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
Oct. 20, 2006 PMDA Janssen Pharmaceutical K.K.

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 748.04 33.93 193 3745 21547 56266582
Anaphylactic reaction 321.18 33.93 129 3809 58866 56229263
Cardiac arrest 143.96 33.93 84 3854 86230 56201899
Bronchospasm 131.01 33.93 47 3891 15622 56272507
Delayed recovery from anaesthesia 122.89 33.93 24 3914 734 56287395
Circulatory collapse 104.27 33.93 43 3895 20760 56267369
Bradycardia 97.64 33.93 60 3878 67444 56220685
Hypotension 94.32 33.93 101 3837 250407 56037722
Neuromuscular block prolonged 81.54 33.93 16 3922 501 56287628
Tachycardia 79.67 33.93 63 3875 105813 56182316
Hyperthermia malignant 75.59 33.93 16 3922 735 56287394
Serotonin syndrome 69.84 33.93 35 3903 26455 56261674
Blood pressure decreased 64.42 33.93 44 3894 59006 56229123
Exposure during pregnancy 58.36 33.93 59 3879 136283 56151846
Anaphylactoid reaction 55.34 33.93 17 3921 3489 56284640
Stress cardiomyopathy 54.90 33.93 21 3917 8315 56279814
Patent ductus arteriosus 53.34 33.93 17 3921 3934 56284195
Anaphylactoid shock 50.66 33.93 10 3928 323 56287806
Pulseless electrical activity 47.35 33.93 18 3920 7006 56281123
Hyperreflexia 44.79 33.93 16 3922 5234 56282895
Clonus 44.14 33.93 15 3923 4234 56283895
Premature delivery 44.09 33.93 26 3912 27034 56261095
Premature baby 40.90 33.93 22 3916 19183 56268946
Ventricular tachycardia 40.65 33.93 21 3917 16880 56271249
Dyskinesia 39.80 33.93 25 3913 29083 56259046
Diabetes insipidus 39.24 33.93 12 3926 2425 56285704
Toxic epidermal necrolysis 38.07 33.93 22 3916 22020 56266109
Drug interaction 38.02 33.93 59 3879 209696 56078433
Fatigue 34.01 33.93 7 3931 788545 55499584

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 514.71 32.08 148 3736 13997 31679463
Anaphylactic reaction 226.68 32.08 97 3787 29456 31664004
Cardiac arrest 149.38 32.08 107 3777 88955 31604505
Hyperthermia malignant 139.34 32.08 35 3849 1949 31691511
Hypotension 120.64 32.08 136 3748 204482 31488978
Delayed recovery from anaesthesia 110.15 32.08 24 3860 713 31692747
Neuromuscular block prolonged 103.31 32.08 21 3863 442 31693018
Bradycardia 99.62 32.08 76 3808 69251 31624209
Trigemino-cardiac reflex 89.18 32.08 16 3868 167 31693293
Bronchospasm 87.17 32.08 36 3848 9936 31683524
Propofol infusion syndrome 85.66 32.08 20 3864 815 31692645
Blood pressure decreased 80.87 32.08 58 3826 48033 31645427
Toxic epidermal necrolysis 78.08 32.08 41 3843 19483 31673977
Airway complication of anaesthesia 72.25 32.08 13 3871 138 31693322
Ventricular fibrillation 68.10 32.08 37 3847 18811 31674649
Drug interaction 64.11 32.08 101 3783 208442 31485018
Kounis syndrome 63.18 32.08 19 3865 2065 31691395
Diabetes insipidus 59.48 32.08 19 3865 2521 31690939
Hypoventilation 55.92 32.08 19 3865 3055 31690405
Drug reaction with eosinophilia and systemic symptoms 54.57 32.08 38 3846 29980 31663480
Seizure like phenomena 53.10 32.08 13 3871 649 31692811
Cardio-respiratory arrest 45.84 32.08 43 3841 51683 31641777
Circulatory collapse 45.54 32.08 29 3855 19715 31673745
Arteriospasm coronary 45.35 32.08 16 3868 2875 31690585
Anaesthetic complication neurological 39.84 32.08 9 3875 316 31693144
Recurrence of neuromuscular blockade 38.96 32.08 8 3876 177 31693283
Anaphylactoid shock 38.67 32.08 9 3875 361 31693099
Sinus arrest 38.34 32.08 12 3872 1489 31691971
Erythema 38.05 32.08 48 3836 80357 31613103
Neuromuscular blockade 36.50 32.08 8 3876 244 31693216
Status epilepticus 36.19 32.08 21 3863 12085 31681375
Rhabdomyolysis 35.02 32.08 41 3843 63540 31629920
Anaphylactoid reaction 34.33 32.08 12 3872 2097 31691363
Tachycardia 33.70 32.08 44 3840 76163 31617297
Death 33.33 32.08 3 3881 360566 31332894

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 1214.35 25.77 339 7481 32151 70888473
Anaphylactic reaction 533.02 25.77 226 7594 74748 70845876
Cardiac arrest 271.78 25.77 186 7634 159648 70760976
Delayed recovery from anaesthesia 217.09 25.77 47 7773 1510 70919114
Bronchospasm 199.75 25.77 80 7740 22712 70897912
Hypotension 192.51 25.77 229 7591 404152 70516472
Hyperthermia malignant 192.03 25.77 47 7773 2614 70918010
Bradycardia 167.77 25.77 126 7694 124489 70796135
Neuromuscular block prolonged 167.40 25.77 35 7785 948 70919676
Circulatory collapse 136.12 25.77 70 7750 35404 70885220
Blood pressure decreased 130.84 25.77 96 7724 91419 70829205
Trigemino-cardiac reflex 117.91 25.77 21 7799 235 70920389
Tachycardia 99.43 25.77 104 7716 158442 70762182
Toxic epidermal necrolysis 99.24 25.77 59 7761 39498 70881126
Diabetes insipidus 96.60 25.77 31 7789 4640 70915984
Propofol infusion syndrome 92.28 25.77 24 7796 1705 70918919
Drug interaction 90.07 25.77 155 7665 381286 70539338
Airway complication of anaesthesia 89.66 25.77 18 7802 396 70920228
Anaphylactoid reaction 86.49 25.77 29 7791 4978 70915646
Kounis syndrome 84.56 25.77 26 7794 3385 70917239
Anaphylactoid shock 84.06 25.77 19 7801 745 70919879
Ventricular fibrillation 82.86 25.77 46 7774 27065 70893559
Pulseless electrical activity 71.49 25.77 33 7787 13182 70907442
Hypoventilation 67.81 25.77 26 7794 6556 70914068
Recurrence of neuromuscular blockade 66.02 25.77 13 7807 258 70920366
Erythema 63.38 25.77 93 7727 199470 70721154
Fatigue 61.50 25.77 9 7811 824310 70096314
Stress cardiomyopathy 60.86 25.77 27 7793 9835 70910789
Serotonin syndrome 59.69 25.77 44 7776 42070 70878554
Ventricular tachycardia 58.36 25.77 41 7779 36382 70884242
Rhabdomyolysis 54.96 25.77 60 7760 95700 70824924
Post procedural complication 52.92 25.77 32 7788 22049 70898575
Upper airway obstruction 50.34 25.77 14 7806 1282 70919342
Sinus arrest 49.17 25.77 17 7803 3198 70917426
Respiratory depression 47.02 25.77 31 7789 24800 70895824
Neuromuscular blockade 45.89 25.77 11 7809 559 70920065
Clonus 44.68 25.77 19 7801 6249 70914375
Seizure like phenomena 42.20 25.77 13 7807 1702 70918922
Death 41.84 25.77 4 7816 510057 70410567
Cardio-respiratory arrest 41.07 25.77 53 7767 100624 70820000
Anaesthetic complication 40.55 25.77 14 7806 2622 70918002
Pain 40.19 25.77 10 7810 628806 70291818
Arteriospasm coronary 38.80 25.77 17 7803 6007 70914617
Arthralgia 38.63 25.77 5 7815 503385 70417239
Drug reaction with eosinophilia and systemic symptoms 37.97 25.77 39 7781 57974 70862650
Urticaria 36.66 25.77 65 7755 162984 70757640
Anaesthetic complication neurological 35.67 25.77 9 7811 566 70920058
Nausea 34.84 25.77 26 7794 852062 70068562
Respiratory arrest 33.04 25.77 35 7785 53898 70866726
Blood pressure immeasurable 32.50 25.77 11 7809 1941 70918683
Procedural hypotension 32.42 25.77 11 7809 1955 70918669
Hyperreflexia 32.36 25.77 16 7804 7426 70913198
Type I hypersensitivity 32.31 25.77 13 7807 3719 70916905
Postoperative delirium 32.16 25.77 7 7813 230 70920394
Electrocardiogram ST segment elevation 32.04 25.77 16 7804 7588 70913036
Fall 30.49 25.77 6 7814 444090 70476534
Subcutaneous emphysema 30.07 25.77 10 7810 1672 70918952
Oxygen saturation decreased 29.56 25.77 49 7771 116380 70804244
Dyskinesia 29.42 25.77 29 7791 41045 70879579
Capillary nail refill test abnormal 28.86 25.77 5 7815 47 70920577
Acute generalised exanthematous pustulosis 28.61 25.77 19 7801 15378 70905246
Exposure during pregnancy 27.96 25.77 41 7779 87676 70832948
Respiratory acidosis 27.50 25.77 16 7804 10265 70910359
Pulmonary alveolar haemorrhage 27.38 25.77 16 7804 10353 70910271
Hypoxic-ischaemic encephalopathy 26.79 25.77 14 7806 7294 70913330
Dizziness 26.65 25.77 9 7811 464132 70456492
Prinzmetal angina 26.51 25.77 9 7811 1603 70919021
Shock 26.13 25.77 27 7793 40398 70880226
Torsade de pointes 25.82 25.77 19 7801 18097 70902527

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
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
132539-07-2 SECONDARY_CAS_RN
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