Apremilast

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WARNING: This product is for research use only, not for human or veterinary use.

Description:Apremilast, also known as CC-10004, is a thalidomide analog and is an orally available small molecule inhibitor of phosphodiesterase 4 (PDE4). Apremilast specifically inhibits PDE4 and inhibits spontaneous production of TNF-alpha from human rheumatoid synovial cells. It has anti-inflammatory activity. Apremilast was approved by the USFDA in March 2014 for treatment of adults with active psoriatic arthritis. It is also being tested for its efficacy in treating other chronic inflammatory diseases such as ankylosing spondylitis, Behcet's disease, and rheumatoid arthritis.

Price and Availability

Apremilast, purity > 98%, is in stock. The same day shipping out after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 205894Name: ApremilastCAS#: 608141-41-9Chemical Formula: C22H24N2O7SExact Mass: 460.13042Molecular Weight: 460.5Elemental Analysis: C, 57.38; H, 5.25; N, 6.08; O, 24.32; S, 6.96

Synonym:CC10004; CC-10004; CC 10004; Apremilast; brand name: Otezla.

IUPAC/Chemical Name:(S)-N-(2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide

InChi Key:IMOZEMNVLZVGJZ-QGZVFWFLSA-N

InChi Code:InChI=1S/C22H24N2O7S/c1-5-31-19-11-14(9-10-18(19)30-3)17(12-32(4,28)29)24-21(26)15-7-6-8-16(23-13(2)25)20(15)22(24)27/h6-11,17H,5,12H2,1-4H3,(H,23,25)/t17-/m1/s1

SMILES Code:CC(NC1=CC=CC(C(N2[C@@H](C3=CC=C(OC)C(OCC)=C3)CS(=O)(C)=O)=O)=C1C2=O)=O

Technical Data

References

1: Thompson BJ, Furniss M, Zhao W, Chakraborty B,Mackay-Wiggan J. An Oral Phosphodiesterase Inhibitor (Apremilast) forInflammatory Rosacea in Adults: A Pilot Study. JAMA Dermatol. 2014 Jul23. doi: 10.1001/jamadermatol.2013.10526. [Epub ahead of print] PubMedPMID: 25054629.

2: Liu Y, Zhou S, Wan Y, Wu A, Palmisano M. The impact ofco-administration of ketoconazole and rifampin on the pharmacokineticsof apremilast in healthy volunteers. Br J Clin Pharmacol. 2014 Jun 24.doi: 10.1111/bcp.12448. [Epub ahead of print] PubMed PMID: 24962564.

3: Schafer PH, Parton A, Capone L, Cedzik D, Brady H, Evans JF, Man HW,Muller GW, Stirling DI, Chopra R. Apremilast is a selective PDE4inhibitor with regulatory effects on innate immunity. Cell Signal. 2014Sep;26(9):2016-29. doi: 10.1016/j.cellsig.2014.05.014. Epub 2014 May 29.PubMed PMID: 24882690.

4: Apremilast (Otezla) for psoriatic arthritis. Med Lett Drugs Ther.2014 May 26;56(1443):41-2. PubMed PMID: 24869713.

5: FitzGerald O. Spondyloarthropathies: Apremilast: welcome advance intreatment of psoriatic arthritis. Nat Rev Rheumatol. 2014Jul;10(7):385-6. doi: 10.1038/nrrheum.2014.77. Epub 2014 May 20. PubMedPMID: 24846499.

6: Poole RM, Ballantyne AD. Apremilast: first global approval. Drugs.2014 May;74(7):825-37. doi: 10.1007/s40265-014-0218-4. PubMed PMID:24797159.

7: Varada S, Tintle SJ, Gottlieb AB. Apremilast for the treatment ofpsoriatic arthritis. Expert Rev Clin Pharmacol. 2014 May;7(3):239-50.doi: 10.1586/17512433.2014.904200. Epub 2014 Apr 4. PubMed PMID:24702658.

8: Kavanaugh A, Mease PJ, Gomez-Reino JJ, Adebajo AO, Wollenhaupt J,Gladman DD, Lespessailles E, Hall S, Hochfeld M, Hu C, Hough D, StevensRM, Schett G. Treatment of psoriatic arthritis in a phase 3 randomised,placebo-controlled trial with apremilast, an oral phosphodiesterase 4inhibitor. Ann Rheum Dis. 2014 Jun;73(6):1020-6. doi:10.1136/annrheumdis-2013-205056. Epub 2014 Mar 4. PubMed PMID: 24595547;PubMed Central PMCID: PMC4033106.

9: Gottlieb AB, Matheson RT, Menter A, Leonardi CL, Day RM, Hu C,Schafer PH, Krueger JG. Efficacy, tolerability, and pharmacodynamics ofapremilast in recalcitrant plaque psoriasis: a phase II open-labelstudy. J Drugs Dermatol. 2013 Aug;12(8):888-97. PubMed PMID: 23986162.

10: Schafer PH, Day RM. Novel systemic drugs for psoriasis: mechanism ofaction for apremilast, a specific inhibitor of PDE4. J Am Acad Dermatol.2013 Jun;68(6):1041-2. doi: 10.1016/j.jaad.2012.10.064. PubMed PMID:23680197.