Home > Compound List > Compound details
118292-40-3 molecular structure
click picture or here to close

ethyl 6-[2-(4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylate

ChemBase ID: 678
Molecular Formular: C21H21NO2S
Molecular Mass: 351.46194
Monoisotopic Mass: 351.12929992
SMILES and InChIs

SMILES:
S1CCC(c2c1ccc(c2)C#Cc1ncc(cc1)C(=O)OCC)(C)C
Canonical SMILES:
CCOC(=O)c1ccc(nc1)C#Cc1ccc2c(c1)C(C)(C)CCS2
InChI:
InChI=1S/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
InChIKey:
OGQICQVSFDPSEI-UHFFFAOYSA-N

Cite this record

CBID:678 http://www.chembase.cn/molecule-678.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
ethyl 6-[2-(4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylate
IUPAC Traditional name
tazarotene
Brand Name
Tazarotene [USAN:INN]
Tazorac
Zorac
Synonyms
Tazorac
Avage
Zora
Tazarotene(Avage)
tazarotene
Tazarotene
Ethyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinate
6-[2-(3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-3-pyridinecarboxylic Acid Ethyl Ester
AGN 190168
Zorac
CAS Number
118292-40-3
PubChem SID
46508992
160964141
PubChem CID
5381

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 5.218718  LogD (pH = 7.4) 5.2187405 
Log P 5.2187405  Molar Refractivity 97.882 cm3
Polarizability 39.30108 Å3 Polar Surface Area 39.19 Å2
Rotatable Bonds Lipinski's Rule of Five false 
Log P 5.15  LOG S -5.67 
Solubility (Water) 7.50e-04 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Soluble expand Show data source
Apperance
Light Yellow Solid expand Show data source
Melting Point
103-105°C expand Show data source
Hydrophobicity(logP)
5.6 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Purity
95+% expand Show data source
97% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals TRC TRC
DrugBank - DB00799 external link
Item Information
Drug Groups approved; investigational
Description Tazarotene (marketed as Tazorac?, Avage? and Zorac?) is a prescription topical retinoid sold as a cream or gel. This medication is approved for treatment of psoriasis, acne, and sun damaged skin (photodamage). [Wikipedia]
Indication Used to treat psoriasis, acne and sun damaged skin (photodamage).
Pharmacology Tazarotene is a prodrug and a member of the acetylenic class of retinoids. Following topical application, tazarotene undergoes esterase hydrolysis to form its active metabolite, tazarotenic acid. When treating acne tazarotene may be taken in conjunction with an oral antibiotic. Tazarotene has been shown in peer-reviewed double blinded studies to reduce: mottling and hyperpigmentation, sallowness, fine wrinkling and coarse wrinkling in sun damaged skin. Histological studies have shown that long term (greater than 1 year) use of Tazarotene is associated with a significant reduction in atypical melanocytes and keratocytes - cells considered to be precursors of skin cancer. Some studies have shown long term use of Tazarotene to be associated with increased collagen production and better organization of skin collagen bundles.
Toxicity Excessive topical use may lead to marked redness, peeling, or discomfort. Oral ingestion of the drug may affect liver function causing hypertriglyceridemia. Other symptoms may include conjunctival irritation, hair loss, headache, edema, fatigue, dermatitis, nausea, and visual disturbances. Oral administration of this material to rats and rabbits at doses of 0.20 mg/kg/day (rabbits) and 0.25 mg/kg/day (rats) resulted in developmental toxicity. A no effect level of 0.05 mg/kg/day was established. Similar teratogenic effects have been reported for other retinoid compounds.
Affected Organisms
Humans and other mammals
Biotransformation Undergoes esterase hydrolysis in skin to form its active metabolite, tazarotenic acid. Tazarotenic acid is further metabolized in skin and, after systemic absorption, hepatically metabolized to sulfoxides, sulfones, and other polar products for elimination.
Absorption Minimal systemic absorption of tazarotene occurs due to its rapid metabolism in the skin to the active metabolite, tazarotenic acid, which can be systemically absorbed and further metabolized. Gender had no influence on the systemic bioavailability of tazarotenic acid.
Half Life The half-life of the active form of the drug, tazarotenic acid, is approximately 18 hours in normal and psoriatic patients.
Protein Binding The active form of the drug, tazarotenic acid, is highly bound to plasma proteins (>99%).
Elimination Tazarotene and tazarotenic acid were metabolized to sulfoxides, sulfones and other polar metabolites which were eliminated through urinary and fecal pathways.
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals - S1569 external link
Research Area: Inflammation
Biological Activity:
Tazarotene is a prescription topical retinoid sold as a cream or gel. This medication is approved for treatment of psoriasis, acne, and sun damaged skin (photodamage). It is commonly sold in two concentrations: 0.05% and 0.1%. In addition to tretinoin, which has been associated with greater skin improvements with high concentrations, tazarotene and isotretinoin creams are also found to be effective for photodamage, but at the expense of skin irritation. More evidence is needed before any recommendations can be made on oral or topical polysaccharides or hydroxy acids. [1][2]
Toronto Research Chemicals - T010050 external link
An acetylenic retinoid prodrug converted to the active metabolite, Tazarotenic acid, with selective affinity for retinoic acid receptors RARβ and RARγ. Antiacne; antipsoriatic. Used in treatment of photodamaged skin.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://en.wikipedia.org/wiki/Tazarotene
  • • Tang-Liu, D.D.-S., et al.: Clin. Pharmacokinet., 37, 273 (1999)
  • • Roeder, A., et al.: Skin Pharmacol. Physiol., 17, 111 (1999)
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle