CAS 1398065-75-2 (±)-Ketoconazole-[d4]

General Information
Catalog: BLP-013923
CAS: 1398065-75-2
Molecular Formula: C26H24D4Cl2N4O4
Molecular Weight: 535.46

General Information

Catalog: BLP-013923

CAS: 1398065-75-2

Molecular Formula: C26H24D4Cl2N4O4

Molecular Weight: 535.46

Chemical Structure

Description	(±)-Ketoconazole-[d4] (cis-isomers) is the labelled analogue of (±)-Ketoconazole, which is a synthetic imidazole antifungal drug used to treat fungal infections.
Synonyms	(+/-)-Ketoconazole-d4 (piperazine-3,3,5,5-d4) (cis-isomers); (±)-Ketoconazole-d4; cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine-d4
IUPAC Name	1-[3,3,5,5-tetradeuterio-4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
Related CAS	65277-42-1 (unlabelled)
Canonical SMILES	CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
InChI	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/i12D2,13D2
InChI Key	XMAYWYJOQHXEEK-DNYYUWHPSA-N
Purity	95% by HPLC; 98% atom D
Solubility	Soluble in Methanol
Appearance	White Powder
Storage	Store at -20°C

(±)-Ketoconazole-[d4], an isotopically labeled compound of ketoconazole predominantly utilized in scientific research, presents a myriad of applications. Here are the key applications:

Pharmacokinetics and Drug Metabolism Studies: By integrating (±)-Ketoconazole-[d4] into pharmacokinetic investigations, researchers can meticulously trace the metabolism and distribution of ketoconazole within the body. Through the utilization of the deuterated variant, scientists can distinguish it from endogenous compounds in mass spectrometry, facilitating a comprehensive comprehension of the drug’s absorption, distribution, metabolism, and excretion (ADME) profiles.

Drug Interaction Research: Positioned at the forefront of drug interaction exploration, this compound plays a pivotal role in unraveling drug-drug interactions, particularly involving cytochrome P450 enzymes. Researchers harness (±)-Ketoconazole-[d4] to scrutinize how ketoconazole influences the metabolism of other drugs. These inquiries are indispensable for assessing potential adverse effects and optimizing co-administration therapies to elevate patient outcomes.

Comparative Studies: In rigorous comparative analyses, (±)-Ketoconazole-[d4] is enlisted to evaluate distinctions between the labeled and non-labeled iterations of the drug. Researchers can meticulously examine the pharmacological and toxicological profiles to ensure that deuteration does not significantly alter the compound’s behavior. Such investigations validate the utilization of deuterated drugs in clinical contexts, guaranteeing safety and efficacy.

Analytical Method Development: Serving as the pinnacle in analytical method advancement, (±)-Ketoconazole-[d4] assists in the precise quantification of ketoconazole in biological samples. By employing this compound as an internal standard in mass spectrometry, the precision and reliability of measurements are significantly enhanced. This plays a pivotal role in ensuring dependable drug monitoring practices and effective therapeutic drug management protocols.