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Home> Encyclopedia >Antibiotic and Antimicrobial Agents>Pharmaceutical Intermediates>Organic Intermediate
Clotrimazole structure
Clotrimazole structure


Iupac Name:1-[(2-chlorophenyl)-diphenylmethyl]imidazole
CAS No.: 23593-75-1
Molecular Weight:344.83678
Modify Date.: 2022-11-05 04:52
Introduction: Clotrimazole is an imidazole derivative, an antifungal compound and is a CYP (cytochrome P450) inhibitor.Target: Antifungal; CYPClotrimazole (brand name Canesten or Lotrimin) is an antifungal medication commonly used in the treatment of fungal infections (of both humans and other animals) such as vaginal yeast infections, oral thrush, and ringworm. It is also used to treat athlete's foot and jock itch.It is commonly available as an over-the-counter substance in various dosage forms, such View more+
1. Names and Identifiers
1.1 Name
1.2 Synonyms

(2-Chlorophenyl)diphenyl-1-imidazolylmethane (Chlorotrityl)imidazole 1-((2-chlorophenyl)diphenylmethyl)-1h-imidazol 1-((2-Chlorophenyl)diphenylmethyl)-1H-imidazole (9CI) 1-(2-Chlorotrityl)imidazole 1-(alpha-(2-Chlorophenyl)benzhydryl)imidazole 1-(o-Chloro-a,a-diphenylbenzyl)imidazole 1-(o-chloro-alpha,alpha-diphenylbenzyl)-imidazol 1-(o-Chlorotrityl)imidazole 1-(o-Chlorotrityl)imidazole,1-(o-Chl 1-(o-Chloro-α,α-diphenylbenzyl)imidazole 1-[(2-Chlorophenyl)(diphenyl)methyl]-1H-imidazole 1-[(2-chlorophenyl)diphenylmethyl]-1h-imidazol 1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole 1-[(2-Chlorophenyl)diphenylmethyl]imidazole 1-[(2-chlorophenyl)-diphenylmethyl]imidazole 1-[(o-Chlorophenyl)diphenylmethyl]imidazole 1-[a-(2-Chlorophenyl)benzhydryl]imidazole 1H-Imidazole, 1-[(2-chlorophenyl)-diphenylmethyl] 1H-Imidazole, 1-[(2-chlorophenyl)diphenylmethyl]- Canesten Canifug Clotrimazole crystalline EINECS 245-764-8 Empecid Fungicip Gyne-Lotrimin Imidazole, 1- (o-chloro-α,α-diphenylbenzyl)- Lotrimin MFCD00057220 Mono-baycuten Mycelex Mycelex G myclo Mycosporin Pedisafe Rimazole Tibatin Trimysten UNII-G07GZ97H65

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1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C22H17ClN2 (isomer)
1.7 Inchi
1.8 InChIkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
2.1 Melting point
2.1 Boiling point
2.1 Refractive index
2.1 Flash Point
2.1 Precise Quality
2.1 PSA
2.1 logP
2.1 Solubility
Soluble in chloroform, DMSO, DMF and alcohols
2.2 Λmax
556nm(Phosphate buffer sol.)(lit.)
2.3 Appearance
Crystals. Odorless.
2.4 Storage
Ambient temperatures.
2.5 Color/Form
2.6 Odor
2.7 PH
2.8 pKa
pKa 4.7(EtOH 50%aq ) (Uncertain)
2.9 Water Solubility
Soluble in chloroform, DMSO, DMF and alcohols
2.10 StorageTemp
3. Use and Manufacturing
3.1 Definition
ChEBI: A member of the class of imidazoles that is 1H-imidazole in which the hydrogen attached to a nitrogen is replaced by a monochlorotrityl group.
3.2 Usage
Clotrimazole is an antifungal agent.
4. Safety and Handling
4.1 Symbol
4.1 Hazard Codes
4.1 Signal Word
4.1 Risk Statements
4.1 Safety Statements
4.1 Exposure Standards and Regulations
Clotrimazole cream. (a) Specifications: Each g of cream contains 10 mg of clotrimazole ... (c) Conditions of use: Apply 1/4 in ribbon of cream per sq in of lesion for 2 to 4 wk ... For the treatment of fungal infections of dogs and cats caused by Microsporum canis and Trichophyton mentagrophytes ... Wash hands thoroughly after use to avoid spread of infection. Federal law restricts this drug to use by or on the order of a licensed veterinarian.
4.2 Hazard Declaration
NONH for all modes of transport
4.2 Caution Statement
P301 + P312 + P330
4.2 Formulations/Preparations
Topical: Lotrimin (Schering), Mycelex (Miles). Cream 1% in 15, 30, 45 (Lotrimin only), and 90 g containers; solution 1% in 10 and 30 ml containers; and lotion 1% (Lotrimin only) in 30 ml containers; intravaginal: Gyne-Lotrimin (Schering) Cream (vaginal) 1% in 45 g containers; tablets (vaginal) 100 and 500 mg; Mycelex-G (Miles) cream (vaginal) 1% in 45 and 90 g containers; tablets 100 and 500 mg; and 500 mg with cream 1% in 7 g containers. Oral: troche 10 mg.
Mycelex 1% cream
4.3 WGK Germany
4.3 Protective Equipment and Clothing
Adverse effects after topical use of clotrimazole include stinging.
4.4 Skin, Eye, and Respiratory Irritations
Adverse effects after topical use of clotrimazole include stinging.
4.5 Safety

Safety Information of?Mycosporin (CAS NO.23593-75-1):
Hazard Codes:Xn?
Risk Statements:22-36/38
22:Harmful if swallowed
36/38:Irritating to eyes and skin??
Safety Statements:26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
36:Wear suitable protective clothing?
WGK Germany:3
Hazardous Substances Data:23593-75-1(Hazardous Substances Data)
Poison by intraperitoneal route. Moderately toxic by ingestion. An experimental teratogen. Human systemic effects by intrvaginal route: primary skin irritations. Experimental reproductive effects. A fungicide. When heated to decomposition it emits very toxic fumes of Cl? and NOx.

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4.6 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral > 1gm/kg (1000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
dog LD50 oral > 2gm/kg (2000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
mammal (species unspecified) LD50 oral 750mg/kg (750mg/kg) ? Antimicrobial Agents and Chemotherapy Vol. -, Pg. 271, 1969.
mouse LD50 intraperitoneal 108mg/kg (108mg/kg) ? Drug and Chemical Toxicology. Vol. 13, Pg. 195, 1990.
mouse LD50 intravenous 198mg/kg (198mg/kg) ? Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
mouse LD50 oral 761mg/kg (761mg/kg) ? Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
mouse LDLo subcutaneous 10gm/kg (10000mg/kg) ? Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1333, 1973.


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.
rat LD50 oral 708mg/kg (708mg/kg) ? Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
rat LDLo subcutaneous 10gm/kg (10000mg/kg) ? Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1333, 1973.
women TDLo intravaginal 28mg/kg/7D (28mg/kg) SKIN AND APPENDAGES (SKIN): PRIMARY IRRITATION: AFTER TOPICAL EXPOSURE Clinical Toxicology. Vol. 18, Pg. 41, 1981.

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2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Signal word


Hazard statement(s)

H302 Harmful if swallowed

H315 Causes skin irritation

H319 Causes serious eye irritation

Precautionary statement(s)

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P280 Wear protective gloves/protective clothing/eye protection/face protection.


P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P321 Specific treatment (see ... on this label).

P332+P313 If skin irritation occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.




P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification


8. Precursor and Product
9. Other Information
9.0 Broad-spectrum antifungal drug
Clotrimazole is an artificially synthetic azole antifungal agent with inhibitory effect on a variety of pathogenic fungi. It is also able to directly kill the fungi at high concentration. Clotrimazole, through interfering with cytochrome P450 activity, inhibits the biosynthesis of the fungal ergosterol and other steroids; cause damage of the fungal cell membrane and change its permeability, causing the leakage of many kinds of important material in the cell; it can also inhibit the biosynthesis of the fungal triglyceride and phosphor-lipid; the product can still inhibit the activity of oxidase and peroxidase, causing the over-accumulation of peroxides in the cell, causing the degeneration and necrosis of the fungal subcellular structures. Clotrimazole has broad-spectrum antifungal activity with excellent anti-fungal activity against Epidermophyton, Trichophyton, aspergillosis, coloring fungi, Cryptococcus and Candida species. It also has certain antifungal effect against sporothrix schenckii,blastomycosis dermatitidis, Blastomyces coccidioides as well as Histoplasma.
Clotrimazole Cream 1%
It has good anti-fungal effect against Candida, Cryptococcus, Aspergillus, algae bacteria, dermatophytes, etc in both in vivo and in vitro. It efficacy in treating skin superficial mycoses is similar as griseofulvin while its efficacy in treating deep fungal disease is similar as amphotericin B. It has excellent efficacy in treating visceral pathogenic fungi such as Candida albicans, Cryptococcus neoformans, coccidioidomycosis and histoplasma. Its effect on the Candida albicans is stronger than nystatin. Fungi are not easy to evolve drug resistance to this kind of product. This product is easily absorbed orally and can be used for the treatment of systemic fungal infection such as aspergillosis fumigatus, candidiasis, cryptococcosis, coccidioidomycosis, histoplasmosis (dogs, cats) and fungal septicemia. For severe fungal infection, it is preferably to use it in combination with amphotericin B. Topically it can also be used for the treatment of superficial fungal infections such as ringworm and livestock comb body and hair tinea. However, it is invalid in treating tinea capitis. Clotrimazole also has certain efficacy in treating some kinds of Gram-positive bacteria and Trichomonas vaginalis.
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9.1 Pharmacokinetics
This product is rarely absorbed after oral administration. Adult, after oral administration of 3, has the peak of the plasma concentration being only 1.29 mg/L at 2 hour while 0.78 mg/L at 6 hours. Upon continuous administration, because of the induction effect of liver enzymes, the serum concentration can in turn decrease. The elimination half-life is 4.5 to 6 hours. Most of the products is metabolic inactivated in the liver and is further excreted by bile with only a small amount (less than 1% of dose) being subject to urine excretion in its prototype. The urine excrete were mostly inactive metabolites. This product is presented at high concentration in the feces including the non-absorption part of oral administration as well as the fraction via biliary excretion. Clotrimazole is widely distributed in the body with high concentration existing in the liver and adipose tissue. It can’t penetrate normal meninges and get into the cerebrospinal fluid. This product has a serum protein binding rate of 50%.
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9.2 Clinical application
Clinical topical usage of 1% clotrimazole cream or solution for treating candidiasis ringworm, tinea versicolor, athlete's foot, nail ringworm and other skin infections. Clotrimazole vaginal tablets (100mg) administration can be used for treating candidiasis and trichomoniasis vaginal infections. Side effects include local irritation and burning sensations. Oral administration can be used for the treatment of deep fungal infection but with serious side effects such as gastrointestinal irritation, neutropenia, and liver function abnormalities.
1. Oral administration: (1) can be used for the treatment of oropharyngeal candidiasis. (2) it can also be used for chemotherapy and the prevention of the oropharynegeal candidiasis infection of immunocompromised or defect patients.
2. Topical: (1) skin candidiasis. (2) Tinea, jork itch and ringworm caused by Trichophyton, Epidermophyton and small spores; tinea versicolor caused by Pityrosporum.
3. Vaginal administration: (1) Vaginitis induced by Candida or other fungi. (2) vaginal infection caused by yeast. (3) Vagina super-infection caused by susceptible strains of the drug.
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9.3 Mechanism
1. Through reducing the activity of cytochrome P450, it inhibit the biosynthesis of ergosterol and other sterols contained in the fungal cell membrane, causing damage of the fungal cell membrane and change its permeability and causing important intracellular material leakage.
2. Clotrimazole can inhibit the biosynthesis of the fungal triglyceride and phospholipid.
3. It can still inhibit the activity of oxidase and peroxidase, leading to the over-accumulation of hydrogen peroxide inside the cell, causing fungal subcellular structures degeneration and necrosis.
4. For Candida albicans, clotrimazole can suppresses the process of its conversion from spores into invasive hyphae.
9.4 Drug Interactions
1, the drug can inhibit the metabolism of drugs like sirolimus and dofetilide mediated by cytochrome P450 3A4 so that the plasma concentration of these drugs increases.
2, when being used in combination with tacrolimus and acamprosate, it can slow down the metabolism of these drugs and increasing its toxicity.
3, when clotrimazole is used in combination with betamethasone, it can make the skin be vulnerable to infection and increase the opportunities for microbial growth; the possible mechanism is through inhibiting the local inflammation.
4, when being used in combination with nystatin, amphotericin B and flucytosine, no synergistic antibacterial effect has been observed for inhibiting Candida albicans; moreover, it has antagonism effect in pharmacodynamic when being used in combination with amphotericin B.
9.5 Side effects
1, Oral administration: (1) gastrointestinal reactions: including loss of appetite, nausea, vomiting, abdominal pain and diarrhea. (2) Liver toxicity: Because most of clotrimazole is subjecting to liver metabolism, it can lead to liver damage and causing increased level of serum bilirubin, alkaline phosphatase and aminotransferase. These symptoms can resume after drug withdrawal. (3) There are occasionally transient neuropsychiatric disorders, manifested as depression, hallucinations and disorientation and so on. Once such reactions occur, treatment must be immediately discontinued. (4) There may be occasionally leukopenia. (5) Some patients, after taking the drug, can get a burning sensation in the urethra. At this time, you should drink more water to ensure a high urine output. However, there is no need for stopping the drug.
2, Topical administration may occasionally cause local irritation, itching or burning sensation. Skin can get erythema, papules, vesicles, scaling and so on. There is also report about contact dermatitis.
3, a small amount of vaginal administrators may get vaginal burning sensation, abdominal cramping, and bloating, frequent urination and so on. There may also be varying degrees of allergic reactions such as skin redness and itching, shortness of breath, hypotension or transient feeling, nausea and diarrhea.
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9.6 Administration instructions
1, the drug can’t be used for systemic fungal infections. Owing to the poor oral absorption of the drug, adverse reactions are common while now we mostly apply topical or vaginal administration.
2, upon using this drug, you should avoid eye contact with the drug.
3, clotrimazole vaginal tablets should be prohibited through oral administration.
4, Administration of the tablets of this product once should overall take 15 to 30 minutes to allow the drug being slowly and completely dissolved. You should avoid chewing or swallowing whole tablet.
5, virginal treatment should be prohibited during menstruation.
6. if there are temporary neuropsychiatric disorder, severe gastrointestinal reactions and local skin allergic reaction happening, you should discontinue the drug immediately.
9.7 Usage
Clotrimazole is an imidazole derivative and an antifungal compound and a CYP (cytochrome P450) inhibitor. Clotrimazole has been shown to block the intermediate-conductance, IK1 channels (Ca2+?activated K+?channels), in cells such as erythrocytes.?In vitro?studies of various yeast strains have demonstrated susceptibility to clotrimazole. Clotrimazole is an activator of MB67 and an inhibitor of CYP3A4 and CYP51A1.
9.8 Merck
9.9 Chemical Properties
It is white powder or colorless crystalline powder. It has a melting point of 147-149 ℃. It is soluble in ethanol, acetone, and chloroform, but almost insoluble in water. It is odorless, tasteless and subject to rapid decomposition in an acid solution. Clotrimazole hydrochloride has a m.p. of 159 ℃.
9.10 Production method
It can be obtained from o-benzoic acid via esterification, addition, hydrolysis, chlorination, and condensation. It may also be obtained by chlorination of o-chlorotoluene into o-chloro benzotrichloride, which, in the presence of aluminum chloride, has condensation reaction with benzene to generate diphenyl-(2-chlorophenyl) methyl chloride, which finally has condensation reaction with imidazole to obtain clotrimazole.
9.11 Description
Clotrimazole is an imidazole antifungal that is active against a wide variety of fungal forms and is effective in many types of fungal infections. It tightly binds sterol 14-α demethylase isoform B from A. fumigatus (KD = 103 nM) and, like other imidazoles, disturbs the fungal cell membrane. In mammalian cells, clotrimazole potently inhibits the calcium-dependent potassium channels Kv1.3 and IK-1 (IC50 = 6.0 and 0.07 μM, respectively).
9.12 Chemical Properties
White or pale yellow, crystalline powder.
9.13 Originator
9.14 Uses
Clotrimazole is an antifungal agent.
9.15 Uses
An antifungal compound and CYP inhibitor.
Clotrimazole (Lotrimin, Mycelex, etc.) is a synthetic imidazole agent. It acts by altering cell membrane permeability. It inhibits the growth of most dermatophyte species, yeast and Malassezia furfur.
9.16 Uses
Clotrimazole formally also is an imidazole derivative because of the presence of an imidazole ring in its structure. It is believed that, like miconazole, econazole, and other “pure” representatives of the imidazole class, it also inhibits the biosynthesis of ergosterin in the cytoplasmatic membrane of fungi.
In terms of pharmacological action, clotrimazole is very similar to miconazole. It has a broad spectrum of antifungal activity. It is effective with respect to dermatophytes, and it also has an antimicrobial effect against streptococci and staphylococci. It is also effective with respect to trichomonases. It is very widely used, both externally and vaginally for treating superficial infections. Synonyms of this drug are canesten, empecid, lotrimin, micosporin, and others.
9.17 Definition
ChEBI: A member of the class of imidazoles that is 1H-imidazole in which the hydrogen attached to a nitrogen is replaced by a monochlorotrityl group.
9.18 Indications
Clotrimazole (Lotrimin, Gyne-Lotrimin, Mycelex) is a broad-spectrum fungistatic imidazole drug used in the topical treatment of oral, skin, and vaginal infections with C. albicans. It is also employed in the treatment of infections with cutaneous dermatophytes.
Topical use results in therapeutic drug concentrations in the epidermis and mucous membranes; less than 10% of the drug is systemically absorbed. Although clotrimazole is generally well tolerated, local abdominal cramping, increased urination, and transient liver enzyme elevations have been reported.
9.19 Manufacturing Process
156.5 g (0.5 mol) o-chlorophenyldiphenylmethyl chloride and 34 g (0.5 mol) imidazole are dissolved in 500 ml acetonitrile, with stirring, and 51 g (0.5 mol) triethylamine are added, whereupon separation of triethylamine hydrochloride occurs even at room temperature. In order to complete the reaction, heating at 50°C is carried out for 3 hours. After cooling, one liter of benzene is added and the reaction mixture is stirred, then washed salt-free with water. The benzene solution is dried over anhydrous sodium sulfate, filtered and concentrated by evaporation; giving 167 g crude 1-(ochlorophenylbisphenylmethyl)-imidazole. By recrystallization from acetone, 115 g (= 71% of the theory) of pure 1-(o-chlorophenylbisphenylmethyl)- imidazole of MP 154° to 156°C are obtained.
9.20 Brand name
Gyne- Lotrimin (Schering-Plough); Gynix (Teva); Lotrimin (Schering-Plough); Mycelex (Bayer).
9.21 Therapeutic Function
9.22 General Description
Chemical structure: imidazole
10. Computational chemical data
  • Molecular Weight: 344.83678g/mol
  • Molecular Formula: C22H17ClN2
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 344.1080262
  • Monoisotopic Mass: 344.1080262
  • Complexity: 396
  • Rotatable Bond Count: 4
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Topological Polar Surface Area: 17.8
  • Heavy Atom Count: 25
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
11. Question & Answer
  • Clotrimazole is a common ingredient in many oral and topical medications. It is said to have excellent effects in treating symptoms of external genital infections in women. But what exactly is Clotrim..
  • Vulvovaginal candidiasis (VVC), also known as vaginal yeast infection, is one of the most common vaginal infections in women. Over the past 30 years, its incidence has significantly increased. Studies..
  • Tinea refers to a series of skin diseases caused by fungal infections. Common types of tinea include athlete's foot, jock itch, ringworm, pityriasis versicolor, and nail fungus. Can Clotrimazole cream..
  • Tolnaftate vs Clotrimazole - both are antifungal medications, but they differ in terms of efficacy and usage. 1. What is Tolnaftate? Tolnaftate is effective against systemic fungal infections. It is b..
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13. Realated Product Infomation