ChemicalBook
Chinese Japanese Germany

Clotrimazole

Broad-spectrum antifungal drug Pharmacokinetics Clinical application Mechanism Drug Interactions Side effects Administration instructions Chemical Properties Production method
Clotrimazole
Clotrimazole
CAS No.
23593-75-1
Chemical Name:
Clotrimazole
Synonyms
CLT;b5097;myclo;fb5097;bay5097;Empecid;FB 5097;Mycelax;Mycelex;Canifug
CBNumber:
CB7404063
Molecular Formula:
C22H17ClN2
Formula Weight:
344.84
MOL File:
23593-75-1.mol

Clotrimazole Properties

Melting point:
147-149°C
Boiling point:
501.14°C (rough estimate)
Density 
1.1095 (rough estimate)
refractive index 
1.5940 (estimate)
storage temp. 
Store at RT.
solubility 
Soluble in chloroform, DMSO, DMF and alcohols
pka
pKa 4.7(EtOH 50%aq ) (Uncertain)
form 
neat
λmax
556nm(Phosphate buffer sol.)(lit.)
Merck 
14,2417
InChIKey
VNFPBHJOKIVQEB-UHFFFAOYSA-N
NIST Chemistry Reference
Clotrimazole(23593-75-1)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  Xn
Risk Statements  22-36/38
Safety Statements  26-36
WGK Germany  3
RTECS  NI4377000
Hazardous Substances Data 23593-75-1(Hazardous Substances Data)
Toxicity LD50 in male mice, rats (mg/kg): 923, 708 orally (Tettenborn)
Symbol(GHS):
Signal word: Warning
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
Precautionary statements:
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P270 Do not eat, drink or smoke when using this product.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P321 Specific treatment (see … on this label).
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313 IF SKIN irritation occurs: Get medical advice/attention.
P501 Dispose of contents/container to..…

Clotrimazole price More Price(14)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich C6019 Clotrimazole 23593-75-1 5g $82.9 2018-11-20 Buy
Sigma-Aldrich 1141002 Clotrimazole United States Pharmacopeia (USP) Reference Standard 23593-75-1 200mg $286.65 2018-11-20 Buy
TCI Chemical C2867 Clotrimazole >98.0%(HPLC)(T) 23593-75-1 5g $47 2018-11-22 Buy
TCI Chemical C2867 Clotrimazole >98.0%(HPLC)(T) 23593-75-1 25g $165 2018-11-22 Buy
Alfa Aesar J63895 Clotrimazole 23593-75-1 5g $61.1 2018-11-13 Buy

Clotrimazole Chemical Properties,Uses,Production

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.
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.

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%.

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.
The above information is edited by the chemicalbook of Dai Xiongfeng.

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.

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.

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.

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.

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 ℃.

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.

Chemical Properties

White or pale yellow, crystalline powder.

Uses

Clotrimazole is an antifungal agent.

Uses

An antifungal compound and CYP inhibitor

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.

brand name

Gyne- Lotrimin (Schering-Plough); Gynix (Teva); Lotrimin (Schering-Plough); Mycelex (Bayer).

Clotrimazole Preparation Products And Raw materials

Raw materials

Preparation Products


Clotrimazole Suppliers

Global( 326)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 20001 58
Hebei Guanlang Biotechnology Co., Ltd.
+86-0311-66562153 whatsapp +8615203118427
+86-0311-66562153 sales@crovellbio.com CHINA 417 50
Liaoning Benyuan Pharmaceutical Co., Ltd
024-45627555
024-45627566 sales@benyuanpharm.com China 62 50
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3218 55
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 22063 58
Shanghai Bojing Chemical Co.,Ltd.
+86-21-37122233
+86-21-37127788 Candy@bj-chem.com CHINA 500 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20795 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32764 55
Rixing Chemical CO.,LTD
13237129059
- info@rixingchemi.com CHINA 235 55
PI & PI BIOTECH INC.
020-81716320
020-81716319 Sales@pipitech.com CHINA 2549 55

View Lastest Price from Clotrimazole manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-12-16 Clotrimazole
23593-75-1
US $7.00 / kg 1kg 99% 100kg career henan chemical co
2018-05-25 clotrimazole
23593-75-1
US $10.00 / KG 10G 99% 1000kg Meihua Biological Technology Co.,Ltd

23593-75-1(Clotrimazole)Related Search:


Copyright 2017 © ChemicalBook. All rights reserved