Structure via PubChem · Public domain (PubChem)
apremilast
Sign in to saveAlso known as CC-10004, Otezla®, CC 10004, CC10004, Apremilastum, Aprémilast, N-{2-[(1S)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide
Apremilast, sold under the brand name Otezla among others, is a medication for the treatment of certain types of psoriasis and psoriatic arthritis. The drug acts as a selective inhibitor of the enzyme phosphodiesterase 4 (PDE4). It is taken by mouth.
In the Vinony graph
Vinony's link graph records 286 inbound references to apremilast, and connects out to psoriasis, cyclosporine and oral administration.
It is catalogued under topics including Acetamides, Catechol ethers and Disease-modifying antirheumatic drugs.
Vinony links it to 19 Wikipedia language editions.
Key facts
- Drug.image
- Apremilast.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 215
- Drug.image2
- Apremilast molecule ball.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 215
- Drug.tradename
- Otezla, others
- Drug.MedlinePlus
- a614022
- Drug.DailyMedID
- Apremilast
- Drug.pregnancy_AU
- B3
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- L04
- Drug.ATC_suffix
- AA32
- Drug.legal_AU
- S4
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.legal_EU
- Rx-only
- Drug.legal_status
- Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C22H24N2O7S
- Molecular weight
- 460.5 g/mol
- IUPAC name
- N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide
- 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
- InChIKey
- IMOZEMNVLZVGJZ-QGZVFWFLSA-N
- XLogP
- 1.8
- Polar surface area
- 127 Ų
- H-bond donors
- 1
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2014
- Admin. routes
- oral
- Indications
- atopic eczema, ankylosing spondylitis, Behcet's syndrome, psoriasis
via ChEMBL · EBI
Research
1,509 papersvia PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 460.13
- Has use
- medication
Show 8 more facts
- chemical formula
- C₂₂H₂₄N₂O₇S
- medical condition treated
- psoriatic arthritis
- 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
- 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
- World Health Organisation international non-proprietary name
- apremilast
- subject has role
- non-steroidal anti-inflammatory drug
- Commons category
- Apremilast
- defined daily dose
- 60
Sources (9)
via Wikidata · CC0
~9 min read
Encyclopedic overview
18 sectionsContents
- Medical uses
- Contraindications
- Adverse effects
- Diarrhea and vomiting
- Psychological
- Weight loss
- Other
- Interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Economics
- Legal status
- Research
- References
{{Infobox drug | image = Apremilast.svg | image_class = skin-invert-image | width = 215 | alt = | image2 = Apremilast molecule ball.png | image_class2 = bg-transparent | width2 = 215 | alt2 =
| pronounce = | tradename = Otezla, others | Drugs.com = | MedlinePlus = a614022 | DailyMedID = Apremilast | pregnancy_AU = B3 | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = By mouth | class = | ATC_prefix = L04 | ATC_suffix = AA32 | ATC_supplemental =
Excerpted from Wikipedia’s “apremilast” article, available under the CC BY-SA 4.0 licence.