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| Targets |
(-)-Talarozole targets cytochrome P450 enzyme CYP26, a family of enzymes responsible for the metabolism of retinoic acid. As a selective retinoic acid metabolism blocking agent (RAMBA), (-)-Talarozole inhibits CYP26-mediated breakdown of endogenous all-trans-retinoic acid. By blocking retinoic acid metabolism, the compound increases intracellular levels of retinoic acid, enhancing its biological effects. This mechanism makes (-)-Talarozole a promising candidate for treating skin disorders where retinoic acid plays a key role.
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| ln Vitro |
In vitro, (-)-Talarozole functions as a potent inhibitor of retinoic acid metabolism by blocking the cytochrome P450 enzyme isoform CYP26. The compound is a new generation all-trans retinoic acid metabolism blocking agent with high specificity for retinoic acid 4-hydroxylase. By inhibiting retinoic acid metabolism, (-)-Talarozole increases intracellular levels of endogenous all-trans retinoic acid, enhancing its biological effects. These in vitro properties establish (-)-Talarozole as a valuable tool for studying retinoic acid signaling.
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| ln Vivo |
In vivo, (-)-Talarozole alleviates hyperproliferation and normalizes differentiation of the epidermis in animal models of psoriasis. As a retinoic acid metabolism blocking agent, the compound increases retinoic acid levels in target tissues, enhancing its biological effects. The compound has been studied for its potential in treating skin disorders like psoriasis and acne, where retinoic acid plays a key role in skin health. Detailed in vivo efficacy data are available in the scientific literature.
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| Enzyme Assay |
(-)-Talarozole is not typically used in standard receptor binding assays. Its activity is assessed through CYP26 enzyme inhibition assays or cell-based assays measuring retinoic acid metabolism. In enzyme inhibition assays, CYP26 activity is measured by monitoring the metabolism of retinoic acid to its metabolites. (-)-Talarozole is incubated with the enzyme and substrate at varying concentrations, and metabolite formation is quantified by HPLC or LC-MS. IC50 values are calculated from concentration-response curves. Nonspecific activity is determined in control reactions without inhibitor.
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| Cell Assay |
Cellular assays for (-)-Talarozole are performed using cell lines that express CYP26 enzymes, such as keratinocytes or other skin cells. Cells are cultured in appropriate media and treated with (-)-Talarozole at varying concentrations for defined time periods. Retinoic acid metabolism is assessed by measuring the levels of retinoic acid and its metabolites in cell lysates or culture supernatant using HPLC or LC-MS. Retinoic acid signaling is assessed by measuring the expression of retinoic acid-responsive genes by qRT-PCR. Cell proliferation and differentiation may also be assessed.
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| Animal Protocol |
In vivo studies with (-)-Talarozole are conducted in animal models of psoriasis and other skin disorders. (-)-Talarozole is administered via oral routes at defined doses and schedules. Skin hyperproliferation and differentiation are assessed by histological analysis and immunohistochemistry. Epidermal thickness and keratinocyte differentiation markers are measured. Pharmacokinetic parameters are determined from plasma samples collected at various time points. The compound's efficacy in alleviating hyperproliferation and normalizing differentiation has been demonstrated in animal models.
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| ADME/Pharmacokinetics |
(-)-Talarozole has a molecular weight of 377.51 and a molecular formula of C21H23N5S. The compound is a potent inhibitor of retinoic acid metabolism. Detailed pharmacokinetic parameters, including oral bioavailability and half-life, have been characterized in preclinical studies. The compound is soluble in DMSO. It should be stored at -20degC. (-)-Talarozole is extracted from patent WO 1997049704 A1.
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| Toxicity/Toxicokinetics |
Comprehensive toxicology data for (-)-Talarozole are not extensively documented in publicly available sources. The compound is intended for research use only and is not approved for human therapeutic applications. Standard laboratory safety practices should be followed when handling this compound, including the use of appropriate personal protective equipment and adherence to institutional biosafety and chemical hygiene guidelines. The compound has a purity of ≥98%.
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| References | |
| Additional Infomation |
N-{4-[2-ethyl-1-(1,2,4-triazol-1-yl)butyl]phenyl}-1,3-benzothiazol-2-amine belongs to the benzothiazolium class of compounds, namely 2-amino-1,3-benzothiazolium, in which one amino hydrogen atom is replaced by 4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl. It belongs to the triazole, benzothiazolium, aromatic amine, and secondary amine classes. Taprazole has been studied for the treatment of psoriasis and skin inflammation. Mechanism of Action: Lanpazol is a new generation all-trans retinoic acid metabolism blocker with high specificity for retinoic acid 4-hydroxylase. This drug can reduce excessive epidermal proliferation and normalize epidermal differentiation in animal models of psoriasis. All-trans retinoic acid (RA) regulates epithelial cell differentiation and growth by activating specific nuclear RA receptors (RAR). Lanbazol's mechanism of action is to inhibit the metabolic breakdown of retinoic acid, thereby enhancing the biological efficacy of RA.
(-)-Talarozole is a selective retinoic acid metabolism blocking agent (RAMBA) that inhibits cytochrome P450 enzyme CYP26, which metabolizes retinoic acid. The compound alleviates hyperproliferation and normalizes differentiation of the epidermis in animal models of psoriasis. (-)-Talarozole has a molecular weight of 377.51 and a molecular formula of C21H23N5S. The compound is for research purposes only. |
| Molecular Formula |
C21H23N5S
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| Molecular Weight |
377.50582242012
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| Exact Mass |
377.167
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| CAS # |
201410-67-5
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| Related CAS # |
Talarozole;201410-53-9;(+)-Talarozole;201410-66-4
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| PubChem CID |
9799888
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| Appearance |
White to off-white solid powder
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| LogP |
6
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
27
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| Complexity |
452
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C(N1N=CN=C1)(C1C=CC(NC2SC3C=CC=CC=3N=2)=CC=1)C(CC)CC
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| InChi Key |
SNFYYXUGUBUECJ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C21H23N5S/c1-3-15(4-2)20(26-14-22-13-23-26)16-9-11-17(12-10-16)24-21-25-18-7-5-6-8-19(18)27-21/h5-15,20H,3-4H2,1-2H3,(H,24,25)
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| Chemical Name |
N-[4-[2-ethyl-1-(1,2,4-triazol-1-yl)butyl]phenyl]-1,3-benzothiazol-2-amine
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ≥ 72.5 mg/mL (~192.05 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6489 mL | 13.2447 mL | 26.4894 mL | |
| 5 mM | 0.5298 mL | 2.6489 mL | 5.2979 mL | |
| 10 mM | 0.2649 mL | 1.3245 mL | 2.6489 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Link: https://clinicaltrials.gov/ct2/show/NCT00716144
Conditions:PsoriasisLink: https://clinicaltrials.gov/ct2/show/NCT00725348
Conditions:PsoriasisLink: https://clinicaltrials.gov/ct2/show/NCT00725439
Conditions:Acne
Title:Study on Anti-inflammatory Effects of Topical R115866 Gel
Status:Completed
updateDate:2011-09-26
Ctid:NCT00719121
Link: https://clinicaltrials.gov/ct2/show/NCT00719121
Conditions:Cutaneous InflammationProducts are for research use only; We do not sell to patients
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