remifentanil 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
opioid receptor agonists, analgesics, fentanyl derivatives 2363 132875-61-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • remifentanil
  • remifentanyl
  • ramifentanyl
  • remifentanil hydrochloride
  • remifentanil HCl
Remifentanil is a mu-opioid agonist with rapid onset and peak effect, and short duration of action.
  • Molecular weight: 376.45
  • Formula: C20H28N2O5
  • CLOGP: 1.96
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 0
  • TPSA: 76.15
  • ALOGS: -2.80
  • ROTB: 9

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.10 % Benet LZ, Broccatelli F, Oprea TI
Vd (Volume of distribution) 0.40 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 37 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.30 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.80 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
July 12, 1996 FDA MYLAN INSTITUTIONAL

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Anaphylactic shock 679.25 30.56 178 3560 19977 50581409
Anaphylactic reaction 311.45 30.56 125 3613 53930 50547456
Cardiac arrest 124.10 30.56 77 3661 83574 50517812
Bronchospasm 123.48 30.56 45 3693 14809 50586577
Delayed recovery from anaesthesia 115.82 30.56 23 3715 726 50600660
Circulatory collapse 103.66 30.56 43 3695 19957 50581429
Hypotension 89.70 30.56 98 3640 235371 50366015
Bradycardia 84.70 30.56 55 3683 64371 50537015
Neuromuscular block prolonged 80.86 30.56 16 3722 495 50600891
Hyperthermia malignant 74.98 30.56 16 3722 723 50600663
Tachycardia 73.57 30.56 60 3678 99703 50501683
Serotonin syndrome 70.35 30.56 35 3703 24678 50576708
Blood pressure decreased 64.45 30.56 44 3694 55865 50545521
Stress cardiomyopathy 54.92 30.56 21 3717 7866 50593520
Anaphylactoid reaction 54.91 30.56 17 3721 3389 50597997
Patent ductus arteriosus 52.99 30.56 17 3721 3803 50597583
Exposure during pregnancy 52.34 30.56 54 3684 120961 50480425
Anaphylactoid shock 50.58 30.56 10 3728 308 50601078
Pulseless electrical activity 46.86 30.56 18 3720 6823 50594563
Hyperreflexia 44.34 30.56 16 3722 5102 50596284
Clonus 43.60 30.56 15 3723 4160 50597226
Premature baby 40.74 30.56 22 3716 18315 50583071
Dyskinesia 39.56 30.56 25 3713 27836 50573550
Diabetes insipidus 38.95 30.56 12 3726 2352 50599034
Toxic epidermal necrolysis 35.33 30.56 21 3717 20971 50580415
Drug interaction 33.70 30.56 56 3682 199565 50401821
Subcutaneous emphysema 31.77 30.56 8 3730 749 50600637
Fatigue 31.47 30.56 7 3731 707594 49893792
Trigemino-cardiac reflex 30.58 30.56 5 3733 50 50601336

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Anaphylactic shock 499.38 31.67 143 3519 13193 29557672
Anaphylactic reaction 212.22 31.67 91 3571 27482 29543383
Cardiac arrest 143.01 31.67 103 3559 85488 29485377
Hypotension 109.79 31.67 127 3535 194227 29376638
Hyperthermia malignant 107.91 31.67 28 3634 1756 29569109
Delayed recovery from anaesthesia 104.78 31.67 23 3639 700 29570165
Neuromuscular block prolonged 103.09 31.67 21 3641 442 29570423
Trigemino-cardiac reflex 89.37 31.67 16 3646 163 29570702
Propofol infusion syndrome 86.14 31.67 20 3642 787 29570078
Bradycardia 82.95 31.67 67 3595 65562 29505303
Blood pressure decreased 76.31 31.67 55 3607 45422 29525443
Bronchospasm 74.66 31.67 32 3630 9577 29561288
Airway complication of anaesthesia 72.12 31.67 13 3649 138 29570727
Toxic epidermal necrolysis 69.05 31.67 37 3625 18116 29552749
Drug interaction 66.12 31.67 100 3562 197285 29373580
Ventricular fibrillation 59.45 31.67 32 3630 15801 29555064
Hypoventilation 57.19 31.67 19 3643 2822 29568043
Kounis syndrome 56.68 31.67 17 3645 1812 29569053
Diabetes insipidus 55.96 31.67 18 3644 2416 29568449
Seizure like phenomena 53.69 31.67 13 3649 613 29570252
Drug reaction with eosinophilia and systemic symptoms 47.23 31.67 34 3628 27958 29542907
Arteriospasm coronary 47.06 31.67 16 3646 2549 29568316
Circulatory collapse 46.75 31.67 29 3633 18644 29552221
Recurrence of neuromuscular blockade 41.22 31.67 8 3654 130 29570735
Cardio-respiratory arrest 40.57 31.67 40 3622 50561 29520304
Erythema 40.03 31.67 48 3614 75558 29495307
Anaesthetic complication neurological 39.74 31.67 9 3653 316 29570549
Sinus arrest 38.65 31.67 12 3650 1435 29569430
Anaphylactoid shock 38.58 31.67 9 3653 361 29570504
Status epilepticus 38.23 31.67 21 3641 10773 29560092
Rhabdomyolysis 36.17 31.67 41 3621 60767 29510098
Anaphylactoid reaction 35.16 31.67 12 3650 1933 29568932
Tachycardia 35.13 31.67 44 3618 72366 29498499

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Anaphylactic shock 1132.77 26.86 319 7078 30009 64461326
Anaphylactic reaction 513.49 26.86 217 7180 68447 64422888
Cardiac arrest 245.63 26.86 175 7222 153889 64337446
Delayed recovery from anaesthesia 204.98 26.86 45 7352 1483 64489852
Bronchospasm 179.93 26.86 74 7323 21608 64469727
Hypotension 176.54 26.86 217 7180 380757 64110578
Neuromuscular block prolonged 166.24 26.86 35 7362 942 64490393
Hyperthermia malignant 158.58 26.86 40 7357 2419 64488916
Bradycardia 138.71 26.86 112 7285 118107 64373228
Circulatory collapse 136.86 26.86 70 7327 33662 64457673
Blood pressure decreased 128.07 26.86 94 7303 86105 64405230
Trigemino-cardiac reflex 118.09 26.86 21 7376 223 64491112
Tachycardia 95.69 26.86 101 7296 149478 64341857
Propofol infusion syndrome 92.94 26.86 24 7373 1593 64489742
Diabetes insipidus 92.32 26.86 30 7367 4491 64486844
Airway complication of anaesthesia 89.04 26.86 18 7379 394 64490941
Toxic epidermal necrolysis 87.55 26.86 54 7343 37112 64454223
Anaphylactoid reaction 86.94 26.86 29 7368 4709 64486626
Drug interaction 86.28 26.86 151 7246 361932 64129403
Anaphylactoid shock 83.57 26.86 19 7378 735 64490600
Ventricular fibrillation 72.82 26.86 41 7356 23819 64467516
Recurrence of neuromuscular blockade 69.20 26.86 13 7384 191 64491144
Hypoventilation 69.14 26.86 26 7371 5980 64485355
Kounis syndrome 65.54 26.86 21 7376 3004 64488331
Pulseless electrical activity 65.22 26.86 31 7366 12708 64478627
Erythema 63.73 26.86 92 7305 186978 64304357
Serotonin syndrome 60.89 26.86 44 7353 39238 64452097
Stress cardiomyopathy 58.26 26.86 26 7371 9231 64482104
Fatigue 56.97 26.86 9 7388 748721 63742614
Rhabdomyolysis 55.15 26.86 60 7337 91666 64399669
Post procedural complication 52.75 26.86 32 7365 21321 64470014
Upper airway obstruction 50.21 26.86 14 7383 1244 64490091
Respiratory depression 47.54 26.86 31 7366 23412 64467923
Sinus arrest 45.33 26.86 16 7381 3074 64488261
Seizure like phenomena 42.17 26.86 13 7384 1639 64489696
Clonus 41.27 26.86 18 7379 6049 64485286
Death 41.03 26.86 4 7393 482701 64008634
Arteriospasm coronary 39.75 26.86 17 7380 5448 64485887
Urticaria 39.63 26.86 65 7332 147252 64344083
Pain 39.12 26.86 8 7389 553503 63937832
Ventricular tachycardia 39.09 26.86 32 7365 34233 64457102
Arthralgia 36.71 26.86 4 7393 442256 64049079
Cardio-respiratory arrest 35.82 26.86 50 7347 98343 64392992
Anaesthetic complication neurological 35.80 26.86 9 7388 536 64490799
Nausea 33.35 26.86 25 7372 785775 63705560
Anaesthetic complication 32.74 26.86 12 7385 2567 64488768
Procedural hypotension 32.44 26.86 11 7386 1875 64489460
Respiratory arrest 32.42 26.86 35 7362 52950 64438385
Hyperreflexia 32.38 26.86 16 7381 7132 64484203
Type I hypersensitivity 32.36 26.86 13 7384 3561 64487774
Blood pressure immeasurable 32.32 26.86 11 7386 1897 64489438
Drug reaction with eosinophilia and systemic symptoms 31.75 26.86 35 7362 54182 64437153
Subcutaneous emphysema 30.12 26.86 10 7387 1599 64489736
Fall 29.47 26.86 6 7391 416820 64074515
Electrocardiogram ST segment elevation 29.22 26.86 15 7382 7244 64484091
Capillary nail refill test abnormal 28.67 26.86 5 7392 47 64491288
Oxygen saturation decreased 28.41 26.86 47 7350 107129 64384206
Dyskinesia 27.64 26.86 28 7369 39360 64451975

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N01AH06 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, GENERAL
Opioid anesthetics
MeSH PA D000700 Analgesics
MeSH PA D000701 Analgesics, Opioid
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D009294 Narcotics
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
CHEBI has role CHEBI:35482 narcotic analgesic
CHEBI has role CHEBI:35717 hypnotics
CHEBI has role CHEBI:38877 intravenous anesthetics
CHEBI has role CHEBI:55322 mu-opioid agonists
FDA MoA N0000175684 Full Opioid Agonists
FDA EPC N0000175690 Opioid Agonist

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
General anesthesia indication 50697003
Local anesthesia indication 386761002
Acute postoperative pain indication 107401000119105
Low blood pressure contraindication 45007003
Bradycardia contraindication 48867003
Decreased respiratory function contraindication 80954004




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.07 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Mu-type opioid receptor GPCR AGONIST WOMBAT-PK CHEMBL
Mu-type opioid receptor GPCR IC50 9.22 CHEMBL

External reference:

IDSource
4024040 VUID
N0000022045 NUI
D01177 KEGG_DRUG
132539-07-2 SECONDARY_CAS_RN
4020990 VANDF
4024040 VANDF
C0246631 UMLSCUI
CHEBI:8802 CHEBI
CHEMBL1005 ChEMBL_ID
DB00899 DRUGBANK_ID
CHEMBL1201120 ChEMBL_ID
D000077208 MESH_DESCRIPTOR_UI
60815 PUBCHEM_CID
7292 IUPHAR_LIGAND_ID
6924 INN_ID
P10582JYYK UNII
236540 RXNORM
181723 MMSL
186043 MMSL
5415 MMSL
d04034 MMSL
006250 NDDF
006251 NDDF
108376001 SNOMEDCT_US
108379008 SNOMEDCT_US
386839004 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
REMIFENTANIL HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0143-9391 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS ANDA 27 sections
REMIFENTANIL HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0143-9392 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 mg INTRAVENOUS ANDA 27 sections
REMIFENTANIL HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0143-9393 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 5 mg INTRAVENOUS ANDA 27 sections
Remifentanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 63323-723 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS ANDA 30 sections
Remifentanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 63323-723 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS ANDA 30 sections
Remifentanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 63323-724 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS ANDA 30 sections
Remifentanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 63323-725 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS ANDA 30 sections
Ultiva HUMAN PRESCRIPTION DRUG LABEL 1 67457-198 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS NDA 30 sections
Ultiva HUMAN PRESCRIPTION DRUG LABEL 1 67457-912 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS NDA 30 sections
Ultiva HUMAN PRESCRIPTION DRUG LABEL 1 67457-913 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS NDA 30 sections
Ultiva HUMAN PRESCRIPTION DRUG LABEL 1 67457-914 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS NDA 30 sections
REMIFENTANIL HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 68475-505 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS ANDA 27 sections
REMIFENTANIL HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 68475-506 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 mg INTRAVENOUS ANDA 27 sections
REMIFENTANIL HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 68475-507 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 5 mg INTRAVENOUS ANDA 27 sections