Levoketoconazole | CAS#142128-57-2 | Cushing's disease

MedKoo Cat#: 558362 | Name: Levoketoconazole

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Description:

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

Levoketoconazole is a treatment of Cushing's Syndrome.

Chemical Structure

Levoketoconazole

CAS#142128-57-2

Theoretical Analysis

MedKoo Cat#: 558362

Name: Levoketoconazole

CAS#: 142128-57-2

Chemical Formula: C26H28Cl2N4O4

Exact Mass: 530.1488

Molecular Weight: 531.43

Elemental Analysis: C, 58.76; H, 5.31; Cl, 13.34; N, 10.54; O, 12.04

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 385.00	2 Weeks
50mg	USD 650.00	2 Weeks

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Synonym

Levoketoconazole; Normocort; 2S,4R-Ketoconazole;

IUPAC/Chemical Name

1-(4-(4-(((2S,4R)-2-((1H-imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)ethan-1-one

InChi Key

XMAYWYJOQHXEEK-ZEQKJWHPSA-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-/m1/s1

SMILES Code

CC(N1CCN(C2=CC=C(OC[C@H]3O[C@@](C4=CC=C(Cl)C=C4Cl)(CN5C=CN=C5)OC3)C=C2)CC1)=O

Appearance

Solid 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

Shelf Life

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

(-)-Ketoconazole ((-)-R 41400) is one of the enantiomer of Ketoconazole. Ketoconazole is a racemic mixture of two enantiomers, levoketoconazole ((2S,4R)-(−)-ketoconazole) and dextroketoconazole ((2R,4S)-(+)-ketoconazole).

In vitro activity:

Levoketoconazole potently inhibits cortisol production in adrenocortical cells, with a variable degree of suppression between specimens. Levoketoconazole inhibits adrenal steroid production more potently compared to RK and might also inhibit ACTH secretion and growth of pituitary adenoma cells. Together with previously reported potential advantages, this indicates that levoketoconazole is a promising novel pharmacotherapy for Cushing's syndrome. Reference: J Clin Endocrinol Metab. 2021 Mar 25;106(4):e1618-e1630. https://pubmed.ncbi.nlm.nih.gov/33399817/

In vivo activity:

The present study assessed the potential of ketoconazole to enhance resistance to carbon tetrachloride-induced hepatotoxicity in vivo in a rat model. Histopathological examination demonstrated ketoconazole pretreatment to extensively prevent liver injury. These results suggest that ketoconazole pretreatment ameliorates carbon tetrachloride-induced acute liver injury in rats, signifying its anti-inflammatory and antioxidant functions. Reference: J Toxicol Sci. 2019;44(6):405-414. https://pubmed.ncbi.nlm.nih.gov/31168027/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	33.3	62.72

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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. Creemers SG, Feelders RA, de Jong FH, Franssen GJH, de Rijke YB, van Koetsveld PM, Hofland LJ. Levoketoconazole, the 2S,4R Enantiomer of Ketoconazole, a New Steroidogenesis Inhibitor for Cushing's Syndrome Treatment. J Clin Endocrinol Metab. 2021 Mar 25;106(4):e1618-e1630. doi: 10.1210/clinem/dgaa989. PMID: 33399817. 2. Prado-Carrillo O, Arenas-Ramírez A, Llaguno-Munive M, Jurado R, Pérez-Rojas J, Cervera-Ceballos E, Garcia-Lopez P. Ketoconazole Reverses Imatinib Resistance in Human Chronic Myelogenous Leukemia K562 Cells. Int J Mol Sci. 2022 Jul 13;23(14):7715. doi: 10.3390/ijms23147715. PMID: 35887063; PMCID: PMC9317189. 3. Akhtar U, Ahmed M, Tayyeb A, Shehzad U, Ali G. Hepatoprotective effect of ketoconazole in chronic liver injury model. Pak J Pharm Sci. 2019 May;32(3):1033-1042. PMID: 31278717. 4. Zhou Y, Peng C, Zhou Z, Huang K. Ketoconazole pretreatment ameliorates carbon tetrachloride-induced acute liver injury in rats by suppressing inflammation and oxidative stress. J Toxicol Sci. 2019;44(6):405-414. doi: 10.2131/jts.44.405. PMID: 31168027.

In vitro protocol:

In vivo protocol:

1. Akhtar U, Ahmed M, Tayyeb A, Shehzad U, Ali G. Hepatoprotective effect of ketoconazole in chronic liver injury model. Pak J Pharm Sci. 2019 May;32(3):1033-1042. PMID: 31278717. 2. Zhou Y, Peng C, Zhou Z, Huang K. Ketoconazole pretreatment ameliorates carbon tetrachloride-induced acute liver injury in rats by suppressing inflammation and oxidative stress. J Toxicol Sci. 2019;44(6):405-414. doi: 10.2131/jts.44.405. PMID: 31168027.

1: Cuevas-Ramos D, Lim DST, Fleseriu M. Update on medical treatment for Cushing's disease. Clin Diabetes Endocrinol. 2016 Sep 13;2:16. doi: 10.1186/s40842-016-0033-9. eCollection 2016. Review. PubMed PMID: 28702250; PubMed Central PMCID: PMC5471955. 2: Fleseriu M, Castinetti F. Updates on the role of adrenal steroidogenesis inhibitors in Cushing's syndrome: a focus on novel therapies. Pituitary. 2016 Dec;19(6):643-653. Review. PubMed PMID: 27600150; PubMed Central PMCID: PMC5080363.