRecruitingBasic SciencePain1
Not AvailableRecruitingDiagnosticAnaesthesia therapy / Pain1
Not AvailableRecruitingOtherPancreatic Cancer or Distal CBD Cancer1
Not AvailableRecruitingPreventionDelirium1
Not AvailableRecruitingPreventionHyperthermia / Neoplasms, Colorectal / Oxaliplatin1
Not AvailableRecruitingPreventionNeoplasms, Thyroid1
Not AvailableRecruitingPreventionPostoperative pain1
Not AvailableRecruitingScreeningShock, Septic1
Not AvailableRecruitingSupportive CareAnaesthesia therapy / Pain1
Not AvailableRecruitingSupportive CareInguinal Hernias / Postoperative pain1
Not AvailableRecruitingSupportive CarePostoperative pain / Undescended Testis1
Not AvailableRecruitingTreatmentAcute Hypercapnic Respiratory Failure1
Not AvailableRecruitingTreatmentAnaesthesia therapy1
Not AvailableRecruitingTreatmentAnaesthesia therapy / Anesthesia Morbidity / Breast Neoplasm Female / Regional Anesthesia / Regional Anesthesia Morbidity1
Not AvailableRecruitingTreatmentAnaesthesia therapy / Nociceptive Pain / Opioids Use / Perioperative/Postoperative Complications1
Not AvailableRecruitingTreatmentBMI >30 kg/m2 / Postoperative pain1
Not AvailableRecruitingTreatmentBariatric Surgery Candidate / Opioids Use / Post Operative Nausea and Vomiting (PONV) / Postoperative pain1
Not AvailableRecruitingTreatmentBreast Cancer1
Not AvailableRecruitingTreatmentElderly Patients / General Anesthetic Drug Adverse Reaction / Postoperative Delirium1
Not AvailableRecruitingTreatmentIntubation; Difficult or Failed1
Not AvailableRecruitingTreatmentMagnesium Sulfate / Opioids Use / Postoperative pain1
Not AvailableRecruitingTreatmentNociceptive Pain / Surgical Procedure, Unspecified1
Not AvailableSuspendedTreatmentAnaesthesia therapy / Children / Pain1
Not AvailableSuspendedTreatmentAnaesthesia therapy / Sedation / Surgery, Cardiac1
Not AvailableSuspendedTreatmentAdjunct to general anesthesia therapy1
Not AvailableTerminatedNot AvailableAnaesthesia therapy1
Not AvailableTerminatedBasic ScienceTachyarrhythmia1
Not AvailableTerminatedDiagnosticParkinson's Disease (PD)1
Not AvailableTerminatedOtherBreast Cancer1
Not AvailableTerminatedPreventionGeneral Surgery1
Not AvailableTerminatedTreatmentAnaesthesia therapy / Surgery, Cardiac1
Not AvailableTerminatedTreatmentBronchoscopy / Sedation2
Not AvailableTerminatedTreatmentChronic Rhinosinusitis1
Not AvailableTerminatedTreatmentDislocation, Shoulder1
Not AvailableTerminatedTreatmentPain1
Not AvailableTerminatedTreatmentAdjunct to general anesthesia therapy1
Not AvailableUnknown StatusNot AvailableLung Cancers / Neoplasms, Lung1
Not AvailableUnknown StatusNot AvailablePediatrics1
Not AvailableUnknown StatusBasic ScienceEffect of Remifentanil / Movement Disorders1
Not AvailableUnknown StatusBasic ScienceLaryngoscopy1
Not AvailableUnknown StatusPreventionIntubation, Intratracheal1
Not AvailableUnknown StatusPreventionPain1
Not AvailableUnknown StatusSupportive CareAdjunct to general anesthesia therapy1
Not AvailableUnknown StatusTreatmentAnalgesia / Pain / Sedation1
Not AvailableUnknown StatusTreatmentBronchoscopy; / Central Airway Stenosis / Interventional; / Noninvasive Positive Pressure Ventilation / Sedation1
Not AvailableUnknown StatusTreatmentHaemodynamic Fluctuations During Off-pump CABG1
Not AvailableUnknown StatusTreatmentLiver Diseases1
Not AvailableUnknown StatusTreatmentLiver Dysfunction / Pain1
Not AvailableWithdrawnPreventionNeoplasms, Brain1

Pharmacoeconomics

Manufacturers
  • Bioniche teoranta
Packagers
  • Abbott Laboratories Ltd.
  • Bioniche Pharma
  • Hospira Inc.
Dosage forms
FormRouteStrength
Powder, for solutionIntravenous
Injection, powder, lyophilized, for solutionIntravenous1 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous2 mg/2mL
Injection, powder, lyophilized, for solutionIntravenous5 mg/5mL
Prices
Unit descriptionCostUnit
Ultiva 5 mg vial118.15USD vial
Ultiva 2 mg vial57.2USD vial
Ultiva 1 mg vial30.19USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5019583No1991-05-282010-07-12Us
US5866591Yes1999-02-022018-03-10Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP1.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.591 mg/mLALOGPS
logP1.75ALOGPS
logP1.52ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)7.51ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area76.15 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity100.56 m3·mol-1ChemAxon
Polarizability40.82 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6136
Blood Brain Barrier+0.9381
Caco-2 permeable-0.5271
P-glycoprotein substrateSubstrate0.7345
P-glycoprotein inhibitor IInhibitor0.8682
P-glycoprotein inhibitor IINon-inhibitor0.6428
Renal organic cation transporterNon-inhibitor0.7077
CYP450 2C9 substrateNon-substrate0.8041
CYP450 2D6 substrateNon-substrate0.8786
CYP450 3A4 substrateSubstrate0.6963
CYP450 1A2 substrateNon-inhibitor0.9355
CYP450 2C9 inhibitorNon-inhibitor0.8788
CYP450 2D6 inhibitorNon-inhibitor0.8838
CYP450 2C19 inhibitorNon-inhibitor0.8201
CYP450 3A4 inhibitorNon-inhibitor0.7827
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7945
Ames testNon AMES toxic0.7388
CarcinogenicityNon-carcinogens0.8554
BiodegradationNot ready biodegradable0.9428
Rat acute toxicity2.6994 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9589
hERG inhibition (predictor II)Inhibitor0.6126
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0009000000-b9035e2706d5ac9b57a7
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-02di-0397000000-c610a2d0adc44d55166b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0930000000-436dbd271b442dcde5bf
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03e9-4900000000-79234a6e65fb22f3b487
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01q9-9700000000-5ce11ade40e1a80e4958

Taxonomy

Description
This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
Piperidinecarboxylic acids / Anilides / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides / Methyl esters / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Alpha-amino acid or derivatives / Piperidinecarboxylic acid / Anilide / Monocyclic benzene moiety / Dicarboxylic acid or derivatives / Piperidine / Benzenoid / Tertiary carboxylic acid amide / Methyl ester / Carboxamide group
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
monocarboxylic acid amide, alpha-amino acid ester, anilide, piperidinecarboxylate ester (CHEBI:8802)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
References
  1. Scott LJ, Perry CM: Remifentanil: a review of its use during the induction and maintenance of general anaesthesia. Drugs. 2005;65(13):1793-823. [PubMed:16114980]
  2. Scott LJ, Perry CM: Spotlight on remifentanil for general anaesthesia. CNS Drugs. 2005;19(12):1069-74. [PubMed:16332149]
  3. Warner DS, Hindman BJ, Todd MM, Sawin PD, Kirchner J, Roland CL, Jamerson BD: Intracranial pressure and hemodynamic effects of remifentanil versus alfentanil in patients undergoing supratentorial craniotomy. Anesth Analg. 1996 Aug;83(2):348-53. [PubMed:8694317]
  4. Guy J, Hindman BJ, Baker KZ, Borel CO, Maktabi M, Ostapkovich N, Kirchner J, Todd MM, Fogarty-Mack P, Yancy V, Sokoll MD, McAllister A, Roland C, Young WL, Warner DS: Comparison of remifentanil and fentanyl in patients undergoing craniotomy for supratentorial space-occupying lesions. Anesthesiology. 1997 Mar;86(3):514-24. [PubMed:9066316]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  6. Hoke JF, Cunningham F, James MK, Muir KT, Hoffman WE: Comparative pharmacokinetics and pharmacodynamics of remifentanil, its principle metabolite (GR90291) and alfentanil in dogs. J Pharmacol Exp Ther. 1997 Apr;281(1):226-32. [PubMed:9103501]
  7. Patel SS, Spencer CM: Remifentanil. Drugs. 1996 Sep;52(3):417-27; discussion 428. [PubMed:8875131]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
References
  1. Stucke AG, Zuperku EJ, Sanchez A, Tonkovic-Capin M, Tonkovic-Capin V, Mustapic S, Stuth EA: Opioid receptors on bulbospinal respiratory neurons are not activated during neuronal depression by clinically relevant opioid concentrations. J Neurophysiol. 2008 Nov;100(5):2878-88. doi: 10.1152/jn.90620.2008. Epub 2008 Sep 24. [PubMed:18815346]
  2. Rodrigues AR, Castro MS, Francischi JN, Perez AC, Duarte ID: Participation of ATP-sensitive K+ channels in the peripheral antinociceptive effect of fentanyl in rats. Braz J Med Biol Res. 2005 Jan;38(1):91-7. Epub 2005 Jan 18. [PubMed:15665994]
  3. Poonawala T, Levay-Young BK, Hebbel RP, Gupta K: Opioids heal ischemic wounds in the rat. Wound Repair Regen. 2005 Mar-Apr;13(2):165-74. [PubMed:15828941]
  4. Sahin AS, Duman A, Atalik EK, Ogun CO, Sahin TK, Erol A, Ozergin U: The mechanisms of the direct vascular effects of fentanyl on isolated human saphenous veins in vitro. J Cardiothorac Vasc Anesth. 2005 Apr;19(2):197-200. [PubMed:15868528]
  5. Darwish M, Tempero K, Kirby M, Thompson J: Pharmacokinetics and dose proportionality of fentanyl effervescent buccal tablets in healthy volunteers. Clin Pharmacokinet. 2005;44(12):1279-86. [PubMed:16372825]
  6. Darwish M, Kirby M, Robertson P Jr, Tracewell W, Jiang JG: Pharmacokinetic properties of fentanyl effervescent buccal tablets: a phase I, open-label, crossover study of single-dose 100, 200, 400, and 800 microg in healthy adult volunteers. Clin Ther. 2006 May;28(5):707-14. [PubMed:16861092]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da
References
  1. Wong GT, Li R, Jiang LL, Irwin MG: Remifentanil post-conditioning attenuates cardiac ischemia-reperfusion injury via kappa or delta opioid receptor activation. Acta Anaesthesiol Scand. 2010 Apr;54(4):510-8. doi: 10.1111/j.1399-6576.2009.02145.x. Epub 2009 Oct 29. [PubMed:19878098]
  2. Pascoe JE, Williams KL, Mukhopadhyay P, Rice KC, Woods JH, Ko MC: Effects of mu, kappa, and delta opioid receptor agonists on the function of hypothalamic-pituitary-adrenal axis in monkeys. Psychoneuroendocrinology. 2008 May;33(4):478-86. doi: 10.1016/j.psyneuen.2008.01.006. Epub 2008 Mar 5. [PubMed:18325678]

Drug created on June 13, 2005 07:24 / Updated on March 30, 2020 22:56

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