Acitretin (Ro 10-1670)

Alias: Etretin, U 0279;U-0279;U0279;RO 10-1670;Ro 10-1670; Ro-10-1670; Ro10-1670; Ro 10-1670/000; Acitretin; Soriatane; Neotigason
Cat No.:V2033 Purity: ≥98%
Acitretin (also known as Etretin, RO 10-1670; Soriatane; Etretin; Neotigason)is a novel, potent, orally bioavailable, second generation retinoid used for psoriasis.
Acitretin (Ro 10-1670) Chemical Structure CAS No.: 55079-83-9
Product category: RAR RXR
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
25mg
50mg
100mg
250mg
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5g
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Other Forms of Acitretin (Ro 10-1670):

  • Acitretin sodium (Ro 10-1670)
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Acitretin (also known as Etretin, RO 10-1670; Soriatane; Etretin; Neotigason) is a novel, potent, orally bioavailable, second generation retinoid used for psoriasis. Acitretin stimulates ADAM10 promoter activity with an EC50 of 1.5 mM and leads to an increase of mature ADAM10 protein that results in a two- to three-fold increase of the ratio between alpha- and beta-secretase activity in neuroblastoma cells. Acitretin (5-20 μM) impairs mitochondrial phosphorylation efficiency as demonstrated by the decrease in the state 3 respiration and ATP levels, and by the increase in the lag phase of ADP phosphorylation cycle, without affecting the membrane potential. Acitretin induces Ca(2+)-mediated mitochondrial permeability transition (MPT) and decreased the adenine nucleotide translocase (ANT) content.

Biological Activity I Assay Protocols (From Reference)
ln Vitro

In vitro activity: Acitretin stimulates ADAM10 promoter activity with an EC(50) of 1.5 mM and leads to an increase of mature ADAM10 protein that results in a two- to three-fold increase of the ratio between alpha- and beta-secretase activity in neuroblastoma cells. Acitretin (5-20 μM) impairs mitochondrial phosphorylation efficiency as demonstrated by the decrease in the state 3 respiration and ATP levels, and by the increase in the lag phase of ADP phosphorylation cycle, without affecting the membrane potential. Acitretin induces Ca(2+)-mediated mitochondrial permeability transition (MPT) and decreased the adenine nucleotide translocase (ANT) content. Acitretin preferentially inhibits the growth of SCL-1 cells in a dose- and time-dependent manner, but not of non-malignant keratinocyte HaCaT cells. Acitretin increases the levels of CD95 (Fas), CD95-ligand and Fas-associated death domain. Acitretin is able to induce apoptosis in skin cancer cells possibly via death receptor CD95 apoptosis pathway without affecting the viability of normal keratinocyte.


Kinase Assay: Acitretin(Ro 10-1670) is a second-generation, systemic retinoid that has been used in the treatment of psoriasis.


Cell Assay: Acitretin is a second-generation, systemic retinoid that has been approved for the treatment of psoriasis since 1997. It can be considered one of the treatments of choice for pustular and erythrodermic psoriasis. However, the efficacy of acitretin as a monotherapy for plaque psoriasis is less, although it is often used in combination therapy with other systemic psoriasis therapies, especially ultraviolet B or psoralen plus ultraviolet A phototherapy, to increase efficacy. Such combination treatments may potentially minimise toxicity by using lower doses of each of the two agent.

ln Vivo
In mice used as models for Alzheimer's disease, citiretin (10 mg/kg; intraperitoneal; ip for 7 days) raises IL-6 in the central nervous system[3].
Animal Protocol
0.75, 1.5 mg/kg/day; Acitretin was given within dimetil sulphoxide (DMSO), which was diluted with saline solution as a ratio of 1/10, in order to increase its solubility.
Thirty-nine male adult Wistar albino rats were divided into 3 groups as two experimental groups and one control group. The first group consisting 14 rats were applied orally standard dose (0.75 mg/kg/day) acitretin and the second group consisting 16 rats were applied high dose (1.5 mg/kg/day) acitretin. Acitretin was given within dimetil sulphoxide (DMSO), which was diluted with saline solution as a ratio of 1/10, in order to increase its solubility. The control group consisting 9 rats were given only saline solution including DMSO for 8 weeks. After 8 weeks of the administration, half of the rats in the first and second groups and the entire control group were sacrificed under deep ether anaesthesia and bilateral orchiectomy was made. The remainingrats were compared with the control group using a similar method at the end of 8 weeks of wash-off period. The orchiectomy materials were histopathologically evaluated under the light microscope for spermatogenesis according to parameters including spermatogenetic activity, spermatogenetic organization, seminiferous tubular diameter, interstitial Leydig cells and fibroblasts. In our study it was concluded that the standard and high doses of acitretin do not have any effect on the spermatogenesis of threats. Clinical indications: Psoriasis FDA Approved Date: Toxicity: nausea; headache; itching; red or flaky skin; dry or red eyes; dry mouth; depression; 0cystitis acne or hair loss.
References
[1]. Lee CS, et al. A review of acitretin, a systemic retinoid for the treatment of psoriasis. Expert Opin Pharmacother. 2005 Aug;6(10):1725-34.
[2]. Sengör B, et al. Effects of acitretin on spermatogenesis of rats. J Eur Acad Dermatol Venereol. 2006 Jul;20(6):689-92.
[3]. Guilherme MDS, et, al. The Synthetic Retinoid Acitretin Increases IL-6 in the Central Nervous System of Alzheimer Disease Model Mice and Human Patients. Front Aging Neurosci. 2019 Jul 23;11:182.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H26O3
Molecular Weight
326.43
CAS #
55079-83-9
Related CAS #
Acitretin sodium;925701-88-8
SMILES
O(C([H])([H])[H])C1C([H])=C(C([H])([H])[H])C(/C(/[H])=C(\[H])/C(=C(\[H])/C(/[H])=C(\[H])/C(=C(\[H])/C(=O)O[H])/C([H])([H])[H])/C([H])([H])[H])=C(C([H])([H])[H])C=1C([H])([H])[H]
InChi Key
IHUNBGSDBOWDMA-AQFIFDHZSA-N
InChi Code
InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+
Chemical Name
(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Synonyms
Etretin, U 0279;U-0279;U0279;RO 10-1670;Ro 10-1670; Ro-10-1670; Ro10-1670; Ro 10-1670/000; Acitretin; Soriatane; Neotigason
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO:20 mg/mL (61.3 mM)
Water:<1 mg/mL
Ethanol:<1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: 2 mg/mL (6.13 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2 mg/mL (6.13 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2 mg/mL (6.13 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.0634 mL 15.3172 mL 30.6344 mL
5 mM 0.6127 mL 3.0634 mL 6.1269 mL
10 mM 0.3063 mL 1.5317 mL 3.0634 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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