apremilast (CHEBI:78540)

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CHEBI:78540 - apremilast

ChEBI ID	CHEBI:78540
ChEBI Name	apremilast
Stars
Definition	A member of the class of isoindoles that is isoindole-1,3-dione substituted at position 4 by an acetamido group and at position 1 by a 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl group. Used for treatment of psoriatic arthritis.
Last Modified	22 February 2017
Submitter	tmorrison
Downloads	Molfile

Formula	C22H24N2O7S
Net Charge	0
Average Mass	460.508
Monoisotopic Mass	460.13042
SMILES	CCOc1cc([C@@H](CS(C)(=O)=O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC
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

Wikipedia

Roles Classification

Biological Roles:

phosphodiesterase IV inhibitor An EC 3.1.4.53 (3',5'-cyclic-AMP phosphodiesterase) inhibitor that specifically blocks the action of phosphodiesterase IV.

antiviral agent A substance that destroys or inhibits replication of viruses.

antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.

Applications:

dermatologic drug A drug used to treat or prevent skin disorders or for the routine care of skin.

anti-ulcer drug One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.

gout suppressant A drug that increases uric acid excretion by the kidney (uricosuric drug), decreases uric acid production (antihyperuricemic), or alleviates the pain and inflammation of acute attacks of gout.

non-steroidal anti-inflammatory drug An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs 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.

antipsoriatic A drug used to treat psoriasis.

ophthalmology drug Any compound used for the treatment of eye conditions or eye diseases.

antirheumatic drug A drug used to treat rheumatoid arthritis.

ChEBI Ontology

Outgoing Relation(s)
	apremilast (CHEBI:78540) has role anti-ulcer drug (CHEBI:49201)
	apremilast (CHEBI:78540) has role antimicrobial agent (CHEBI:33281)
	apremilast (CHEBI:78540) has role antipsoriatic (CHEBI:50748)
	apremilast (CHEBI:78540) has role antirheumatic drug (CHEBI:35842)
	apremilast (CHEBI:78540) has role antiviral agent (CHEBI:22587)
	apremilast (CHEBI:78540) has role dermatologic drug (CHEBI:50177)
	apremilast (CHEBI:78540) has role gout suppressant (CHEBI:35845)
	apremilast (CHEBI:78540) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
	apremilast (CHEBI:78540) has role ophthalmology drug (CHEBI:66981)
	apremilast (CHEBI:78540) has role phosphodiesterase IV inhibitor (CHEBI:68844)
	apremilast (CHEBI:78540) is a N-acetylarylamine (CHEBI:13790)
	apremilast (CHEBI:78540) is a aromatic ether (CHEBI:35618)
	apremilast (CHEBI:78540) is a phthalimides (CHEBI:82851)
	apremilast (CHEBI:78540) is a sulfone (CHEBI:35850)

IUPAC Name
N-{2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide

INNs	Source
apremilast	WHO MedNet
apremilast	ChemIDplus
aprémilast	WHO MedNet
apremilastum	WHO MedNet

Synonyms	Source
CC 10004	ChemIDplus
CC-10004	ChemIDplus
CC10004	ChemIDplus

Brand Names	Source
Apremilast accord	ChEMBL
OTEZLA	KEGG DRUG

Manual Xrefs	Databases
4829	DrugCentral
Apremilast	Wikipedia
D08860	KEGG DRUG

Registry Numbers	Sources
Reaxys:12446985	Reaxys
CAS:608141-41-9	KEGG DRUG
CAS:608141-41-9	ChemIDplus

Citations