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1356508

USP

Ketoconazole

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

(±)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine

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About This Item

Empirical Formula (Hill Notation):
C26H28Cl2N4O4
CAS Number:
Molecular Weight:
531.43
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

ketoconazole

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

SMILES string

CC(=O)N1CCN(CC1)c2ccc(OC[C@H]3CO[C@@](Cn4ccnc4)(O3)c5ccc(Cl)cc5Cl)cc2

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

InChI key

XMAYWYJOQHXEEK-OZXSUGGESA-N

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Ketoconazole USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:
  • Ketoconazole Compounded Oral Suspension
  • Ketoconazole Tablets
CYP3A4 inhibitor

Biochem/physiol Actions

Antifungal agent

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

Sales restrictions may apply.

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1B - STOT RE 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Drug safety, 20(5), 451-458 (1999-05-29)
The definition of hormone refractory prostate cancer is changing. It has become clear that patients with advanced prostate cancer whose disease has progressed following treatment with luteinising hormone releasing hormone agonists and antiandrogens can respond to additional hormonal manoeuvres. Ketoconazole
J J Berwaerts et al.
Journal of the American Geriatrics Society, 46(7), 880-884 (1998-07-22)
Cushing's syndrome is a rare disorder. The corticotropin (ACTH)-dependent form of this syndrome generally results either from excessive ACTH secretion by a pituitary adenoma or ectopic secretion by a malignant tumor. Theoretically, the latter type can be assumed to occur
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Seborrhoeic dermatitis (SD) is a chronic, inflammatory skin disorder, affecting areas of the head and body where sebaceous glands are most prominent and active. The disorder commonly affects hair-bearing areas of the head, including the scalp. Involvement on the face
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European journal of immunology, 44(6), 1781-1790 (2014-03-20)
The active vitamin D metabolite 1α,25-dihydroxyvitamin D (1,25[OH]₂ D) potently inhibits DC priming of T-cell activation, suggesting that it mediates a homeostatic role in this context. Therefore, careful regulation of 1,25[OH]₂ D levels is necessary to avoid inappropriate inhibition of
Avivit Peer et al.
The Prostate, 74(4), 433-440 (2013-12-18)
Abiraterone, a potent CYP 17 inhibitor, is standard treatment in docetaxel refractory, metastatic castrate resistant prostate cancer (mCRPC). However, in countries where abiraterone has not been approved yet, or for patients who cannot afford it, ketoconazole is used as an

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