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118292-40-3

Tazarotene

CAS: 118292-40-3

Molecular Formula: C21H21NO2S

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118292-40-3 - Names and Identifiers

Name Tazarotene
Synonyms Zorac
Avage
Tazorac
agn190168
TAZAROTENE
Tazarotene
AGN 190168
UNII-81BDR9Y8PS
Ethyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinate
ethyl 6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl]pyridine-3-carboxylate
3-pyridinecarboxylicacid,6-((3,4-dihydro-4,4-dimethyl-2h-1-benzothiopyran-6-y
6-[(3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran)-6-yl]nicotinic acid ethyl ester
ethyl 6-[(4,4-dimethyl-3,4-dihydro-2H-thiochromen-6-yl)ethynyl]pyridine-3-carboxylate
3-Pyridinecarboxylic acid, 6-((3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl)-, ethyl ester
6-[2-(3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]- 3-pyridinecarboxylic Acid Ethyl Ester
CAS 118292-40-3
EINECS 601-516-4
InChI InChI=1/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3

118292-40-3 - Physico-chemical Properties

Molecular FormulaC21H21NO2S
Molar Mass351.46
Density1.22±0.1 g/cm3(Predicted)
Melting Point95-98°C
Boling Point499.8±45.0 °C(Predicted)
Flash Point256.1°C
Solubility DMSO: >15mg/mL
Vapor Presure4.03E-10mmHg at 25°C
Appearancepowder
Colorwhite to very faintly yellow
Merck14,9081
pKa0.04±0.29(Predicted)
Storage Condition2-8°C
Refractive Index1.624
Physical and Chemical PropertiesOff-white or light-yellow solid
In vitro studyIn HL-60 human myeloid leukemia cells, Tazarotene causes ERK activation, RB tumor suppressor protein phosphorylation, G0 arrest, and myeloid differentiation. Tazarotene is able to push the early or late part of the period leading to differentiation or G0 arrest and is interchangeable with RARalpha-selective ligands. Tazarotene modulates three important pathogenic factors in psoriasis by interacting with specific nuclear retinoic acid receptors (RARs) to therapeutically regulate gene transcription. Tazarotene inhibits fibroblast proliferation and synthesis of DNA and collagen. Tazarotene down-regulates keratinocyte differentiation, keratinocyte proliferation, and markers of inflammation. Tazarotene also upregulates three novel genes, TIG-1 (tazarotene-induced gene -1),TIG-2, and TIG-3, which may mediate antiproliferative effects. In retinoid-responsive breast cancer cell lines, Tazarotene causes growth inhibition by upregulating tig3.
In vivo studyIn UV-and ionizing radiation-treated Ptch1 /− mice, Tazarotene treatment reduced the number and size of onlookers basal cell carcinomas (BCCs).

118292-40-3 - Risk and Safety

WGK Germany3
RTECSUS5675100

118292-40-3 - Standard

Authoritative Data Verified Data

This product is 6 - [( 3, 4-dihydro-4, 4-dimethyl-2-1-benzothian-6-yl) ethynyl]-3-pyridinecarboxylic acid ethyl ester. The content of C21H21NO2S shall be 98.5% to 101.5% calculated as the dried product.

Last Update:2024-01-02 23:10:35

118292-40-3 - Trait

Authoritative Data Verified Data
  • This product is white to light yellow crystal or crystalline powder; Odorless.
  • This product is soluble in benzyl alcohol, soluble in ethyl acetate, slightly soluble in acetonitrile, slightly soluble in ethanol, almost insoluble in water.

melting point

The melting point of this product (General 0612) is 102~105°C.

Last Update:2022-01-01 11:39:13

118292-40-3 - Preparation solution concentration reference

 1mg5mg10mg
1 mM2.845 ml14.226 ml28.453 ml
5 mM0.569 ml2.845 ml5.691 ml
10 mM0.285 ml1.423 ml2.845 ml
5 mM0.057 ml0.285 ml0.569 ml
Last Update:2024-01-02 23:10:35

118292-40-3 - Differential diagnosis

Authoritative Data Verified Data
  1. take about 5mg of this product, add 2 drops of sulfuric acid, that is red; Add 2ml of water, red disappeared.
  2. in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
  3. This product is dissolved in methanol and diluted to make a solution containing about 4ug per lml, and then determined by UV-Vis spectrophotometry (General 0401), there is maximum absorption at a wavelength of 259nm and 351nm; The solution shows yellow-green fluorescence when viewed under a UV lamp (365mn).
  4. take the product and tazarotene control, respectively, plus ethyl acetate dissolved and diluted to make each 1 mL solution containing about 1 mg. According to the thin layer chromatography (General 0502) test, absorb the above two solutions of 10 u1, respectively, on the same silica gel GF254 thin layer plate, with methanol as the developing agent, expand, take out, dry, view under UV light (365nm). The position and color of the main spot displayed by the test solution should be the same as that of the reference solution.
  5. The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 1116).
  6. two items (2) and (4) above can be selected as one item.
Last Update:2022-01-01 11:39:13

118292-40-3 - Exam

Authoritative Data Verified Data

Related substances

take this product, add acetonitrile to dissolve and dilute to make a solution containing about 80ug per lml as a test solution; Take lml from precision children and put it in a 100m l measuring flask, as a control solution, it was diluted to the scale with acetonitrile and shaken. According to the chromatographic conditions under the content determination item, 20 u1 of the test solution and the control solution are respectively injected into the liquid chromatograph, and the chromatogram is recorded to 2 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the sum of each impurity peak area shall not be greater than 1.5 times (1.5%) of the main peak area of the control solution.


loss on drying

take this product, at 60°C under reduced pressure drying to constant weight, weight loss should not exceed 1.0% (General rule 0831).


ignition residue

take l.Og of this product and check it according to law (General rule 0841). The residue left shall not exceed 0.1%.


Heavy metals

The residue left under the item of taking the ignition residue shall not contain more than 20 parts per million of heavy metal when examined by law (General rule 0821, Law II).

Last Update:2022-01-01 11:39:14

118292-40-3 - Content determination

Authoritative Data Verified Data

measured by high performance liquid chromatography (General 0512).


chromatographic conditions and system suitability test

silica gel bonded with eighteen alkyl silane was used as a filler; Isopropanol-acetonitrile-water (38:27:35) was used as a mobile phase; The detection wavelength was 325nm. The number of theoretical plates shall not be less than 5000 calculated by tazarotene peak, and the separation degree between tazarotene peak and adjacent impurity peaks shall meet the requirements.


assay

take about 16mg of this product, accurately weigh, put it in a 100ml measuring flask, add acetonitrile to dissolve and dilute to the scale, shake well, take 5ml accurately, put it in a 50ml measuring flask, dilute with acetonitrile to scale, shake, as a test solution, accurately take 20u1 injection liquid chromatography, record chromatogram; Tazarotene control, the same method. According to the external standard method to calculate the peak area, that is.

Last Update:2022-01-01 11:39:15

118292-40-3 - Category

Authoritative Data Verified Data

antikeratotic agents.

Last Update:2022-01-01 11:39:15

118292-40-3 - Storage

Authoritative Data Verified Data

sealed and stored in a cool and dry place.

Last Update:2022-01-01 11:39:15

118292-40-3 - Tazarotene gel

Authoritative Data Verified Data

This product contains tazarotene (C21H21N02S) should be 90.0% to 110.0% of the label.


trait

This product is colorless to light yellow gel.


identification

  1. take an appropriate amount of this product (about 0.2mg of tazarotene), add 50ml of methanol, shake, dissolve tazarotene, centrifuge, and take the supernatant, as determined by UV-Vis spectrophotometry (General rule 0401), there is a maximum absorption at a wavelength of 351nm, and the solution shows bright yellow-green fluorescence when viewed under a UV lamp (365nm).
  2. in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.

examination

  • pH value: take 2.0g of this product, add 30ml of water to dissolve it, and measure it according to law (General rule 0631). The pH value should be 6.0~8.3.
  • others shall comply with the relevant provisions under the item of gel (General rule 0114).

Content determination

take an appropriate amount of this product (about 0.8mg equivalent to tazarotene), weigh it accurately, put it in a 50ml measuring flask, add an appropriate amount of acetonitrile, and fully shake to dissolve tazarotene, dilute with acetonitrile to the scale, shake, centrifuge, take the supernatant as the test solution, take 20 u1 with precision, and measure according to the method under the content determination item of tazarotene.


category

Same as tazarotene.


specification

(l )15g:7.5mg (2)30g:15mg (3)30g:30mg


storage

sealed and stored in a cool place.

Last Update:2022-01-01 11:39:16
118292-40-3
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Shanghai Macklin Biochemical Co., Ltd
Featured ProductsSpot supply
Product Name: Tazarotene Visit Supplier Webpage Request for quotation
CAS: 118292-40-3
Tel: +86-18821248368
Email: Int06@meryer.com
Mobile: +86-18821248368
QQ: 495145328 Click to send a QQ message
WhatsApp: +86-18821248368
Shanghai Amole Biotechnology Co., Ltd.
Multiple SpecificationsSpot supply
Product Name: Tazarotene Request for quotation
CAS: 118292-40-3
Tel: 400-968-2212
Email: 3623107365@qq.com
Mobile: 18916960931
QQ: 3623107365 Click to send a QQ message
Wechat: 18916960931
SHANGHAI ACMEC BIOCHEMICAL TECHNOLOGY CO., LTD.
Spot supply
Product Name: Tazarotene Visit Supplier Webpage Request for quotation
CAS: 118292-40-3
Tel: +86-400-900-4166
Email: product@acmec-e.com
Mobile: +86-18621343501
QQ: 2881950922 Click to send a QQ message
Wechat: 18621343501
WhatsApp: +86-18621343501
MedChemExpress (MCE)
Multiple SpecificationsSpot supply
Product Name: AGN 190168 Visit Supplier Webpage Request for quotation
CAS: 118292-40-3
Tel: 609-228-6898
Email: sales@medchemexpress.com
     tech@medchemexpress.com
Mobile: 609-228-6898
SKYRUN INDUSTRIAL CO.,LTD
Spot supply
Product Name: Tazarotene Visit Supplier Webpage Request for quotation
CAS: 118292-40-3
Tel: +86 0571-86722205
Email: sales@chinaskyrun.com
Mobile: +8618958170122
QQ: 2531159185 Click to send a QQ messageSend QQ message
Wechat: chinaskyrun
Shanghai Yuanye Bio-Technology Co., Ltd.
Spot supply
Product Name: Tazarotene Visit Supplier Webpage Request for quotation
CAS: 118292-40-3
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409 Click to send a QQ message
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118292-40-3
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