Alitretinoin

Names

[ Name ]:
Alitretinoin

[Synonym ]:
9-cis-Tretinoin,Alitretinoin
(9cis)-Retinoic acid
Alitretinoin
(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
9-cis-retinoic acid
MFCD00270072
9Z-retinoic acid
9-cis-Tretinoin
9-cis Retinoic Acid
Panretin Gel
(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
Retinoic acid, (9cis)-
9(Z)-Retinoic acid

Biological Activity

[Description]:

9-cis-Retinoic acid (ALRT1057), a vitamin A derivative, is a potent RAR/RXR agonist. 9-cis-Retinoic acid induces apoptosis, regulates cell cycle and has anticancer, anti-inflammatory and neuroprotection activities[1][2][3][4][5].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

Research Areas >> Neurological Disease

Signaling Pathways >> Metabolic Enzyme/Protease >> RAR/RXR

[In Vitro]

9-cis-Retinoic acid (1-10 μM; 0-5 days; CA 9-22 and NA cells) treatment significantly decreases proliferation in a dose-dependent manner in CA 9-22 and NA cells[1]. 9-cis-Retinoic acid (1 μM; 24 hours) treatment significantly increases PPARγ functional activity by >200% in CA 9-22 and NA aerodigestive cells[1]. 9-cis-Retinoic acid treatment results in the formation of a nuclear PPARγ-RXRα heterodimer supershift complex in CA 9-22 cells[1]. 9-cis-Retinoic acid inhibits proliferation and induces apoptosis in cutaneous T-cell lymphoma (CTCL) in a dose-dependent and time-dependent manner. 9-cis-Retinoic acid also induces G0/G1 cell cycle arrest by downregulation of cyclin D1. 9-cis-Retinoic acid significantly decreases phosphorylation of JAK1, STAT3, and STAT5 and downregulated Bcl-xL and cyclin D1[2]. Cell Proliferation Assay[1] Cell Line: CA 9-22 and NA cells Concentration: 1 μM, 10 μM Incubation Time: 0 day, 1 day, 3 days, 5 days Result: Significantly decreased proliferation.

[In Vivo]

9-cis-Retinoic acid (1 mg/kg; intravenous injection; daily; for 10 days; male C57BL/6J mice) treatment significantly decreases the serum ALT and AST level, alleviates hepatic necrosis of the bile duct ligation (BDL)-mice[3]. Animal Model: Male C57BL/6J mice (6-8 weeks; 19-22 g) treatment with bile duct ligated[3] Dosage: 1 mg/kg Administration: Intravenous injection; daily; for 10 days Result: Significantly decreased the serum ALT and AST level, alleviated hepatic necrosis.

[References]

[1]. Raul Rosas, et al. Retinoids Augment Thiazolidinedione PPARγ Activation in Oral Cancer Cells. Anticancer Res. 2020 Jun;40(6):3071-3080.

[2]. Hua Yang, et al. Effects of 9-cis-retinoic Acid on the Proliferation and Apoptosis of Cutaneous T-cell Lymphoma Cells. Anticancer Drugs. 2019 Jan;30(1):56-64.

[3]. Zhiqing Yuan, et al. 9-cis-retinoic Acid Elevates MRP3 Expression by Inhibiting Sumoylation of RXRα to Alleviate Cholestatic Liver Injury. Biochem Biophys Res Commun. 2018 Sep 3;503(1):188-194.

[4]. V M Manzano, et al. Human Renal Mesangial Cells Are a Target for the Anti-Inflammatory Action of 9-cis Retinoic Acid. Br J Pharmacol. 2000 Dec;131(8):1673-83.

[5]. Gro H Mathisen, et al. Delayed Translocation of NGFI-B/RXR in Glutamate Stimulated Neurons Allows Late Protection by 9-cis Retinoic Acid. Biochem Biophys Res Commun. 2011 Oct 14;414(1):90-5.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
462.8±14.0 °C at 760 mmHg

[ Melting Point ]:
189-191ºC

[ Molecular Formula ]:
C₂₀H₂₈O₂

[ Molecular Weight ]:
300.435

[ Flash Point ]:
350.6±11.0 °C

[ Exact Mass ]:
300.208923

[ PSA ]:
37.30000

[ LogP ]:
6.83

[ Vapour Pressure ]:
0.0±2.5 mmHg at 25°C

[ Index of Refraction ]:
1.556

[ Storage condition ]:
−20°C

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

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H315-H319-H335-H360

[ Precautionary Statements ]:
P201-P261-P305 + P351 + P338-P308 + P313

[ Personal Protective Equipment ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R36/37/38;R61

[ Safety Phrases ]:
S26-S36/37/39-S45-S53

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2916209090

Customs

[ HS Code ]: 2916209090

[ Summary ]:
2916209090 other cyclanic, cyclenic or cyclotherpenic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0%

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Related Compounds

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