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Usage

Uses

Used in Pharmaceutical Industry:
(4R)-4-[(3S,5R,8S,9S,10S,12S,13R,14S)-1,3,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid is used as a pharmaceutical agent for its potential therapeutic effects. Its unique structure and functional groups may allow it to interact with biological targets, such as enzymes or receptors, to modulate their activity and produce desired pharmacological effects.
Used in Chemical Research:
In the field of chemical research, (4R)-4-[(3S,5R,8S,9S,10S,12S,13R,14S)-1,3,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid can serve as a valuable compound for studying its synthesis, properties, and potential applications. Researchers can explore its reactivity, stability, and interactions with other molecules to gain insights into its potential uses and optimize its synthesis for large-scale production.
Used in Drug Metabolism Studies:
(4R)-4-[(3S,5R,8S,9S,10S,12S,13R,14S)-1,3,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid, being a metabolite of Taurodeoxycholic Acid, can be used in drug metabolism studies to understand its role in the body's detoxification and elimination processes. This knowledge can help in the development of new drugs with improved pharmacokinetic properties and reduced side effects.

Upstream product

• 104839-75-0 (R)-methyl 4-((1R,3S,5R,8S,9S,10S,12S,13R,14S,17R)-12-acetoxy-1,3-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate 
• 83-44-3 Deoxycholic acid 
• 104881-54-1 methyl 12α-acetoxy-2β-bromo-3-oxo-5β-cholan-24-oate 
• 104854-44-6 (R)-methyl 4-((1R,5R,8S,9S,10S,12S,13R,14S,17R)-12-acetoxy-1-hydroxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate 
• 99598-09-1 (R)-4-((1S,2S,5R,8S,9S,10S,12S,13R,14S,17R)-12-Hydroxy-10,13-dimethyl-3-oxo-hexadecahydro-20-oxa-cyclopropa[1,2]cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 
• 99598-21-7 2,4-dibromo-3-oxo deoxycholic acid methyl ester 
• 99598-05-7 (R)-4-((5R,8R,9S,10R,12S,13R,14S,17R)-12-Hydroxy-10,13-dimethyl-3-oxo-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 
• 99598-13-7 (R)-4-((1R,5R,8S,9S,10S,12S,13R,14S,17R)-1,12-Dihydroxy-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 
• 91097-45-9 1β,3α,12α-trihydroxy-5β-cholan-24-oic acid methyl ester 
• 104854-43-5 (R)-methyl 4-[(1S,2S,5R,8S,9S,10S,12S,13R,14S,17R)-12-acetoxy-1,2-epoxy-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate 
• 104839-67-0 methyl 12α-acetoxy-2β,4β-dibromo-3-oxo-5β-cholan-24-oate 
• 7753-75-5 (R)-methyl 4-((5R,8R,9S,10S,12S,13R,14S,17R)-12-acetoxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate 
• 10538-58-6 methyl 12α-hydroxy-3-oxo-5β-cholan-24-oate 
• 3245-38-3 methyl deoxycholate 

Relevant academic research and scientific papers

Synthesis of 1β-hydroxydeoxycholic acid in H-2 and unlabeled forms

1β–hydroxydeoxycholic acid in unlabeled and stable isotope labeled forms was required for use as a biomarker for Cytochrome P450 3A4/5 activity. A lengthy synthesis was undertaken to deliver the unlabeled compound and in the process, to develop a route to the deuterium labeled compound. The synthesis of the unlabeled compound was completed but in a very low yield. Concurrent with the synthetic approach, a biosynthetic route was pursued and this approach proved to be much more rapid and afforded the compound in both unlabeled and deuterium labeled forms in a 1-step oxidation from deoxycholic acid and [D4]deoxycholic acid, respectively.

CYP3A specifically catalyzes 1β-hydroxylation of deoxycholic acid: Characterization and enzymatic synthesis of a potential novel urinary biomarker for CYP3A activity

The endogenous bile acid metabolite 1β-hydroxy-deoxycholic acid (1β-OH-DCA) excreted in human urine may be used as a sensitive CYP3A biomarker in drug development reflecting in vivo CYP3A activity. An efficient and stereospecific enzymatic synthesis of 1β-OH-DCA was developed using a Bacillus megaterium (BM3) cytochrome P450 (P450) mutant, and its structure was confirmed by nuclear magnetic resonance (NMR) spectroscopy. A [2H4]-labeled analog of 1β-OH-DCA was also prepared. The major hydroxylated metabolite of deoxycholic acid (DCA) in human liver microsomal incubations was identified as 1β-OH-DCA by comparison with the synthesized reference analyzed by UPLC-HRMS. Its formation was strongly inhibited by CYP3A inhibitor ketoconazole. Screening of 21 recombinant human cytochrome P450 (P450) enzymes showed that, with the exception of extrahepatic CYP46A1, the most abundant liver P450 subfamily CYP3A, including CYP3A4, 3A5, and 3A7, specifically catalyzed 1β-OH-DCA formation. This indicated that 1β-hydroxylation of DCA may be a useful marker reaction for CYP3A activity in vitro. The metabolic pathways of DCA and 1β-OHDCA in human hepatocytes were predominantly via glycine and, to a lesser extent, via taurine and sulfate conjugation. The potential utility of 1β-hydroxylation of DCA as a urinary CYP3A biomarker was illustrated by comparing the ratio of 1β-OH-DCA:DCA in a pooled spot urine sample from six healthy control subjects to a sample from one patient treated with carbamazepine, a potent CYP3A inducer; 1β-OH-DCA:DCA was considerably higher in the patient versus controls (ratio 2.8 vs. 0.4). Our results highlight the potential of 1β-OH-DCA as a urinary biomarker in clinical CYP3A DDI studies.