Entry

D02219                      Drug

Name

Terbinafine hydrochloride (JP18/USP);
Lamisil (TN)

Product

Generic

TERBINAFINE (Bryant Ranch Prepack), TERBINAFINE (Chartwell RX), TERBINAFINE (Cipla USA), TERBINAFINE (Exelan Pharmaceuticals), TERBINAFINE (Proficient Rx LP), TERBINAFINE HYDROCHLORIDE (Proficient Rx LP), TERBINAFINE (REMEDYREPACK), TERBINAFINE (direct rx), TERBINAFINE (A-S Medication Solutions), TERBINAFINE HYDROCHLORIDE (A-S Medication Solutions), TERBINAFINE (A-S Medication Solutions), TERBINAFINE HYDROCHLORIDE (Aphena Pharma Solutions - Tennessee), TERBINAFINE (Aurobindo Pharma Limited), TERBINAFINE HYDROCHLORIDE (Bionpharma), TERBINAFINE HYDROCHLORIDE (Breckenridge Pharmaceutical), TERBINAFINE HYDROCHLORIDE (Bryant Ranch Prepack), TERBINAFINE HYDROCHLORIDE (Bryant Ranch Prepack), TERBINAFINE (Bryant Ranch Prepack), TERBINAFINE HYDROCHLORIDE (Bryant Ranch Prepack), TERBINAFINE HYDROCHLORIDE (Bryant Ranch Prepack), TERBINAFINE HYDROCHLORIDE (Bryant Ranch Prepack), TERBINAFINE HYDROCHLORIDE (Denton Pharma), TERBINAFINE HYDROCHLORIDE (DirectRX), TERBINAFINE HYDROCHLORIDE (Dr.Reddys Laboratories Limited), TERBINAFINE HYDROCHLORIDE (Golden State Medical Supply), TERBINAFINE HYDROCHLORIDE (Harris Pharmaceutical), TERBINAFINE (Lake Erie Medical DBA Quality Care Products LLC), TERBINAFINE (NorthStar Rx LLC), TERBINAFINE HYDROCHLORIDE (Northwind Pharmaceuticals), TERBINAFINE HYDROCHLORIDE (NuCare Pharmaceuticals), TERBINAFINE HYDROCHLORIDE (NuCare Pharmaceuticals), TERBINAFINE HYDROCHLORIDE (NuCare Pharmaceuticals), TERBINAFINE (NuCare Pharmaceuticals), TERBINAFINE (NuCare Pharmaceuticals), TERBINAFINE HYDROCHLORIDE (NuCare Pharmaceuticals), TERBINAFINE (NuCare Pharmaceuticals), TERBINAFINE HYDROCHLORIDE (OrchidPharma), TERBINAFINE HYDROCHLORIDE (PD-Rx Pharmaceuticals), TERBINAFINE HYDROCHLORIDE (PD-Rx Pharmaceuticals), TERBINAFINE HYDROCHLORIDE (Preferred Pharmaceuticals), TERBINAFINE (Preferred Pharmaceuticals), TERBINAFINE (Proficient Rx LP), TERBINAFINE HYDROCHLORIDE (Proficient Rx LP), TERBINAFINE (Proficient Rx LP), TERBINAFINE HYDROCHLORIDE (Proficient Rx LP), TERBINAFINE HYDROCHLORIDE (REMEDYREPACK), TERBINAFINE (REMEDYREPACK), TERBINAFINE (RPK Pharmaceuticals), TERBINAFINE HYDROCHLORIDE (Wockhardt USA LLC.), TERBINAFINE HYDROCHLORIDE (Cipla USA), TERBINAFINE HYDROCHLORIDE (NuCare Pharmaceuticals), TERBINAFINE HYDROCHLORIDE (REMEDYREPACK)

Formula

C21H25N. HCl

Exact mass

327.1754

Mol weight

327.8908

Structure

Simcomp

Class

Metabolizing enzyme substrate
DG01892  CYP1A2 substrate
DG02918  CYP2C8 substrate
DG01642  CYP2C9 substrate
DG01639  CYP2C19 substrate
DG01633  CYP3A/CYP3A4 substrate
  DG02913  CYP3A4 substrate
Metabolizing enzyme inhibitor
DG01645  CYP2D6 inhibitor

Remark

Therapeutic category:

2659 6290

ATC code:

D01AE15 D01BA02

Chemical structure group:

DG00375

Product (DG00375):

D02219<JP/US>

Efficacy

Antifungal, Ergosterol biosynthesis inhibitor

Disease

Onychomycosis [DS:H01316]
Tinea unguium [DS:H01316]
Tinea capitis [DS:H01316]

Comment

Allylamine derivative

Target

squalene epoxidase [KO:K00511]

Pathway

ko00100

Steroid biosynthesis

Metabolism

Enzyme: CYP2C9 [HSA:1559], CYP1A2 [HSA:1544], CYP3A4 [HSA:1576], CYP2C8 [HSA:1558], CYP2C19 [HSA:1557]

Interaction

CYP inhibition: CYP2D6 [HSA:1565]

Structure map

map07026

Antifungal agents

map07114

Naphthalene family

Brite

Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
D DERMATOLOGICALS
  D01 ANTIFUNGALS FOR DERMATOLOGICAL USE
   D01A ANTIFUNGALS FOR TOPICAL USE
    D01AE Other antifungals for topical use
     D01AE15 Terbinafine
      D02219  Terbinafine hydrochloride (JP18/USP) <JP/US>
   D01B ANTIFUNGALS FOR SYSTEMIC USE
    D01BA Antifungals for systemic use
     D01BA02 Terbinafine
      D02219  Terbinafine hydrochloride (JP18/USP) <JP/US>
USP drug classification [BR:br08302]
Antifungals
  Terbinafine
   D02219  Terbinafine hydrochloride (JP18/USP)
Dermatological Agents
  Topical Anti-infectives
   Antifungals, dermatological
    Terbinafine
     D02219  Terbinafine hydrochloride (JP18/USP)
Therapeutic category of drugs in Japan [BR:br08301]
2  Agents affecting individual organs
  26  Epidermides
   265  Antiparasitic dermatosis agents
    2659  Others
     D02219  Terbinafine hydrochloride (JP18/USP)
6  Agents against pathologic organisms and parasites
  62  Chemotherapeutics
   629  Miscellaneous
    6290  Miscellaneous
     D02219  Terbinafine hydrochloride (JP18/USP)
Classification of Japanese OTC drugs [BR:br08313]
Agents for integumentary system
  58 Ringworm drugs
   D02219  Terbinafine hydrochloride (JP18/USP)
Risk category of Japanese OTC drugs [BR:br08312]
Designated second-class OTC drugs
  Inorganic and organic chemicals
   Terbinafine
    D02219  Terbinafine hydrochloride (JP18/USP)
Second-class OTC drugs
  Inorganic and organic chemicals
   Terbinafine
    D02219  Terbinafine hydrochloride (JP18/USP)
Drug groups [BR:br08330]
Metabolizing enzyme substrate
  DG01892  CYP1A2 substrate
   DG00375  Terbinafine
    D02219  Terbinafine hydrochloride
  DG02918  CYP2C8 substrate
   DG00375  Terbinafine
    D02219  Terbinafine hydrochloride
  DG01642  CYP2C9 substrate
   DG00375  Terbinafine
    D02219  Terbinafine hydrochloride
  DG01639  CYP2C19 substrate
   DG00375  Terbinafine
    D02219  Terbinafine hydrochloride
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00375  Terbinafine
     D02219  Terbinafine hydrochloride
Metabolizing enzyme inhibitor
  DG01645  CYP2D6 inhibitor
   DG00375  Terbinafine
    D02219  Terbinafine hydrochloride
Antimicrobials [BR:br08307]
Antifungals
  Ergosterol biosynthesis inhibitor
   Other ergosterol biosynthesis inhibitor
    D02219  Terbinafine hydrochloride (JP18/USP) <JP/US>
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
Chemicals
  D02219  Terbinafine hydrochloride
  D02219  Terbinafine hydrochloride tablets
  D02219  Terbinafine hydrochloride solution
  D02219  Terbinafine hydrochloride spray
  D02219  Terbinafine hydrochloride cream
Drug metabolizing enzymes and transporters [br08309.html]
Drug metabolizing enzymes
  D02219
Rx-to-OTC switch list in the USA [br08315.html]
D02219
Rx-to-OTC switch list in Japan [br08314.html]
D02219
Drug groups [BR:br08330]
Metabolizing enzyme substrate
  DG01892  CYP1A2 substrate
   DG00375  Terbinafine
  DG02918  CYP2C8 substrate
   DG00375  Terbinafine
  DG01642  CYP2C9 substrate
   DG00375  Terbinafine
  DG01639  CYP2C19 substrate
   DG00375  Terbinafine
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00375  Terbinafine
Metabolizing enzyme inhibitor
  DG01645  CYP2D6 inhibitor
   DG00375  Terbinafine
Antimicrobials abbreviations [BR:br08327]
Antifungals
  Ergosterol biosynthesis inhibitor
   Other ergosterol biosynthesis inhibitor
    DG00375  Terbinafine

Other DBs

CAS:	78628-80-5

PubChem:

7849278

ChEBI:

77614

LigandBox:

D02219

NIKKAJI:

J257.267B

KCF data

ATOM        23
            1   X   Cl   36.1001  -19.8424
            2   C8x C    25.4100  -18.8300
            3   C8x C    25.4100  -20.2300
            4   C8x C    26.6700  -20.9300
            5   C8y C    27.8600  -20.2300
            6   C8y C    27.8600  -18.8300
            7   C8x C    26.6700  -18.1300
            8   C8x C    29.0500  -20.9300
            9   C8x C    30.3100  -20.2300
            10  C8x C    30.3100  -18.8300
            11  C8y C    29.0500  -18.1300
            12  C1b C    29.0500  -16.7300
            13  N1c N    30.3100  -16.0300
            14  C1b C    31.5000  -16.7300
            15  C1a C    30.3100  -14.6300
            16  C2b C    32.6900  -16.0300
            17  C2b C    33.8800  -16.7300
            18  C3b C    35.0700  -16.0300
            19  C3b C    36.2600  -15.3300
            20  C1d C    37.5200  -14.6300
            21  C1a C    38.7100  -13.9300
            22  C1a C    36.8200  -13.3700
            23  C1a C    38.2200  -15.8200
BOND        23
            1     2   3 2
            2     3   4 1
            3     4   5 2
            4     5   6 1
            5     6   7 2
            6     2   7 1
            7     5   8 1
            8     8   9 2
            9     9  10 1
            10   10  11 2
            11    6  11 1
            12   11  12 1
            13   12  13 1
            14   13  14 1
            15   13  15 1
            16   14  16 1
            17   16  17 2
            18   17  18 1
            19   18  19 3
            20   19  20 1
            21   20  21 1
            22   20  22 1
            23   20  23 1