Ketoconazole 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.
  • y_2017, m_9, d_23, h_22
  • bvseo_bulk, prod_bvrr, vn_bulk_2.0.3
  • cp_1, bvpage1
  • co_hasreviews, tv_0, tr_1
  • loc_en_US, sid_200496, prod, sort_[SortEntry(order=SUBMISSION_TIME, direction=DESCENDING)]
  • clientName_scbt
  • bvseo_sdk, java_sdk, bvseo-3.2.0
  • CLOUD, getAggregateRating, 5ms
  • REVIEWS, PRODUCT
| See product citations (12)
Synonym: (±)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine
Application: 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.
* Refer to Certificate of Analysis for lot specific data (including water content).
Submit a review for this product and receive 15 CruzCredits

Ordering Information

PRODUCT NAME CATALOG # UNIT PRICE QTY FAVORITES
Ketoconazole sc-200496 50 mg $54.00
Ketoconazole sc-200496A 500 mg $249.00

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
Transport :
UN 2811, Class 6.1, Packing group III
PubChem CID :
456201
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[C@H]3CO[C@](O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl

Download SDS (MSDS)

Certificate of Analysis

Adobe Acrobat Reader is required to reliably view,
print and comment on PDF documents

You May Also Like

Ketoconazole Product Citations

See how others have used Ketoconazole. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 12 total

PMID: # 25652406
Cunningham, D. et al. 2015. Analysis of hedgehog signaling in cerebellar granule cell precursors in a conditional Nsdhl allele demonstrates an essential role for cholesterol in postnatal CNS development. Hum. Mol. Genet.. 24: 2808-25.

PMID: # 20146553
Patel, MR. et al. 2011. Investigating effect of microemulsion components: In vitro permeation of ketoconazole. Pharm Dev Technol. 16: 250-258.

PMID: # 20228983
Khozeimeh, F. et al. 2010. Comparative evaluation of ketoconazole tablet and topical ketoconazole 2% in orabase in treatment of Candida-infected denture stomatitis. J Contemp Dent Pract. 11: 017-024.

PMID: # 20346873
Seneca, N. et al. 2010. Effects of ketoconazole on the biodistribution and metabolism of [11C]loperamide and [11C]N-desmethyl-loperamide in wild-type and P-gp knockout mice. Nucl. Med. Biol.. 37: 335-345.

PMID: # 20233203
Shin, KH. et al. 2010. Effect of ketoconazole on the pharmacokinetics of udenafil in healthy Korean subjects. Br J Clin Pharmacol. 69: 307-310.

PMID: # 20337383
Morsy, MA. et al. 2009. Electron paramagnetic resonance method for the quantitative assay of ketoconazole in pharmaceutical preparations. Anal. Chem.. 81: 6991-6995.

PMID: # 2677377
Van Wauwe, JP. et al. 1989. Is there a case for P-450 inhibitors in cancer treatment? J. Med. Chem.. 32: 2231-2239.

PMID: # 3361885
Nardone, PA. et al. 1988. Ketoconazole: a thromboxane synthetase and 5-lipoxygenase inhibitor with antimetastatic activity in B16-F10 melanoma. J. Surg. Res.. 44: 425-429.

PMID: # 2832292
Boscaro, M. et al. 1987. ACTH response to corticotropin releasing hormone in Cushing's disease before and after ketoconazole: in vivo and in vitro studies. Horm. Metab. Res. Suppl.. 16: 60-62.

PMID: # 3006695
Beetens, JR. et al. 1986. Ketoconazole inhibits the biosynthesis of leukotrienes in vitro and in vivo. Biochem. Pharmacol.. 35: 883-891.

Citations 1 to 10 of 12 total

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 scbt@scbt.com, or using the Live Chat function on our website.
Answered by: Tech Service 8
Date published: 2017-01-20
  • y_2017, m_9, d_23, h_22CST
  • bvseo_bulk, prod_bvqa, vn_bulk_2.0.3
  • cp_1, bvpage1
  • co_hasquestionsanswers, tq_2
  • loc_en_US, sid_200496, prod, sort_[SortEntry(order=LAST_APPROVED_ANSWER_SUBMISSION_TIME, direction=DESCENDING)]
  • clientName_scbt
  • bvseo_sdk, java_sdk, bvseo-3.2.0
  • CLOUD, getContent, 42ms
  • QUESTIONS, PRODUCT
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
  • y_2017, m_9, d_23, h_22
  • bvseo_bulk, prod_bvrr, vn_bulk_2.0.3
  • cp_1, bvpage1
  • co_hasreviews, tv_0, tr_1
  • loc_en_US, sid_200496, prod, sort_[SortEntry(order=SUBMISSION_TIME, direction=DESCENDING)]
  • clientName_scbt
  • bvseo_sdk, java_sdk, bvseo-3.2.0
  • CLOUD, getReviews, 5ms
  • REVIEWS, PRODUCT

Santa Cruz Biotechnology, Inc. is a world leader in the development of products for the biomedical research market. Call us Toll Free at 1-800-457-3801.
Copyright © 2007-2017 Santa Cruz Biotechnology, Inc. All Rights Reserved. "Santa Cruz Biotechnology", and the Santa Cruz Biotechnology, Inc. logo, "Santa Cruz Animal Health", "San Juan Ranch", "Supplement of Champions", the San Juan Ranch logo, "Ultracruz", "Chemcruz", "Immunocruz", "Exactacruz", and "EZ Touch" are registered trademarks of Santa Cruz Biotechnology, Inc.
All trademarks are the property of their respective owners.