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Drug

D0422 | Clotrimazole

Molecular Formula C22H17ClN2
Molecular Weight 344.8
Structure
State solid
Volume of distribution The topical form is minimally absorbed in the serum and tissues [F3088]. Clotrimazole is a lipophilic drug [A174118], and has been shown to be secreted in breastmilk in animal studies [F3088]. There are limited data available regarding the volume of distribution following oral troche administration.
Route of elimination Mainly hepatic [L5173].
Protein binding 98% [L5170]
Absorption Because clotrimazole is generally not significantly absorbed, drug interactions are not a major issue with its use [A174094].

D

G

A

G01AF20 Combinations of imidazole derivatives


[G01AF] Imidazole derivatives


[G01A] ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS


[G01] GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS


[G] Genitourinary system and reproductive hormones

G01AF02 Clotrimazole


[G01AF] Imidazole derivatives


[G01A] ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS


[G01] GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS


[G] Genitourinary system and reproductive hormones

D01AC01 Clotrimazole


[D01AC] Imidazole and triazole derivatives


[D01A] ANTIFUNGALS FOR TOPICAL USE


[D01] ANTIFUNGALS FOR DERMATOLOGICAL USE


[D] Dermatological drugs

A01AB18 Clotrimazole


[A01AB] Antiinfectives and antiseptics for local oral treatment


[A01A] STOMATOLOGICAL PREPARATIONS


[A01] STOMATOLOGICAL PREPARATIONS


[A] Alimentary tract and metabolism

Toxicity Dose Time Species Model Method Action Positive criterion Reference
MEMBRANE POTENTIAL 23.9 µM 30 mins mouse liver mitochondria Rh123 fluorescence (excitation 485 nm, emission 535 nm) are recorded using a fluorescence multi-well plate reader (mCICCP (20 µM) treatments was considered as the 100% baseline for ΔΨm loss) decrease EC20 36
RESPIRATION 2.9 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. decrease EC20 36
RESPIRATION ND 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. Negative EC20 36
GLYCOLYSIS decrease 35
SWELLING ND 30 mins mouse liver mitochondria swelling assay: Absorbance at 545 nm using a fluorescence multi-well plate reader (CaCl2 (50 µM) was considered as the 100% baseline for the swelling ) Negative EC20 36
APOPTOSIS 40 µM 12 hours human CAL27 western blot increase 2.1875-fold decrease 5
APOPTOSIS 40 µM 12 hours human UM1 western blot increase 1.35-fold decrease 5
APOPTOSIS 40 µM 24 hours human CAL27 western blot increase 3.1818-fold decrease 5
APOPTOSIS 40 µM 24 hours human UM1 western blot increase 1.5-fold decrease 5
APOPTOSIS 40 µM 48 hours human CAL27 western blot increase 3.3333-fold decrease 5
APOPTOSIS 40 µM 48 hours human UM1 western blot increase 1.5882-fold decrease 5
APOPTOSIS 40 µM 12 hours human CAL27 western blot increase 1.3953-fold increase 5
APOPTOSIS 40 µM 12 hours human UM1 western blot Negative No increase 5
APOPTOSIS 40 µM 24 hours human CAL27 western blot increase 1.3953-fold increase 5
APOPTOSIS 40 µM 24 hours human UM1 western blot increase 1.2623-fold increase 5
APOPTOSIS 40 µM 48 hours human CAL27 western blot increase 2.3256-fold increase 5
APOPTOSIS 40 µM 48 hours human UM1 western blot increase 1.6223-fold increase 5
APOPTOSIS 150 mg/kg/day 6 days a week for two weeks human CAL27(xenograft tumors)/mouse Immunohistochemistry increase 1.5-fold decrease 5
APOPTOSIS 150 mg/kg/day 6 days a week for two weeks human CAL27(xenograft tumors)/mouse western blot analysis increase 2.0-fold increase 5
EARLY APOPTOSIS 30 μmol/L 24 hours human CAL27 Apoptosis measurement increase p < 0.05 5
EARLY APOPTOSIS 30 μmol/L 24 hours human SCC25 Apoptosis measurement increase p < 0.05 5
EARLY APOPTOSIS 30 μmol/L 24 hours human UM1 Apoptosis measurement increase p < 0.05 5
EARLY APOPTOSIS 40 μmol/L 24 hours human CAL27 Apoptosis measurement increase p < 0.01 5
EARLY APOPTOSIS 40 μmol/L 24 hours human SCC25 Apoptosis measurement increase p < 0.01 5
EARLY APOPTOSIS 40 μmol/L 24 hours human UM1 Apoptosis measurement increase p < 0.01 5
LATE APOPTOSIS 30 μmol/L 24 hours human CAL27 Apoptosis measurement increase p < 0.05 5
LATE APOPTOSIS 30 μmol/L 24 hours human SCC25 Apoptosis measurement increase p < 0.05 5
LATE APOPTOSIS 30 μmol/L 24 hours human UM1 Apoptosis measurement increase p < 0.05 5
LATE APOPTOSIS 40 μmol/L 24 hours human CAL27 Apoptosis measurement increase p < 0.01 5
LATE APOPTOSIS 40 μmol/L 24 hours human SCC25 Apoptosis measurement increase p < 0.01 5
LATE APOPTOSIS 40 μmol/L 24 hours human UM1 Apoptosis measurement increase p < 0.01 5

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase 2.9 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. inhibit EC20 36
Succinate dehydrogenase ND 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. Negative EC20 36
Apoptosis regulator Bcl-2 40 µM 12 hours human CAL27 western blot inhibitor 2.1875-fold decrease 5
Apoptosis regulator Bcl-2 40 µM 12 hours human UM1 western blot inhibitor 1.35-fold decrease 5
Apoptosis regulator Bcl-2 40 µM 24 hours human CAL27 western blot inhibitor 3.1818-fold decrease 5
Apoptosis regulator Bcl-2 40 µM 24 hours human UM1 western blot inhibitor 1.5-fold decrease 5
Apoptosis regulator Bcl-2 40 µM 48 hours human CAL27 western blot inhibitor 3.3333-fold decrease 5
Apoptosis regulator Bcl-2 40 µM 48 hours human UM1 western blot inhibitor 1.5882-fold decrease 5
Apoptosis regulator Bcl-2 150 mg/kg/day 6 days a week for two weeks human CAL27(xenograft tumors)/mouse Immunohistochemistry inhibitor 1.5-fold decrease 5
Apoptosis regulator BAX 40 µM 12 hours human CAL27 western blot activate 1.3953-fold increase 5
Apoptosis regulator BAX 40 µM 12 hours human UM1 western blot Negative No increase 5
Apoptosis regulator BAX 40 µM 24 hours human CAL27 western blot activate 1.3953-fold increase 5
Apoptosis regulator BAX 40 µM 24 hours human UM1 western blot activate 1.2623-fold increase 5
Apoptosis regulator BAX 40 µM 48 hours human CAL27 western blot activate 2.3256-fold increase 5
Apoptosis regulator BAX 40 µM 48 hours human UM1 western blot activate 1.6223-fold increase 5
Apoptosis regulator BAX 150 mg/kg/day 6 days a week for two weeks human CAL27(xenograft tumors)/mouse western blot analysis activate 2.0-fold increase 5
Cytochrome c > 800 µM 30 mins mouse liver mitochondria Cytochrome c release was evaluated using ELISA kit ( 20 µg/ml Alamethicin was used as 100% baseline) release EC20 36

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 331 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


Reported as not meeting GHS hazard criteria by 3 of 331 companies. For more detailed information, please visit ECHA C&L website


Of the 12 notification(s) provided by 328 of 331 companies with hazard statement code(s):


H302 (99.09%): Harmful if swallowed [Warning Acute toxicity, oral]


H311 (10.67%): Toxic in contact with skin [Danger Acute toxicity, dermal]


H315 (80.18%): Causes skin irritation [Warning Skin corrosion/irritation]


H319 (90.85%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H361 (10.67%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


H373 (10.67%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]


H400 (83.84%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]


H410 (84.45%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P201, P202, P260, P264, P270, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P312, P314, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P391, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
mammal (species unspecified) LD50 oral 750mg/kg (750mg/kg) Antimicrobial Agents and Chemotherapy Vol. -, Pg. 271, 1969.
women TDLo intravaginal 28mg/kg/7D (28mg/kg) skin and appendages (skin): primary irritation: after topical exposure Clinical Toxicology. Vol. 18, Pg. 41, 1981.
rat LDLo subcutaneous 10gm/kg (10000mg/kg) Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1333, 1973.
mouse LD50 intravenous 198mg/kg (198mg/kg) Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
cat LD50 oral > 1gm/kg (1000mg/kg) gastrointestinal: nausea or vomiting Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
rabbit LD50 oral > 1gm/kg (1000mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
rat LD50 oral 708mg/kg (708mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
mouse LD50 oral 761mg/kg (761mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
mouse LD50 intraperitoneal 108mg/kg (108mg/kg) Drug and Chemical Toxicology. Vol. 13, Pg. 195, 1990.
dog LD50 oral > 2gm/kg (2000mg/kg) gastrointestinal: nausea or vomiting Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
rat LD50 intraperitoneal 445mg/kg (445mg/kg) Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1333, 1973.
mouse LDLo subcutaneous 10gm/kg (10000mg/kg) Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1333, 1973.


  • (2-Chlorophenyl)diphenyl-1-imidazolylmethane (Chlorotrityl)imidazole 1-((2-Chlorophenyl)diphenylmethyl)-1H-imidazole
    1-((2-Chlorophenyl)diphenylmethyl)-1H-imidazole (9CI) 1-((o-Chloro-phenyl)diphenylmethyl)imidazole 1-(.alpha.-(2-Chlorophenyl)benzhydryl)imidazole
    1-(2-Chloro-?,?-diphenylbenzyl)imidazole 1-(2-chlorotrityl)imidazole 1-(alpha-(2-Chlorophenyl)benzhydryl)imidazole
    1-(o-Chloro-.alpha.,.alpha.-diphenylbenzyl)imidazole 1-(o-Chloro-alpha,alpha-diphenylbenzyl)imidazole 1-(o-Chloro-|A,|A-diphenylbenzyl)imidazole
    1-(o-Chlorophenyldiphenylmethyl)imidazole 1-(o-Chlorotrityl)imidazole 1-(o-Chlorotrityl)imidazole
    1-(o-chloro-a,a-diphenylbenzyl)imidazole 1-[(2-Chloro-phenyl)-diphenyl-methyl]-1H-imidazole 1-[(2-Chlorophenyl)diphenylmethyl]-1H-imidazole
    1-[(2-Chlorophenyl)diphenylmethyl]-1H-imidazole 1-[(2-Chlorophenyl)diphenylmethyl]imidazole 1-[(2-chlorophenyl)(diphenyl)methyl]-1H-imidazole
    1-[(2-chlorophenyl)-di(phenyl)methyl]imidazole 1-[(2-chlorophenyl)-diphenyl-methyl]imidazole 1-[(2-chlorophenyl)-diphenylmethyl]imidazole
    1H-Imidazole, 1-((2-chlorophenyl)diphenylmethyl)- 1H-Imidazole, 1-[(2-chlorophenyl)-diphenylmethyl] 1H-Imidazole, 1-[(2-chlorophenyl)diphenylmethyl]-
    23593-75-1 3ACDFDF8-38E3-4368-85D0-BDF8AE1E6591 455-EP2272972A1
    455-EP2272973A1 455-EP2275420A1 455-EP2277872A1
    455-EP2281816A1 455-EP2292595A1 455-EP2295055A2
    455-EP2295416A2 455-EP2298748A2 455-EP2298764A1
    455-EP2298765A1 455-EP2305642A2 455-EP2311453A1
    455-EP2311808A1 455-EP2311829A1 5-23-04-00291 (Beilstein Handbook Reference)
    593C751 A816789 AB00051951
    AB00051951-14 AB00051951_15 AB00051951_16
    AB0015989 AB1009401 AKOS005607024
    API0002086 AS-13816 B 5097
    BAY 5097 BAY b 5097 BAY b5097
    BAY-5097 BAYb 5097 BCP02150
    BDBM31774 BIDD:GT0450 BIDD:PXR0036
    BPBio1_000126 BRD-K15916496-001-14-7 BRN 0622318
    BSPBio_000114 BSPBio_002057 Bay b 9057
    Bay-B 5097 Bis-fenil-(2-clorofenil)-1-imidazolil-metano Bis-fenil-(2-clorofenil)-1-imidazolil-metano [Italian]
    Bis-phenyl-(2-chlorophenyl)(1-imidazoyl)methane Bis-phenyl-(2-chlorophenyl)-1-imidazoyl)methane Bisphenyl-(2-chlorphenyl)-1-imidazolyl-methan
    Bisphenyl-(2-chlorphenyl)-1-imidazolyl-methan [German] C 6019 C06922
    CAS-23593-75-1 CCG-35563 CCRIS 6245
    CHEBI:3764 CHEMBL104 CLT
    CPD000058306 CS-1926 Canesten
    Canesten 1-Day Cream Combi-Pak Canesten 1-Day Therapy Canesten 3-Day Therapy
    Canesten 6-Day Therapy Canesten Combi-Pak 1-Day Therapy Canesten Combi-Pak 3-Day Therapy
    Canesten Cream Canesten Solution Canestene
    Canestine Canifug Certified Reference Material
    Chlotrimazole Clomatin Clotrimaderm
    Clotrimaderm Cream Clotrimazol Clotrimazol [INN-Spanish]
    Clotrimazole (Canesten) Clotrimazole (JP17/USP/INN) Clotrimazole [USAN:INN:BAN:JAN]
    Clotrimazole [USAN:USP:INN:BAN:JAN] Clotrimazole for peak identification, European Pharmacopoeia (EP) Reference Standard Clotrimazole(Canesten)
    Clotrimazole, British Pharmacopoeia (BP) Reference Standard Clotrimazole, European Pharmacopoeia (EP) Reference Standard Clotrimazole, Pharmaceutical Secondary Standard
    Clotrimazole, United States Pharmacopeia (USP) Reference Standard Clotrimazole, VETRANAL(TM), analytical standard Clotrimazole,(S)
    Clotrimazolum Clotrimazolum [INN-Latin] Cutistad
    D00282 DB-046195 DB00257
    DRG-0072 DSSTox_CID_9871 DSSTox_GSID_29871
    DSSTox_RID_78827 DTXSID7029871 Desamix F
    Diphenyl(2-chlorophenyl)(1-imidazolyl)methane Diphenyl-(2-chlorophenyl)-1-imidazolylmethane DivK1c_000665
    EINECS 245-764-8 EU-0100315 Empecid
    Esparol FB 5097 FB b 5097
    FT-0603193 Fem Care FemCare
    G07GZ97H65 GNF-Pf-3499 GTPL2330
    Gino-Lotremine Gyne lotrimin Gyne-Lotrimin
    Gyne-Lotrimin 3 Gyne-Lotrimin 3 Combination Pack Gyne-Lotrimin Combination Pack
    Gyne-Lotrimin3 Gyne-Lotrimin3 Combination Pack Gynix
    HMS1568F16 HMS1920O21 HMS2051E11
    HMS2091G10 HMS2095F16 HMS2235E20
    HMS3260P12 HMS3369I03 HMS3393E11
    HMS3655I09 HMS3712F16 HMS502B07
    HSDB 3266 HY-10882 IDI1_000665
    Imidazole, 1-(o-chloro-.alpha.,.alpha.-diphenylbenzyl)- Imidazole, 1-(o-chloro-alpha,alpha-diphenylbenzyl)- Imidazole,.alpha.-diphenylbenzyl)-
    J10369 Jidesheng KBio1_000665
    KBio2_001823 KBio2_004391 KBio2_006959
    KBio3_001277 KBioGR_000850 KBioSS_001823
    KS-00000XNX Kanesten Klotrimazole
    LP00315 LS-78271 Lopac-C-6019
    Lopac0_000315 Lotrimax Lotrimin
    Lotrimin (TN) Lotrimin AF Cream Lotrimin AF Jock-Itch Cream
    Lotrimin AF Lotion Lotrimin AF Solution Lotrimin Af
    Lotrimin Cream Lotrimin Lotion Lotrimin Solution
    MCULE-6862012558 MFCD00057220 MLS000028502
    MLS000758243 MLS001423972 MRF-0000070
    Methane, bis-phenyl-(2-chlorophenyl)-1-imidazolyl- Mono-baycuten Monobaycuten
    Mycelax Mycelex Mycelex (TN)
    Mycelex 7 Mycelex Cream Mycelex G
    Mycelex OTC Mycelex Solution Mycelex Troches
    Mycelex Twin Pack Mycelex-7 Mycelex-7 Combination Pack
    Mycelex-G Mycelex: MycosporinRimazole Myclo Cream
    Myclo Solution Myclo Spray Solution Myclo-Gyne
    Mycofug Mycosporin Mykosporin
    N713 NC00035 NCGC00015251-01
    NCGC00015251-02 NCGC00015251-03 NCGC00015251-04
    NCGC00015251-05 NCGC00015251-06 NCGC00015251-07
    NCGC00015251-08 NCGC00015251-09 NCGC00015251-10
    NCGC00015251-11 NCGC00015251-13 NCGC00015251-14
    NCGC00093761-01 NCGC00093761-02 NCGC00093761-03
    NCGC00093761-04 NCGC00093761-05 NCGC00093761-06
    NCGC00254538-01 NCGC00261000-01 NCIMech_000609
    NINDS_000665 NSC 257473 NSC-257473
    NSC-756700 NSC257473 NSC756700
    Nalbix Neo-Zol Cream Otomax
    Pan-Fungex Pedisafe Pharmakon1600-01500200
    Prestwick0_000267 Prestwick1_000267 Prestwick2_000267
    Prestwick3_000267 Prestwick_120 Q413546
    QTL1_000024 Rimazole SAM001247056
    SB17418 SBI-0050303.P004 SC-17936
    SCHEMBL3850 SMR000058306 SPBio_000176
    SPBio_002333 SPECTRUM1500200 SR-01000075771
    SR-01000075771-1 SR-01000075771-10 SR-01000075771-6
    SR-01000075771-8 ST50994242 STK700023
    SW196431-5 Spectrum2_000128 Spectrum3_000359
    Spectrum4_000295 Spectrum5_000781 Spectrum_001343
    Stiemazol Tibatin Tox21_110111
    Tox21_110111_1 Tox21_300415 Tox21_500315
    Trimysten Trivagizole 3 UNII-G07GZ97H65
    VNFPBHJOKIVQEB-UHFFFAOYSA-N Veltrim W-107394
    ZINC3807804 [(2-chlorophenyl)diphenylmethyl]imidazole chlortrimazole
    cid_2812 clortrimazole clotrimazole
    clotrimazole crystalline clotrimeizol component of Lotrimax (Salt/Mix)
    component of Otomax (Salt/Mix) s1606

    DrugBank Name Clotrimazole
    DrugBank DB00257
    CAS Number 117829-71-7, 1185076-41-8, 23593-75-1
    PubChem Compound 2812
    KEGG Compound ID C06922
    KEGG Drug D00282
    PubChem.Substance 46507927
    ChEBI 3764
    PharmGKB PA449057
    ChemSpider 2710
    BindingDB 31774.0
    TTD DAP000138
    Wikipedia Clotrimazole