WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 205894
CAS#: 608141-41-9
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.
MedKoo Cat#: 205894
Name: Apremilast
CAS#: 608141-41-9
Chemical Formula: C22H24N2O7S
Exact Mass: 460.13042
Molecular Weight: 460.5
Elemental 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
Appearance: White to off-white powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 460.5 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Thompson BJ, Furniss M, Zhao W, Chakraborty B, Mackay-Wiggan J. An Oral Phosphodiesterase Inhibitor (Apremilast) for Inflammatory Rosacea in Adults: A Pilot Study. JAMA Dermatol. 2014 Jul 23. doi: 10.1001/jamadermatol.2013.10526. [Epub ahead of print] PubMed PMID: 25054629.
2: Liu Y, Zhou S, Wan Y, Wu A, Palmisano M. The impact of co-administration of ketoconazole and rifampin on the pharmacokinetics of 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 PDE4 inhibitor with regulatory effects on innate immunity. Cell Signal. 2014 Sep;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 in treatment of psoriatic arthritis. Nat Rev Rheumatol. 2014 Jul;10(7):385-6. doi: 10.1038/nrrheum.2014.77. Epub 2014 May 20. PubMed PMID: 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 of psoriatic 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, Stevens RM, Schett G. Treatment of psoriatic arthritis in a phase 3 randomised, placebo-controlled trial with apremilast, an oral phosphodiesterase 4 inhibitor. 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 of apremilast in recalcitrant plaque psoriasis: a phase II open-label study. J Drugs Dermatol. 2013 Aug;12(8):888-97. PubMed PMID: 23986162.
10: Schafer PH, Day RM. Novel systemic drugs for psoriasis: mechanism of action 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.
