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 analgesic drug. It is given to patients during surgery to relieve pain and as an adjunct to an anaesthetic. Remifentanil is a specific mu-type-opioid receptor agonist. Hence, it causes a reduction in sympathetic nervous system tone, respiratory depression and analgesia.

Structure
Thumb
Synonyms
  • REMIFENTANIL
  • 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 solution1 mgIntravenousTeva2014-06-05Not applicableCanada
Remifentanil for InjectionPowder, for solution2 mgIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Remifentanil for InjectionPowder, for solution2 mgIntravenousTeva2014-06-05Not applicableCanada
Remifentanil for InjectionPowder, for solution1 mgIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Remifentanil Hydrochloride for InjectionPowder, for solution1 mgIntravenousSterimax Inc2011-09-27Not applicableCanada
Remifentanil Hydrochloride for InjectionPowder, for solution5 mgIntravenousSterimax IncNot applicableNot applicableCanada
Remifentanil Hydrochloride for InjectionPowder, for solution2 mgIntravenousSterimax Inc2011-09-29Not applicableCanada
UltivaPowder, for solution2 mgIntravenousAbbvie1997-04-072013-10-02Canada
UltivaInjection, powder, lyophilized, for solution1 mg/1mLIntravenousMylan Institutional1996-11-06Not applicableUs
UltivaInjection, powder, lyophilized, for solution2 mg/2mLIntravenousAbbott1996-07-172012-11-29Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Remifentanil HydrochlorideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousFresenius Kabi2018-01-19Not applicableUs
Remifentanil HydrochlorideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousFresenius Kabi2018-01-19Not applicableUs
Remifentanil HydrochlorideInjection, powder, lyophilized, for solution1 mg/1mLIntravenousFresenius Kabi2018-01-19Not applicableUs
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
Human
UDelta-type opioid receptor
agonist
Human
UKappa-type opioid receptor
agonist
Human
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
DrugInteraction
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.
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may increase the analgesic activities of Remifentanil.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may increase the analgesic activities of Remifentanil.
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-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the central nervous system depressant (CNS depressant) and hypertensive activities of Remifentanil.
AcebutololRemifentanil may increase the bradycardic activities of Acebutolol.
AcepromazineThe risk or severity of adverse effects can be increased when Remifentanil is combined with Acepromazine.
AceprometazineThe risk or severity of adverse effects can be increased when Remifentanil is combined with Aceprometazine.
AcetazolamideThe risk or severity of adverse effects can be increased when Remifentanil is combined with Acetazolamide.
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 Compound
C08021
PubChem Compound
60815
PubChem Substance
46504538
ChemSpider
54803
BindingDB
50012491
ChEBI
8802
ChEMBL
CHEMBL1005
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
0RecruitingBasic ScienceSleep Apnea Syndrome1
1CompletedNot AvailablePain1
1CompletedDiagnosticDepth of Anaesthesia1
1CompletedTreatmentPain / Stress1
1RecruitingHealth Services ResearchRespiratory Depression1
1Unknown StatusSupportive CareSleep Apnea, Obstructive1
1, 2Active Not RecruitingPreventionAnaesthesia therapy / Cesarean Section1
1, 2CompletedSupportive CareInfant, Preterm1
1, 2CompletedTreatmentDrug Overdose1
1, 2CompletedTreatmentHematologic Diseases / Neoplasms1
1, 2CompletedTreatmentPain, Acute / Respiration stimulated / Sedation therapy1
1, 2TerminatedSupportive CareMechanical Ventilator Care / Preterm Infants1
2Active Not RecruitingSupportive CareAnalgesic Adverse Reaction1
2CompletedPreventionPre-Eclampsia, Severe / Pregnancy1
2CompletedSupportive CareIdiopathic Scoliosis1
2CompletedTreatmentAnaesthesia therapy / Hysterectomy / Ketamine / Morphine1
2CompletedTreatmentHyperalgesia1
2CompletedTreatmentProgressive Infantile Idiopathic Scoliosis1
2CompletedTreatmentAdjunct to general anesthesia therapy1
2RecruitingTreatmentHyperalgesia1
2RecruitingTreatmentPain, Acute1
2TerminatedBasic ScienceHealthy Volunteers1
2, 3RecruitingTreatmentAnalgesia, Obstetrical / Obstetrical Anesthesia / Postpartum Depression1
2, 3Unknown StatusTreatmentObesity, Morbid1
3CompletedNot AvailableCognitive Ability, General1
3CompletedSupportive CareArterial Hypotension / Bradycardia1
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
3RecruitingTreatmentAnaesthesia therapy / Child's Development / Neurotoxicity1
3RecruitingTreatmentAnaesthesia therapy / Opioid-Related Disorders1
3RecruitingTreatmentStrokes1
3TerminatedTreatmentAnalgesia1
3Unknown StatusBasic SciencePostherpetic Neuralgia1
4Active Not RecruitingOtherCardiac Diseases1
4Active Not RecruitingPreventionAnesthesia, Intratracheal / Hernia / Intravenous Anesthesia / Pain, Acute / Pain, Chronic1
4Active Not RecruitingTreatmentAnaesthesia therapy1
4CompletedNot AvailableAnaesthesia therapy1
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
4CompletedPreventionAcute Agitation1
4CompletedPreventionAnaesthesia therapy / Palonosetron / Ponv1
4CompletedPreventionAortic Valve Stenosis / Ischaemic Heart Diseases1
4CompletedPreventionCervical Disc Herniation / Cervical Spinal Stenosis / Cervical Spine Damage1
4CompletedPreventionChronic Rhinosinusitis1
4CompletedPreventionCoronary Artery Disease1
4CompletedPreventionCoughing1
4CompletedPreventionDrug Usage1
4CompletedPreventionElective Thyroidectomy1
4CompletedPreventionEndovascular Repair of Aortic Aneurysm / Endovascular Treatment of Arteriosclerosis Obliterans of Lower Extremities1
4CompletedPreventionFentanyl / Pain, Chronic / Remifentanil / Sternotomy1
4CompletedPreventionHeart Diseases / Hyperglycemias1
4CompletedPreventionHyperalgesia2
4CompletedPreventionIntubation, Endotracheal1
4CompletedPreventionMyocardial Ischemic Reperfusion Injury1
4CompletedPreventionOpen Craniotomy1
4CompletedPreventionPostoperative Confusion1
4CompletedPreventionPostoperative pain2
4CompletedPreventionSleep Apnea Syndromes / Sleep Apnea, Obstructive1
4CompletedPreventionSupratentorial Neoplasms1
4CompletedPreventionThyroidectomy1
4CompletedPreventionUpper Respiratory Infections1
4CompletedScreeningAnaesthesia therapy / Neuromuscular Blockade1
4CompletedScreeningPatients Undergoing Major Abdominal Surgery / Postoperative Confusion1
4CompletedSupportive CareColonoscopy1
4CompletedSupportive CareHypothermia1
4CompletedSupportive CareIntubation; Difficult1
4CompletedSupportive CareRespiratory Distress Syndrome (RDS)1
4CompletedSupportive CareTranscervical Resection of Endometrium / Transcervical Resection of Fibroids / Transcervical Resection of Polyp1
4CompletedSupportive CareUnderdosing of Unspecified General Anesthetics1
4CompletedTreatmentAdverse Effects / Labour Pain / Satisfaction1
4CompletedTreatmentAnaesthesia therapy2
4CompletedTreatmentAnesthetics / Anesthetics, Intravenous / Cardiopulmonary Bypass / Pharmacology1
4CompletedTreatmentChronic Calculous Cholecystitis1
4CompletedTreatmentCoughing / High Blood Pressure (Hypertension)1
4CompletedTreatmentDeep Sedation / Delayed Emergence From Anesthesia1
4CompletedTreatmentDiagnostic Colonoscopy Screening1
4CompletedTreatmentDrug Usage1
4CompletedTreatmentEfficacy and Safety of Mivacurium Chloride for Pediatric Patients1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Myocardial Ischemia / Tachycardia1
4CompletedTreatmentInduction of Anaesthesia1
4CompletedTreatmentLabour Pain1
4CompletedTreatmentLabour / Pain1
4CompletedTreatmentLung Function1
4CompletedTreatmentMuscle Relaxation1
4CompletedTreatmentOpioid Induced Pharyngeal and Esophageal Dysfunction1
4CompletedTreatmentOpioid Induced Swallowing Disorders1
4CompletedTreatmentOsteoarthritis (OA) / Pain, Chronic1
4CompletedTreatmentPain4
4CompletedTreatmentPain Relief in Labour1
4CompletedTreatmentFunctional disorders of the biliary tract / Pancreatic Diseases1
4CompletedTreatmentPancreatic Stone Disease1
4CompletedTreatmentPediatric Rigid Bronchoscopy1
4CompletedTreatmentRenal Stones1
4CompletedTreatmentRespiration, Artificial / Respiratory Insufficiency / Sedation, Conscious1
4CompletedTreatmentSedation therapy1
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
4Enrolling by InvitationTreatmentAnterior Cervical Discectomy and Fusion (ACDF)1
4Not Yet RecruitingPreventionCritical Illness1
4Not Yet RecruitingScreeningCerebral Oxygen Saturation / Hypotension Drug-Induced1
4Not Yet RecruitingSupportive CareBronchoscopy1
4Not Yet RecruitingSupportive CareIntubating Conditions1
4Not Yet RecruitingTreatmentAnaesthesia therapy / Electroconvulsive Therapy1
4RecruitingNot AvailableGeneral Surgery1
4RecruitingBasic SciencePharyngeal Dysfunction / Pharyngeal Swallowing1
4RecruitingDiagnosticBispectral Index / Induction of anesthesia therapy / Target Controlled Infusion (TCI)1
4RecruitingPreventionDrug Usage1
4RecruitingPreventionIntra-abdominal and Intrapelvic Surgery / Intra-abdominal Surgery1
4RecruitingSupportive CareAnaesthesia therapy1
4RecruitingSupportive CareAnesthesia, Conduction / Drug Interactions1
4RecruitingSupportive CareLocal Anesthesia1
4RecruitingTreatmentLabour Pain1
4RecruitingTreatmentPostoperative pain1
4RecruitingTreatmentRespiratory Distress Syndrome, Newborn1
4TerminatedDiagnosticVentricular Dysfunction / Young Healthy Adults1
4TerminatedPreventionCarotid Artery Stenosis1
4TerminatedSupportive CarePain1
4TerminatedTreatmentAnaesthesia therapy1
4TerminatedTreatmentAnalgesia / Sedation therapy1
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 StatusNot AvailablePolyps, Nasal1
4Unknown StatusBasic ScienceHyperalgesia4
4Unknown StatusPreventionAcute Agitation1
4Unknown StatusPreventionDelirium1
4Unknown StatusSupportive CareLung Cancers1
4Unknown StatusTreatmentAdrenal Suppression / Hemodynamics Instability1
4Unknown StatusTreatmentAnaesthesia therapy / Hemodynamics / Oxidative Stress1
4Unknown StatusTreatmentGoiter, Nodular1
4Unknown StatusTreatmentHaemodynamic Rebound1
4Unknown StatusTreatmentHemodynamics / Hysteroscopy / Sedation therapy1
Not AvailableCompletedNot AvailableAnaesthesia therapy2
Not AvailableCompletedNot AvailableAnaesthesia therapy / Effects of Dexmedetomidine / Elderly Patients / Emergence From Anesthesia / Recovery From Anesthesia1
Not AvailableCompletedNot AvailableAnalgesia1
Not AvailableCompletedNot AvailableCardiac Dysrhythmia / Coronary Artery Bypass Graft / Dexmedetomidine / Hypokalaemia / Remifentanil1
Not AvailableCompletedNot AvailableComplication of Labor and/or Delivery1
Not AvailableCompletedNot AvailableEpilepsies1
Not AvailableCompletedNot AvailableHead and Neck Disorder / Pain1
Not AvailableCompletedNot AvailableHypotension, Controlled1
Not AvailableCompletedNot AvailableTraumatic Brain Injury (TBI)1
Not AvailableCompletedBasic ScienceCritical Care / Deep Sedation / Sedation, Conscious1
Not AvailableCompletedBasic ScienceDrug Overdose1
Not AvailableCompletedBasic ScienceLumbar Surgery1
Not AvailableCompletedDiagnosticAnaesthesia therapy1
Not AvailableCompletedDiagnosticCancer of the Ovary / Cervical Cancers / Gallbladder Inflammation / Ovarian Cysts / Uterine Leiomyomas1
Not AvailableCompletedDiagnosticEndoscopic Sinus Surgery1
Not AvailableCompletedHealth Services ResearchPain1
Not AvailableCompletedOtherAnaesthesia therapy / General Surgery / Ophthalmic1
Not AvailableCompletedOtherObese1
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 AvailableCompletedPreventionGeneral Surgery With Endotracheal Intubation1
Not AvailableCompletedPreventionGeneral Surgery / Prostate Cancer1
Not AvailableCompletedPreventionHealthy Volunteers2
Not AvailableCompletedPreventionHemodynamic Responses During Tracheal Intubation1
Not AvailableCompletedPreventionIntraoperative Awareness1
Not AvailableCompletedPreventionIntubation, Intratracheal1
Not AvailableCompletedPreventionPain2
Not AvailableCompletedPreventionPostoperative pain1
Not AvailableCompletedPreventionProphylaxis against postoperative nausea and vomiting1
Not AvailableCompletedPreventionRespiratory Complications2
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 CareStrabismus1
Not AvailableCompletedTreatmentAdult Intracranial Tumor / Adult Solid Tumor1
Not AvailableCompletedTreatmentAdverse Effect of Other General Anesthetics1
Not AvailableCompletedTreatmentAnaesthesia therapy1
Not AvailableCompletedTreatmentAnaesthesia therapy / Neuromuscular Blockade1
Not AvailableCompletedTreatmentAnaesthesia therapy / Pain1
Not AvailableCompletedTreatmentAnxiety Preoperative / Midazolam Premedication / Premedication1
Not AvailableCompletedTreatmentDrug Usage1
Not AvailableCompletedTreatmentFractures, Compression1
Not AvailableCompletedTreatmentIschaemic Heart Diseases1
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 AvailableCompletedTreatmentShort Duration Analgesia / Skull Pin Insertion1
Not AvailableCompletedTreatmentSurgical Blood Loss1
Not AvailableNot Yet RecruitingPreventionEndoscopic Sinus Surgery2
Not AvailableNot Yet RecruitingPreventionRobotic-assisted Laparoscopic Radical Prostatectomy1
Not AvailableNot Yet RecruitingSupportive CareAnaesthesia therapy / Pain1
Not AvailableNot Yet RecruitingSupportive CareCardiovascular Disease (CVD)1
Not AvailableNot Yet RecruitingTreatmentAnaesthesia therapy / Sedation therapy / Surgery, Cardiac1
Not AvailableNot Yet RecruitingTreatmentNociceptive Pain / Surgical Procedure, Unspecified1
Not AvailableNot Yet RecruitingTreatmentSurgery, Cardiac1
Not AvailableRecruitingNot AvailableAnaesthesia therapy1
Not AvailableRecruitingNot AvailableGeneral Anesthetics Toxicity / Lymphocyte Destruction / Metastatic Colorectal Cancers / Molecular Mechanism of Pharmacological Action / Survival Rate1
Not AvailableRecruitingNot AvailableIntravenous Anesthesia1
Not AvailableRecruitingNot AvailableLabor; Prolonged, First Stage / Labor; Prolonged, Second Stage / Labour Pain1
Not AvailableRecruitingNot AvailableOocyte Retrieval / Sedation, Conscious / Ventilatory Depression1
Not AvailableRecruitingBasic SciencePain1
Not AvailableRecruitingDiagnosticAnaesthesia therapy / Pain1
Not AvailableRecruitingOtherPancreatic Cancer or Distal CBD Cancer1
Not AvailableRecruitingOtherShort Stature1
Not AvailableRecruitingPreventionCoughing1
Not AvailableRecruitingPreventionDelirium1
Not AvailableRecruitingPreventionNeoplasms, Thyroid1
Not AvailableRecruitingPreventionPeripheral Obliterative Arteriopathy1
Not AvailableRecruitingScreeningShock, Septic1
Not AvailableRecruitingSupportive CareInguinal Hernias / Postoperative pain1
Not AvailableRecruitingSupportive CarePostoperative pain / Undescended Testis1
Not AvailableRecruitingTreatmentAcute Hypercapnic Respiratory Failure1
Not AvailableRecruitingTreatmentAnaesthesia therapy / Children / Pain1
Not AvailableRecruitingTreatmentBariatric Surgery Candidate / Opioids Use / Postoperative pain / Prophylaxis against postoperative nausea and vomiting1
Not AvailableRecruitingTreatmentBrain / Sedation therapy1
Not AvailableRecruitingTreatmentBronchoscopy / Sedation therapy2
Not AvailableRecruitingTreatmentColonoscopy1
Not AvailableRecruitingTreatmentAdjunct to general anesthesia therapy1
Not AvailableTerminatedNot AvailableAnaesthesia therapy1
Not AvailableTerminatedDiagnosticParkinson's Disease (PD)1
Not AvailableTerminatedPreventionGeneral Surgery1
Not AvailableTerminatedTreatmentAnaesthesia therapy / Surgery, Cardiac1
Not AvailableTerminatedTreatmentChronic Rhinosinusitis1
Not AvailableTerminatedTreatmentPain1
Not AvailableTerminatedTreatmentShoulder Dislocation1
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 StatusTreatmentHaemodynamic Fluctuations During Off-pump CABG1
Not AvailableWithdrawnPreventionNeoplasms, Brain1

Pharmacoeconomics

Manufacturers
  • Bioniche teoranta
Packagers
  • Abbott Laboratories Ltd.
  • Bioniche Pharma
  • Hospira Inc.
Dosage forms
FormRouteStrength
Powder, for solutionIntravenous1 mg
Powder, for solutionIntravenous2 mg
Injection, powder, lyophilized, for solutionIntravenous1 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous2 mg/2mL
Injection, powder, lyophilized, for solutionIntravenous5 mg/5mL
Powder, for solutionIntravenous5 mg
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)
US5019583No1993-07-122010-07-12Us
US5866591Yes1998-03-102018-03-10Us

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
Human
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
Human
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
Human
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 September 21, 2018 00:06