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    Synopsis

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    Chemistry

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    Also known as: 608141-41-9, Otezla, Cc-10004, Cc 10004, Apremilast (cc-10004), Cc10004
    Molecular Formula
    C22H24N2O7S
    Molecular Weight
    460.5  g/mol
    InChI Key
    IMOZEMNVLZVGJZ-QGZVFWFLSA-N
    FDA UNII
    UP7QBP99PN
    Apremilast
    Apremilast is an orally bioavailable, small molecule inhibitor of phosphodiesterase 4 (PDE4), with potential anti-inflammatory activity. Upon oral administration, apremilast targets, binds to and inhibits the activity of PDE4, thereby blocking cyclic adenosine monophosphate (cAMP) degradation and increasing intracellular cAMP levels. This may decrease the production of the proinflammatory cytokines including tumor necrosis factor-alpha (TNF-alpha). PDE4 is an enzyme that plays an important role in the degradation of cAMP and in cytokine production in inflammatory cells.
    1 2D Structure

    Apremilast

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide
    2.1.2 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
    2.1.3 InChI Key
    IMOZEMNVLZVGJZ-QGZVFWFLSA-N
    2.1.4 Canonical SMILES
    CCOC1=C(C=CC(=C1)C(CS(=O)(=O)C)N2C(=O)C3=C(C2=O)C(=CC=C3)NC(=O)C)OC
    2.1.5 Isomeric SMILES
    CCOC1=C(C=CC(=C1)[C@@H](CS(=O)(=O)C)N2C(=O)C3=C(C2=O)C(=CC=C3)NC(=O)C)OC
    2.2 Other Identifiers
    2.2.1 UNII
    UP7QBP99PN
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Cc 10004

    2. Cc-10004

    3. Cc10004

    4. Otezla

    2.3.2 Depositor-Supplied Synonyms

    1. 608141-41-9

    2. Otezla

    3. Cc-10004

    4. Cc 10004

    5. Apremilast (cc-10004)

    6. Cc10004

    7. (s)-n-(2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide

    8. Chebi:78540

    9. Up7qbp99pn

    10. Chembl514800

    11. N-{2-[(1s)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1h-isoindol-4-yl}acetamide

    12. N-[2-[(1s)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide

    13. (s)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione

    14. N-{2-[(1s)-1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethyl]-1,3-dioxo-2,3-dihydro-1h-isoindol-4-yl}acetamide

    15. (+)-n-(2-((1s)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxo- 2,3-dihydro-1h-isoindol-4-yl)acetamide

    16. Apremilast [usan]

    17. Apremilast [usan:inn]

    18. Unii-up7qbp99pn

    19. Apremilastum

    20. Mfcd18782607

    21. Hsdb 8221

    22. Apremilast- Bio-x

    23. Otezla (tn)

    24. Apremilast [mi]

    25. Apremilast [inn]

    26. Apremilast [jan]

    27. Apremilast (jan/usan)

    28. Apremilast [vandf]

    29. Apremilast [who-dd]

    30. Schembl302992

    31. Amy371

    32. Gtpl7372

    33. Apremilast [orange Book]

    34. Dtxsid30976289

    35. Ex-a336

    36. Cas:608141-41-9;apremilast

    37. 608141-44-2

    38. Bcp03783

    39. Bcp25283

    40. Bdbm50248919

    41. S8034

    42. Zinc30691736

    43. Akos016339660

    44. Bcp9000311

    45. Ccg-269336

    46. Cs-0671

    47. Db05676

    48. Fk-0727

    49. Ac-27650

    50. Ba164215

    51. Hy-12085

    52. Bcp0726000109

    53. Sw219856-1

    54. D08860

    55. Q2858961

    56. (s)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione(apremilast)

    57. (s)-n-{2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1h-isoindol-4-yl}-acetamide

    58. 4-[[5 Pound Not7-dihydroxy-2 Pound Not2-dimethyl-8-(2-methylpropanoyl)chromen-6-yl]methy L]-3 Pound Not5-dihydroxy-6 Pound Not6-dimethyl-2-(2-methylpropanoyl)cyclohexa-2 Pound Not4-dien- 1-one

    59. A9l

    60. Acetamide, N-(2-((1s)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)- 2,3-dihydro-1,3-dioxo-1h-isoindol-4-yl)-

    61. Acetamide, N-[2-[(1s)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-2,3-dihydro-1,3-dioxo-1h-isoindol-4-yl]-

    62. N-[2-[(1s)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-2,3-dihydro-1,3-dioxo-1h-isoindol-4-yl]acetamide

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 460.5 g/mol
    Molecular Formula C22H24N2O7S
    XLogP31.8
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count8
    Exact Mass460.13042228 g/mol
    Monoisotopic Mass460.13042228 g/mol
    Topological Polar Surface Area128 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity825
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    Anti-Inflammatory Agents, Non-Steroidal; Phosphodiesterase Inhibitors

    National Library of Medicine's Medical Subject Headings. Apremilast. Online file (MeSH, 2014). Available from, as of December 18, 2014: https://www.nlm.nih.gov/mesh/2014/mesh_browser/MBrowser.html

    Otezla is indicated for the treatment of adult patients with active psoriatic arthritis. /Included in US product label/

    NIH; DailyMed. Current Medication Information for Otezla (Apremilast) Tablet, Film Coated (Revised: October 2014). Available from, as of December 31, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3acf6751-827d-11e2-9e96-0800200c9a66

    Otezla is indicated for the treatment of patients with moderate to severe plaque psoriasis who are candidates for phototherapy or systemic therapy. /Included in US product label/

    NIH; DailyMed. Current Medication Information for Otezla (Apremilast) Tablet, Film Coated (Revised: October 2014). Available from, as of December 31, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3acf6751-827d-11e2-9e96-0800200c9a66

    EXPL THER /The purpose of this study is/ to evaluate the efficacy and safety of an oral phosphodiesterase 4 inhibitor, apremilast, in treatment of ankylosing spondylitis (AS) by monitoring symptoms and signs in a pilot study including exploratory investigation of effects of PDE4 inhibition on blood biomarkers of bone biology. In this double-blind, placebo-controlled, single-centre, Phase II study, patients with symptomatic AS with active disease on MRI were randomized to apremilast 30 mg BID or placebo over 12 weeks. Bath Indices were monitored serially. Patients were followed for 4 weeks after stopping medication. Bone biomarkers were assessed at baseline and day 85. 38 subjects were randomised and 36 subjects completed the study. Although the primary end-point (change in BASDAI at week 12) was not met, apremilast was associated with numerically greater improvement from baseline for all clinical assessments compared with placebo with mean change in BASDAI (-1.59 + or - 1.48 vs -0.77 + or - 1.47), BASFI (-1.74 + or - 1.91 vs -0.28 + or - 1.61) and BASMI (-0.51 + or - 1.02 vs -0.21 + or - 0.67); however, differences did not achieve statistical significance. The clinical indices returned to baseline values by 4 weeks after cessation of apremilast. Six apremilast patients (35.3%) vs 3 placebo (15.8%) achieved ASAS20 responses (p=0.25). There were statistically significant decreases in serum RANKL and RANKL:osteoprotegrin ratio and plasma sclerostin but no significant changes in serum DKK-1, bone alkaline phosphatase, TRAP5b, MMP3, osteoprotegrin, or osteocalcin. Although a small pilot study, these results suggest that apremilast may be effective and well tolerated in AS and modulates biomarkers of bone biology. These data support further research of apremilast in axial inflammation.

    PMID:22984171 Pathan E et al; Ann Rheum Dis 72 (9): 1475-80 (2013)

    EXPL THER Discoid lupus erythematosus (DLE) is a chronic inflammatory disorder mediated by Th1 cells. Apremilast is a novel oral PDE4 enzyme inhibitor capable of blocking leukocyte production of IL-12, IL-23, TNF-a, INF- with subsequent suppression of Th1 and Th17-mediated immune responses, and proven clinical efficacy for psoriasis as well as rheumatoid and psoriatic arthritis. Cutaneous Lupus Erythematosus Disease Area and Severity Index (CLASI) showed a significant (P<0.05) decrease after 85 days of treatment with apremilast 20 mg twice daily in 8 patients with active discoid lupus. The adverse events related to the drug were mild and transient. This is the first open label study to use apremilast as a treatment modality for discoid lupus. Our observations indicate that apremilast may constitute a safe and effective therapeutic option for DLE.

    PMID:23134988 De Souza A et al; J Drugs Dermatol 11 (10): 1224-6 (2012)

    4.2 Drug Warning

    Treatment with Otezla is associated with an increase in adverse reactions of depression. Before using Otezla in patients with a history of depression and/or suicidal thoughts or behavior prescribers should carefully weigh the risks and benefits of treatment with Otezla in such patients. Patients, their caregivers, and families should be advised of the need to be alert for the emergence or worsening of depression, suicidal thoughts or other mood changes, and if such changes occur to contact their healthcare provider. Prescribers should carefully evaluate the risks and benefits of continuing treatment with Otezla if such events occur.

    NIH; DailyMed. Current Medication Information for Otezla (Apremilast) Tablet, Film Coated (Revised: October 2014). Available from, as of February 25, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3acf6751-827d-11e2-9e96-0800200c9a66

    The safety and effectiveness of Otezla in pediatric patients less than 18 years of age have not been established.

    NIH; DailyMed. Current Medication Information for Otezla (Apremilast) Tablet, Film Coated (Revised: October 2014). Available from, as of February 25, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3acf6751-827d-11e2-9e96-0800200c9a66

    It is not known whether Otezla or its metabolites are present in human milk; however apremilast was detected in milk of lactating mice. Because many drugs are present in human milk, caution should be exercised when Otezla is administered to a nursing woman.

    NIH; DailyMed. Current Medication Information for Otezla (Apremilast) Tablet, Film Coated (Revised: October 2014). Available from, as of February 25, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3acf6751-827d-11e2-9e96-0800200c9a66

    FDA Pregnancy Risk Category: C /RISK CANNOT BE RULED OUT. Adequate, well controlled human studies are lacking, and animal studies have shown risk to the fetus or are lacking as well. There is a chance of fetal harm if the drug is given during pregnancy; but the potential benefits may outweigh the potential risk./

    NIH; DailyMed. Current Medication Information for Otezla (Apremilast) Tablet, Film Coated (Revised: October 2014). Available from, as of February 25, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3acf6751-827d-11e2-9e96-0800200c9a66

    For more Drug Warnings (Complete) data for Apremilast (11 total), please visit the HSDB record page.

    4.3 Drug Indication

    Apremilast is indicated for the treatment of adults with active psoriatic arthritis and adults with oral ulcers associated with Behcet's Disease. In addition, apremilast is indicated for the treatment of plaque psoriasis, of any severity, in adult patients who are candidates for phototherapy or systemic therapy.

    * Psoriatic arthritis :

    Otezla, alone or in combination with Disease Modifying Antirheumatic Drugs (DMARDs), is indicated for the treatment of active psoriatic arthritis (PsA) in adult patients who have had an inadequate response or who have been intolerant to a prior DMARD therapy.

    * Psoriasis:

    Otezla is indicated for the treatment of moderate to severe chronic plaque psoriasis in adult patients who failed to respond to or who have a contraindication to, or are intolerant to other systemic therapy including cyclosporine, methotrexate or psoralen and ultraviolet-A light (PUVA).

    Treatment of Behcet disease

    Treatment of chronic idiopathic arthritis (including rheumatoid arthritis , ankylosing spondylitis, psoriatic arthritis and juvenile idiopathic arthritis )

    Treatment of psoriasis

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Apremilast reduces but does not completely inhibit various inflammatory cytokines such as IL-1, IL-6, IL-8, IL-10 MCP-1, MIP-1, MMP-3, and TNF-, relieving the symptoms of psoriasis and Behcet's disease, which are caused by an increase in these inflammatory mediators. This drug has also been proven to be effective in relieving the pain associated with oral ulcers in Behcet's disease. Apremilast may cause unwanted weight loss and worsen depression, leading to suicidal thoughts or actions. It is advisable to monitor for symptoms of depression and seek medical attention if they occur, especially in patients with pre-existing depression. The need for apremilast should be carefully assessed along with the risk of worsening depression and suicide. If weight loss occurs, the degree of weight loss should be evaluated, and consideration should be made for the possible discontinuation of apremilast.

    5.2 MeSH Pharmacological Classification

    Anti-Inflammatory Agents, Non-Steroidal

    Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

    Phosphodiesterase 4 Inhibitors

    Compounds that specifically inhibit PHOSPHODIESTERASE 4. (See all compounds classified as Phosphodiesterase 4 Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Pharmacological Classes
    Phosphodiesterase 4 Inhibitors [MoA]; Phosphodiesterase 4 Inhibitor [EPC]
    5.4 ATC Code

    L04AA32

    L - Antineoplastic and immunomodulating agents

    L04 - Immunosuppressants

    L04A - Immunosuppressants

    L04AA - Selective immunosuppressants

    L04AA32 - Apremilast

    5.5 Absorption, Distribution and Excretion

    Absorption

    An oral dose of apremilast is well-absorbed and the absolute bioavailability is approximately 73%. Tmax is approximately 2.5 hours and Cmax has been reported to be approximately 584 ng/mL in one pharmacokinetic study. Food intake does not appear to affect apremilast absorption.

    Route of Elimination

    Only 3% and 7% of an apremilast dose are detected in the urine and feces as unchanged drug, respectively, indicating extensive metabolism and high absorption.

    Volume of Distribution

    The average apparent volume of distribution (Vd) is about 87 L, suggesting that apremilast is distributed in the extravascular compartment.

    Clearance

    In healthy patients, the plasma clearance of apremilast is about 10 L/hour.

    Human plasma protein binding of apremilast is approximately 68%. Mean apparent volume of distribution (Vd) is 87 L.

    NIH; DailyMed. Current Medication Information for Otezla (Apremilast) Tablet, Film Coated (Revised: October 2014). Available from, as of February 25, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3acf6751-827d-11e2-9e96-0800200c9a66

    The lacteal excretion of apremilast was evaluated following oral administration of apremilast to lactating CD-1 mice. In this study, female mice approximately 13 days postpartum received a single oral dose of apremilast at 10 mg/kg, administered by oral gavage in a volume of 10 mL/kg. Milk and blood samples from 5 animals per time point were obtained at 1, 6, and 24 hr postdose and apremilast concentrations determined in plasma and milk using LC-MS/MS analysis. The mean apremilast plasma concentrations at 1 and 6 hr post-dose were 984 and 138 ng/mL, while concentrations in milk were 1441 and 186 ng/mL, respectively. The resulting mean milk-to-plasma ratios ranged from 1.46 to 1.62, indicating transfer of apremilast into milk in mice. Plasma and milk concentrations were below the detection limit of 3 ng/mL in the 24-hr samples.

    European Medicines Agency (EMA), Committee for Medicinal Products for Human Use (CHMP), European Public Assessment Report (EPAR): Otezla (Apremilast) p.35 (November 20, 2014). Available from, as of February 26, 2015: https://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/003746/WC500182629.pdf

    In monkeys, pregnant animals were administered daily oral doses of apremilast beginning on gestation day 20 through gestation day 50, and a single oral dose on gestation day 100 at dosages of 20, 50, 200, and 1000 mg/kg/day (n = 16/group at the beginning of the study). Maternal and fetal blood was collected at 5 hr postdose on gestation Day 100. In all dosage groups, the fetal-to-maternal plasma concentration ratios were between 0.3 and 0.4, indicating apremilast crossed the placenta in monkeys.

    European Medicines Agency (EMA), Committee for Medicinal Products for Human Use (CHMP), European Public Assessment Report (EPAR): Otezla (Apremilast) p.34-5 (November 20, 2014). Available from, as of February 26, 2015: https://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/003746/WC500182629.pdf

    As part of fertility and developmental toxicity study in female CD-1 mice and an embryo-fetal development study in cynomolgus monkeys, the transport of apremilast across the placenta was assessed. In mice, following daily oral administration of apremilast beginning 15 days prior to cohabitation and continuing through Day 15 of presumed gestation at doses of 10, 20, 40, and 80 mg/kg/day, blood was collected from pregnant mice (n = 3/time point) at 0.5, 2, 4, 8, and 24 hr postdose on gestation Day 15. Blood was collected from fetuses) at the time of sacrifice in the 24 hr postdose mice. Maternal plasma apremilast concentrations increased in a less than dose proportional manner. The fetal plasma concentrations at 24 hr were highly variable, with six of the ten litters evaluated being below the limit of quantification (1 ng/mL). In fetal plasma from four of the ten litters evaluated, apremilast was quantified, with concentrations ranging from 14.5 to 2813 ng/mL. The mean fetal-to-maternal plasma concentration ratios ranged from 0.3 to 1.07, indicating apremilast crossed the placenta in mice.

    European Medicines Agency (EMA), Committee for Medicinal Products for Human Use (CHMP), European Public Assessment Report (EPAR): Otezla (Apremilast) p.34 (November 20, 2014). Available from, as of February 26, 2015: https://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/003746/WC500182629.pdf

    For more Absorption, Distribution and Excretion (Complete) data for Apremilast (13 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    Apremilast is heavily metabolized by various pathways, which include oxidation, hydrolysis, in addition to conjugation. About 23 metabolites are produced from its metabolism. The CYP3A4 primarily mediates the oxidative metabolism of this drug, with smaller contributions from CYP1A2 and CYP2A6 enzymes. The main metabolite of apremilast, M12, is an inactive glucuronide conjugate form of the O-demethylated drug. Some other major metabolites, M14 and M16, are significantly less active in the inhibition of PDE4 and inflammatory mediators than their parent drug, apremilast. After an oral dose, unchanged apremilast (45%) and the inactive metabolite, O-desmethyl apremilast glucuronide (39%) are found in the plasma. Minor metabolites M7 and M17 are active, but are only present in about 2% or less of apremilast concentrations, and likely not significant contributors to the actions of apremilast.

    The plasma clearance of apremilast is about 10 L/hr in healthy subjects, with a terminal elimination half-life of approximately 6-9 hours. Following oral administration of radio-labeled apremilast, about 58% and 39% of the radioactivity is recovered in urine and feces, respectively, with about 3% and 7% of the radioactive dose recovered as apremilast in urine and feces, respectively.

    NIH; DailyMed. Current Medication Information for Otezla (Apremilast) Tablet, Film Coated (Revised: October 2014). Available from, as of February 25, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3acf6751-827d-11e2-9e96-0800200c9a66

    Following oral administration in humans, apremilast is a major circulating component (45%) followed by inactive metabolite M12 (39%), a glucuronide conjugate of O-demethylated apremilast. It is extensively metabolized in humans with up to 23 metabolites identified in plasma, urine and feces. Apremilast is metabolized by both cytochrome (CYP) oxidative metabolism with subsequent glucuronidation and non-CYP mediated hydrolysis. In vitro, CYP metabolism of apremilast is primarily mediated by CYP3A4, with minor contributions from CYP1A2 and CYP2A6.

    NIH; DailyMed. Current Medication Information for Otezla (Apremilast) Tablet, Film Coated (Revised: October 2014). Available from, as of February 25, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3acf6751-827d-11e2-9e96-0800200c9a66

    In /an/ oral study, concentrations of both total radioactivity (e.g., parent compound plus any metabolites) and of parent compound in plasma were greater in females than in males. In males, the total radioactivity AUC values were 25 to 96 times greater than those for parent compound, whereas in females the difference was only 2- to 3-fold, suggesting that metabolism was more extensive in male than in female rats. In the same study following six daily doses, accumulation was indicated by Cmax and AUC values in females, but not in males.

    European Medicines Agency (EMA), Committee for Medicinal Products for Human Use (CHMP), European Public Assessment Report (EPAR): Otezla (Apremilast) p.32 (November 20, 2014). Available from, as of February 26, 2015: https://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/003746/WC500182629.pdf

    In a bile-duct cannulated male mouse study following a single 10 mg/kg oral dose of (14)C-apremilast, 54% and 16% of the radioactive dose was excreted via the biliary and urinary routes, suggesting that at least 70% of the radioactive dose was absorbed in mice, indicating apremilast is subject to moderate first pass metabolism. Toxicokinetic evaluation in mice suggests exposure increases dose-proportionally and less than dose-proportionally at doses over 100 mg/kg/day. The studies do not indicate sex-related differences or inversion of apremilast to its R enantiomer in mice.

    European Medicines Agency (EMA), Committee for Medicinal Products for Human Use (CHMP), European Public Assessment Report (EPAR): Otezla (Apremilast) p.32 (November 20, 2014). Available from, as of February 26, 2015: https://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/003746/WC500182629.pdf

    For more Metabolism/Metabolites (Complete) data for Apremilast (6 total), please visit the HSDB record page.

    5.7 Biological Half-Life

    The average elimination half-life of this drug ranges from 6-9 hours.

    terminal elimination half-life of approximately 6-9 hours

    NIH; DailyMed. Current Medication Information for Otezla (Apremilast) Tablet, Film Coated (Revised: October 2014). Available from, as of February 25, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3acf6751-827d-11e2-9e96-0800200c9a66

    5.8 Mechanism of Action

    The full mechanism of action of this drug is not fully established, however, it is known that apremilast is an inhibitor of phosphodiesterase 4 (PDE4), which mediates the activity of cyclic adenosine monophosphate (cAMP), a second messenger. The inhibition of PDE4 by apremilast leads to increased intracellular cAMP levels. An increase in cAMP results in the suppression of inflammation by decreasing the expression of TNF-, IL-17, IL-23, and other inflammatory mediators. The above inflammatory mediators have been implicated in various psoriatic conditions as well as Behcet's disease, leading to their undesirable inflammatory symptoms such as mouth ulcers, skin lesions, and arthritis. Apremilast administration leads to a cascade which eventually decreases the levels of the above mediators, relieving inflammatory symptoms.

    Apremilast is an orally administered phosphodiesterase-4 inhibitor, currently in phase 2 clinical studies of psoriasis and other chronic inflammatory diseases. The inhibitory effects of apremilast on pro-inflammatory responses of human primary peripheral blood mononuclear cells (PBMC), polymorphonuclear cells, natural killer (NK) cells and epidermal keratinocytes were explored in vitro, and in a preclinical model of psoriasis. Apremilast was tested in vitro against endotoxin- and superantigen-stimulated PBMC, bacterial peptide and zymosan-stimulated polymorphonuclear cells, immunonoglobulin and cytokine-stimulated NK cells, and ultraviolet B light-activated keratinocytes. Apremilast was orally administered to beige-severe combined immunodeficient mice, xenotransplanted with normal human skin and triggered with human psoriatic NK cells. Epidermal skin thickness, proliferation index and inflammation markers were analysed. Apremilast inhibited PBMC production of the chemokines CXCL9 and CXCL10, cytokines interferon-gamma and tumour necrosis factor (TNF)-alpha, and interleukins (IL)-2, IL-12 and IL-23. Production of TNF-alpha by NK cells and keratinocytes was also inhibited. In vivo, apremilast significantly reduced epidermal thickness and proliferation, decreased the general histopathological appearance of psoriasiform features and reduced expression of TNF-alpha, human leukocyte antigen-DR and intercellular adhesion molecule-1 in the lesioned skin. Apremilast displayed a broad pattern of anti-inflammatory activity in a variety of cell types and decreased the incidence and severity of a psoriasiform response in vivo. Inhibition of TNF-alpha, IL-12 and IL-23 production, as well as NK and keratinocyte responses by this phosphodiesterase-4 inhibitor suggests a novel approach to the treatment of psoriasis.

    PMID:20050849 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2829210 Schafer PH et al; Br J Pharmacol 159 (4): 842-55 (2010)

    Psoriasis and psoriatic arthritis are common clinical conditions that negatively impact health-related quality of life and are linked to serious medical comorbidities. Disease mechanisms involve local and systemic chronic inflammatory processes. Available biologic therapies specifically target single inflammatory mediators, such as tumor necrosis factor-a (TNF-a), in the context of a larger inflammatory signaling cascade. To interrupt this pathological cascade earlier in the response or further upstream, and return pro-inflammatory and anti-inflammatory signaling to a homeostatic balance, the use of a phosphodiesterase4 (PDE4) inhibitor has been explored. PDE4 is the major enzyme class responsible for the hydrolysis of cyclic adenosine monophosphate (cAMP), an intracellular second messenger that controls a network of pro-inflammatory and anti-inflammatory mediators. With PDE4 inhibition, and the resulting increases in cAMP levels in immune and non-immune cell types, expression of a network of pro-inflammatory and anti-inflammatory mediators can be modulated. Apremilast is an orally available targeted PDE4 inhibitor that modulates a wide array of inflammatory mediators involved in psoriasis and psoriatic arthritis, including decreases in the expression of inducible nitric oxide synthase, TNF-a, and interleukin (IL)-23 and increases IL-10. In phase II studies of subjects with psoriasis and psoriatic arthritis, apremilast reversed features of the inflammatory pathophysiology in skin and joints and significantly reduces clinical symptoms. The use of an oral targeted PDE4 inhibitor for chronic inflammatory diseases, like psoriasis and psoriatic arthritis, represents a novel treatment approach that does not target any single mediator, but rather focuses on restoring a balance of pro-inflammatory and anti-inflammatory signals.

    PMID:22257911 Schafer P; Biochem Pharmacol 83 (12): 1583-90 (2012)

    Apremilast, a small-molecule inhibitor of phosphodiesterase 4 (PDE4), works intracellularly to modulate a network of pro-inflammatory and anti-inflammatory mediators. Phosphodiesterase 4 inhibition elevates intracellular cAMP levels, thereby reducing the inflammatory response by modulating the expression of tumor necrosis factor-alpha (TNF-a), interleukin-23 (IL-23), IL-17 and IL-10.

    Health Canada; Product Monograph for Otezla (Apremilast), Drug Identification Number (DIN): 02434318 p.13 (Date of Preparation: November 12, 2014). Available from, as of February 25, 2015: https://webprod5.hc-sc.gc.ca/dpd-bdpp/start-debuter.do?lang=eng

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    Polpharma

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    About the Company : Polpharma API. European CDMO partner and API manufacturer since 1951. Poland-based CDMO and API producer, delivering products to pharmaceutical companies worldwide. Aiming at the c...

    Polpharma API. European CDMO partner and API manufacturer since 1951. Poland-based CDMO and API producer, delivering products to pharmaceutical companies worldwide. Aiming at the continuous development of Polpharma and caring for the future of patients, business partners and our employees, we are launching a specialized facility for the R&D and Production of HPAPI with an OEL value of 10 ng/m3 (OEB 6). The HP API investment includes separate process laboratories (PDL), analytical laboratories (ADL) with the possibility of performing QC analyses, and a GMP kilo-lab production line with volume up to 1.5 kg with potential volume increase.
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    Established in 2004, Metrochem API is one of the fastest-growing APIs, pellets & intermediates manufacturers. It has 6 dedicated manufacturing facilities for its 3 core product ...

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    About the Company : Founded in 1984, DRL is well-known for its generic APIs and its track record in drug product development. It is one of the earliest pharma API manufacturers with a diverse portfoli...

    Founded in 1984, DRL is well-known for its generic APIs and its track record in drug product development. It is one of the earliest pharma API manufacturers with a diverse portfolio that provides high-quality, low-cost APIs to leading pharma companies in 80+ countries. It has 8 USFDA-inspected facilities – 6 in India & 1 each in Mexico & the UK & are inspected by international regulatory authorities on a regular basis. Its facilities are supplemented by formulation facilities that provide a wide range of dosage forms. Product(s) under patent(s) are offered only for R&D purposes U/S 107A of the Patent Act and not for commercial sale
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    About the Company : Aarti Pharmalab, earlier the pharma division of Aarti Industries, is a leading Indian manufacturer of APIs. It has dedicated facilities to manufacture HPAPIs, corticosteroids, cyto...

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    About the Company : HRV Global is a leading global manufacturer, seller & exporter of a wide range of APIs, advanced intermediates, pellets, food grade chemicals, food additives & food ingredients. It...

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    Neuland Laboratories

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    Arene Lifesciences

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    Globofarm International

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    About the Company : Globofarm International Pvt Ltd is a well-informed, highly efficient, Swiftly functioning competitive sourcing entity. We serve private, institutional, and corporate clients worldw...

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    About the Company : Piramal Pharma Solutions (PPS) is a CDMO that provides end-to-end solutions for drug development and manufacturing across the drug life cycle to its clients in North America, Europ...

    Piramal Pharma Solutions (PPS) is a CDMO that provides end-to-end solutions for drug development and manufacturing across the drug life cycle to its clients in North America, Europe and Asia through a globally integrated network of facilities. It offers a range of services from drug discovery to commercial supply of APIs and finished dosage forms, along with specialized services like HPAPIs, antibody drug conjugations, sterile fill/finish, peptide products and services and potent solid oral drug products. PPS also provides services for biologics, including vaccines, gene therapies and monoclonal antibodies through its subsidiary Yapan Bio.
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    13-Jan-2021
    01-Jun-2024
    KGS
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