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HomeProduct name list9-CIS-RETINOIC ACID

9-CIS-RETINOIC ACID

Synonym(s):9-cis-Tretinoin;Alitretinoin

  • CAS NO.:5300-03-8
  • Empirical Formula: C20H28O2
  • Molecular Weight: 300.44
  • MDL number: MFCD00270072
  • EINECS: 1533716-785-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 15:53:33
9-CIS-RETINOIC ACID Structural

What is 9-CIS-RETINOIC ACID?

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)

The Uses of 9-CIS-RETINOIC ACID

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.

The Uses of 9-CIS-RETINOIC ACID

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.

What are the applications of Application

9-cis-Retinoic acid is a Cox-2 inhibitor that prevents cell proliferation and induces cell differentiation.

Background

An important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth; and embryonic development. An excess of tretinoin can be teratogenic. It is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute).

Indications

For topical treatment of cutaneous lesions in patients with AIDS-related Kaposi's sarcoma.

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.

Pharmacokinetics

Alitretinoin (9-cis-retinoic acid) is a naturally-occurring endogenous retinoid indicated for topical treatment of cutaneous lesions in patients with AIDS-related Kaposi's sarcoma. Alitretinoin inhibits the growth of Kaposi's sarcoma (KS) cells in vitro.

Metabolism

Not Available

Properties of 9-CIS-RETINOIC ACID

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 (
form  Light yellow to orange crystalline powder.
pka 4.73±0.33(Predicted)
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 for 9-CIS-RETINOIC ACID

Signal word Danger
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
H360:Reproductive toxicity
Precautionary Statement Codes P201:Obtain special instructions before use.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P308+P313:IF exposed or concerned: Get medical advice/attention.

Computed Descriptors for 9-CIS-RETINOIC ACID

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