13-cis-Retinoic acid (CAS 4759-48-2)

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Alternativa namn: Isotretinoin; Accutane; Amnesteem; Claravis

Ansökan 13-cis-Retinoic acid is a vitamin A analog that inhibits cell proliferation

CAS Nr: 4759-48-2

Renhet: ≥98%

Molekylvikt: 300.44

Molekylär formel: C₂₀H₂₈O₂

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

* Refer to Certificate of Analysis for lot specific data (including water content).

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13-cis-Retinoic acid is a vitamin A analog that inhibits cell proliferation and induces cell differentiation. Clinically, 13-cis-Retinoic acid is primarily used in the treatment of severe recalcitrant nodular acne. Its effects include reducing the production of sebum, shrinking the size of the sebaceous glands, stabilizing keratinization, preventing comedones from forming, and reducing inflammation of inflammatory acne. Though the exact mechanism of action of 13-cis-Retinoic acid is not fully understood, studies have suggested that the compound alters DNA transcription and induces apoptosis in select types of cells throughout the body.

Konferenser

1. Samokyszyn, V.M., et al. 1987. J. Biol. Chem. 262: 14119-14133. PMID: 3115987
2. Samokyszyn, V.M., et al. 1997. Chem. Res. Toxicol. 10: 795-801. PMID: 9250414
3. Chang, H.C., et al. 2000. Kaohsiung J. Med. Sci. 16: 387-392. PMID: 11221542

Appearance :

Powder

Physical State :

Solid

Solubility :

Soluble in chloroform (50 mg/ml), DMSO (60 mg/ml at 25° C), water (<1 mg/ml at 25° C), ethanol (25 mg/ml), and ether (sparingly).

LAGRING :

Store at -20° C

Melting Point :

172-175° C (lit.)

Boiling Point :

~462.80° C at 760 mmHg (Predicted)

Density :

1.01 g/cm³ (Predicted)

Refractive Index :

n²⁰_D 1.56 (Predicted)

IC50 :

ERK 2: IC₅₀ = 0.46 µM (human); SR-2B: IC₅₀ = 0.85 µM (human); Cellular retinoic acid-binding protein I: IC₅₀ = 0.9 µM (red junglefowl); Retinoic acid receptor α: IC₅₀ >1 µM (mouse); Retinoic acid receptor γ: IC₅₀ >1 µM (mouse)

Ki Data :

SR-2B: K_i= 0.54 µM (human); Adenosine A3-R: K_i= 2.36 µM (human); α2B-AR: K_i= 3.02 µM (human); Dictyostelium discoideum AX2 RNase P: K_i= 20 µM

pK Values :

pK_a: 4.76 (Predicted)

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

WGK Germany :

RTECS :

VH6440000

PubChem CID :

5282379

Merck Index :

14: 5228

MDL Number :

MFCD00079542

EC Number :

225-296-0

Beilstein Registry :

1885770

SMILES :

CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C\\C(=O)O)/C)/C

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Certificate of Analysis

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13-cis-Retinoic acid (CAS 4759-48-2) Produkt Citat

See how others have used 13-cis-Retinoic acid (CAS 4759-48-2). Click on the entry to view the PubMed entry .

Citations 1 to 7 of 7 total

PMID: # 10955779 Dahl, AR. et al. 2000. Clin. Cancer Res. 6: 3015-3024.

PMID: # 10550153 Ayoub, J. et al. 1999. J. Clin. Oncol. 17: 3546-3552.

PMID: # 1734084 Lippman, SM. et al. 1992. J. Natl. Cancer Inst. 84: 235-241.

PMID: # 2764704 Klug, S. et al. 1989. Arch. Toxicol. 63: 185-192.

PMID: # 3278754 Koeffler, HP. et al. 1988. Blood. 71: 703-708.

PMID: # 6219631 Leyden, JJ. et al. 1982. Arch. Dermatol. Res. 272: 331-337.

PMID: # 6930601 Shklar, G. et al. 1980. Oral Surg. Oral Med. Oral Pathol. 50: 45-52.

Citations 1 to 7 of 7 total

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