Chemical Property of Alitretinoin
Chemical Property:
- Appearance/Colour:Pale yellow solid
- Melting Point:189-191 °C
- Boiling Point:462.801 °C at 760 mmHg
- PKA:4.73±0.33(Predicted)
- Flash Point:350.596 °C
- PSA：37.30000
- Density:1.011 g/cm3
- LogP:5.60260
- Storage Temp.:−20°C
- Sensitive.:Moisture & Light Sensitive
- Solubility.:Acetonitrile (Very Slightly), Chloroform (Slightly), DMSO (Slightly), Ethanol (
- Water Solubility.:Soluble in chloroform (50 mg/ml), DMSO (~25 mg/ml), ethanol (25 mg/ml), and acetone (25 mg/ml). Insoluble in water.
- XLogP3:6.3
- Hydrogen Bond Donor Count:1
- Hydrogen Bond Acceptor Count:2
- Rotatable Bond Count:5
- Exact Mass:300.208930132
- Heavy Atom Count:22
- Complexity:567
- Purity/Quality:
-
98% *data from raw suppliers
9-cis Retinoic Acid *data from reagent suppliers
Safty Information:
- Pictogram(s):
T
- Hazard Codes:T
- Statements:
61-36/37/38
- Safety Statements:
53-26-36/37/39-45
- MSDS Files:
-
SDS file from LookChem
Useful:
- Canonical SMILES:CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C
- Isomeric SMILES:CC1=C(C(CCC1)(C)C)/C=C/C(=C\C=C\C(=C\C(=O)O)\C)/C
- Recent ClinicalTrials:Follow-up Efficacy and Safety of Alitretinoin in Severe Chronic Hand Dermatitis
- Recent EU Clinical Trials:A 24 week, randomised, assessor blinded, active-controlled, parallel group, phase 3, 2 arm trial to compare the efficacy and safety of delgocitinib cream 20 mg/g twice-daily with alitretinoin capsules once-daily in adult participants with severe chronic hand eczema
-
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.
-
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. 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.
-
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.
