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118292-40-3 872333-04-5
1246815-76-8 864841-56-5

118292-40-3

118292-40-3 structure
118292-40-3 structure
  • Name: Tazarotene
  • Chemical Name: tazarotene
  • CAS Number: 118292-40-3
  • Molecular Formula: C21H21NO2S
  • Molecular Weight: 351.462
  • Catalog: API Special medicine Dermatology medication
  • Create Date: 2018-05-09 08:00:00
  • Modify Date: 2024-01-02 16:52:36
  • Tazarotene is a selective retinoic acid receptor (RAR) agonist for the treatment of plaque psoriasis and acne vulgaris.
Name tazarotene
Synonyms 3-pyridinecarboxylic acid, 6-[(3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-, ethyl ester
Avage
Ethyl 6-[(4,4-dimethyl-3,4-dihydro-2H-thiochromen-6-yl)ethynyl]nicotinate
ethyl 6-[2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)ethynyl]pyridine-3-carboxylate
6-[(4,4-diméthyl-3,4-dihydro-2H-thiochromén-6-yl)éthynyl]pyridine-3-carboxylate d'éthyle
6-[(3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-3-pyridinecarboxylic acid ethyl ester
Ethyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinate
Ethyl 6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl] nicotinate
Tazorac
3-Pyridinecarboxylic acid, 6-[2-(3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-, ethyl ester
Tazarotene
Zorac
Ethyl-6-[(4,4-dimethyl-3,4-dihydro-2H-thiochromen-6-yl)ethinyl]pyridin-3-carboxylat
ethyl 6-[(4,4-dimethyl-3,4-dihydro-2H-thiochromen-6-yl)ethynyl]pyridine-3-carboxylate
MFCD00867628
Description Tazarotene is a selective retinoic acid receptor (RAR) agonist for the treatment of plaque psoriasis and acne vulgaris.
Related Catalog
In Vitro Tazarotene, in both gel and cream formulations, has been used both as monotherapy and as an adjuvant therapy. For psoriasis it has been combined with steroids, calcipotriene and phototherapy, and for acne, with antibiotics. Tazarotene has been shown to upregulate the tumor suppressor, tazarotene induced gene 3, which is overexpressed in psoriasis and skin cancer[1]. In human epidermal cell cultures, tazarotene suppresses the gene expression of 2 marker proteins, MRP-8 (calgranulin A) and SKALP (skin derived anti-leukoproteinase), highly elevated in psoriatic epidermis[2].
In Vivo Topical gel application provides direct delivery of tazarotene into the skin. At 10 hours after a topical application of 0.1% tazarotene gel to the skin of healthy individuals and patients with psoriasis, approximately 4 to 6% of the dose resides in the stratum corneum and 2% of the dose distributed to the viable epidermis and dermis. Tazarotene is designed to undergo rapid and complete metabolism to its active metabolite tazarotenic acid. Tazarotenic acid has a short systemic residence time and limited tissue distribution in animals[3].When topically applied, tazarotene blocks the induction of ornithine decarboxylase (ODC) activity by the tumour promoter 12-O-tetradecanoylphorbol 13-acetate (TPA) in the epidermis of the hairless mouse[3].
References

[1]. Talpur R, et al. Efficacy and safety of topical tazarotene: a review. Expert Opin Drug Metab Toxicol. 2009 Feb;5(2):195-210.

[2]. Nagpal S, et al. Negative regulation of two hyperproliferative keratinocyte differentiation markers by a retinoic acidreceptor-specific retinoid: insight into the mechanism of retinoid action in psoriasis. Cell Growth Differ. 1996 Dec;7(12):1783-91.

[3]. Tang-Liu DD, et al. Clinical pharmacokinetics and drug metabolism of tazarotene: a novel topical treatment for acne and psoriasis. Clin Pharmacokinet. 1999 Oct;37(4):273-87.
Density 1.2±0.1 g/cm3
Boiling Point 499.8±45.0 °C at 760 mmHg
Melting Point 97-98ºC
Molecular Formula C21H21NO2S
Molecular Weight 351.462
Flash Point 256.1±28.7 °C
Exact Mass 351.129303
PSA 64.49000
LogP 6.22
Vapour Pressure 0.0±1.3 mmHg at 25°C
Index of Refraction 1.625
Storage condition Store at +4°C
Tazarotene
SAFETY DATA SHEET
Section1. IDENTIFICATION
Product name:Tazarotene
5.3
Section2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDSNot classified
HEALTH HAZARDS
Skin corrosion/irritationCategory 3
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
None
Pictograms or hazard symbols
Signal wordWarning
Causes mild skin irritation
Hazard statements
Precautionary statements:
If skin irritation occurs: Get medical advice/attention.
[Response]
Section3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture:Substance
Components:Tazarotene
Percent:>98.0%(GC)
CAS Number:118292-40-3
C21H21NO2S
Chemical Formula:
Section4. FIRST AID MEASURES
Inhalation:Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact:Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact:Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion:Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.
Section5. FIRE-FIGHTING MEASURES
Suitable extinguishingDry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical:generate poisonous fume.
Tazarotene
Section5. FIRE-FIGHTING MEASURES
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protectiveWhen extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:
Section6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.
Section7. HANDLING AND STORAGE
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions:Keep container tightly closed. Store in a refrigerator.
Store away from incompatible materials such as oxidizing agents.
Heat-sensitive
Packaging material:Comply with laws.
Section8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls:Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection:Protective gloves.
Eye protection:Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.
Section9. PHYSICAL AND CHEMICAL PROPERTIES
Solid
Physical state (20°C):
Form:Crystal- Powder
Colour:Very pale yellow - Yellow
No data available
Odour:
pH: No data available
Melting point/freezing point:105°C
Boiling point/range:No data available
No data available
Flash point:
Flammability or explosive
limits:
Lower:No data available
No data available
Upper:
Relative density:No data available
Solubility(ies):
[Water]No data available
No data available
[Other solvents]
Log Pow:5.25
Tazarotene
Section10. STABILITY AND REACTIVITY
Chemical stability:Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Sulfur oxides
products:
Section11. TOXICOLOGICAL INFORMATION
Acute Toxicity:orl-rat LD:>2 g/kg
Skin corrosion/irritation: skn-hmn 0.1%/12W-I open
Serious eyeNo data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC =No data available
No data available
NTP =
Reproductive toxicity:No data available
US5675100
RTECS Number:
Section12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish:No data available
Crustacea:No data available
Algae:No data available
Persistence / degradability: No data available
BioaccumulativeNo data available
potential(BCF):
Mobility in soil
Log Pow:5.25
Soil adsorption (Koc):No data available
Henry's LawNo data available
constant(PaM3/mol):
Section13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.
Section14. TRANSPORT INFORMATION
Hazards Class:Does not correspond to the classification standard of the United Nations
UN-No:Not listed
Section15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.
Tazarotene

SECTION 16 - ADDITIONAL INFORMATION
N/A

CHEMICAL IDENTIFICATION

RTECS NUMBER :
US5675100
CHEMICAL NAME :
3-Pyridinecarboxylic acid, 6-((3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl )ethynyl)-, ethyl ester
CAS REGISTRY NUMBER :
118292-40-3
LAST UPDATED :
199801
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C21-H21-N-O2-S

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JAADDB Journal of the American Academy of Dermatology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63141) 1979- Volume(issue)/page/year: 37(Suppl),S25,1997 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
22750 ug/kg/13W-I
TOXIC EFFECTS :
Musculoskeletal - other changes
REFERENCE :
JAADDB Journal of the American Academy of Dermatology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63141) 1979- Volume(issue)/page/year: 37(Suppl),S25,1997
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
35 mg/kg/26W-I
TOXIC EFFECTS :
Musculoskeletal - other changes
REFERENCE :
JAADDB Journal of the American Academy of Dermatology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63141) 1979- Volume(issue)/page/year: 37(Suppl),S25,1997
RIDADR NONH for all modes of transport
HS Code 2942000000
118292-06-1 structure

118292-06-1
49608-01-7 structure

49608-01-7

~61%

118292-40-3 structure

118292-40-3
Literature: INDOCO REMEDIES LIMITED Patent: WO2009/116075 A2, 2009 ; Location in patent: Page/Page column 12 ;
118292-06-1 structure

118292-06-1

~%

118292-40-3 structure

118292-40-3
Literature: WO2006/59345 A2, ; Page/Page column 20-21 ;
64-17-5 structure

64-17-5
118292-41-4 structure

118292-41-4

~%

118292-40-3 structure

118292-40-3
Literature: US2007/238881 A1, ; Page/Page column 6 ;
78-39-7 structure

78-39-7
118292-41-4 structure

118292-41-4

~%

118292-40-3 structure

118292-40-3
Literature: US2007/238881 A1, ; Page/Page column 7 ;
952294-18-7 structure

952294-18-7
78-39-7 structure

78-39-7

~%

118292-40-3 structure

118292-40-3
Literature: US2007/238881 A1, ; Page/Page column 7 ;
112110-44-8 structure

112110-44-8

~%

118292-40-3 structure

118292-40-3
Literature: Organic Process Research and Development, , vol. 9, # 5 p. 646 - 650
864841-54-3 structure

864841-54-3

~%

118292-40-3 structure

118292-40-3
Literature: Organic Process Research and Development, , vol. 9, # 5 p. 646 - 650
864841-55-4 structure

864841-55-4

~%

118292-40-3 structure

118292-40-3
Literature: Organic Process Research and Development, , vol. 9, # 5 p. 646 - 650
HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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