sufentanil Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
opioid receptor agonists, analgesics, fentanyl derivatives 2491 56030-54-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • sulfentanyl
  • sulfentanil
  • sulfentanil citrate
  • sufentanil
  • sufentanil citrate
An opioid analgesic that is used as an adjunct in anesthesia, in balanced anesthesia, and as a primary anesthetic agent.
  • Molecular weight: 386.55
  • Formula: C22H30N2O2S
  • CLOGP: 3.59
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 0
  • TPSA: 32.78
  • ALOGS: -4.51
  • ROTB: 8

  • 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) 6 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.06 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 0 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 9.40 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 15 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.08 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 14 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
May 4, 1984 FDA AKORN

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 1257.88 29.72 317 4955 19957 46660833
Hypotension 264.58 29.72 214 5058 232375 46448415
Bronchospasm 242.47 29.72 84 5188 15623 46665167
Exposure during pregnancy 144.85 29.72 110 5162 108102 46572688
Maternal exposure during delivery 115.23 29.72 25 5247 791 46679999
Anaphylactoid shock 113.75 29.72 21 5251 284 46680506
Anaphylactic reaction 113.36 29.72 72 5200 53040 46627750
Tachycardia 100.71 29.72 86 5186 99536 46581254
Circulatory collapse 94.63 29.72 47 5225 21577 46659213
Cardiac arrest 75.32 29.72 70 5202 90329 46590461
Shock 74.04 29.72 40 5232 21805 46658985
Oliguria 70.03 29.72 29 5243 8730 46672060
Hepatocellular injury 67.89 29.72 42 5230 29480 46651310
Hepatorenal failure 65.45 29.72 15 5257 611 46680179
Respiratory depression 65.33 29.72 30 5242 11570 46669220
Peripheral nerve injury 61.44 29.72 13 5259 364 46680426
Delayed recovery from anaesthesia 60.70 29.72 15 5257 846 46679944
Haemodynamic instability 59.81 29.72 25 5247 7700 46673090
Suspected product quality issue 58.32 29.72 11 5261 168 46680622
Spinal epidural haemorrhage 56.93 29.72 10 5262 100 46680690
Hypocapnia 55.88 29.72 12 5260 361 46680429
Type I hypersensitivity 54.04 29.72 17 5255 2329 46678461
Erythema 50.65 29.72 71 5201 142749 46538041
Ventricular fibrillation 47.36 29.72 24 5248 11472 46669318
Unwanted awareness during anaesthesia 47.05 29.72 10 5262 286 46680504
Bradycardia 46.98 29.72 47 5225 66251 46614539
Stress cardiomyopathy 46.56 29.72 21 5251 7763 46673027
Patent ductus arteriosus 45.73 29.72 17 5255 3845 46676945
Fatigue 43.88 29.72 8 5264 608689 46072101
Foetal exposure during pregnancy 42.62 29.72 32 5240 30715 46650075
Serotonin syndrome 42.27 29.72 29 5243 24191 46656599
Oxygen saturation decreased 40 29.72 44 5228 69120 46611670
Cauda equina syndrome 39.03 29.72 10 5262 653 46680137
Anaesthetic complication 37.04 29.72 12 5260 1805 46678985
Acute generalised exanthematous pustulosis 36.89 29.72 19 5253 9386 46671404
Epidural haemorrhage 36.35 29.72 7 5265 120 46680670
Cardio-respiratory arrest 36.21 29.72 39 5233 59830 46620960
Myoglobin blood increased 35.56 29.72 11 5261 1425 46679365
Paralysis 35.31 29.72 18 5254 8703 46672087
Cholestasis 35.09 29.72 27 5245 26866 46653924
Post procedural stroke 34.25 29.72 6 5266 59 46680731
Foetal growth restriction 33.91 29.72 16 5256 6551 46674239
Eosinophilia 33.51 29.72 23 5249 19194 46661596
Suspected product contamination 32.21 29.72 5 5267 21 46680769
Metabolic acidosis 32.17 29.72 30 5242 38750 46642040
Carcinoid crisis 31.63 29.72 7 5265 243 46680547
Diarrhoea 31.51 29.72 12 5260 559590 46121200
Haemodilution 31.26 29.72 6 5266 101 46680689
Foetal heart rate abnormal 30.89 29.72 8 5264 545 46680245
Maternal exposure during pregnancy 30.54 29.72 47 5225 102502 46578288

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 811.05 31.83 216 3907 13777 29934578
Bronchospasm 170.10 31.83 61 4062 10277 29938078
Hypertransaminasaemia 133.32 31.83 40 4083 3845 29944510
Anaphylactic reaction 111.75 31.83 61 4062 27921 29920434
Hypotension 105.08 31.83 133 3990 200432 29747923
Hyperthermia malignant 104.19 31.83 28 4095 1806 29946549
Tachycardia 75.76 31.83 70 4053 73669 29874686
Circulatory collapse 69.57 31.83 40 4083 20174 29928181
Toxic epidermal necrolysis 68.50 31.83 38 4085 17902 29930453
Septic shock 58.82 31.83 57 4066 63550 29884805
Haemodynamic instability 57.33 31.83 26 4097 7989 29940366
Rhabdomyolysis 56.97 31.83 56 4067 63524 29884831
Multiple organ dysfunction syndrome 53.33 31.83 54 4069 63433 29884922
Shock 52.59 31.83 35 4088 22824 29925531
Victim of crime 50.75 31.83 11 4112 282 29948073
Hepatorenal failure 47.77 31.83 12 4111 592 29947763
Anaphylactoid shock 46.86 31.83 11 4112 407 29947948
Hepatocellular injury 44.60 31.83 33 4090 25438 29922917
Type I hypersensitivity 42.40 31.83 12 4111 936 29947419
Patent ductus arteriosus 42.10 31.83 16 4107 3153 29945202
Erythema 41.27 31.83 52 4071 77399 29870956
Suspected product contamination 39.13 31.83 7 4116 63 29948292
Coma 38.76 31.83 37 4086 40412 29907943
Infantile apnoea 38.62 31.83 11 4112 878 29947477
Suspected product quality issue 38.52 31.83 8 4115 166 29948189
Stress cardiomyopathy 36.59 31.83 12 4111 1537 29946818
Fear 36.10 31.83 21 4102 10804 29937551
Injury 35.47 31.83 27 4096 21704 29926651
Post procedural haemorrhage 33.62 31.83 18 4105 7892 29940463
Fibrinolysis increased 33.06 31.83 5 4118 13 29948342
Agitation neonatal 32.76 31.83 10 4113 1015 29947340
Anaesthetic complication 32.35 31.83 10 4113 1059 29947296

Pharmacologic Action:

SourceCodeDescription
ATC N01AH03 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, GENERAL
Opioid anesthetics
MeSH PA D000759 Adjuvants, Anesthesia
FDA MoA N0000175684 Full Opioid Agonists
FDA EPC N0000175690 Opioid Agonist
MeSH PA D000700 Analgesics
MeSH PA D000701 Analgesics, Opioid
MeSH PA D000777 Anesthetics
MeSH PA D018686 Anesthetics, Intravenous
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:38877 intravenous anesthetics
CHEBI has role CHEBI:55322 mu opioid agonist
CHEBI has role CHEBI:60807 anaesthesia adjuvants

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
General anesthesia indication 50697003
Postoperative pain indication 213299007
Asthenia contraindication 13791008
Chronic disease of respiratory system contraindication 17097001
Decreased cardiac function contraindication 43650005
Bradycardia contraindication 48867003
Injury of head contraindication 82271004
Kidney disease contraindication 90708001 DOID:557
Disease of liver contraindication 235856003 DOID:409

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.37 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 0.03MG BASE DSUVIA ACELRX PHARMS N209128 Nov. 2, 2018 RX TABLET SUBLINGUAL Nov. 2, 2021 NEW PRODUCT

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Mu-type opioid receptor GPCR AGONIST EC50 8.13 WOMBAT-PK CHEMBL
Delta-type opioid receptor GPCR Ki 7.30 PDSP
Kappa-type opioid receptor GPCR EC50 6.70 WOMBAT-PK
Opioid receptor GPCR Ki 10.70 CHEMBL
Mu-type opioid receptor GPCR Ki 9.66 CHEMBL

External reference:

IDSource
4019936 VUID
N0000148021 NUI
D00845 KEGG_DRUG
60561-17-3 SECONDARY_CAS_RN
4019269 VANDF
4019936 VANDF
C0143993 UMLSCUI
CHEBI:9316 CHEBI
CHEMBL658 ChEMBL_ID
CHEMBL1201163 ChEMBL_ID
D017409 MESH_DESCRIPTOR_UI
3534 IUPHAR_LIGAND_ID
4048 INN_ID
DB00708 DRUGBANK_ID
AFE2YW0IIZ UNII
41693 PUBCHEM_CID
56795 RXNORM
10199 MMSL
32203 MMSL
5519 MMSL
d00378 MMSL
001570 NDDF
004630 NDDF
370275005 SNOMEDCT_US
37527009 SNOMEDCT_US
49998007 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Sufentanil Citrate HUMAN PRESCRIPTION DRUG LABEL 1 0409-3382 INJECTION, SOLUTION 50 ug EPIDURAL ANDA 32 sections
Sufentanil Citrate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6110 INJECTION 0.05 mg EPIDURAL ANDA 27 sections
Sufentanil Citrate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6111 INJECTION 0.05 mg EPIDURAL ANDA 27 sections
Sufentanil Citrate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6112 INJECTION 0.05 mg EPIDURAL ANDA 27 sections
Sufentanil Citrate HUMAN PRESCRIPTION DRUG LABEL 1 17478-050 INJECTION 50 ug INTRAVENOUS NDA 29 sections
Dsuvia Human Prescription Drug Label 1 61621-430 TABLET 30 ug SUBLINGUAL NDA 30 sections