remifentanil 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 591.17 28.93 166 3953 20108 46661835
Anaphylactic reaction 249.58 28.93 112 4007 53000 46628943
Delayed recovery from anaesthesia 173.75 28.93 34 4085 827 46681116
Bronchospasm 127.37 28.93 49 4070 15658 46666285
Circulatory collapse 115.49 28.93 50 4069 21574 46660369
Cardiac arrest 106.15 28.93 77 4042 90322 46591621
Bradycardia 97.80 28.93 65 4054 66233 46615710
Hypotension 96.20 28.93 110 4009 232479 46449464
Serotonin syndrome 88.42 28.93 43 4076 24177 46657766
Tachycardia 86.59 28.93 71 4048 99551 46582392
Neuromuscular block prolonged 82.81 28.93 17 4102 529 46681414
Blood pressure decreased 77.00 28.93 53 4066 57106 46624837
Hyperthermia malignant 66.47 28.93 15 4104 734 46681209
Anaphylactoid reaction 63.82 28.93 20 4099 3471 46678472
Stress cardiomyopathy 62.05 28.93 24 4095 7760 46674183
Pulseless electrical activity 60.35 28.93 23 4096 7144 46674799
Respiratory depression 55.99 28.93 25 4094 11575 46670368
Drug interaction 55.09 28.93 78 4041 203016 46478927
Patent ductus arteriosus 49.84 28.93 17 4102 3845 46678098
Anaphylactoid shock 49.22 28.93 10 4109 295 46681648
Apnoea 45.89 28.93 19 4100 7320 46674623
Exposure during pregnancy 42.54 28.93 50 4069 108162 46573781
Diabetes insipidus 42.02 28.93 13 4106 2161 46679782
Clonus 41.33 28.93 15 4104 4065 46677878
Hyperreflexia 41.16 28.93 16 4103 5238 46676705
Dyskinesia 36.97 28.93 26 4093 28899 46653044
Procedural hypotension 35.58 28.93 10 4109 1192 46680751
Dystonia 35.18 28.93 18 4101 11239 46670704
Premature baby 34.74 28.93 21 4098 18091 46663852
Upper airway obstruction 33.04 28.93 8 4111 532 46681411
Atrioventricular block second degree 31.29 28.93 12 4107 3787 46678156
Respiratory arrest 31.19 28.93 25 4094 33791 46648152
Foetal exposure during pregnancy 31.09 28.93 24 4095 30723 46651220
Toxic epidermal necrolysis 30.75 28.93 21 4098 22257 46659686
Subcutaneous emphysema 29.66 28.93 8 4111 819 46681124
Erythema 28.95 28.93 48 4071 142772 46539171

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 432.31 29.40 131 3791 13862 29934694
Anaphylactic reaction 225.57 29.40 97 3825 27885 29920671
Cardiac arrest 170.72 29.40 121 3801 92729 29855827
Hyperthermia malignant 115.19 29.40 30 3892 1804 29946752
Delayed recovery from anaesthesia 115.00 29.40 25 3897 686 29947870
Neuromuscular block prolonged 106.67 29.40 21 3901 348 29948208
Bradycardia 103.37 29.40 78 3844 65448 29883108
Hypotension 99.14 29.40 126 3796 200439 29748117
Propofol infusion syndrome 88.82 29.40 21 3901 845 29947711
Blood pressure decreased 83.07 29.40 60 3862 47015 29901541
Bronchospasm 73.87 29.40 33 3889 10305 29938251
Ventricular fibrillation 67.61 29.40 35 3887 15103 29933453
Trigemino-cardiac reflex 61.09 29.40 11 3911 109 29948447
Toxic epidermal necrolysis 56.67 29.40 33 3889 17907 29930649
Airway complication of anaesthesia 53.34 29.40 10 3912 126 29948430
Drug interaction 53.06 29.40 94 3828 199474 29749082
Hypoventilation 51.14 29.40 18 3904 3005 29945551
Seizure like phenomena 49.48 29.40 12 3910 538 29948018
Erythema 46.70 29.40 54 3868 77397 29871159
Arteriospasm coronary 45.87 29.40 16 3906 2602 29945954
Diabetes insipidus 44.35 29.40 15 3907 2224 29946332
Anaphylactoid shock 42.15 29.40 10 3912 408 29948148
Kounis syndrome 40.32 29.40 13 3909 1660 29946896
Rhabdomyolysis 39.43 29.40 45 3877 63535 29885021
Anaesthetic complication neurological 38.97 29.40 9 3913 326 29948230
Nodal rhythm 38.19 29.40 12 3910 1411 29947145
Sinus arrest 37.41 29.40 12 3910 1508 29947048
Tachycardia 37.22 29.40 47 3875 73692 29874864
Anaphylactoid reaction 36.91 29.40 13 3909 2173 29946383
Ventricular tachycardia 36.61 29.40 28 3894 23834 29924722
Urticaria 34.44 29.40 39 3883 54567 29893989
Circulatory collapse 33.85 29.40 25 3897 20189 29928367
Respiratory depression 33.27 29.40 20 3902 11483 29937073
Cardio-respiratory arrest 32.91 29.40 39 3883 57267 29891289
Drug reaction with eosinophilia and systemic symptoms 32.25 29.40 28 3894 28460 29920096
Status epilepticus 31.38 29.40 19 3903 11053 29937503
Electrocardiogram ST segment elevation 31.14 29.40 14 3908 4428 29944128
Death 30.83 29.40 5 3917 357278 29591278
Prinzmetal angina 29.87 29.40 9 3913 920 29947636
Recurrence of neuromuscular blockade 29.45 29.40 6 3916 119 29948437
Capillary nail refill test abnormal 29.44 29.40 5 3917 34 29948522

Pharmacologic Action:

SourceCodeDescription
ATC N01AH06 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, GENERAL
Opioid anesthetics
FDA MoA N0000175684 Full Opioid Agonists
FDA EPC N0000175690 Opioid Agonist
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 analgesics
CHEBI has role CHEBI:35717 sedatives
CHEBI has role CHEBI:38877 intravenous anesthetics
CHEBI has role CHEBI:55322 mu opioid agonist

Drug Use (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

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

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
CHEMBL1201120 ChEMBL_ID
D000077208 MESH_DESCRIPTOR_UI
DB00899 DRUGBANK_ID
7292 IUPHAR_LIGAND_ID
6924 INN_ID
P10582JYYK UNII
60815 PUBCHEM_CID
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 31 sections
Ultiva HUMAN PRESCRIPTION DRUG LABEL 1 67457-912 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS NDA 31 sections
Ultiva HUMAN PRESCRIPTION DRUG LABEL 1 67457-913 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS NDA 31 sections
Ultiva HUMAN PRESCRIPTION DRUG LABEL 1 67457-914 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS NDA 31 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