9-CIS-RETINOIC ACID Chemical Properties

Melting point:

189-191°C

Boiling point:

462.8±14.0 °C(Predicted)

Density 

1.011±0.06 g/cm3(Predicted)

RTECS 

VH6450000

storage temp. 

-20°C

solubility 

Acetonitrile (Very Slightly), Chloroform (Slightly), DMSO (Slightly), Ethanol (

pka

4.73±0.33(Predicted)

form 

Light yellow to orange crystalline powder.

color 

Pale Yellow to Yellow

Water Solubility 

Soluble in chloroform (50 mg/ml), DMSO (~25 mg/ml), ethanol (25 mg/ml), and acetone (25 mg/ml). Insoluble in water.

Sensitive 

Moisture & Light Sensitive

Stability:

Store Dry in Freezer at -20°C for up to 1 year; in Solution at -20°C for up to 3 Months.

CAS DataBase Reference

5300-03-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

61-36/37/38

Safety Statements 

53-26-36/37/39-45

WGK Germany 

3

HS Code 

29162090

Hazardous Substances Data

5300-03-8(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich

9-CIS-RETINOIC ACID Usage And Synthesis

Description

Alitretinoin was introduced in the US for the topical treatment of cutaneous lesions in patients with Kaposi's sarcoma (KS), the most frequent malignancy observed in AIDS patients. It is a derivative of 9-cis-retinoic acid (9- cis-RA) identified as an endogenous hormone in mammalian tissues. Alitretinoin binds to all isoforms of the intracellular retinoid X (RXR) and retinoid A (RAR) receptors thus inducing cell differentiation, increasing cell apoptosis and inhibiting cellular proliferation in experimental models of human cancer. In an international phase III trial in patients with KS, 42% of 82 patients treated with 0.1% gel formulation experienced complete or partial responses cf 7% for controls. Alitretinoin is the first topical therapy for KS and is expected to be a new option to its traditional management.

Chemical Properties

Pale Yellow Solid

Originator

Ligand (US)

Uses

9-cis-Retinoic acid is a vitamin A analog that inhibits cell proliferation and induces cell differentiation. 9-cis-Retinoic acid is an inhibitor of Cox-2 and an activator of RAR α, RAR β, RAR γ and RXR.

Uses

An endogenous retinoic acid isomer, which is capable of binding to both retinoic acid receptors (RAR) and retinoid X receptors (RXR). A biologically active ligand for members of the RAR and RXR subfamilies, implying that it may play a critical role in regulating retinoid-responsive pathways.

Definition

ChEBI: A retinoic acid in which the exocyclic double bonds have 7E,9Z,11E,13E geometry.

Indications

Alitretinoin (Panretin) is a naturally occurring endogenous retinoid that binds to and activates all known retinoid receptors (both RARs and RXRs). It is approved for the topical treatment of cutaneous lesions of Kaposi’s sarcoma. Most patients have local irritation while using alitretinoin gel; however, the irritation rarely necessitates discontinuation of therapy.

brand name

Panretin (Ligand).

Biochem/physiol Actions

Ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR) that act as transcription factors to regulate the growth and differentiation of normal and malignant cells.

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