Apremilast

• CAT Number: I004295
• CAS Number: 608141-41-9
• Molecular Formula: C₂₂H₂₄N₂O₇S
• Molecular Weight: 460.5
• Purity: ≥95%
• Target: PDE
• Solubility: in DMSO > 10 mM
• Storage: Store at -20°C
• IC50: 74 nM
• IUPAC Name: N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide
• InChI: 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
• InChIKey: IMOZEMNVLZVGJZ-QGZVFWFLSA-N
• SMILES: CCOC1=C(C=CC(=C1)C(CS(=O)(=O)C)N2C(=O)C3=C(C2=O)C(=CC=C3)NC(=O)C)OC

Apremilast (Cat.No:I004295) is a small-molecule drug that works as a phosphodiesterase 4 (PDE4) inhibitor, used in the treatment of psoriatic arthritis, psoriasis, and oral ulcers associated with Behcet’s disease. It is orally administered and has a favorable safety profile. Apremilast reduces inflammation and modulates the immune response by increasing intracellular cyclic adenosine monophosphate (cAMP) levels. 

Reference

1:Apremilast in the treatment of moderate to severe hidradenitis suppurativa: A case series of 9 patients. Weber P, Seyed Jafari SM, Yawalkar N, Hunger RE.J Am Acad Dermatol. 2017 Jun;76(6):1189-1191. doi: 10.1016/j.jaad.2017.02.026. No abstract available. PMID: 28522043 2:The phosphodiesterase 4 inhibitor apremilast inhibits Th1 but promotes Th17 responses induced by 6-sulfo LacNAc (slan) dendritic cells. Oehrl S, Prakash H, Ebling A, Trenkler N, Wölbing P, Kunze A, Döbel T, Schmitz M, Enk A, Schäkel K.J Dermatol Sci. 2017 Apr 20. pii: S0923-1811(16)30797-6. doi: 10.1016/j.jdermsci.2017.04.005. [Epub ahead of print] PMID: 28499587 3:A Novel Apremilast Nail Lacquer Formulation for the Treatment of Nail Psoriasis. Kushwaha AS, Repka MA, Narasimha Murthy S.AAPS PharmSciTech. 2017 Apr 28. doi: 10.1208/s12249-017-0776-3. [Epub ahead of print] PMID: 28455829 4:Identification and characterization of process-related substances and degradation products in apremilast: Process optimization and degradation pathway elucidation. Lu Y, Shen X, Hang T, Song M.J Pharm Biomed Anal. 2017 Jul 15;141:70-78. doi: 10.1016/j.jpba.2017.03.067. Epub 2017 Apr 2. PMID: 28454058 5:Apremilast for a psoriasis patient with HIV and hepatitis C. Reddy SP, Shah VV, Wu JJ.J Eur Acad Dermatol Venereol. 2017 Apr 27. doi: 10.1111/jdv.14301. [Epub ahead of print] No abstract available. PMID: 28449227 6:Novel use of apremilast for adjunctive treatment of recalcitrant pyoderma gangrenosum. Laird ME, Tong LX, Lo Sicco KI, Kim RH, Meehan SA, Franks AG Jr.JAAD Case Rep. 2017 Apr 14;3(3):228-229. doi: 10.1016/j.jdcr.2017.02.019. eCollection 2017 May. No abstract available. PMID: 28443317 Free PMC Article7:Long-term safety and tolerability of apremilast in patients with psoriasis: Pooled safety analysis for ≥156 weeks from 2 phase 3, randomized, controlled trials (ESTEEM 1 and 2). Crowley J, Thaçi D, Joly P, Peris K, Papp KA, Goncalves J, Day RM, Chen R, Shah K, Ferrándiz C, Cather JC.J Am Acad Dermatol. 2017 Apr 14. pii: S0190-9622(17)30146-9. doi: 10.1016/j.jaad.2017.01.052. [Epub ahead of print] PMID: 28416342 8:Treatment of recalcitrant erosive oral lichen planus and desquamative gingivitis with oral apremilast. AbuHilal M, Walsh S, Shear N.J Dermatol Case Rep. 2016 Nov 30;10(3):56-57. doi: 10.3315/jdcr.2016.1232. eCollection 2016 Nov 30. PMID: 28400896 Free PMC Article9:Apremilast, an oral phosphodiesterase 4 inhibitor, in the treatment of Japanese patients with moderate to severe plaque psoriasis: Efficacy, safety and tolerability results from a phase 2b randomized controlled trial. Ohtsuki M, Okubo Y, Komine M, Imafuku S, Day RM, Chen P, Petric R, Maroli A, Nemoto O.J Dermatol. 2017 Apr 9. doi: 10.1111/1346-8138.13829. [Epub ahead of print] PMID: 28391657 10:Apremilast and suicidality – a retrospective analysis of three large databases: the FAERS, EudraVigilance and a large single-centre US patient population. Vakharia PP, Orrell KA, Lee D, Rangel SM, Lund E, Laumann AE, West DP, Nardone B.J Eur Acad Dermatol Venereol. 2017 Apr 5. doi: 10.1111/jdv.14256. [Epub ahead of print] No abstract available. PMID: 28380251