Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H24N2O7S |
| Molecular Weight | 460.5 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC1=CC(=CC=C1OC)[C@@H](CS(C)(=O)=O)N2C(=O)C3=CC=CC(NC(C)=O)=C3C2=O
InChI
InChIKey=IMOZEMNVLZVGJZ-QGZVFWFLSA-N
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
| Molecular Formula | C22H24N2O7S |
| Molecular Weight | 460.5 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Apremilast (brand name Otezla) selective inhibitor of phosphodiesterase 4 is used for the treatment of patients with moderate to severe plaque psoriasis. OTEZLA is the first and only PDE4 inhibitor approved for the treatment of plaque psoriasis, a chronic inflammatory disease of the skin resulting from an uncontrolled immune response. Apremilast also inhibits spontaneous production of TNF-alpha from human rheumatoid synovial cells. It has anti-inflammatory activity. By inhibiting PDE-4, apremilast increases intracellular levels of cAMP and thereby inhibits the production of multiple proinflammatory mediators including PDE-4, TNF-alpha, interleukin-2 (IL-2), interferon-gamma, leukotrienes, and nitric oxide synthase.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| The effects of selective cytokine inhibitory drugs (CC-10004 and CC-1088) on VEGF and IL-6 expression and apoptosis in myeloma and endothelial cell co-cultures. | 2004 Feb |
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| CC-10004 . | 2005 May |
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| Discovery of (S)-N-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl] acetamide (apremilast), a potent and orally active phosphodiesterase 4 and tumor necrosis factor-alpha inhibitor. | 2009 Mar 26 |
|
| Disposition, metabolism and mass balance of [(14)C]apremilast following oral administration. | 2011 Dec |
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| Novel systemic drugs under investigation for the treatment of psoriasis. | 2012 Jul |
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| Novel systemic drugs for psoriasis: mechanism of action for apremilast, a specific inhibitor of PDE4. | 2013 Jun |
|
| Apremilast: a PDE4 inhibitor for the treatment of psoriatic arthritis. | 2015 May |
Sample Use Guides
The recommended initial dosage titration of OTEZLA (apremilast) from Day 1 to Day 5 is from 10 mg till 30 mg corresponding. Following the 5-day titration, the recommended maintenance dosage is 30 mg twice daily taken orally starting on Day 6. This titration is intended to reduce the gastrointestinal symptoms associated with initial therapy.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Mar 06 10:33:25 UTC 2018
by
admin
on
Tue Mar 06 10:33:25 UTC 2018
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| Record UNII |
UP7QBP99PN
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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NDF-RT |
N0000182961
Created by
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WHO-ATC |
L04AA32
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EMA ASSESSMENT REPORTS |
OTEZLA (AUTHORIZED: ARTHRITIS, PSORIATIC)
Created by
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WHO-VATC |
QL04AA32
Created by
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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7372
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PRIMARY | |||
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N0000182960
Created by
admin on Tue Mar 06 10:33:25 UTC 2018 , Edited by admin on Tue Mar 06 10:33:25 UTC 2018
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PRIMARY | Phosphodiesterase 4 Inhibitors [MoA] | ||
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8872
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PRIMARY | |||
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608141-41-9
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PRIMARY | |||
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M2010
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PRIMARY | Merck Index | ||
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C505730
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PRIMARY | |||
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11561674
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PRIMARY | |||
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SUB130837
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PRIMARY | |||
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CHEMBL514800
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1492727
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PRIMARY | RxNorm | ||
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608141-41-9
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PRIMARY |
| Related Record | Type | Details | ||
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EXCRETED UNCHANGED |
URINE
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TARGET -> INHIBITOR |
IC50
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TARGET -> INHIBITOR |
IC50
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TARGET -> INHIBITOR |
IC50
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TARGET -> INHIBITOR |
IC50
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TARGET -> INHIBITOR |
Apremilast is a selective inhibitor of PDE4 that regulates inflammatory mediators.
COMPETITIVE INHIBITOR
IC50
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TARGET -> INHIBITOR |
INHIBITS PDE4 AND INCREASES cAMP CONCENTRATION
INDIRECT
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BINDER -> LIGAND |
BINDING
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLITE -> PARENT |
MINOR
PLASMA; URINE
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METABOLITE -> PARENT |
Metabolites M7 and M17,which were present at trace levels in plasma, did retain some PDE4 and TNF-.alpha. inhibition activity, with IC 50 values similar to those of apremilast.
FECAL
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METABOLITE INACTIVE -> PARENT |
MAJOR
PLASMA; URINE
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METABOLITE -> PARENT |
MINOR
FECAL
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METABOLITE -> PARENT |
MINOR
FECAL
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METABOLITE -> PARENT |
MINOR
FECAL
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METABOLITE -> PARENT |
Metabolites M7 and M17,which were present at trace levels in plasma, did retain some PDE4 and TNF-.alpha. inhibition activity, with IC 50 values similar to those of apremilast.
FECAL; URINE
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METABOLITE -> PARENT |
Major fecal
MAJOR
FECAL
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METABOLITE -> PARENT |
MINOR
PLASMA; URINE
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METABOLITE INACTIVE -> PARENT | |||
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METABOLITE -> PARENT |
MINOR
URINE
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METABOLITE -> PARENT |
MINOR
FECAL
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METABOLITE -> PARENT |
MINOR
PLASMA; URINE
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METABOLITE -> PARENT |
MINOR
FECAL
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
|---|---|---|---|---|---|---|
| Volume of Distribution | PHARMACOKINETIC |
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| Biological Half-life | PHARMACOKINETIC |
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