biotransformation

Isonicotinic acid, a metabolite of isoniazid and a useful isomer of nicotinic acid, is formed from isoniazid by hydrazinolysis and can be catalyzed by cytochrome P450 enzymes, such as CYP2C.

Naringinase is a hydrolytic enzymatic complex that exhibits α-L-rhamnosidase and β-D-glucosidase activities. It is widely found in nature and is primarily utilized for the biotransformation of steroids, antibiotics, and glycosides.

Cevimeline hydrochloride hemihydrate ((-)-SNI-2011), a novel muscarinic receptor agonist, is being explored as a potential treatment for xerostomia in Sjogren's syndrome, exhibiting an IC50 value indicative of its affinity for mAChR. This compound's pharmacological effects on the gastrointestinal, urinary, and reproductive systems, alongside its impact on various tissues, were thoroughly examined in species including mice, rats, guinea pigs, rabbits, and dogs. The metabolic breakdown of (-)-SNI-2011 was studied in vitro using rat and dog liver microsomes to assess its biotransformation. Upon oral administration, peak plasma concentrations were reached within an hour in both rats and dogs, showcasing rapid absorption and a subsequent decrease in concentration with a half-life ranging from 0.4 to 1.1 hours. Bioavailability was noted at 50% in rats and 30% in dogs. Metabolic pathways highlighted significant species differences, with both S- and N-oxidized metabolites identified in rats, but only N-oxidized metabolites in dogs. Additionally, gender differences in pharmacokinetics were observed in rats but were absent in dogs. In vitro studies pinpointed the involvement of cytochrome P450 (CYP) and flavin-containing monooxygenase (FMO) in the metabolism of (-)-SNI-2011, specifically through sulfoxidation and N-oxidation processes, respectively. CYP2D and CYP3A were identified as the primary enzymes responsible for sulfoxidation in rat liver microsomes.

Nebicapone is a reversible catechol-O-methyltransferase (COMT) inhibitor and is mainly metabolized by glucuronidation. Nebicapone is mainly peripherally acting inhibitor that decreases the biotransformation of L-DOPA to 3-O-methyl-DOPA by inhibition of CO

Alanycarb (OK-135) is a broad-spectrum oxime carbamate insecticide that exhibits both contact and oral toxicity. Effective against a variety of pests, it is considered a proinsecticide. Upon biotransformation within target organisms, the primary active compound produced is methomyl.

Clopidogrel is an antithrombic compound whose active metabolite is a selective, irreversible antagonist of the platelet purinergic P2Y12 receptor (IC50 = 100 nM). Clopidogrel inhibits ADP-induced platelet aggregation ex vivo and functions as a prodrug whereupon biotransformation to its active metabolite via CYP2C19 in the liver enables its anti-aggregating activity. Marketed under the name Plavix , clopidogrel in combination with aspirin has been shown to be beneficial in the prevention of vascular ischemic events for patients without deficiencies in CYP2C19-related metabolism.

rac-trans-4-hydroxy Glyburide, an active metabolite of the SUR1/Kir6.2 sulfonylurea inhibitor glyburide, is formed by the cytochrome P450 (CYP) isoforms CYP2C8 and CYP2C9. It inhibits glyburide binding to rat brain synaptosomes at high and low affinity sites of SUR1/Kir6.2 with IC50 values of 0.95 and 100 nM, respectively.

Vaccarin is a major flavonoid glycoside in Vaccariae semen, its biotransformation pathways involves methylation, hydroxylation, glycosylation and deglycosylation.

1. Biotransformation of glucoAurantio-obtusin towards Aurantio-obtusin increased the toxicity of irinotecan through increased inhibition of SN-38 glucuronidation. 2. Aurantio-obtusin, stimulated chemotactic migration of MC3T3-E1 osteoblast cells in a conc

Diaphorase, derived from anaerobic sludge organisms, catalyzes the denitrification biotransformation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) [1].

7-Hydroxy-TSU-68, a derivative and metabolite of TSU-68, originates from the self-induced hydroxylation of TSU-68 in human liver microsomes, indicating its biotransformation pathway [1].

4'-Demethylpodophyllotoxone, an intermediate in the biotransformation pathway of Alternaria alternata S-f6, undergoes further modification with 4-(2,3,5,6-tetramethylpyrazine-1) (4-TMP). This modification yields a novel compound that exhibits potent inhibitory effects on the human gastric cancer cell line BGC-823 [1].

(±)-Lavandulol, an atypical monoterpene alcohol, undergoes biotransformation by the fungal strain Rhizopus oryzae to yield its oxygenated metabolite [1].

8-Chloroadenosine-5'-triphosphate (8-chloro ATP), a potent metabolite of the anticancer agent 8-chloro cyclic AMP (cAMP) and a nucleotide derivative, is produced through the biotransformation of 8-chloro cAMP into 8-chloroadenosine, followed by mono- and diphosphate intermediates. Accumulating for up to 12 hours after the administration of 8-chloro cAMP or 8-chloroadenosine, 8-chloro ATP inhibits cell growth, diminishes endogenous ATP levels, and reduces RNA synthesis without affecting DNA synthesis in multiple myeloma cells derived from patients. Moreover, it obstructs topoisomerase II-α-mediated relaxation of supercoiled pUC19 DNA at concentrations ranging from 1.5 to 8 mM and decreases topoisomerase II-α-enhanced ATP hydrolysis by 50% at a concentration of 1 mM in K562 human myelocytic leukemia cells.

5-(3'-Hydroxyphenyl)-γ-Valerolactone (3'-OH-PVL) is a major phenolic catabolite produced from the fermentation of flavan-3-ols (such as catechin and epicatechin) by the gut microbiota. The compound serves as a key biomarker for investigating the biotransformation pathways and stoichiometry of dietary polyphenols within the colon, enabling the assessment of bioavailability and the potential health contributions of flavan-3-ols with varying degrees of polymerization through monitoring its production levels.

10,11-Dihydro-10,11-dihydroxy Carbamazepine, a metabolite of the anticonvulsant carbamazepine and the antiepileptic prodrug oxcarbazepine, is produced through the biotransformation of carbamazepine via a carbamazepine 10,11-epoxide intermediate by epoxide hydrolase, and from oxcarbazepine via a 10,11-dihydro-10-hydroxy carbamazepine intermediate. This compound has been detected in wastewater effluent, highlighting its environmental presence following pharmaceutical use.

(±)-Lavandulol (Standard) is a reference standard for research and analysis in studies involving (±)-Lavandulol. (±)-Lavandulol, an atypical monoterpene alcohol, undergoes biotransformation by the fungal strain Rhizopus oryzae to yield its oxygenated metabolite [1].

Aurantio-obtusin (Standard) is a reference standard for research and analysis in studies involving Aurantio-obtusin. 1. Biotransformation of glucoAurantio-obtusin towards Aurantio-obtusin increased the toxicity of irinotecan through increased inhibition of SN-38 glucuronidation. 2. Aurantio-obtusin, stimulated chemotactic migration of MC3T3-E1 osteoblast cells in a concentration-dependent manner. Besides migration, the compound stimulated osteoblast differentiation and mineralization. 3. Aurantio-obtusin is a promising osteoanabolic compound of natural origin with potential therapeutic applications in the prevention of osteoporosis and other metabolic bone diseases.

Flufiprole (Standard) is a reference standard substance of flufiprole developed for quantitative analysis, analytical quality control, and biochemical research applications. Flufiprole is classified as a phenylpyrazole pesticide that exhibits enantioselective metabolic behavior in both human and rat liver microsome systems, thereby providing a useful model compound for toxicological evaluation, metabolic profiling, and stereoselective biotransformation studies.

Vaccarin (Standard) is a reference standard for research and analysis in studies involving Vaccarin. Vaccarin is a major flavonoid glycoside in Vaccariae semen, its biotransformation pathways involves methylation, hydroxylation, glycosylation and deglycosylation.

Vomifoliol is a plant-derived compound likely serving as the immediate precursor of dehydrovomifoliol due to its metabolic conversion from abscisic acid. Vomifoliol, in conjunction with Stigmasterol, exhibits antiproliferative activity on human lung cancer cell lines, making Vomifoliol relevant in studies of plant metabolite biotransformation and anticancer bioactivity.

3-epi-Resibufogenin (compound 2) is an anticancer agent obtained through the biotransformation of Resibufogenin by Actinomucor elegans AS 3.2778. It demonstrates cytotoxicity against cancer cells, with IC50 values of 42.5 μM (A549) and 48.4 μM (H1299).