| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| Other Sizes |
Purity: ≥98%
| Targets |
Tazarotene targets retinoic acid receptors (RARs), which are nuclear receptors that mediate the effects of retinoic acid on gene transcription. The active metabolite, tazarotenic acid, is a potent and selective agonist of RARs that binds to RARα, RARβ, and RARγ with EC50 values of 11, 2.5, and 11 nM, respectively. Tazarotenic acid relatively selectively activates RARβ and RARγ. By activating RARs, tazarotene modulates gene expression involved in cell differentiation, proliferation, and inflammation, which underlies its therapeutic effects in acne and psoriasis.
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| ln Vitro |
In vitro, tazarotenic acid (the active metabolite) is a potent and selective RAR agonist that binds to RARα, RARβ, and RARγ with EC50 values of 11, 2.5, and 11 nM, respectively. It induces reporter gene expression in DK7-NR cells expressing human RARs. Tazarotenic acid relatively selectively activates RARβ and RARγ. The conversion of tazarotene to tazarotenic acid has been studied in various skin models, confirming the prodrug activation mechanism. These in vitro studies establish the pharmacological profile of tazarotene's active metabolite.
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| ln Vivo |
Analyzing the tazarotenic acid (compound AGN 190299) pharmacokinetic (PK) profile in rats after intravenous dose of AGN 190168 [1]. Male Female Male Dose (mg kg-1) 4.4 4.4 0.49 AUC (μg h mL-1) 9.31 (2.14) 9.78 (1.36) 0.594 (0.95) CL (mL min-1 kg-1) 7.96 (1.59) 7.62 (0.85 ) 14.0 (2.2) k (h-1) 0.562 (0.339) 0.820 (0.146) 0.741 (0.115) T1/2 (h) 1.64 (0.92) 0.86 (0.14) 0.95 (0.15) V\ (L kg-1) - 1.14 (0.09) Vmax (μg min-1) 9.08 (2.89) 6.09 (1.22) - Km (μg mL-1) 7.09 (1.35 ) 5.12 (1.19) -
In vivo, tazarotene is a widely prescribed topical retinoid for acne vulgaris and plaque psoriasis. It is applied topically to the skin, where it is converted to its active metabolite, tazarotenic acid. The compound's efficacy in treating acne and psoriasis has been demonstrated in numerous clinical studies. Tazarotene is associated with skin irritation, dryness, flaking, and photosensitivity as common side effects. The compound is approved for topical use in the treatment of these dermatological conditions. |
| Enzyme Assay |
In vitro receptor binding assays for tazarotenic acid measure its affinity for RARα, RARβ, and RARγ. Membranes from cells expressing the respective RAR subtypes are incubated with a radiolabeled RAR ligand and varying concentrations of tazarotenic acid. The Ki values are determined from competition binding curves. Functional assays measure the activation of RAR-mediated transcription using reporter gene assays. Cells are transfected with a RAR response element (RARE)-luciferase reporter and treated with tazarotenic acid. The EC50 for transcriptional activation is determined for each RAR subtype.
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| Cell Assay |
In vitro cell-based assays for tazarotenic acid are conducted using keratinocytes or other skin cells to study its effects on cell differentiation and proliferation. Cells are treated with tazarotenic acid at various concentrations, and the expression of RAR target genes is measured by quantitative PCR. Cell proliferation is assessed using standard assays such as BrdU incorporation or MTT. The compound's effects on keratinocyte differentiation can be assessed by measuring the expression of differentiation markers such as involucrin and transglutaminase. These assays confirm the biological activity of tazarotenic acid in skin cells.
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| Animal Protocol |
In vivo animal experiments for tazarotene are conducted in animal models of skin diseases, such as the rhino mouse model for acne or the mouse tail model for psoriasis. Tazarotene is applied topically to the skin, and the effects on epidermal thickness, keratinocyte differentiation, and inflammation are assessed. These studies confirm the efficacy of tazarotene in treating skin disorders and provide insights into its mechanism of action. However, specific protocols for tazarotene are not detailed in standard product descriptions, as the compound is an approved drug.
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| ADME/Pharmacokinetics |
Tazarotene has a molecular weight of 383.51 g/mol and a molecular formula of C21H21NO2S. It is a solid compound. For research use, tazarotenic acid (the active metabolite) is supplied as a solid with a purity of ≥99%. It is soluble in DMSO at 20 mg/mL. For storage, it is recommended to keep the powder at -20°C. Tazarotene is a prodrug that is converted to tazarotenic acid in the skin. Pharmacokinetic properties of tazarotene and its active metabolite have been characterized in clinical studies. Tazarotene is applied topically and has minimal systemic absorption.
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| Toxicity/Toxicokinetics |
Detailed toxicity data for tazarotene is available from its clinical use. Common side effects include skin irritation, dryness, flaking, and photosensitivity. Tazarotene is contraindicated in pregnancy due to its teratogenic potential. As a topical retinoid, it should be used under medical supervision. For research use of tazarotenic acid, standard laboratory safety precautions should be followed when handling the compound.
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| References |
[1]. Chandraratna RA. Tazarotene--first of a new generation of receptor-selective retinoids. Br J Dermatol. 1996;135 Suppl 49:18-25.
[2]. Hsyu PH, et al. Pharmacokinetics of a novel retinoid AGN 190168 and its metabolite AGN 190299 after intravenous administration of AGN 190168 to rats. Biopharm Drug Dispos. 1994;15(5):347-357. [3]. Abramovits W, et al. Treatment of warty dyskeratoma with tazarotenic acid. J Am Acad Dermatol. 2002;46(2 Suppl Case Reports):S4. |
| Additional Infomation |
Tazarotenic acid is a thiochromic acid compound with an acetylene structure, wherein the hydrogen atoms are replaced by 5-carboxypyridin-2-yl and 4,4-dimethylthiochromic-6-yl. It is the active form of the prodrug tazarotenic acid. It has keratolytic and teratogenic effects. It is a monocarboxylic acid, a thiochromic acid compound, a retinol-like compound, and also a pyridine compound.
Tazarotene (AGN-190299) is an approved drug for the topical treatment of acne vulgaris and plaque psoriasis. It is a retinoid prodrug that is metabolized to its active form, tazarotenic acid, a potent and selective agonist of retinoic acid receptors (RARs). Tazarotenic acid binds to RARα, RARβ, and RARγ with EC50 values of 11, 2.5, and 11 nM, respectively. The compound is associated with skin irritation as a common side effect. Tazarotene is also used as a research compound to study retinoid receptor signaling and skin biology. |
| Exact Mass |
323.097
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|---|---|
| CAS # |
118292-41-4
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| Related CAS # |
Tazarotenic acid-d6;1794760-38-5
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| PubChem CID |
147525
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| Appearance |
Light yellow to light brown solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
527.5±50.0 °C at 760 mmHg
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| Flash Point |
272.9±30.1 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.671
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| LogP |
4.95
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
23
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| Complexity |
518
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
IQIBKLWBVJPOQO-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C19H17NO2S/c1-19(2)9-10-23-17-8-4-13(11-16(17)19)3-6-15-7-5-14(12-20-15)18(21)22/h4-5,7-8,11-12H,9-10H2,1-2H3,(H,21,22)
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| Chemical Name |
6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinic acid
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| Synonyms |
AGN 190299 AGN-190299 AGN190299 Tazarotenic acid.
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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 : ~100 mg/mL (~309.21 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.) |
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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT02411955 | COMPLETED | Drug: Tazarotene Cream 0.1% Drug: Tazorac® Drug: Placebo |
Acne Vulgaris | Taro Pharmaceuticals USA | 2014-06 | Phase 1 |
| NCT02886702 | COMPLETEDWITH RESULTS | Drug: Tazarotene Cream 0.05% Drug: TAZORAC® (tazarotene) Cream 0.05% Drug: Placebo |
Plaque Psoriasis | Fougera Pharmaceuticals Inc. | 2016-09-19 | Phase 3 |
| NCT02886715 | COMPLETEDWITH RESULTS | Drug: Tazarotene Cream 0.1% Drug: Tazorac® Drug: Placebo |
Acne Vulgaris | Fougera Pharmaceuticals Inc. | 2016-09-21 | Phase 3 |
| NCT00648986 | COMPLETED | Drug: Tazorac | Brittle Nails | Columbia University | 2005-08 | Phase 4 |
| NCT02218034 | COMPLETED | Drug: AGN-190168 Formulation 1 Drug: AGN-190168 Formulation 2 Drug: tazarotene gel 0.1% Drug: tazarotene cream 0.1% |
Acne Vulgaris | Allergan | 2014-08 | Phase 1 |
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