remifentanil 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,AKT2,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,ITK,JAK2,MAP3K21,MAP3K7,MAPK12,MAPK7,MAPK9,MAPKAPK2,MET,MTOR,NTRK2,PAK4,PDK1,PDK2,PDK4,PDPK1,PIK3CB,PIM2,PLK1,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TTK 45
kinase-selectivity-class AXL,EPHB4,GRK2,PDK4,STK33 5
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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 1111.21 34.54 278 5282 31339 90591548
Anaphylactic reaction 510.51 34.54 194 5366 87330 90535557
Cardiac arrest 229.85 34.54 117 5443 104818 90518069
Anaesthetic complication neurological 217.86 34.54 38 5522 703 90622184
Hypotension 216.14 34.54 170 5390 325227 90297660
Bronchospasm 180.64 34.54 62 5498 20647 90602240
Bradycardia 161.96 34.54 86 5474 83761 90539126
Delayed recovery from anaesthesia 148.88 34.54 29 5531 1001 90621886
Circulatory collapse 126.15 34.54 50 5510 24854 90598033
Tachycardia 118.76 34.54 89 5471 157584 90465303
Drug interaction 96.81 34.54 101 5459 276352 90346535
Premature delivery 92.82 34.54 46 5514 38716 90584171
Blood pressure decreased 91.38 34.54 57 5503 74838 90548049
Procedural hypotension 86.47 34.54 20 5540 1580 90621307
Neuromuscular block prolonged 85.95 34.54 17 5543 635 90622252
Serotonin syndrome 82.02 34.54 42 5518 37845 90585042
Hyperthermia malignant 74.29 34.54 17 5543 1281 90621606
Recurrence of neuromuscular blockade 70.65 34.54 12 5548 188 90622699
Oxygen saturation decreased 70.61 34.54 56 5504 107427 90515460
Anaphylactoid reaction 70.43 34.54 21 5539 4447 90618440
Pulseless electrical activity 63.55 34.54 23 5537 8909 90613978
Exposure during pregnancy 60.92 34.54 74 5486 238336 90384551
Stress cardiomyopathy 57.92 34.54 24 5536 13331 90609556
Maternal exposure during delivery 55.98 34.54 17 5543 3829 90619058
Hypoxia 54.69 34.54 41 5519 72358 90550529
Diabetes insipidus 54.57 34.54 16 5544 3196 90619691
Patent ductus arteriosus 53.09 34.54 17 5543 4552 90618335
Apnoea 51.51 34.54 20 5540 9394 90613493
Transcranial electrical motor evoked potential monitoring abnormal 50.48 34.54 7 5553 24 90622863
Anaphylactoid shock 49.23 34.54 10 5550 428 90622459
Sinus tachycardia 48.70 34.54 27 5533 28486 90594401
Respiratory depression 48.00 34.54 22 5538 15553 90607334
Hyperreflexia 46.82 34.54 17 5543 6640 90616247
Hypoventilation 46.70 34.54 16 5544 5280 90617607
Premature baby 46.29 34.54 25 5535 25052 90597835
Fatigue 45.71 34.54 8 5552 1154015 89468872
Clonus 45.41 34.54 16 5544 5734 90617153
Ventricular tachycardia 41.11 34.54 23 5537 24685 90598202
Local anaesthetic systemic toxicity 40.57 34.54 13 5547 3487 90619400
Dystonia 40.35 34.54 20 5540 16799 90606088
Erythema 39.85 34.54 59 5501 229187 90393700
Respiratory arrest 39.70 34.54 25 5535 33286 90589601
Torsade de pointes 39.26 34.54 19 5541 15163 90607724
Toxic epidermal necrolysis 37.73 34.54 24 5536 32504 90590383
Dyskinesia 37.58 34.54 25 5535 36509 90586378
Postoperative delirium 36.91 34.54 7 5553 209 90622678

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 802.07 30.03 238 5407 23279 42592411
Anaesthetic complication neurological 300.17 30.03 56 5589 680 42615010
Anaphylactic reaction 275.02 30.03 127 5518 42616 42573074
Hyperthermia malignant 243.83 30.03 59 5586 2599 42613091
Cardiac arrest 184.43 30.03 136 5509 109184 42506506
Hypotension 163.90 30.03 185 5460 257446 42358244
Delayed recovery from anaesthesia 160.43 30.03 36 5609 1133 42614557
Diabetes insipidus 149.90 30.03 43 5602 3670 42612020
Bradycardia 147.74 30.03 108 5537 85376 42530314
Neuromuscular block prolonged 118.14 30.03 25 5620 594 42615096
Drug interaction 98.92 30.03 147 5498 266852 42348838
Bronchospasm 94.39 30.03 42 5603 12843 42602847
Trigemino-cardiac reflex 94.28 30.03 19 5626 352 42615338
Propofol infusion syndrome 91.45 30.03 23 5622 1186 42614504
Toxic epidermal necrolysis 88.75 30.03 51 5594 26699 42588991
Negative pressure pulmonary oedema 84.40 30.03 19 5626 606 42615084
Recurrence of neuromuscular blockade 81.25 30.03 16 5629 262 42615428
Blood pressure decreased 75.11 30.03 62 5583 58270 42557420
Airway complication of anaesthesia 74.04 30.03 14 5631 183 42615507
Drug reaction with eosinophilia and systemic symptoms 72.15 30.03 53 5592 42022 42573668
Respiratory depression 70.78 30.03 39 5606 18829 42596861
Rhabdomyolysis 66.99 30.03 66 5579 77953 42537737
Hypoventilation 61.64 30.03 22 5623 3780 42611910
Ventricular fibrillation 58.64 30.03 41 5604 30082 42585608
Laryngospasm 58.34 30.03 18 5627 1970 42613720
Airway peak pressure increased 57.01 30.03 11 5634 161 42615529
Cardio-respiratory arrest 56.74 30.03 53 5592 58583 42557107
Kounis syndrome 56.54 30.03 20 5625 3348 42612342
Circulatory collapse 50.31 30.03 34 5611 23602 42592088
Seizure like phenomena 45.58 30.03 13 5632 1084 42614606
Tachycardia 45.10 30.03 61 5584 101026 42514664
Status epilepticus 44.55 30.03 27 5618 15551 42600139
Fatigue 43.28 30.03 4 5641 435637 42180053
Sinus arrest 40.80 30.03 14 5631 2142 42613548
Anaphylactoid shock 40.72 30.03 10 5635 467 42615223
Oxygen saturation decreased 40.00 30.03 46 5599 64641 42551049
Arteriospasm coronary 39.74 30.03 17 5628 4721 42610969
Intensive care unit acquired weakness 39.32 30.03 12 5633 1266 42614424
Haematuria traumatic 38.60 30.03 9 5636 336 42615354
Death 38.24 30.03 8 5637 471177 42144513
Upper airway obstruction 35.66 30.03 10 5635 784 42614906
Erythema 34.58 30.03 56 5589 108737 42506953
Hypercapnia 34.57 30.03 16 5629 5345 42610345
Prinzmetal angina 34.45 30.03 11 5634 1346 42614344
Haemodynamic instability 33.95 30.03 21 5624 12536 42603154
Neuromuscular blockade 33.24 30.03 8 5637 343 42615347
Pulseless electrical activity 33.17 30.03 18 5627 8419 42607271
Hyperkalaemia 32.04 30.03 46 5599 80412 42535278
Hypothermia 31.50 30.03 20 5625 12495 42603195

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 1854.61 27.02 511 10550 51035 110527203
Anaphylactic reaction 768.71 27.02 322 10739 113978 110464260
Cardiac arrest 397.36 27.02 246 10815 196507 110381731
Hypotension 369.22 27.02 349 10712 523500 110054738
Delayed recovery from anaesthesia 293.37 27.02 63 10998 2152 110576086
Hyperthermia malignant 283.54 27.02 68 10993 3832 110574406
Bradycardia 282.47 27.02 182 10879 155335 110422903
Bronchospasm 253.30 27.02 100 10961 30139 110548099
Diabetes insipidus 202.67 27.02 58 11003 6512 110571726
Drug interaction 191.19 27.02 242 10819 499941 110078297
Neuromuscular block prolonged 179.52 27.02 38 11023 1209 110577029
Circulatory collapse 164.32 27.02 82 10979 42911 110535327
Blood pressure decreased 161.68 27.02 115 10946 114976 110463262
Tachycardia 154.96 27.02 149 10912 226496 110351742
Trigemino-cardiac reflex 125.67 27.02 24 11037 447 110577791
Recurrence of neuromuscular blockade 121.50 27.02 23 11038 408 110577830
Negative pressure pulmonary oedema 116.22 27.02 24 11037 675 110577563
Toxic epidermal necrolysis 114.27 27.02 71 10990 56656 110521582
Respiratory depression 110.47 27.02 57 11004 31944 110546294
Procedural hypotension 104.34 27.02 28 11033 2477 110575761
Hypoventilation 101.54 27.02 36 11025 8045 110570193
Airway complication of anaesthesia 99.35 27.02 21 11040 663 110577575
Propofol infusion syndrome 98.76 27.02 27 11034 2562 110575676
Rhabdomyolysis 97.34 27.02 87 10974 120314 110457924
Kounis syndrome 96.28 27.02 32 11029 5893 110572345
Anaphylactoid reaction 91.84 27.02 32 11029 6794 110571444
Pulseless electrical activity 91.83 27.02 41 11020 16716 110561522
Ventricular fibrillation 89.04 27.02 54 11007 41259 110536979
Fatigue 87.20 27.02 10 11051 1215948 109362290
Laryngospasm 87.13 27.02 28 11033 4640 110573598
Anaphylactoid shock 86.36 27.02 20 11041 966 110577272
Oxygen saturation decreased 84.86 27.02 91 10970 156891 110421347
Serotonin syndrome 82.73 27.02 59 11002 59094 110519144
Airway peak pressure increased 72.29 27.02 16 11045 629 110577609
Erythema 70.94 27.02 114 10947 291333 110286905
Hypoxia 68.08 27.02 74 10987 129441 110448797
Drug reaction with eosinophilia and systemic symptoms 67.66 27.02 60 11001 82035 110496203
Local anaesthetic systemic toxicity 67.04 27.02 24 11037 5513 110572725
Stress cardiomyopathy 65.87 27.02 32 11029 15774 110562464
Haemodynamic instability 65.53 27.02 36 11025 22852 110555386
Cardio-respiratory arrest 64.07 27.02 68 10993 115768 110462470
Ventricular tachycardia 63.38 27.02 47 11014 49962 110528276
Hypercapnia 63.38 27.02 28 11033 11131 110567107
Postoperative delirium 61.59 27.02 15 11046 900 110577338
Pain 61.06 27.02 11 11050 954944 109623294
Upper airway obstruction 60.49 27.02 17 11044 1785 110576453
Arthralgia 59.49 27.02 5 11056 779627 109798611
Sinus arrest 57.50 27.02 20 11041 4222 110574016
Type I hypersensitivity 56.50 27.02 22 11039 6371 110571867
Post procedural complication 55.26 27.02 34 11027 26624 110551614
Status epilepticus 54.82 27.02 36 11025 31535 110546703
Premature delivery 53.36 27.02 35 11026 30597 110547641
Apnoea 49.10 27.02 25 11036 13614 110564624
Neuromuscular blockade 49.08 27.02 12 11049 732 110577506
Arteriospasm coronary 49.00 27.02 22 11039 9078 110569160
Anaesthetic complication 48.87 27.02 17 11044 3589 110574649
Respiratory arrest 48.81 27.02 43 11018 58256 110519982
Seizure like phenomena 47.03 27.02 15 11046 2426 110575812
Nausea 46.08 27.02 34 11027 1235656 109342582
Haematuria traumatic 45.90 27.02 10 11051 365 110577873
Transcranial electrical motor evoked potential monitoring abnormal 44.00 27.02 7 11054 41 110578197
Clonus 43.55 27.02 20 11041 8696 110569542
Death 40.62 27.02 10 11051 698859 109879379
Dizziness 40.56 27.02 10 11051 698183 109880055
Intensive care unit acquired weakness 39.36 27.02 13 11048 2346 110575892
Fall 38.41 27.02 7 11054 603475 109974763
Shock 37.97 27.02 36 11025 53552 110524686
Maternal exposure during delivery 37.75 27.02 14 11047 3551 110574687
Diarrhoea 36.76 27.02 36 11025 1139469 109438769
Hypothermia 36.22 27.02 26 11035 26276 110551962
Headache 35.89 27.02 22 11039 882355 109695883
Pulmonary alveolar haemorrhage 35.03 27.02 23 11038 20127 110558111
Procedural complication 34.97 27.02 17 11044 8388 110569850
Hyperkalaemia 34.19 27.02 54 11007 135742 110442496
Sinus tachycardia 33.66 27.02 31 11030 44462 110533776
Dyskinesia 33.51 27.02 33 11028 51413 110526825
Muscle contracture 33.35 27.02 12 11049 2796 110575442
Hyperreflexia 33.02 27.02 17 11044 9468 110568770
Torsade de pointes 32.64 27.02 23 11038 22577 110555661
Prinzmetal angina 31.92 27.02 11 11050 2258 110575980
Anaesthetic complication neurological 31.31 27.02 9 11052 1024 110577214
Blood pressure immeasurable 31.22 27.02 11 11050 2412 110575826
Hypoxic-ischaemic encephalopathy 31.21 27.02 16 11045 8831 110569407
Acute generalised exanthematous pustulosis 31.18 27.02 22 11039 21642 110556596
Subcutaneous emphysema 30.52 27.02 11 11050 2573 110575665
Respiratory acidosis 29.59 27.02 18 11043 13808 110564430
Decreased appetite 29.25 27.02 6 11055 475840 110102398
Thyrotoxic crisis 29.13 27.02 10 11051 2030 110576208
Unwanted awareness during anaesthesia 29.04 27.02 7 11054 402 110577836
Procedural haemorrhage 28.84 27.02 13 11048 5414 110572824
Nasopharyngitis 28.78 27.02 3 11058 394358 110183880
Metabolic acidosis 28.40 27.02 42 11019 99702 110478536
Dystonia 27.74 27.02 22 11039 25783 110552455
Nodal rhythm 27.52 27.02 11 11050 3412 110574826
Exposure during pregnancy 27.22 27.02 55 11006 167369 110410869

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 D002492 Central Nervous System Depressants
MeSH PA D009294 Narcotics
MeSH PA D018689 Sensory System Agents
FDA MoA N0000175684 Full Opioid Agonists
FDA EPC N0000175690 Opioid Agonist
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35482 opioid analgesic
CHEBI has role CHEBI:35554 cardiovascular drug
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:35717 sedative
CHEBI has role CHEBI:38877 intravenous anaesthetic
CHEBI has role CHEBI:55322 μ-opioid receptor agonist
CHEBI has role CHEBI:74518 anti-obesity agent

Related Drugs by ATC class:

N01AH Opioid anesthetics 5 drugs
alfentanilanileridinefentanylphenoperidinesufentanil

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
P10582JYYK INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
REMIFENTANIL HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0143-9391 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS ANDA 30 sections
REMIFENTANIL HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0143-9392 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 mg INTRAVENOUS ANDA 30 sections
REMIFENTANIL HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0143-9393 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 5 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 63323-723 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 67457-912 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS NDA 32 sections
Ultiva HUMAN PRESCRIPTION DRUG LABEL 1 67457-913 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS NDA 32 sections
Ultiva HUMAN PRESCRIPTION DRUG LABEL 1 67457-914 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS NDA 32 sections
Ultiva HUMAN PRESCRIPTION DRUG LABEL 1 72078-034 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS NDA 34 sections
Ultiva HUMAN PRESCRIPTION DRUG LABEL 1 72078-035 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS NDA 34 sections
Ultiva HUMAN PRESCRIPTION DRUG LABEL 1 72078-036 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS NDA 34 sections
Remifentanil hydrochloride Human Prescription Drug Label 1 75834-230 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS ANDA 31 sections
Remifentanil hydrochloride Human Prescription Drug Label 1 75834-231 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 mg INTRAVENOUS ANDA 31 sections
Remifentanil hydrochloride Human Prescription Drug Label 1 75834-232 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 5 mg INTRAVENOUS ANDA 31 sections