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    Synopsis

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    Chemistry

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    Also known as: Phentanyl, Fentanil, Fentanest, Fentora, 437-38-7, Duragesic
    Molecular Formula
    C22H28N2O
    Molecular Weight
    336.5  g/mol
    InChI Key
    PJMPHNIQZUBGLI-UHFFFAOYSA-N
    FDA UNII
    UF599785JZ
    Fentanyl
    A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078)
    Fentanyl is an Opioid Agonist. The mechanism of action of fentanyl is as a Full Opioid Agonist.
    1 2D Structure

    Fentanyl

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
    2.1.2 InChI
    InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3
    2.1.3 InChI Key
    PJMPHNIQZUBGLI-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3
    2.2 Other Identifiers
    2.2.1 UNII
    UF599785JZ
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Duragesic

    2. Durogesic

    3. Fentanest

    4. Fentanyl Citrate

    5. Fentora

    6. Phentanyl

    7. R 4263

    8. R-4263

    9. R4263

    10. Sublimaze

    11. Transmucosal Oral Fentanyl Citrate

    2.3.2 Depositor-Supplied Synonyms

    1. Phentanyl

    2. Fentanil

    3. Fentanest

    4. Fentora

    5. 437-38-7

    6. Duragesic

    7. Sublimaze

    8. Fentanylum

    9. Fentanila

    10. Sentonil

    11. Sublimase

    12. Duragesic-100

    13. Matrifen

    14. Ionsys

    15. N-(1-phenethylpiperidin-4-yl)-n-phenylpropionamide

    16. Duragesic-12

    17. Duragesic-25

    18. Duragesic-50

    19. Duragesic-75

    20. Fentanyl-12

    21. Fentanyl-25

    22. Fentanyl-50

    23. Fentanyl-75

    24. Fentanylum [inn-latin]

    25. Fentanila [inn-spanish]

    26. Fentanyl-100

    27. 1-phenethyl-4-n-propionylanilinopiperidine

    28. Recuvyra

    29. Pecfent

    30. Fentanyl Cii

    31. N-(1-phenethyl-4-piperidyl)propionanilide

    32. N-phenyl-n-[1-(2-phenylethyl)piperidin-4-yl]propanamide

    33. N-phenethyl-4-(n-propionylanilino)piperidine

    34. 1-phenethyl-4-(n-phenylpropionamido)piperidine

    35. R 4263

    36. Fendrop

    37. Abstral-

    38. N-(1-phenethyl-4-piperidinyl)-n-phenylpropionamide

    39. Durogesic D-trans

    40. N-phenyl-n-(1-(2-phenylethyl)-4-piperidinyl)propanamide

    41. N02ab03

    42. Chebi:119915

    43. N-(1-phenethyl-piperidin-4-yl)-n-phenyl-propionamide

    44. Propionanilide, N-(1-phenethyl-4-piperidyl)-

    45. Durogesic

    46. Chembl596

    47. Ids-nf-001

    48. R4263

    49. En3267

    50. Propanamide, N-phenyl-n-(1-(2-phenylethyl)-4-piperidinyl)-

    51. Propanamide, N-phenyl-n-[1-(2-phenylethyl)-4-piperidinyl]-

    52. Uf599785jz

    53. Ad 923

    54. Ad-923

    55. En-3267

    56. Ncgc00168252-01

    57. Subsys

    58. Fentanil [dcit]

    59. Durotep Mt

    60. Hsdb 3329

    61. Einecs 207-113-6

    62. Fentanyl Transdermal System

    63. Jns020qd

    64. Brn 0494484

    65. Unii-uf599785jz

    66. Fentanyl [usan:usp:inn:ban]

    67. Duragesic (tn)

    68. Subsys (tn)

    69. Fentanyl-hcl

    70. Fentanyl [hsdb]

    71. Fentanyl [usan]

    72. Fentanyl [inn]

    73. Fentanyl [jan]

    74. Fentanyl [mi]

    75. Fentanyl [vandf]

    76. Dsstox_cid_3049

    77. Fentanyl [mart.]

    78. Epitope Id:153507

    79. Fentanyl [who-dd]

    80. Schembl8804

    81. Fentanyl (jan/usp/inn)

    82. Dsstox_rid_76851

    83. Fentanyl [ema Epar]

    84. Dsstox_gsid_23049

    85. Oprea1_152073

    86. Oprea1_207148

    87. 5-22-08-00049 (beilstein Handbook Reference)

    88. Bidd:gt0555

    89. Fentanyl [green Book]

    90. Fentanyl [ep Impurity]

    91. Fentanyl [orange Book]

    92. Fentanyl Cii [usp-rs]

    93. Gtpl1626

    94. Fentanyl [ep Monograph]

    95. Dtxsid9023049

    96. Fentanyl [usp Monograph]

    97. Fentanyl 0.1 Mg/ml In Methanol

    98. Fentanyl 1.0 Mg/ml In Methanol

    99. N-(1-(2-phenylethyl)-4-piperidinyl)-n-phenylpropanamide

    100. Zinc2522669

    101. Tox21_112611

    102. Bdbm50008984

    103. Hy-u00158

    104. Pdsp1_000860

    105. Pdsp2_000846

    106. Fentanyl [ema Epar Veterinary]

    107. Cs-7211

    108. Db00813

    109. Cas-437-38-7

    110. N-(1-phenylethyl-4-piperidinyl)propionanilide

    111. D00320

    112. 1-(2-phenylethyl)-4-(n-propananilido)piperidine

    113. L001275

    114. Q407541

    115. N-phenyl-n-[1-(2-phenylethyl)-4-piperidinyl]propanamide #

    116. N-(1-phenethyl-piperidin-4-yl)-n-phenyl-propionamide(fentanyl)

    117. Propanamide, N-phenyl-n-(1-(2-phenylethyl)-4-piperidinyl)

    118. Fentanyl Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

    119. Fentanyl Solution, 100 Mug/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 336.5 g/mol
    Molecular Formula C22H28N2O
    XLogP34
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count6
    Exact Mass336.220163521 g/mol
    Monoisotopic Mass336.220163521 g/mol
    Topological Polar Surface Area23.6 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity391
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 24  
    Drug NameDuragesic-100
    PubMed HealthFentanyl (Into the mouth)
    Drug ClassesAnalgesic
    Drug LabelFENTORA (fentanyl buccal tablet) is a potent opioid analgesic, intended for buccal mucosal administration. FENTORA is designed to be placed and retained within the buccal cavity for a period sufficient to allow disintegration of the tablet and absorp...
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength100mcg/hr
    Market StatusPrescription
    CompanyJanssen Pharms

    2 of 24  
    Drug NameDuragesic-12
    Drug LabelSUBSYS (fentanyl sublingual spray) is a potent opioid analgesic intended for sublingual mucosal administration.SUBSYS is formulated to be sprayed underneath the tongue to allow for absorption of fentanyl across the sublingual mucosa.Active Ingredient...
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength12.5mcg/hr
    Market StatusPrescription
    CompanyJanssen Pharms

    3 of 24  
    Drug NameDuragesic-25
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength25mcg/hr
    Market StatusPrescription
    CompanyJanssen Pharms

    4 of 24  
    Drug NameDuragesic-50
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength50mcg/hr
    Market StatusPrescription
    CompanyJanssen Pharms

    5 of 24  
    Drug NameDuragesic-75
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength75mcg/hr
    Market StatusPrescription
    CompanyJanssen Pharms

    6 of 24  
    Drug NameFentanyl-100
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength100mcg/hr
    Market StatusPrescription
    CompanyWatson Labs; Mylan Technologies; Mallinckrodt; Aveva; Lavipharm Labs; Par Pharm

    7 of 24  
    Drug NameFentanyl-12
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength12.5mcg/hr
    Market StatusPrescription
    CompanyMylan Technologies

    8 of 24  
    Drug NameFentanyl-25
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength25mcg/hr
    Market StatusPrescription
    CompanyWatson Labs; Mylan Technologies; Mallinckrodt; Aveva; Lavipharm Labs; Par Pharm

    9 of 24  
    Drug NameFentanyl-50
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength50mcg/hr
    Market StatusPrescription
    CompanyWatson Labs; Mylan Technologies; Mallinckrodt; Aveva; Lavipharm Labs; Par Pharm

    10 of 24  
    Drug NameFentanyl-75
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength75mcg/hr
    Market StatusPrescription
    CompanyWatson Labs; Mylan Technologies; Mallinckrodt; Aveva; Lavipharm Labs; Par Pharm

    11 of 24  
    Drug NameFentora
    Active IngredientFentanyl citrate
    Dosage FormTablet
    RouteBuccal, sublingual
    Strengtheq 0.1mg base; eq 0.8mg base; eq 0.6mg base; eq 0.4mg base; eq 0.2mg base
    Market StatusPrescription
    CompanyCephalon

    12 of 24  
    Drug NameSubsys
    Active IngredientFentanyl
    Dosage FormSpray
    RouteSublingual
    Strength0.8mg; 1.2mg; 1.6mg; 0.4mg; 0.1mg; 0.6mg; 0.2mg
    Market StatusPrescription
    CompanyInsys Therap

    13 of 24  
    Drug NameDuragesic-100
    PubMed HealthFentanyl (Into the mouth)
    Drug ClassesAnalgesic
    Drug LabelFENTORA (fentanyl buccal tablet) is a potent opioid analgesic, intended for buccal mucosal administration. FENTORA is designed to be placed and retained within the buccal cavity for a period sufficient to allow disintegration of the tablet and absorp...
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength100mcg/hr
    Market StatusPrescription
    CompanyJanssen Pharms

    14 of 24  
    Drug NameDuragesic-12
    Drug LabelSUBSYS (fentanyl sublingual spray) is a potent opioid analgesic intended for sublingual mucosal administration.SUBSYS is formulated to be sprayed underneath the tongue to allow for absorption of fentanyl across the sublingual mucosa.Active Ingredient...
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength12.5mcg/hr
    Market StatusPrescription
    CompanyJanssen Pharms

    15 of 24  
    Drug NameDuragesic-25
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength25mcg/hr
    Market StatusPrescription
    CompanyJanssen Pharms

    16 of 24  
    Drug NameDuragesic-50
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength50mcg/hr
    Market StatusPrescription
    CompanyJanssen Pharms

    17 of 24  
    Drug NameDuragesic-75
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength75mcg/hr
    Market StatusPrescription
    CompanyJanssen Pharms

    18 of 24  
    Drug NameFentanyl-100
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength100mcg/hr
    Market StatusPrescription
    CompanyWatson Labs; Mylan Technologies; Mallinckrodt; Aveva; Lavipharm Labs; Par Pharm

    19 of 24  
    Drug NameFentanyl-12
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength12.5mcg/hr
    Market StatusPrescription
    CompanyMylan Technologies

    20 of 24  
    Drug NameFentanyl-25
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength25mcg/hr
    Market StatusPrescription
    CompanyWatson Labs; Mylan Technologies; Mallinckrodt; Aveva; Lavipharm Labs; Par Pharm

    21 of 24  
    Drug NameFentanyl-50
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength50mcg/hr
    Market StatusPrescription
    CompanyWatson Labs; Mylan Technologies; Mallinckrodt; Aveva; Lavipharm Labs; Par Pharm

    22 of 24  
    Drug NameFentanyl-75
    Active IngredientFentanyl
    Dosage FormFilm, extended release
    RouteTransdermal
    Strength75mcg/hr
    Market StatusPrescription
    CompanyWatson Labs; Mylan Technologies; Mallinckrodt; Aveva; Lavipharm Labs; Par Pharm

    23 of 24  
    Drug NameFentora
    Active IngredientFentanyl citrate
    Dosage FormTablet
    RouteBuccal, sublingual
    Strengtheq 0.1mg base; eq 0.8mg base; eq 0.6mg base; eq 0.4mg base; eq 0.2mg base
    Market StatusPrescription
    CompanyCephalon

    24 of 24  
    Drug NameSubsys
    Active IngredientFentanyl
    Dosage FormSpray
    RouteSublingual
    Strength0.8mg; 1.2mg; 1.6mg; 0.4mg; 0.1mg; 0.6mg; 0.2mg
    Market StatusPrescription
    CompanyInsys Therap

    4.2 Therapeutic Uses

    Analgesics, Opioid; Adjuvants, Anesthesia; Narcotics; Anesthetics, Intravenous

    National Library of Medicine's Medical Subject Headings. Fentanyl. Online file (MeSH, 2017). Available from, as of April 26, 2017: https://www.nlm.nih.gov/mesh/2017/mesh_browser/MBrowser.html

    /CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Fentanyl is included in the database.

    NIH/NLM; ClinicalTrials.Gov. Available from, as of June 20, 2017: https://clinicaltrials.gov/

    Fentanyl citrate is a strong analgesic used preoperatively, during surgery, and in the immediate postoperative period for its analgesic action. In addition, the drug may be used to prevent