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Chemical Structure| 65277-42-1 Chemical Structure| 65277-42-1

Structure of Ketoconazole
CAS No.: 65277-42-1

Chemical Structure| 65277-42-1

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Ketoconazole is an imidazole anti-fungal agent which inhibits cyclosporine oxidase and testosterone 6 beta-hydroxylase with IC50 of 0.19 mM and 0.22 mM, respectively.

Synonyms: Ketoconazol; R 41400; Ketoconazole, Nizoral, Kuric, Fungoral, Ketoderm, Xolegel, Extina

4.5 *For Research Use Only !

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Product Details of Ketoconazole

CAS No. :65277-42-1
Formula : C26H28Cl2N4O4
M.W : 531.43
SMILES Code : ClC1=CC=C([C@]2(CN3C=CN=C3)OC[C@@H](COC4=CC=C(N5CCN(C(C)=O)CC5)C=C4)O2)C(Cl)=C1
Synonyms :
Ketoconazol; R 41400; Ketoconazole, Nizoral, Kuric, Fungoral, Ketoderm, Xolegel, Extina
MDL No. :MFCD00058579

Safety of Ketoconazole

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H360-H373-H410
Precautionary Statements:P201-P202-P260-P264-P270-P273-P280-P301+P310+P330-P308+P313-P391-P405-P501
Class:6.1
UN#:2811
Packing Group:

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Human Corneal Epithelial Cells 1 mg/ml 4 hours To evaluate the cytotoxicity of Ketoconazole-ion sensitive gel, the results showed that cell viability was over 80% at concentrations of 1 mg/ml and below, indicating safety at this concentration. PMC11562027

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
New Zealand White Rabbits Ocular Administration Model Topical Administration 50 µl Single dose, lasting 180 minutes To evaluate the pharmacokinetics of Ketoconazole-ion sensitive gel in rabbit eyes, the results showed that the formulation significantly increased the bioavailability of Ketoconazole, with a 47-fold increase in drug concentration in the cornea. PMC11562027

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT01584297 Granulosa Cell Tumour of the O... More >>vary Less << PHASE2 TERMINATED 2025-11-14 Complejo Hospitalario Universi... More >>tario de Santiago de Compostela, Santiago de Compostela, A Coru?a, 15706, Spain|Hospital Central de Asturias, Oviedo, Asturias, 33006, Spain|Hospital Universitario Fundación Alcorcón, Alcorcón, Madrid, 28922, Spain|Hospital del Mar, Barcelona, 08003, Spain|Hospital Reina Sofía, Cordoba, 14004, Spain|Hospital La Paz, Madrid, 28046, Spain|Hospital Morales Meseguer, Murcia, 30008, Spain|Complejo Hospitalario de Navarra, Navarra, 31008, Spain|Hospital Son Llatzer, Palma de Mallorca, 07198, Spain|Hospital Universitario y Politécnico La Fe, Valencia, 46026, Spain Less <<
NCT04869449 Glioblastoma|Glioblastoma Mult... More >>iforme|Glioblastoma Multiforme of Brain|Glioblastoma Multiforme, Adult Less << EARLY_PHASE1 RECRUITING 2025-12-25 Penn State Milton S Hershey Me... More >>dical Center, Hershey, Pennsylvania, 17033, United States Less <<
NCT00703846 Dermatitis, Seborrheic PHASE4 COMPLETED 2025-04-10 -
NCT00384917 Healthy PHASE1 COMPLETED 2025-09-06 -

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

1.88mL

0.38mL

0.19mL

9.41mL

1.88mL

0.94mL

18.82mL

3.76mL

1.88mL

References

[1]Oliver WR Jr, Shenk JL, et al. A selective peroxisome proliferator-activated receptor delta agonist promotes reverse cholesterol transport. Proc Natl Acad Sci U S A. 2001 Apr 24;98(9):5306-11.

[2]Eil C. Ketoconazole binds to the human androgen receptor. Horm Metab Res. 1992 Aug;24(8):367-70.

[3]Awasthi A, Dutta GP, et al. Resistance reversal action of ketoconazole against mefloquine resistance of Plasmodium yoelii nigeriensis. Exp Parasitol. 2004 Jul-Aug;107(3-4):115-9.

[4]Saadeddin A, Peris JE, et al. Pharmacokinetic interaction between efavirenz and ketoconazole in rats. Xenobiotica. 2009 Feb;39(2):135-9.

[5]Ward KW, Stelman GJ, et al. Development of an in vivo preclinical screen model to estimate absorption and first-pass hepatic extraction of xenobiotics. II. Use of ketoconazole to identify P-glycoprotein/CYP3A-limited bioavailability in the monkey. Drug Metab Dispos. 2004 Feb;32(2):172-7.

[6]Eil C. Ketoconazole binds to the human androgen receptor. Horm Metab Res. 1992 Aug;24(8):367-70. doi: 10.1055/s-2007-1003337. PMID: 1526623.

[7]Forgue-Lafitte ME, Coudray AM, Fagot D, Mester J. Effects of ketoconazole on the proliferation and cell cycle of human cancer cell lines. Cancer Res. 1992 Dec 15;52(24):6827-31. PMID: 1458471.

[8]Gupta AK, Kohli Y, Li A, Faergemann J, Summerbell RC. In vitro susceptibility of the seven Malassezia species to ketoconazole, voriconazole, itraconazole and terbinafine. Br J Dermatol. 2000 Apr;142(4):758-65. doi: 10.1046/j.1365-2133.2000.03294.x. PMID: 10792228.

[9]Goeders NE, Peltier RL, Guerin GF. Ketoconazole reduces low dose cocaine self-administration in rats. Drug Alcohol Depend. 1998 Dec 1;53(1):67-77. doi: 10.1016/s0376-8716(98)00108-2. PMID: 10933341.

[10]Salphati L, Benet LZ. Effects of ketoconazole on digoxin absorption and disposition in rat. Pharmacology. 1998 Jun;56(6):308-13. doi: 10.1159/000028214. PMID: 9654217.

 

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