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Ketoconazole (CAS 65277-42-1)

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Application:
Ketoconazole is an inhibitor of CYP proteins, thromboxane synthetase, and 5-LO
CAS Number:
65277-42-1
Purity:
≥99%
Molecular Weight:
531.43
Molecular Formula:
C26H28Cl2N4O4
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Ketoconazole is an imidazole-containing small molecule inhibitor of cytochrome P-450-dependent steps in the biosynthesis of steroid hormoness, also inhibits TXA Synthase (thromboxane synthetase) and 5-LO (5-lipoxygenase) activity. Ketoconazole exhibits antimetastatic, antineoplastic, and antipsoriatic activity. Inhibition of 5-LO (5-lipoxygenase) by Ketoconazole interrupts arachidonic acid (sc-200770)-derived leukotriene production, which was correlated to a suppression of leukotriene-mediated anaphylactic bronchoconstriction in guinea pigs. Ketoconazole is described as reducing platelet cellular levels of thromboxane A2, suppressing thromboxane A2-mediated increase of microvascular permeability in response to ischemia insults. Ketoconazole produces an antiandrogen effect through inhibition of adrenocorticoid biosynthesis, suppressing the adrenal secretion of androgens and attenuating cortisol response. Ketoconazole is an inhibitor of CYP17A1, CYP3A4 and CYP3A5.


Ketoconazole (CAS 65277-42-1) References

  1. Anti-androgens and other hormonal therapies for prostate cancer.  |  Richie, JP. 1999. Urology. 54: 15-8. PMID: 10606279
  2. Secondary hormonal manipulations in the management of advanced prostate cancer.  |  Chaudhary, UB., et al. 2005. Can J Urol. 12: 2666-76. PMID: 16011813
  3. Sources of variability in ketoconazole inhibition of human cytochrome P450 3A in vitro.  |  Greenblatt, DJ., et al. 2010. Xenobiotica. 40: 713-20. PMID: 20712450
  4. Ketoconazole inhibits ovulation as a result of arrest of follicular steroidogenesis in the rat ovary.  |  Gal, M. and Orly, J. 2014. Clin Med Insights Reprod Health. 8: 37-44. PMID: 24987273
  5. ACTH response to corticotropin releasing hormone in Cushing's disease before and after ketoconazole: in vivo and in vitro studies.  |  Boscaro, M., et al. 1987. Horm Metab Res Suppl. 16: 60-2. PMID: 2832292
  6. Ketoconazole inhibits the biosynthesis of leukotrienes in vitro and in vivo.  |  Beetens, JR., et al. 1986. Biochem Pharmacol. 35: 883-91. PMID: 3006695
  7. The effect of ketoconazole on adrenal and testicular steroidogenesis in vitro.  |  Lambert, A., et al. 1986. Biochem Pharmacol. 35: 3999-4004. PMID: 3022746
  8. Effects of ketoconazole, voriconazole, and itraconazole on the pharmacokinetics of apatinib in rats.  |  Lou, D., et al. 2019. Drug Dev Ind Pharm. 45: 689-693. PMID: 30632818
  9. Ketoconazole-induced transient hypoadrenocorticism in a dog.  |  Sullivant, AM. and Lathan, P. 2020. Can Vet J. 61: 407-410. PMID: 32255827
  10. Ketoconazole: a thromboxane synthetase and 5-lipoxygenase inhibitor with antimetastatic activity in B16-F10 melanoma.  |  Nardone, PA., et al. 1988. J Surg Res. 44: 425-9. PMID: 3361885
  11. Arylacetamide deacetylase knockout mice are sensitive to ketoconazole-induced hepatotoxicity and adrenal insufficiency.  |  Nagaoka, M., et al. 2022. Biochem Pharmacol. 195: 114842. PMID: 34798123
  12. Ketoconazole and other imidazole derivatives as inhibitors of steroidogenesis.  |  Feldman, D. 1986. Endocr Rev. 7: 409-20. PMID: 3536461
  13. Thromboxane A2 moderates permeability after limb ischemia.  |  Lelcuk, S., et al. 1985. Ann Surg. 202: 642-6. PMID: 3840349
  14. Inhibition of ischemia-induced thromboxane synthesis in man.  |  Lelcuk, S., et al. 1984. J Trauma. 24: 393-6. PMID: 6325720
  15. Ketoconazole attenuates the cortisol response but not the subjective effects of smoked cocaine in humans.  |  Ward, AS., et al. 1998. Behav Pharmacol. 9: 577-86. PMID: 9862083

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Ketoconazole, 50 mg

sc-200496
50 mg
$63.00

Ketoconazole, 500 mg

sc-200496A
500 mg
$265.00

Why is this compound $403 USD on Sigma for 10 mg but $54 for 50 mg here? What is the catch?

Asked by: carodriguez
Thank you for your question. For accurate availability, pricing and shipping information regarding this chemical, please contact your our customer service department for assistance.
Answered by: Technical Service 3
Date published: 2020-11-20

Is the about solubility in water of ketoconazole "water (<1 mg/mL)" stupid?

Asked by: Jack112233
Thank you for your question. This product is soluble in DMSO (20 mg/mL warm), ethanol (20 mg/mL warm), chloroform, water (<1 mg/mL), and methanol. Please contact our Technical Service Department by phone, e-mail or live chat if you have any further questions.
Answered by: Tech Service
Date published: 2017-08-14

What is the appearance of the compound?

Asked by: two2igm05
Thank you for your question. The compound, sc-200496, is provided as a white to off-white crystalline powder. if you have any further questions or concerns, please feel free to contact our Technical Service department by calling 800-457-3801 option 2, emailing scbt@scbt.com, or using the Live Chat function on our website.
Answered by: Tech Service 8
Date published: 2017-01-20
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Rated 5 out of 5 by from Richie et alRichie et al. (PubMed ID 10606279) found that ketoconazole suppressed adrenal secretion of androgens in men with hormone refractory prostate cancer. -SCBT Publication Review
Date published: 2015-03-15
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Ketoconazole is rated 5.0 out of 5 by 1.
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