r-isomer

MKC-963 is a platelet aggregation inhibitor and autoinducer of CYP3A4.

Midodrine is a vasopressor/antihypertensive agent for the treatment of symptomatic postural hypotension.

Oxybutynin R-isomer , also known as Aroxybutynin, is a muscarinic receptor antagonist. Aroxybutynin is the optically avtice inhibitor of proliferation and supresses gene expression in bladder smooth muscle cells. Oxybutynin exerts direct antispasmodic effect on smooth muscle and inhibits the muscarinic action of acetylcholine on smooth muscle. It exhibits one-fifth of the anticholinergic activity of atropine on the rabbit detrusor muscle, but four to ten times the antispasmodic activity. No blocking effects occur at skeletal neuromuscular junctions or autonomic ganglia (antinicotinic effects).

BAY-598 R-isomer is the R-isomer of BAY589, which is used as a reference compound. It is is an inhibitor of lysine N-methyltransferase (SMYD2) and is selective for SMYD2 over protease-activated receptor 1 (PAR1).

BAY-6035 is an inhibitor of the methylation of MEKK2 peptide.

INCB3344 is a potent CCR2 antagonist. INCB3344 R-isomer is the R-isomer of INCB3344.

(S, R)-LSN 3318839 is an allosteric modulator of the glucagon-like peptide-3318839 receptor (GLP-1R) that has demonstrated powerful hypoglycemic effects in animal models alone or in combination with sitagliptin.

(R)-CR8 ((R)-Isomer) is a potent and selective CDK inhibitor.

(R)-CR8 trihydrochloride (CR8, (R)-Isomer trihydrochloride) is a CDK1/2/5/7/9 inhibitor that acts as a molecular glue degrader with neuroprotective activity and induces apoptosis.

(R)-pyrrolidine-2-carboxylic acid (D-Proline) is an isomer of the naturally occurring amino acid L-Proline. D-amino acids, including D-Proline, are found in relatively high abundance in human plasma and saliva, potentially originating from bacterial sources or endogenous production via amino acid racemase activity.

(R)-Lansoprazole (T 168390) is the R-isomer of lansoprazole and a substituted benzimidazole prodrug with selective and irreversible proton pump inhibitor activity.Lansoprazole (AG 1749) is a potent brain penetrant neutral sphingomyelinase (N-SMase) inhibitor (exosome inhibitor)

(R)-Naroparcil is an isomer of Naroparcil. Naroparcil, a 4-methylumbelliferyl beta-D-xyloside analog, is associated with vascular smooth muscle cell proliferation and inhibits thrombus formation in the Wessler slough model.

1,2-Diphenylpropan-2-amine is the monohydrochloride metabolite of the (S,R)-isomer of Remacemide.1,2-Diphenylpropan-2-amine has anticonvulsant properties.

(R)-AZD 9639 is the R-isomer of AZD 9639, a novel respiratory syncytial virus (RSV) fusion inhibitor with antiviral activity.

(R)-Carisbamate is the R-isomer of Carisbamate . Carisbamate is an experimental anticonvulsant drug.

Benzo[b]thiophene-7-propanoic acid, α-methoxy-4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-, (αR)- is a dual PPARα/γ agonist with EC50 of 0.358μM and 1.21μM. Benzo[b]thiophene-7-propanoic acid, α-methoxy-4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-, (αR)- is the R-isomer of Aleglitazar.

Seviteronel R enantiomer (VT-464 R enantiomer) is a Seviteronel isomer produced during the manufacturing process.

(Rac)-Etavopivat ((Rac)-FT-4202), an isomer of Etavopivat, is an orally active erythrocyte pyruvate kinase-R (PKR) activator used in sickle cell disease and haemoglobinopathy research [1].

(R)-JAK2/STAT3-IN-10a is the R-isomer of JAK2/STAT3-IN-1.JAK2/STAT3-IN-1 is a GP130 D1 structural domain inhibitor with antitumor activity that inhibits the phosphorylation of JAK2 and STAT3. The KD value of (R)-JAK2/STAT3-IN-1 on GP130 protein is 3.8 μM.

(S)-KT109 is the (S) isomer of the diacylglycerol lipase β (DAGLβ) inhibitor KT109 . (S)-KT109 is a less potent inhibitor of DAGLβ (IC50 = 39.81 nM), DAGLα-mediated hydrolysis of 1-stearoyl-2-arachidonoyl-sn-glycerol (IC50 = 794.3 nM), and α/β-hydrolase domain-containing protein 6 (ABHD6; IC50 = 630.9 nM) than (R)-KT109 .

19(R)-Hydroxylated prostaglandins (PGs) are present at µg/ml concentrations in the semen of some mammalian species, notably primates, with the majority being from the PGE series and featuring a 15(S),19(R) hydroxyl stereochemistry. These compounds are also observed in marsupials' seminal plasma, where F-type 1 and 2-series compounds are predominant. The 15(R)-hydroxy epimer represents the inverse or unnatural isomer at C-15 for these 19-hydroxylated PGs. Although the biological function of 19(R)-hydroxylated PGs remains unclear, 19(R)-hydroxylation in the F-series leads to a notable reduction in receptor-mediated biological activity in certain assays.

BW 737C89 is a highly potent dopamine D1 receptor antagonist; BW-737C is the (S)-isomer; BW-736C is the (R)-isomer.

(R)-Amlodipine is the R isomer of Amlodipine, a medication used to prevent chest pain and lower blood pressure.

Dexlansoprazole-d4 is a deuterated compound of Dexlansoprazole. Dexlansoprazole has a CAS number of 138530-94-6. Dexlansoprazole is the R-isomer of lansoprazole and a substituted benzimidazole prodrug with selective and irreversible proton pump inhibitor activity.Lansoprazole (AG 1749) is a potent brain penetrant neutral sphingomyelinase (N-SMase) inhibitor (exosome inhibitor)

8-iso-15(R)-Prostaglandin F2α (8-iso-15(R) PGF2α) is a chemically distinct member within a broad group of prostaglandin-like eicosanoids, produced through the free radical peroxidation of arachidonic acid contained in membrane phospholipids. It represents the C-15 epimer of 8-isoPGF2α, distinguished as the sole isoprostane isomer extensively examined across numerous biological systems.

15(S)-Fluprostenol, an isomer of the FP receptor agonist fluprostenol, serves as a potential active metabolite of 15(S)-fluprostenol isopropyl ester. It can function as an agonist at FP receptors, though with lower potency compared to its 15(R) epimer, fluprostenol.

(R)-Afatinib ((R)-BIBW 2992), an isomer of Afatinib, is a potent, orally administered, irreversible inhibitor targeting the ErbB family (EGFR and HER2) with IC50 values of 0.5 nM for EGFR wt, 0.4 nM for EGFR L858R, 10 nM for EGFR L858R T790M, and 14 nM for HER2, holding potential for research into esophageal squamous cell carcinoma (ESCC), non-small cell lung cancer (NSCLC), and gastric cancer [1].

(R)-BAY-899 is an R-isomer of BAY-899. BAY-899 is a selective, orally active luteinizing hormone receptor (LH-R) antagonist that acts on hLH (human LH) (IC50: 185 nM) and rLH (rat LH) (IC50: 46 nM).

(R)-NVS-ZP7-4 is the R-isomer of NVS-ZP7-4, a Zinc transporter SLC39A7 (ZIP7) inhibitor and the first reported chemical tool to explore the effects of modulating ER zinc levels and investigate ZIP7 as a novel druggable node in the Notch pathway.

(Rac)-Nebivolol ((Rac)-R 065824) is a racemic isomer of Nebivolol, a selective β1-adrenergic receptor antagonist (IC50 = 0.8 nM). Nebivolol exhibits vasodilatory activity and can prevent Nox2 NADPH oxidase up-regulation and lipoperoxidation in early stages of ethanol-induced cardiac toxicity.

(±)18-HETE is the racemic version of a cytochrome P450 (CYP450) metabolite of arachidonic acid. When formed by the CYP2E1 isoform, 18-HETE is comprised 100% of the (R) isomer. 18(R)-HETE dose-dependently stimulates vasodilation of the rabbit kidney, whereas 18(S)-HETE does not affect perfusion pressure. 18-HETE has negligible effects on ATPase activity. 18(R)-HETE at 1 μM completely blocks 20-HETE-induced vasoconstriction of renal arterioles.

Electrolyte and fluid transport in the kidney are regulated in part by arachidonic acid and its metabolites. (±)17-HETE is the racemic version of a cytochrome P450 (CYP450) metabolite of arachidonic acid that has stereospecific effects on sodium transport in the kidney. At a concentration of 2 μM the (S)-enantiomer of 17-HETE inhibits proximal tubule ATPase activity by as much as 70%, whereas the (R)-isomer is inactive.

AMG-628, (R)- is the R isomer of AMG-628 --- a potent, ATP-competitive inhibitor of Raf kinases. AMG-628 displays selectivity for Raf kinases and inhibits activation of tyrosine protein kinases such as VEGFR2, Lyn, Flt1 and Fms. AMG-628 has shown to inhibit growth, and induces cell cycle arrest and apoptosis in colon and melanoma cell lines with the B-RafV600E mutation.

Fmoc-Gly-Gly-D-Phe-OtBu, an ADC cleavable linker, is utilized in the synthesis of antibody-drug conjugates. It is the R-isomer of Fmoc-Gly-Gly-Phe-OtBu [1].

NS1219 ((R)-SPD502), an isomer of NS1209, functions as a selective antagonist for AMPA receptors, exhibiting neuroprotective properties. This compound is utilized in research related to stroke, neuropathic pain, and epilepsy.

17-phenyl trinor Prostaglandin F2α N-ethyl amide (17-phenyl trinor PGF2α) is an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug, sold under the Allergan trade name 17-phenyl trinor PGF2α ethyl amide. Investigations in our lab have shown that 17-phenyl trinor PGF2α ethyl amide is converted by an amidase enzymatic activity in the human cornea to yield the corresponding free acid, with a conversion rate of about 25 μg/cornea/24 hours. The free acid, 17-phenyl trinor PGF2α, is a potent FP receptor agonist. 15(R)-17-phenyl trinor PGF2α is the 15-epi, or unnatural isomer of this active free acid metabolite. It has much diminished FP receptor-mediated activity

5(S),6(R)-11-trans DiHETE is a C-11 double bond isomer of 5(S),6(R)-DiHETE that is formed by the enzymatic isomerization of 5(S),6(R)-DiHETE by a membrane bound factor. 5(S),6(R)-11-trans DiHETE has been found in rat kidney homogenates and is potentially formed by the epoxide hydrolase pathway in this tissue. The isomerase activity responsible for the conversion of leukotriene B4 (LTB4) to 6-trans LTB4 in rat kidney homogenates has also been implicated in its formation. 5(S),6(R)-11-trans DiHETE is not a substrate for soybean lipoxygenase. The biological activity of 5(S),6(R)-11-trans DiHETE has not been reported.

(R)-Omeprazole is the inactive isomer of omeprazole , a gastric proton-pump inhibitor. A stereoselective hydroxylation of (R)-omeprazole is mediated primarily by cytochrome P450 (CYP) 2C19, whereas CYP3A4 favors sulfoxidation of the active (S)-enantiomer . (R)-Omeprazole has been shown to act as a reversible direct-acting and metabolism-dependent inhibitor of CYP2C19 in pooled human liver microsomes (IC50 = 8.1 μM).

Epoxide hydrolases convert the EETs into vicinal diols, with the concurrent loss of much of their biological activity. The 8(S),9(R)-EET isomer is metabolized by platelet COX to form 8(S),9(R),11(R)-THETA, a trihydroxy fatty acid which may act as a renal vasoconstrictor.

The lipoxins are trihydroxy fatty acids containing a 7,9,11,13-conjugated tetraene. Lipoxin A4 (LXA4) was first described as a metabolite of 15-HpETE and/or 15-HETE when added in vitro to isolated human leukocytes. The material obtained in this manner consists of at least four distinct isomers: 5(S), 6(S); 5(S), 6(R); and the 11-trans and 11-cis isomers of each of these. 6(S)-LXA4 is one of the original four metabolites first identified by Serhan, Nicolaou, and Samuelsson. It was considered to be an artifact by these authors because it lacked the potency of the 5(S),6(R) isomer with respect to contraction of isolated guinea pig lung parenchymal strips. It has not been possible to isolate natural LXA4 from humans or other mammals in amounts sufficient for determination of absolute stereochemistry. Most authors refer to LXA4 as the 5(S)

(R)-(+)-Deoxyarbutin, an isomer of deoxyarbutin, acts as a tyrosinase inhibitor. Effective at a concentration of 21 µM, it diminishes tyrosinase activity and has been demonstrated to lighten the skin in hairless guinea pigs with dark, medium, and light pigmentation when applied at a 1% concentration.

15(S)-Fluprostenol isopropyl ester, an isomer of the prostaglandin F2α analog, fluprostenol isopropyl ester, serves as a possible prodrug to 15(S)-fluprostenol. It has the potential to act as an agonist at FP receptors, albeit with lower potency compared to the 15(R) epimer and the FP receptor agonist, fluprostenol. Additionally, it may be present as a potential impurity in commercial formulations of fluprostenol isopropyl ester.

Alprenolol tartrate, (R)-, is the R isomer of Alprenolol tartrate.

Adrafinil, (R)- is the R isomer of Adrafinil -- a eugeroic that was formerly used to promote alertness, attention, wakefulness, mood, and other parameters, particularly in the elderly.

(R)-Viloxazine Hydrochloride is the R-isomer of Viloxazine, a selective norepinephrine reuptake inhibitor (NRI) used as an antidepressant.

(R)-Ofloxacin is a R-isomer of Ofloxacin, an antibiotic used to treat a number of bacterial infections.

(±)8-HEPE is produced by the non-enzymatic oxidation of EPA, containing equal amounts of 8(S)-HEPE and 8(R)-HEPE. The ability of (±)8-HEPE to induce hatching of E. modestus and B. balanoides eggs is probably due to the presence of the 8(R) isomer within the racemic mixture.[1][2]

(R)-PD 0325901CL, an isomer of PD 0325901CL, acts as a selective inhibitor of mitogen-activated protein kinase kinase (MEK), playing a crucial role in cancer research. It effectively inhibits the growth of cancer cells both in vitro and in vivo.

(±)12-HEPE is produced by non-enzymatic oxidation of EPA, resulting in equal amounts of 12(S)-HEPE and 12(R)-HEPE. The biological activity of (±)12-HEPE is likely mediated by one of the individual isomers, primarily the 12(S) isomer in mammalian systems. 12-HEPE inhibits platelet aggregation with an IC50 of 24 μM, similar to 12-HETE (IC50 = 25 μM), and both compounds also inhibit U46619-induced contraction of rat aorta with IC50 values between 8.6-8.8 μM. [1][2]

Leukotriene B4 (LTB4) compounds are produced by both enzymatic and non-enzymatic processes. The products of enzymatic origin, via Leukotriene A4 (LTA4) hydrolase, are stereospecifically 12(R). Non-enzymatic hydrolysis products are 50:50 mixtures at C-12, but are almost exclusively trans at C-6. Thus, the non-enzymatic hydrolysis product of LTA4 is 6-trans-12-epi LTB4. 12-epi LTB4 is an isomer which would not be expected to occur in either non-enzymatic hydrolysis products, or in the enzymatic products of LTA4 hydrolase. Compared to LTB4, 12-epi LTB4 has significantly reduced activity for the LTB4 receptor on human neutrophils (IC50 of 7.5 mM), and on guinea pig lung membranes with a (Ki of 4.7 mM). 12-epi LTB4 is an weak agonist at both the recombinant human BLT1 and BLT2 receptors, requiring approximately 10 mM for full activation of the receptor.