Entry

D00320                      Drug

Name

Fentanyl (JAN/USP/INN);
Duragesic (TN);
Subsys (TN)

Product

SUBSYS (Insys Therapeutics), DURAGESIC (Janssen Pharmaceuticals), SUBSYS (West Therapeutics Development)

Generic

FENTANYL SYSTEM (Alvogen), FENTANYL (Apotex Corp.), FENTANYL (Apotex Corp.), FENTANYL (Bryant Ranch Prepack), FENTANYL (Bryant Ranch Prepack), FENTANYL (Bryant Ranch Prepack), FENTANYL (Bryant Ranch Prepack), FENTANYL (Bryant Ranch Prepack), FENTANYL (Bryant Ranch Prepack), FENTANYL (Bryant Ranch Prepack), FENTANYL (Bryant Ranch Prepack), FENTANYL (Bryant Ranch Prepack), FENTANYL (Bryant Ranch Prepack), FENTANYL (DirectRX), FENTANYL (DirectRX), FENTANYL SYSTEM (Lake Erie Medical DBA Quality Care Products LLC), FENTANYL (Mylan Pharmaceuticals), FENTANYL SYSTEM (Quality Care Products), FENTANYL (Quality Care Products), FENTANYL SYSTEM (Quality Care Products), FENTANYL TRANSDERMAL (Bryant Ranch Prepack), FENTANYL TRANSDERMAL (Bryant Ranch Prepack), FENTANYL TRANSDERMAL (Bryant Ranch Prepack), FENTANYL TRANSDERMAL (SpecGx LLC), FENTANYL TRANSDERMAL SYSTEM (Bryant Ranch Prepack)

Formula

C22H28N2O

Exact mass

336.2202

Mol weight

336.4705

Structure

Simcomp

Class

Neuropsychiatric agent
DG02030  Anesthetics
  DG02027  General anesthetics
   DG02026  Opioid anesthetics
DG01564  Opioid receptor agonist
  DG01563  mu-Opioid receptor agonist
Analgesic
DG01984  Opioid analgesics
Metabolizing enzyme substrate
DG01633  CYP3A/CYP3A4 substrate
  DG02913  CYP3A4 substrate

Remark

Therapeutic category:

8219

ATC code:

N01AH01 N02AB03

Chemical structure group:

DG00791

Product (DG00791):

D00320<JP/US> D01399<JP/US>

Efficacy

Analgesic (narcotic), Opioid receptor agonist

Comment

synthetic-opioid
Phenylpiperidine derivative

Target

OPRM1 [HSA:4988] [KO:K04215]

Pathway

hsa04080

Neuroactive ligand-receptor interaction

Metabolism

Enzyme: CYP3A4 [HSA:1576]

Interaction

Structure map

map07039

Opioid analgesics

map07224

Opioid receptor agonists/antagonists

Brite

Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
N NERVOUS SYSTEM
  N01 ANESTHETICS
   N01A ANESTHETICS, GENERAL
    N01AH Opioid anesthetics
     N01AH01 Fentanyl
      D00320  Fentanyl (JAN/USP/INN) <JP/US>
  N02 ANALGESICS
   N02A OPIOIDS
    N02AB Phenylpiperidine derivatives
     N02AB03 Fentanyl
      D00320  Fentanyl (JAN/USP/INN) <JP/US>
USP drug classification [BR:br08302]
Analgesics
  Opioid Analgesics, Long-acting
   Fentanyl
    D00320  Fentanyl (JAN/USP/INN)
  Opioid Analgesics, Short-acting
   Fentanyl
    D00320  Fentanyl (JAN/USP/INN)
Therapeutic category of drugs in Japan [BR:br08301]
8  Narcotics
  82  Non-alkaloidal narcotics
   821  Synthetic narcotics
    8219  Others
     D00320  Fentanyl (JAN/USP/INN)
Drug groups [BR:br08330]
Neuropsychiatric agent
  DG02030  Anesthetics
   DG02027  General anesthetics
    DG02026  Opioid anesthetics
     DG00791  Fentanyl
      D00320  Fentanyl
  DG01564  Opioid receptor agonist
   DG01563  mu-Opioid receptor agonist
    DG00791  Fentanyl
     D00320  Fentanyl
Analgesic
  DG01984  Opioid analgesics
   DG00791  Fentanyl
    D00320  Fentanyl
Metabolizing enzyme substrate
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00791  Fentanyl
     D00320  Fentanyl
Target-based classification of drugs [BR:br08310]
G Protein-coupled receptors
  Rhodopsin family
   Opioid
    OPRM1
     D00320  Fentanyl (JAN/USP/INN) <JP/US>
Drug metabolizing enzymes and transporters [br08309.html]
Drug metabolizing enzymes
  D00320
Drug groups [BR:br08330]
Neuropsychiatric agent
  DG02030  Anesthetics
   DG02027  General anesthetics
    DG02026  Opioid anesthetics
     DG00791  Fentanyl
  DG01564  Opioid receptor agonist
   DG01563  mu-Opioid receptor agonist
    DG00791  Fentanyl
Analgesic
  DG01984  Opioid analgesics
   DG00791  Fentanyl
Metabolizing enzyme substrate
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00791  Fentanyl

Other DBs

CAS:

437-38-7

PubChem:

7847386

ChEBI:

119915

PDB-CCD:

7V7[PDBj]

LigandBox:

D00320

NIKKAJI:

J5.736C

KCF data

ATOM        25
            1   N1c N    28.2800  -14.2100
            2   C1y C    29.5400  -14.9100
            3   C8y C    27.0900  -14.9100
            4   C5a C    28.2800  -12.8100
            5   C1x C    29.5400  -16.3100
            6   C1x C    30.7300  -14.2100
            7   C8x C    25.9000  -14.2100
            8   C8x C    27.0900  -16.3100
            9   C1b C    29.5400  -12.1100
            10  O5a O    27.0900  -12.1100
            11  C1x C    30.7300  -17.0100
            12  C1x C    31.9200  -14.9100
            13  C8x C    24.6400  -14.9100
            14  C8x C    25.8300  -17.0100
            15  C1a C    30.7300  -12.8100
            16  N1y N    31.9200  -16.3100
            17  C8x C    24.6400  -16.2400
            18  C1b C    33.1800  -17.0100
            19  C1b C    34.3700  -16.3100
            20  C8y C    35.5600  -17.0100
            21  C8x C    35.5600  -18.4100
            22  C8x C    36.8200  -16.3100
            23  C8x C    36.8200  -19.1100
            24  C8x C    38.0100  -17.0100
            25  C8x C    38.0100  -18.4100
BOND        27
            1     1   2 1
            2     1   3 1
            3     1   4 1
            4     2   5 1
            5     2   6 1
            6     3   7 2
            7     3   8 1
            8     4   9 1
            9     4  10 2
            10    5  11 1
            11    6  12 1
            12    7  13 1
            13    8  14 2
            14    9  15 1
            15   11  16 1
            16   13  17 2
            17   16  18 1
            18   18  19 1
            19   19  20 1
            20   20  21 1
            21   20  22 2
            22   21  23 2
            23   22  24 1
            24   23  25 1
            25   12  16 1
            26   14  17 1
            27   24  25 2