APREMILAST

Search structure
Trade Names:
Synonyms:
Status: Approved (2014)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: L04AA32
UNII: UP7QBP99PN

Structure
InChI Key IMOZEMNVLZVGJZ-QGZVFWFLSA-N
Smile 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

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H24N2O7S
Molecular Weight 460.51
AlogP 2.43
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 8.0
Polar Surface Area 119.08
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 32.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Phosphodiesterase 4 inhibitor DailyMed
Primary Target
phosphodiesterase 4A
phosphodiesterase 4B
phosphodiesterase 4C
phosphodiesterase 4D
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4A
- 74-110 - - 8-91
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4B
- 24-74 - - -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4C
- 74-110 - - -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4D
- 33-540 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Psoriasis 4 D011565 ClinicalTrials
Psoriasis 4 D011565 ClinicalTrials
Arthritis, Psoriatic 4 D015535 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Behcet Syndrome 3 D001528 ClinicalTrials
Spondylitis, Ankylosing 3 D013167 ClinicalTrials
Dermatitis, Atopic 2 D003876 ClinicalTrials
Alcoholism 2 D000437 ClinicalTrials
Vitiligo 2 D014820 ClinicalTrials
Dermatitis, Allergic Contact 2 D017449 ClinicalTrials
Eczema 2 D004485 ClinicalTrials
Dermatomyositis 2 D003882 ClinicalTrials
Lichen Planus, Oral 2 D017676 ClinicalTrials
Dermatitis 2 D003872 ClinicalTrials
Lichen Planus 2 D008010 ClinicalTrials
Arthritis, Rheumatoid 2 D001172 ClinicalTrials
Acne Vulgaris 2 D000152 ClinicalTrials
Colitis, Ulcerative 2 D003093 ClinicalTrials
Gout 2 D006073 ClinicalTrials
Prostatitis 2 D011472 ClinicalTrials
Rosacea 2 D012393 ClinicalTrials
Hidradenitis Suppurativa 2 D017497 ClinicalTrials
Lupus Erythematosus, Discoid 1 D008179 ClinicalTrials
Uveitis 1 D014605 ClinicalTrials
Stomatitis, Aphthous 0 D013281 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Diarrhoea 9.26
Gastrointestinal disorders Nausea 8.92
Gastrointestinal disorders Diarrhoea 7.71
Gastrointestinal disorders Nausea 7.44
Nervous system disorders Headache 5.88
Nervous system disorders Headache 4.83
Infections and infestations Upper respiratory tract infection 3.85
Gastrointestinal disorders Vomiting 3.25
Gastrointestinal disorders Nausea
Infections and infestations Nasopharyngitis 2.64
Nervous system disorders Headache
Gastrointestinal disorders Abdominal pain upper 2.03
Infections and infestations Upper respiratory tract infection
Nervous system disorders Headache
Gastrointestinal disorders Diarrhoea 1.8
Gastrointestinal disorders Nausea 1.8
Gastrointestinal disorders Diarrhoea
Infections and infestations Nasopharyngitis
Gastrointestinal disorders Nausea
Gastrointestinal disorders Diarrhoea
Nervous system disorders Headache 1.2
Gastrointestinal disorders Vomiting 0.805
Infections and infestations Upper respiratory tract infection
Gastrointestinal disorders Abdominal pain upper 0.604
Infections and infestations Upper respiratory tract infection 0.604
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Abdominal pain upper
Infections and infestations Nasopharyngitis
Infections and infestations Nasopharyngitis 0.201

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Gastrointestinal disorders
24.73
General disorders and administration site conditions
12.94
Nervous system disorders
10.84
Skin and subcutaneous tissue disorders
10.47
Immune system disorders
6.95
Musculoskeletal and connective tissue disorders
5.87
Psychiatric disorders
5.32
Respiratory, thoracic and mediastinal disorders
4.68
Infections and infestations
3.46
Investigations
2.72
Vascular disorders
2.55
Injury, poisoning and procedural complications
2.39
Cardiac disorders
2.23

Cross References

Resources Reference
CAS NUMBER 608141-41-9
ChEBI 78540
ChEMBL CHEMBL514800
DrugBank DB05676
DrugCentral 4829
FDA SRS UP7QBP99PN
Guide to Pharmacology 7372
KEGG D08860
PDB A9L
PubChem 11561674
SureChEMBL SCHEMBL302992
ZINC ZINC000030691736
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