sufentanil ๐Ÿถ Veterinary Use | 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 ยตM/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 1435.28 29.26 356 5695 19799 50579274
Hypotension 271.93 29.26 224 5827 235245 50363828
Bronchospasm 253.94 29.26 87 5964 14767 50584306
Exposure during pregnancy 147.12 29.26 119 5932 120896 50478177
Maternal exposure during delivery 135.77 29.26 30 6021 976 50598097
Anaphylactic reaction 133.26 29.26 82 5969 53973 50545100
Cardiac arrest 122.71 29.26 92 5959 83559 50515514
Anaphylactoid shock 111.67 29.26 21 6030 297 50598776
Tachycardia 106.35 29.26 91 5960 99672 50499401
Circulatory collapse 101.55 29.26 49 6002 19951 50579122
Shock 76.79 29.26 41 6010 20609 50578464
Oliguria 73.62 29.26 30 6021 8186 50590887
Hepatocellular injury 70.66 29.26 42 6009 25905 50573168
Stress cardiomyopathy 67.95 29.26 28 6023 7859 50591214
Delayed recovery from anaesthesia 67.08 29.26 16 6035 733 50598340
Ventricular fibrillation 66.37 29.26 30 6021 10529 50588544
Mixed liver injury 65.93 29.26 22 6029 3429 50595644
Respiratory depression 65.74 29.26 31 6020 11979 50587094
Hepatorenal failure 65.16 29.26 15 6036 588 50598485
Eosinophilia 63.68 29.26 35 6016 18617 50580456
Cardio-respiratory arrest 63.20 29.26 52 5999 53840 50545233
Myoclonus 60.26 29.26 31 6020 14439 50584634
Peripheral nerve injury 59.86 29.26 13 6038 389 50598684
Fatigue 58.23 29.26 8 6043 707593 49891480
Haemodynamic instability 57.51 29.26 25 6026 7999 50591074
Spinal epidural haemorrhage 56.36 29.26 10 6041 100 50598973
Suspected product quality issue 56.21 29.26 11 6040 194 50598879
Hypocapnia 55.99 29.26 12 6039 337 50598736
Multiple organ dysfunction syndrome 53.70 29.26 46 6005 50291 50548782
Type I hypersensitivity 52.80 29.26 17 6034 2368 50596705
Bradycardia 51.37 29.26 50 6001 64376 50534697
Rash maculo-papular 49.77 29.26 34 6017 26607 50572466
Erythema 49.00 29.26 73 5978 146341 50452732
Unwanted awareness during anaesthesia 46.86 29.26 10 6041 275 50598798
Patent ductus arteriosus 44.97 29.26 17 6034 3803 50595270
Serotonin syndrome 44.89 29.26 31 6020 24682 50574391
Hyperlactacidaemia 40.54 29.26 14 6037 2419 50596654
Myoglobin blood increased 40.39 29.26 12 6039 1281 50597792
Cholestasis 39.53 29.26 29 6022 25372 50573701
Oxygen saturation decreased 39.17 29.26 46 6005 73202 50525871
Metabolic acidosis 38.41 29.26 34 6017 38791 50560282
Paralysis 37.34 29.26 19 6032 8645 50590428
Cauda equina syndrome 37.19 29.26 10 6041 744 50598329
Uterine hypotonus 37.08 29.26 7 6044 101 50598972
Anaesthetic complication 36.95 29.26 12 6039 1718 50597355
Postpartum haemorrhage 36.78 29.26 12 6039 1742 50597331
Acute generalised exanthematous pustulosis 36.78 29.26 19 6032 8919 50590154
Epidural haemorrhage 36.01 29.26 7 6044 119 50598954
Post procedural stroke 34.29 29.26 6 6045 55 50599018
Mydriasis 33.69 29.26 19 6032 10608 50588465
Foetal growth restriction 32.90 29.26 16 6035 6611 50592462
Anticholinergic syndrome 32.53 29.26 11 6040 1784 50597289
Torsade de pointes 31.79 29.26 19 6032 11816 50587257
Carcinoid crisis 31.78 29.26 7 6044 224 50598849
Foetal exposure during pregnancy 31.21 29.26 26 6025 27333 50571740
Suspected product contamination 31.21 29.26 5 6046 25 50599048
Diarrhoea 30.91 29.26 16 6035 588460 50010613
Foetal heart rate abnormal 30.83 29.26 8 6043 518 50598555
Haemodilution 29.99 29.26 6 6045 119 50598954
Toxic encephalopathy 29.45 29.26 14 6037 5501 50593572

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 879.99 31.37 236 4548 13100 29556643
Bronchospasm 164.78 31.37 61 4723 9548 29560195
Hypertransaminasaemia 129.86 31.37 40 4744 3566 29566177
Hyperthermia malignant 123.80 31.37 33 4751 1751 29567992
Hypotension 117.32 31.37 150 4634 194204 29375539
Anaphylactic reaction 113.99 31.37 65 4719 27508 29542235
Rash maculo-papular 94.35 31.37 55 4729 24234 29545509
Toxic epidermal necrolysis 86.47 31.37 47 4737 18106 29551637
Circulatory collapse 82.48 31.37 46 4738 18627 29551116
Drug reaction with eosinophilia and systemic symptoms 82.16 31.37 53 4731 27939 29541804
Tachycardia 78.27 31.37 76 4708 72334 29497409
Eosinophilia 72.61 31.37 45 4739 22116 29547627
Rhabdomyolysis 64.13 31.37 63 4721 60745 29508998
Haemodynamic instability 56.16 31.37 27 4757 8046 29561697
Septic shock 55.39 31.37 59 4725 62501 29507242
Shock 51.87 31.37 36 4748 21368 29548375
Injury 50.82 31.37 34 4750 19012 29550731
Hepatic cytolysis 49.37 31.37 25 4759 8322 29561421
Multiple organ dysfunction syndrome 48.04 31.37 55 4729 63061 29506682
Hepatorenal failure 47.38 31.37 12 4772 519 29569224
Cholestasis 46.65 31.37 35 4749 23427 29546316
Anaphylactoid shock 46.42 31.37 11 4773 359 29569384
Victim of crime 46.34 31.37 11 4773 362 29569381
Rash morbilliform 43.32 31.37 16 4768 2477 29567266
Erythema 43.17 31.37 57 4727 75549 29494194
Hepatocellular injury 42.93 31.37 32 4752 21211 29548532
Stress cardiomyopathy 41.94 31.37 14 4770 1610 29568133
Patent ductus arteriosus 39.78 31.37 16 4768 3115 29566628
Type I hypersensitivity 39.03 31.37 12 4772 1060 29568683
Suspected product quality issue 38.80 31.37 8 4776 135 29569608
Suspected product contamination 38.11 31.37 7 4777 62 29569681
Infantile apnoea 36.91 31.37 11 4773 874 29568869
Coma 36.29 31.37 38 4746 39412 29530331
Fear 35.48 31.37 21 4763 9483 29560260
Symmetrical drug-related intertriginous and flexural exanthema 35.05 31.37 8 4776 221 29569522
Fibrinolysis increased 32.53 31.37 5 4779 12 29569731
Post procedural haemorrhage 31.81 31.37 18 4766 7473 29562270
Anaesthetic complication 31.55 31.37 10 4774 976 29568767

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 2255.23 26.17 585 9473 29743 64458931
Bronchospasm 404.37 26.17 145 9913 21537 64467137
Hypotension 251.42 26.17 302 9756 380672 64108002
Anaphylactic reaction 247.07 26.17 146 9912 68518 64420156
Tachycardia 176.25 26.17 162 9896 149417 64339257
Circulatory collapse 168.34 26.17 89 9969 33643 64455031
Anaphylactoid shock 141.98 26.17 31 10027 723 64487951
Hyperthermia malignant 137.11 26.17 38 10020 2421 64486253
Hypertransaminasaemia 129.80 26.17 47 10011 7144 64481530
Cardiac arrest 126.17 26.17 137 9921 153927 64334747
Maternal exposure during delivery 126.10 26.17 29 10029 861 64487813
Rash maculo-papular 118.77 26.17 80 9978 46946 64441728
Shock 118.56 26.17 74 9984 38166 64450508
Eosinophilia 113.82 26.17 72 9986 38004 64450670
Hepatorenal failure 108.09 26.17 27 10031 1145 64487529
Toxic epidermal necrolysis 105.43 26.17 68 9990 37098 64451576
Drug reaction with eosinophilia and systemic symptoms 104.01 26.17 78 9980 54139 64434535
Hepatocellular injury 102.53 26.17 72 9986 45163 64443511
Stress cardiomyopathy 101.09 26.17 42 10016 9215 64479459
Suspected product quality issue 96.91 26.17 19 10039 255 64488419
Erythema 87.99 26.17 126 9932 186944 64301730
Type I hypersensitivity 86.20 26.17 29 10029 3545 64485129
Multiple organ dysfunction syndrome 84.34 26.17 91 9967 101322 64387352
Fatigue 82.75 26.17 10 10048 748720 63739954
Delayed recovery from anaesthesia 82.37 26.17 23 10035 1505 64487169
Cholestasis 80.41 26.17 62 9996 44810 64443864
Respiratory depression 79.35 26.17 48 10010 23395 64465279
Haemodynamic instability 79.06 26.17 41 10017 14871 64473803
Oliguria 71.36 26.17 38 10020 14538 64474136
Rhabdomyolysis 68.81 26.17 78 9980 91648 64397026
Suspected product contamination 68.51 26.17 12 10046 82 64488592
Septic shock 66.42 26.17 82 9976 105355 64383319
Mixed liver injury 63.68 26.17 26 10032 5455 64483219
Anaesthetic complication 62.49 26.17 21 10037 2558 64486116
Rash morbilliform 61.83 26.17 25 10033 5116 64483558
Cardio-respiratory arrest 61.13 26.17 76 9982 98317 64390357
Hepatic cytolysis 53.37 26.17 31 10027 14018 64474656
Myoclonus 52.32 26.17 38 10020 25080 64463594
Ventricular fibrillation 51.77 26.17 37 10021 23823 64464851
Bradycardia 51.68 26.17 77 9981 118142 64370532
Symmetrical drug-related intertriginous and flexural exanthema 50.80 26.17 13 10045 608 64488066
Peripheral nerve injury 50.49 26.17 13 10045 623 64488051
Diarrhoea 47.49 26.17 27 10031 722677 63765997
Torsade de pointes 47.32 26.17 31 10027 17332 64471342
Hypocapnia 46.55 26.17 12 10046 578 64488096
Coma 45.55 26.17 62 9996 87553 64401121
Acute pulmonary oedema 45.34 26.17 27 10031 12782 64475892
Victim of crime 45.25 26.17 11 10047 416 64488258
Carcinoid crisis 44.58 26.17 11 10047 443 64488231
Dizziness 44.44 26.17 7 10051 430156 64058518
Spinal epidural haemorrhage 44.37 26.17 9 10049 145 64488529
Oxygen saturation decreased 44.27 26.17 68 9990 107108 64381566
Unwanted awareness during anaesthesia 44.21 26.17 10 10048 275 64488399
Fibrinolysis increased 43.73 26.17 7 10051 25 64488649
Headache 42.21 26.17 15 10043 529452 63959222
Neuromuscular block prolonged 40.56 26.17 12 10046 965 64487709
Ventricular tachycardia 39.99 26.17 37 10021 34228 64454446
Fear 38.60 26.17 29 10029 20142 64468532
Fall 38.36 26.17 9 10049 416817 64071857
Uterine hypotonus 36.98 26.17 7 10051 77 64488597
Altered state of consciousness 36.82 26.17 37 10021 37865 64450809
Hyperlactacidaemia 36.70 26.17 17 10041 4827 64483847
Dermatitis bullous 36.50 26.17 23 10035 12031 64476643
Postpartum haemorrhage 35.92 26.17 12 10046 1435 64487239
Tonic clonic movements 35.88 26.17 13 10045 1976 64486698
Acute generalised exanthematous pustulosis 35.65 26.17 24 10034 14034 64474640
Device issue 35.62 26.17 29 10029 22619 64466055
Nervous system disorder 35.15 26.17 29 10029 23049 64465625
Cauda equina syndrome 34.92 26.17 11 10047 1092 64487582
Foetal heart rate abnormal 34.45 26.17 8 10050 248 64488426
Renal injury 33.63 26.17 24 10034 15405 64473269
Exposure during pregnancy 33.07 26.17 50 10008 77625 64411049
Injury 32.76 26.17 42 10016 55950 64432724
Malaise 31.94 26.17 11 10047 396236 64092438
Epidural haemorrhage 31.66 26.17 7 10051 173 64488501
Respiratory acidosis 30.33 26.17 19 10039 9836 64478838
Leukocytosis 29.82 26.17 33 10025 37707 64450967
Mydriasis 29.26 26.17 22 10036 15290 64473384
Metabolic acidosis 29.25 26.17 45 10013 70913 64417761
Post procedural stroke 29.00 26.17 6 10052 107 64488567
Cough 28.84 26.17 6 10052 302142 64186532
Cardiogenic shock 28.50 26.17 30 10028 32397 64456277
Myoglobin blood increased 28.43 26.17 12 10046 2735 64485939
Vasoplegia syndrome 28.34 26.17 12 10046 2755 64485919
Anaphylactoid reaction 27.93 26.17 14 10044 4724 64483950
Haemodilution 27.47 26.17 6 10052 140 64488534
Third stage postpartum haemorrhage 27.40 26.17 4 10054 6 64488668
Arthralgia 26.92 26.17 18 10040 442242 64046432
Hypercapnia 26.66 26.17 16 10042 7678 64480996
Post procedural haemorrhage 26.32 26.17 19 10039 12412 64476262

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N01AH03 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, GENERAL
Opioid anesthetics
CHEBI has role CHEBI:35482 narcotic analgesic
CHEBI has role CHEBI:38877 intravenous anesthetics
CHEBI has role CHEBI:55322 mu-opioid agonists
CHEBI has role CHEBI:60807 anaesthestic adjuvant
FDA MoA N0000175684 Full Opioid Agonists
FDA EPC N0000175690 Opioid Agonist
MeSH PA D000759 Adjuvants, Anesthesia
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

Drug Use | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 0.03MG BASE DSUVIA ACELRX PHARMS N209128 Nov. 2, 2018 RX TABLET SUBLINGUAL 10245228 Jan. 5, 2027 TREATMENT OF ACUTE PAIN
EQ 0.03MG BASE DSUVIA ACELRX PHARMS N209128 Nov. 2, 2018 RX TABLET SUBLINGUAL 10507180 Jan. 5, 2027 TREATMENT OF ACUTE PAIN
EQ 0.03MG BASE DSUVIA ACELRX PHARMS N209128 Nov. 2, 2018 RX TABLET SUBLINGUAL 8226978 Jan. 5, 2027 TREATMENT OF ACUTE PAIN
EQ 0.03MG BASE DSUVIA ACELRX PHARMS N209128 Nov. 2, 2018 RX TABLET SUBLINGUAL 8535714 Jan. 5, 2027 TREATMENT OF ACUTE PAIN
EQ 0.03MG BASE DSUVIA ACELRX PHARMS N209128 Nov. 2, 2018 RX TABLET SUBLINGUAL 8778393 Jan. 5, 2027 TREATMENT OF ACUTE PAIN
EQ 0.03MG BASE DSUVIA ACELRX PHARMS N209128 Nov. 2, 2018 RX TABLET SUBLINGUAL 8778394 Jan. 5, 2027 TREATMENT OF ACUTE PAIN
EQ 0.03MG BASE DSUVIA ACELRX PHARMS N209128 Nov. 2, 2018 RX TABLET SUBLINGUAL 8865211 Jan. 5, 2027 TREATMENT OF ACUTE PAIN
EQ 0.03MG BASE DSUVIA ACELRX PHARMS N209128 Nov. 2, 2018 RX TABLET SUBLINGUAL 9320710 Jan. 5, 2027 TREATMENT OF ACUTE PAIN
EQ 0.03MG BASE DSUVIA ACELRX PHARMS N209128 Nov. 2, 2018 RX TABLET SUBLINGUAL 8202535 Oct. 22, 2030 TREATMENT OF ACUTE PAIN
EQ 0.03MG BASE DSUVIA ACELRX PHARMS N209128 Nov. 2, 2018 RX TABLET SUBLINGUAL 8865743 Oct. 22, 2030 TREATMENT OF ACUTE PAIN

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 EC50 8.13 WOMBAT-PK CHEMBL
Kappa-type opioid receptor GPCR EC50 6.70 WOMBAT-PK
Delta-type opioid receptor GPCR Ki 7.30 PDSP
Solute carrier family 22 member 1 Transporter IC50 4.71 CHEMBL
Mu-type opioid receptor GPCR Ki 9.66 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane other IC50 5.68 CHEMBL
Opioid receptor GPCR Ki 10.70 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
DB00708 DRUGBANK_ID
CHEMBL1201163 ChEMBL_ID
D017409 MESH_DESCRIPTOR_UI
41693 PUBCHEM_CID
3534 IUPHAR_LIGAND_ID
4048 INN_ID
AFE2YW0IIZ UNII
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