Ketoconazole CAS: 65277-42-1
MF: C26H28Cl2N4O4
MW: 531.43
An inhibitor of CYP proteins, thromboxane synthetase, and 5-LO.

Ketoconazole (CAS 65277-42-1)

Ketoconazole | CAS 65277-42-1 is rated 5.0 out of 5 by 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 (including water content).
DISCOUNT: Bulk orders of Chemicals totaling $1,000 or more receive a 5% discount.
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Ketoconazole is an imidazole-containing small molecule inhibitor of cytochrome P-450-dependent steps in the biosynthesis of steroid hormones; 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.


References

1. Lelcuk, S., et al. 1984. J Trauma. 24: 393-396. PMID: 6325720
2. Lelcuk, S., et al. 1985. Ann. Surg. 202: 642-646. PMID: 3840349
3. Lambert, A., et al. 1986. Biochem. Pharmacol. 35: 3999-4004. PMID: 3022746
4. Beetens, J.R., et al. 1986. Biochem. Pharmacol. 35: 883-891. PMID: 3006695
5. Boscaro, M., et al. 1987. Horm. Metab. Res. Suppl. 16: 60-62. PMID: 2832292
6. Nardone, P.A., et al. 1988. J. Surg. Res. 44: 425-429. PMID: 3361885
7. Ward, A.S., et al. 1998. Behav Pharmacol. 9: 577-586. PMID: 9862083
8. Richie, J.P. 1999. Urology. 54: 15-18. PMID: 10606279
9. Chaudhary, U.B., et al. 2005. Can J Urol. 12: 2666-2676. PMID: 16011813

Physical State :
Solid
Solubility :
Soluble in DMSO (20 mg/mL warm), ethanol (20 mg/mL warm), chloroform and methanol. Low water solubility (<1 mg/mL).
Storage :
Store at room temperature
Melting Point :
147° C
Boiling Point :
~753.4° C at 760 mmHg (Predicted)
Density :
~1.4 g/cm3 (Predicted)
Refractive Index :
n20D 1.64
Optical Activity :
α20/D -10.5°, c = 0.4 in chloroform
IC50 :
Cytochrome P450 3A4: IC50 = 13 nM (human); Filobasidiella neoformans: IC50 = 20 nM (Cryptococcus neoformans); Candida parapsilosis: IC50 = 40 nM (Candida parapsilosis)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
TK7912300
PubChem CID :
Merck Index :
14: 5302
MDL Number :
MFCD00058579
EC Number :
265-667-4
Beilstein Registry :
634785
SMILES :
CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OC[[email protected]]3CO[[email protected]](O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl

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Certificate of Analysis

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Ketoconazole (CAS 65277-42-1)  Product Citations

See how others have used Ketoconazole (CAS 65277-42-1). Click on the entry to view the PubMed entry .

Citations 1 to 10 of 20 total

PMID: # 34842434  Hargrove, TY.|Wawrzak, Z.|Rachakonda, G.|Nes, WD.|Villalta, F.|Guengerich, FP.|Lepesheva, GI.| et al. 2021. J Med Chem.

PMID: # 28461309  Hargrove, TY. et al. 2017. Antimicrob. Agents Chemother. 61:

PMID: # 25652406  Cunningham, D. et al. 2015. Hum. Mol. Genet. 24: 2808-25.

PMID: # 26379312  Khalil, MS. et al. 2015. Acta Histochem Cytochem. 48: 103-13.

PMID: # 20146553  Patel, MR. et al. 2011. Pharm Dev Technol. 16: 250-258.

PMID: # 20346873  Seneca, N. et al. 2010. Nucl. Med. Biol. 37: 335-345.

PMID: # 20233203  Shin, KH. et al. 2010. Br J Clin Pharmacol. 69: 307-310.

PMID: # 20228983  Khozeimeh, F. et al. 2010. J Contemp Dent Pract. 11: 017-024.

PMID: # 20337383  Morsy, MA. et al. 2009. Anal. Chem. 81: 6991-6995.

PMID: # 2677377  Van Wauwe, JP. et al. 1989. J. Med. Chem. 32: 2231-2239.

Citations 1 to 10 of 20 total

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 &quot;water (&lt;1 mg/mL)&quot; 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 (&lt;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 [email protected], 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 al Richie 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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