Ketoconazole | CAS#65277-42-1 | Antifungal

Ketoconazole
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318079

CAS#: 65277-42-1

Description: Ketoconazole is a synthetic imidazole antifungal drug used primarily to treat fungal infections. It is sold commercially as a tablet for oral administration (although this use has been discontinued in a number of countries), and in a variety of formulations for topical administration, such as creams (used to treat tinea; cutaneous candidiasis, including candidal paronychia; and pityriasis versicolor) and shampoos (used primarily to treat dandruff—seborrhoeic dermatitis of the scalp).

Chemical Structure

Ketoconazole

CAS# 65277-42-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318079
Name: Ketoconazole
CAS#: 65277-42-1
Chemical Formula: C26H28Cl2N4O4
Exact Mass: 530.15
Molecular Weight: 531.431
Elemental Analysis: C, 58.76; H, 5.31; Cl, 13.34; N, 10.54; O, 12.04

Price and Availability

Size	Price	Availability
1g	USD 250
5g	USD 450	2 Weeks
10g	USD 750	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Ketoconazole, Nizoral, Kuric, Fungoral, Ketoderm, Xolegel, Extina

IUPAC/Chemical Name: 1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone

InChi Key: XMAYWYJOQHXEEK-OZXSUGGESA-N

InChi Code: InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m0/s1

SMILES Code: CC(N1CCN(C2=CC=C(OC[C@@H]3O[C@@](CN4C=CN=C4)(C5=CC=C(Cl)C=C5Cl)OC3)C=C2)CC1)=O

Appearance: White to off-white crystalline powder.

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO (50 mg/mL)

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot# C22B04B28

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	Ketoconazole (R-41400) is an imidazole anti-fungal agent, a CYP3A4 and CYP24A1 inhibitor.
In vitro activity:	Additional binding studies performed with ketoconazole in the presence of increasing amounts of [3H]R1881 showed that the interaction of ketoconazole with AR was competitive when the data were analyzed by the Scatchard method. Reference: Horm Metab Res. 1992 Aug;24(8):367-70. https://pubmed.ncbi.nlm.nih.gov/1526623/
In vivo activity:	KTZ (ketoconazole) effectively inhibited time-dependent calcitriol-inducible CYP24A1 protein expression and enzyme activity in PC3 cells and C3H/HeJ mouse kidney tissues. Systemic calcitriol exposure area under the curve was higher in mice treated with a combination of calcitriol and KTZ than with calcitriol alone. Reference: Endocrinology. 2010 Sep;151(9):4301-12. https://pubmed.ncbi.nlm.nih.gov/20591973/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	5.0	9.41
	DMF:PBS (pH 7.2) (1:1)	0.5	0.94
	DMSO	22.3	41.94
	Ethanol	13.8	25.94

Preparing Stock Solutions

The following data is based on the product molecular weight 531.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. 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. 2. Ayub M, Levell MJ. Inhibition of human adrenal steroidogenic enzymes in vitro by imidazole drugs including ketoconazole. J Steroid Biochem. 1989 Apr;32(4):515-24. doi: 10.1016/0022-4731(89)90384-1. PMID: 2724954. 3. Doheny D, Manore S, Sirkisoon SR, Zhu D, Aguayo NR, Harrison A, Najjar M, Anguelov M, Cox AO, Furdui CM, Watabe K, Hollis T, Thomas A, Strowd R, Lo HW. An FDA-Approved Antifungal, Ketoconazole, and Its Novel Derivative Suppress tGLI1-Mediated Breast Cancer Brain Metastasis by Inhibiting the DNA-Binding Activity of Brain Metastasis-Promoting Transcription Factor tGLI1. Cancers (Basel). 2022 Aug 31;14(17):4256. doi: 10.3390/cancers14174256. PMID: 36077791; PMCID: PMC9454738. 4. Muindi JR, Yu WD, Ma Y, Engler KL, Kong RX, Trump DL, Johnson CS. CYP24A1 inhibition enhances the antitumor activity of calcitriol. Endocrinology. 2010 Sep;151(9):4301-12. doi: 10.1210/en.2009-1156. Epub 2010 Jun 30. PMID: 20591973; PMCID: PMC2940491.
In vitro protocol:	1. 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. 2. Ayub M, Levell MJ. Inhibition of human adrenal steroidogenic enzymes in vitro by imidazole drugs including ketoconazole. J Steroid Biochem. 1989 Apr;32(4):515-24. doi: 10.1016/0022-4731(89)90384-1. PMID: 2724954.
In vivo protocol:	1. Doheny D, Manore S, Sirkisoon SR, Zhu D, Aguayo NR, Harrison A, Najjar M, Anguelov M, Cox AO, Furdui CM, Watabe K, Hollis T, Thomas A, Strowd R, Lo HW. An FDA-Approved Antifungal, Ketoconazole, and Its Novel Derivative Suppress tGLI1-Mediated Breast Cancer Brain Metastasis by Inhibiting the DNA-Binding Activity of Brain Metastasis-Promoting Transcription Factor tGLI1. Cancers (Basel). 2022 Aug 31;14(17):4256. doi: 10.3390/cancers14174256. PMID: 36077791; PMCID: PMC9454738. 2. Muindi JR, Yu WD, Ma Y, Engler KL, Kong RX, Trump DL, Johnson CS. CYP24A1 inhibition enhances the antitumor activity of calcitriol. Endocrinology. 2010 Sep;151(9):4301-12. doi: 10.1210/en.2009-1156. Epub 2010 Jun 30. PMID: 20591973; PMCID: PMC2940491.

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*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

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1: Gupta AK, Lyons DC. The Rise and Fall of Oral Ketoconazole. J Cutan Med Surg. 2015 Jul-Aug;19(4):352-7. doi: 10.1177/1203475415574970. Epub 2015 Mar 5. Review. PubMed PMID: 25775613.

2: Gupta AK, Daigle D, Foley KA. Drug safety assessment of oral formulations of ketoconazole. Expert Opin Drug Saf. 2015 Feb;14(2):325-34. doi: 10.1517/14740338.2015.983071. Epub 2014 Nov 20. Review. PubMed PMID: 25409549.

3: Greenblatt HK, Greenblatt DJ. Liver injury associated with ketoconazole: review of the published evidence. J Clin Pharmacol. 2014 Dec;54(12):1321-9. doi: 10.1002/jcph.400. Epub 2014 Oct 1. Review. PubMed PMID: 25216238.

4: Gal M, Orly J. Ketoconazole inhibits ovulation as a result of arrest of follicular steroidogenesis in the rat ovary. Clin Med Insights Reprod Health. 2014 Jun 9;8:37-44. doi: 10.4137/CMRH.S15887. eCollection 2014. Review. PubMed PMID: 24987273; PubMed Central PMCID: PMC4071760.

5: Yan JY, Nie XL, Tao QM, Zhan SY, Zhang YD. Ketoconazole associated hepatotoxicity: a systematic review and meta- analysis. Biomed Environ Sci. 2013 Jul;26(7):605-10. doi: 10.3967/0895-3988.2013.07.013. Review. PubMed PMID: 23895707.

6: Greenblatt DJ, Venkatakrishnan K, Harmatz JS, Parent SJ, von Moltke LL. Sources of variability in ketoconazole inhibition of human cytochrome P450 3A in vitro. Xenobiotica. 2010 Oct;40(10):713-20. doi: 10.3109/00498254.2010.506224. Review. PubMed PMID: 20712450.

7: Arakaki R, Welles B. Ketoconazole enantiomer for the treatment of diabetes mellitus. Expert Opin Investig Drugs. 2010 Feb;19(2):185-94. doi: 10.1517/13543780903381411. Review. PubMed PMID: 20047506.

8: Faergemann J, Borgers M, Degreef H. A new ketoconazole topical gel formulation in seborrhoeic dermatitis: an updated review of the mechanism. Expert Opin Pharmacother. 2007 Jun;8(9):1365-71. Review. PubMed PMID: 17563270.

9: Ketoconazole foam--connetics: connetics ketoconazole foam. Drugs R D. 2003;4(5):323-5. Review. PubMed PMID: 12952504.

10: Chakrapee-Sirisuk S, Amornpichetkul K, Visudhiphan S, Sangruchi T, Srimuninnimit V, Sinlarat P. Ketoconazole and Flutamide in the treatment of disseminated intravascular clotting from prostate cancer: a case report and review. J Med Assoc Thai. 2001 Oct;84(10):1495-501. Review. PubMed PMID: 11804262.

11: Peehl DM, Seto E, Feldman D. Rationale for combination ketoconazole/ vitamin D treatment of prostate cancer. Urology. 2001 Aug;58(2 Suppl 1):123-6. Review. PubMed PMID: 11502466.

12: Brown ES, Bobadilla L, Rush AJ. Ketoconazole in bipolar patients with depressive symptoms: a case series and literature review. Bipolar Disord. 2001 Feb;3(1):23-9. Review. PubMed PMID: 11256460.

13: Bok RA, Small EJ. The treatment of advanced prostate cancer with ketoconazole: safety issues. Drug Saf. 1999 May;20(5):451-8. Review. PubMed PMID: 10348095.

14: Akpuaka FC, Gugnani HC, Iregbulam LM. African histoplasmosis: report of two patients treated with amphotericin B and ketoconazole. Mycoses. 1998 Nov;41(9-10):363-4. Review. PubMed PMID: 9916457.

15: Berwaerts JJ, Verhelst JA, Verhaert GC, Verhaegen AA, Abs RE. Corticotropin-dependent Cushing's syndrome in older people: presentation of five cases and therapeutical use of ketoconazole. J Am Geriatr Soc. 1998 Jul;46(7):880-4. Review. PubMed PMID: 9670876.

16: Rheney CC, Saddler CM. Oral ketoconazole in cutaneous fungal infections. Ann Pharmacother. 1998 Jun;32(6):709-11. Review. PubMed PMID: 9640491.

17: DeVries A, Semchuk WM, Betcher JG. Ketoconazole in the prevention of acute respiratory distress syndrome. Pharmacotherapy. 1998 May-Jun;18(3):581-7. Review. PubMed PMID: 9620108.

18: Sarver RG, Dalkin BL, Ahmann FR. Ketoconazole-induced adrenal crisis in a patient with metastatic prostatic adenocarcinoma: case report and review of the literature. Urology. 1997 May;49(5):781-5. Review. PubMed PMID: 9145992.

19: Miossec P, Archambeaud-Mouveroux F, Teissier MP. [Inhibition of steroidogenesis by ketoconazole. Therapeutic uses]. Ann Endocrinol (Paris). 1997;58(6):494-502. Review. French. PubMed PMID: 9686009.

20: Chapman SA, Lake KD, Solbrack DF, Milfred SK, Marshall PS, Kamps MA. Considerations for using ketoconazole in solid organ transplant recipients receiving cyclosporine immunosuppression. J Transpl Coord. 1996 Sep;6(3):148-54. Review. PubMed PMID: 9188374.

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