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 856.67 91.84 147 564 4139 2353235
Hypotension 407.26 91.84 115 596 32321 2325053
Exposure during pregnancy 276.85 91.84 81 630 25138 2332236
Bronchospasm 180.18 91.84 38 673 2986 2354388
Anaphylactoid shock 114.46 91.84 16 695 96 2357278
Drug ineffective 108.43 91.84 61 650 101563 2255811
Circulatory collapse 92.57 91.84 23 688 3697 2353677

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 451.94 82.58 81 362 2818 1743520
Bronchospasm 128.18 82.58 27 416 2055 1744283
Hypotension 119.05 82.58 45 398 29609 1716729
Anaphylactic reaction 99.26 82.58 27 416 6086 1740252
Circulatory collapse 83.63 82.58 21 422 3446 1742892

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 opioid analgesic
CHEBI has role CHEBI:55322 mu-opioid receptor agonist
CHEBI has role CHEBI:60807 anaesthesia adjuvant
CHEBI has role CHEBI:38877 intravenous anaesthetic

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)

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)

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
C0143993 UMLSCUI
D00845 KEGG_DRUG
370275005 SNOMEDCT_US
4019936 VANDF
56795 RXNORM
d00378 MMSL
004630 NDDF
49998007 SNOMEDCT_US
AFE2YW0IIZ UNII
4048 INN_ID
CHEMBL658 ChEMBL_ID
DB00708 DRUGBANK_ID
60561-17-3 SECONDARY_CAS_RN
CHEBI:9316 CHEBI
CHEMBL1201163 ChEMBL_ID
D017409 MESH_DESCRIPTOR_UI
41693 PUBCHEM_CID
3534 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Sufentanil Citrate HUMAN PRESCRIPTION DRUG LABEL 1 0409-3382 INJECTION, SOLUTION 50 ug EPIDURAL ANDA 19 sections
Sufentanil Citrate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6110 INJECTION 0.05 mg EPIDURAL ANDA 17 sections
Sufentanil Citrate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6111 INJECTION 0.05 mg EPIDURAL ANDA 17 sections
Sufentanil Citrate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6112 INJECTION 0.05 mg EPIDURAL ANDA 17 sections
Sufentanil Citrate HUMAN PRESCRIPTION DRUG LABEL 1 17478-050 INJECTION 50 ug INTRAVENOUS NDA 18 sections
Dsuvia HUMAN PRESCRIPTION DRUG LABEL 1 61621-430 TABLET 30 ug SUBLINGUAL NDA 19 sections