Apremilast

Highest phase reached

Approved

www.ebi.ac.uk

Drug type

Small molecule

www.ebi.ac.uk

First approval year

2014

www.ebi.ac.uk

First approval year: 2014
www.ebi.ac.uk

Listing at source: Listed

Highest phase reached: Approved
www.ebi.ac.uk

Drug type: Small molecule
www.ebi.ac.uk

Drug name: Apremilast
www.ebi.ac.uk

Molecular weight: 460.51
www.ebi.ac.uk

Structure (SMILES): CCOc1cc([C@@H](CS(C)(=O)=O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC
www.ebi.ac.uk

apremilast accord
Apremilast accord
otezla
Otezla

apremilast
Apremilast
Apremilast (CC-10004)
Apremilast [INN]
Apremilast [JAN]
Apremilast [MI]
Apremilast [ORANGE BOOK]
Apremilast [USAN]
Apremilast [VANDF]
Apremilast [WHO-DD]
Apremilast 10mg
Apremilast 20 mg
Apremilast 20mg
Apremilast 30 mg
Apremilast 30 mg Tablets
Apremilast 30mg
Apremilast 60mg
Apremilast Immediate Release
apremilast inn
Apremilast IR
apremilast jan
apremilast mi
Apremilast Oral Suspension
Apremilast Oral Tablet
apremilast orange book

And 13 more, listed on the interactive page.

ATC classification codes

L04AA32

Sources for recorded values

www.ebi.ac.uk

CAS registry numbers

608141-41-9

ChEMBL ID: CHEMBL514800
www.ebi.ac.uk

InChIKey: IMOZEMNVLZVGJZ-QGZVFWFLSA-N
www.ebi.ac.uk

PubChem compound IDs

11561674

RxNorm IDs (RxCUI)

1492727

FDA ingredient codes (UNII)

UP7QBP99PN

Applicant: AMGEN INC
Approval date: 21 Mar 2014
Application number: NDA205437

Status: Authorised
Status date: 15 Jan 2015
Authorisation date: 15 Jan 2015
Approved indications: Psoriatic arthritisOtezla, 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. PsoriasisOtezla is indicated for the treatment of moderate to severe chronic plaque psoriasis (PSOR) 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). Paediatric psoriasisOtezla is indicated for the treatment of moderate to severe plaque psoriasis in children and adolescents from the age of 6 years and weighing at least 20 kg who are candidates for systemic therapy.Behçet’s diseaseOtezla is indicated for the treatment of adult patients with oral ulcers associated with Behçet’s disease (BD) who are candidates for systemic therapy.
Product number: EMEA/H/C/003746
Authorisation holder: Amgen Europe B.V.
Priority medicines scheme: No
Generic: No
Biosimilar: No
Generic medicines: 1
Biosimilar medicines: 0
Advanced therapy: No
Conditional approval: No
Additional monitoring: No
Accelerated assessment: No
Exceptional circumstances: No

Therapeutic areas

Arthritis, Psoriatic
Behcet Syndrome
Psoriasis

European medicines record

www.ema.europa.eu

Patents: 13
Designations: 1
Earliest recorded loss of exclusivity: 27 May 2042
First in class: Yes
Fast track: No
Breakthrough designation: No
Orphan designation: No
Priority review: No
Orphan exclusivity: No
Accelerated approval: No
Availability: Prescription only

Pharmacology name: apremilast
Type: Synthetic organic
Drug name stem: -ast
Approval recorded by Guide to Pharmacology: Yes

Administration routes

Oral

Action
Inhibition
Action type
Inhibitor
Target
phosphodiesterase 4A
Gene symbol
PDE4A
Protein identifier
P27815
Median affinity
7.85
Affinity units
pIC50
Primary target
Yes
Action
Inhibition
Action type
Inhibitor
Target
phosphodiesterase 4B
Gene symbol
PDE4B
Protein identifier
Q07343
Affinity units
pIC50
Primary target
Yes
Action
Inhibition
Action type
Inhibitor
Target
phosphodiesterase 4C
Gene symbol
PDE4C
Protein identifier
Q08493
Median affinity
6.93
Affinity units
pIC50
Primary target
Yes
Action
Inhibition
Action type
Inhibitor
Target
phosphodiesterase 4D
Gene symbol
PDE4D
Protein identifier
Q08499
Median affinity
7.48
Affinity units
pIC50
Primary target
Yes
Mechanism
Phosphodiesterase 4 inhibitor
Action type
Inhibitor
Target
Phosphodiesterase 4
Protein identifier
P27815
Mechanism
Phosphodiesterase 4 inhibitor
Action type
Inhibitor
Target
Phosphodiesterase 4
Protein identifier
Q07343
Mechanism
Phosphodiesterase 4 inhibitor
Action type
Inhibitor
Target
Phosphodiesterase 4
Protein identifier
Q08493
Mechanism
Phosphodiesterase 4 inhibitor
Action type
Inhibitor
Target
Phosphodiesterase 4
Protein identifier
Q08499

Open Targets mechanisms

Mechanism
Phosphodiesterase 4 inhibitor
Action type
Inhibitor
Target
Phosphodiesterase 4

Action type
Inhibitor
Gene symbol
PDE4A
Protein identifier
P27815
Organism
Homo sapiens
Target development level
Clinical
Action type
Inhibitor
Gene symbol
PDE4B
Protein identifier
Q07343
Organism
Homo sapiens
Target development level
Clinical
Action type
Inhibitor
Gene symbol
PDE4C
Protein identifier
Q08493
Organism
Homo sapiens
Target development level
Clinical
Action type
Inhibitor
Gene symbol
PDE4D
Protein identifier
Q08499
Organism
Homo sapiens
Target development level
Clinical

Condition
Dermatitis, Atopic
Highest recorded phase
2
Condition identifier
EFO:0000274
Subject identifier
D003876
Condition
Dermatomyositis
Highest recorded phase
2
Condition identifier
EFO:0000398
Subject identifier
D003882
Condition
Immune System Diseases
Highest recorded phase
4
Condition identifier
EFO:0000540
Subject identifier
D007154
Condition
Psoriasis
Highest recorded phase
4
Condition identifier
EFO:0000676
Subject identifier
D011565
Condition
Arthritis, Rheumatoid
Highest recorded phase
2
Condition identifier
EFO:0000685
Subject identifier
D001172
Condition
Colitis, Ulcerative
Highest recorded phase
2
Condition identifier
EFO:0000729
Subject identifier
D003093
Condition
Pneumonia
Highest recorded phase
3
Condition identifier
EFO:0003106
Subject identifier
D011014
Condition
Arthritis, Psoriatic
Highest recorded phase
4
Condition identifier
EFO:0003778
Subject identifier
D015535
Condition
Behcet Syndrome
Highest recorded phase
4
Condition identifier
EFO:0003780
Subject identifier
D001528
Condition
Prostatitis
Highest recorded phase
2
Condition identifier
EFO:0003830
Subject identifier
D011472
Condition
Acne Vulgaris
Highest recorded phase
2
Condition identifier
EFO:0003894
Subject identifier
D000152
Condition
Spondylitis, Ankylosing
Highest recorded phase
3
Condition identifier
EFO:0003898
Subject identifier
D013167
Condition
Vitiligo
Highest recorded phase
2
Condition identifier
EFO:0004208
Subject identifier
D014820
Condition
Gout
Highest recorded phase
2
Condition identifier
EFO:0004274
Subject identifier
D006073
Condition
Influenza, Human
Highest recorded phase
3
Condition identifier
EFO:0007328
Subject identifier
D007251
Condition
Lichen Planus, Oral
Highest recorded phase
2
Condition identifier
EFO:0008517
Subject identifier
D017676
Condition
Dermatitis, Allergic Contact
Highest recorded phase
2
Condition identifier
EFO:1000668
Subject identifier
D017449
Condition
Erythema Multiforme
Highest recorded phase
2
Condition identifier
EFO:1000694
Subject identifier
D004892
Condition
Hidradenitis Suppurativa
Highest recorded phase
2
Condition identifier
EFO:1000710
Subject identifier
D017497
Condition
Lichen Planus
Highest recorded phase
2
Condition identifier
EFO:1000726
Subject identifier
D008010
Condition
Rosacea
Highest recorded phase
2
Condition identifier
EFO:1000760
Subject identifier
D012393
Condition
Uveitis
Highest recorded phase
1
Condition identifier
EFO:1001231
Subject identifier
D014605
Condition
Psoriasis
Highest recorded phase
4
Condition identifier
EFO:1001494
Subject identifier
D011565
Condition
Oral Ulcer
Highest recorded phase
4
Condition identifier
HP:0000155
Subject identifier
D019226
Condition
Eczema
Highest recorded phase
2
Condition identifier
HP:0000964
Subject identifier
D004485

And 5 more, listed on the interactive page.

Condition identifier
EFO_0000274
Highest recorded phase
2
Condition identifier
EFO_0000398
Highest recorded phase
2
Condition identifier
EFO_0000540
Condition identifier
EFO_0000676
Condition identifier
EFO_0000685
Highest recorded phase
2
Condition identifier
EFO_0000729
Highest recorded phase
2
Condition identifier
EFO_0003778
Condition identifier
EFO_0003780
Condition identifier
EFO_0003830
Highest recorded phase
2
Condition identifier
EFO_0003894
Highest recorded phase
2
Condition identifier
EFO_0003898
Highest recorded phase
3
Condition identifier
EFO_0004192
Condition identifier
EFO_0004208
Highest recorded phase
2
Condition identifier
EFO_0004274
Highest recorded phase
2
Condition identifier
EFO_0008517
Highest recorded phase
2
Condition identifier
EFO_1000694
Highest recorded phase
2
Condition identifier
EFO_1000710
Highest recorded phase
2
Condition identifier
EFO_1000726
Highest recorded phase
2
Condition identifier
EFO_1000760
Highest recorded phase
2
Condition identifier
EFO_1001231
Condition identifier
EFO_1001494
Condition identifier
EFO_1001494
Highest recorded phase
4
Condition identifier
HP_0000155
Condition identifier
HP_0000155
Highest recorded phase
4
Condition identifier
HP_0000964
Highest recorded phase
2

And 38 more, listed on the interactive page.

Event
abdominal discomfort
Reports
3,970
Reporting signal score
5,092.68
Event
abdominal pain upper
Reports
2,060
Reporting signal score
1,034.86
Event
depression
Reports
2,768
Reporting signal score
1,585.35
Event
diarrhoea
Reports
15,222
Reporting signal score
16,178.2
Event
dyspnoea
Reports
553
Reporting signal score
880.838
Event
frequent bowel movements
Reports
649
Reporting signal score
891.029
Event
gastric disorder
Reports
787
Reporting signal score
914.793
Event
headache
Reports
10,604
Reporting signal score
8,865.59
Event
nausea
Reports
14,410
Reporting signal score
12,137.8
Event
product dose omission issue
Reports
1,371
Reporting signal score
1,170.38
Event
psoriasis
Reports
11,827
Reporting signal score
25,170.9
Event
psoriatic arthropathy
Reports
3,292
Reporting signal score
7,019.72
Event
therapy non-responder
Reports
1,419
Reporting signal score
1,523.6
Event
weight decreased
Reports
2,841
Reporting signal score
1,515

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And 59 more, listed on the interactive page.

Dose: 30 mg
Route: Oral
How often: Twice daily

Do not crush, split, or chew
Swallow tablets whole

Hydrogen bond acceptors: 7
Hydrogen bond donors: 1
Polar surface area: 119.08
Calculated partition coefficient (ALogP): 2.43
Calculated partition coefficient (XLogP): 1.8
Prodrug: No
Chirality: Single enantiomer
Inorganic: No
Rule-of-five violations: 0
Rotatable bonds: 8
Heavy atoms: 32
Molecular formula: C22H24N2O7S
Monoisotopic mass: 460.13042228
Natural product: Yes

55513-137
55513-369
55513-485
55513-497
55513-508
55513-516
55513-519
55513-996

Recorded assays: 188
Active assays: 45

Confirmatory
Other

Anti-Inflammatory Agents, Non-Steroidal
id.nlm.nih.gov
Phosphodiesterase 4 Inhibitors
id.nlm.nih.gov

These details could not be displayed.

Related records

Trials (148)

[18F]PF-06445974 to Image PDE4B in Major Depressive Disorder Using PET
A 20-Week Study Assessing the Efficacy of Apremilast in Patients with EB Simplex Generalized
A Drug-Drug Interaction Study to Evaluate the Effect of Rifampin on the Pharmacokinetics of Apremilast
A Long-term Extension Study of Apremilast (CC-10004) in Pediatric Subjects From 6 Through 17 Years of Age With Moderate to Severe Plaque Psoriasis
A Phase 3 Randomized, Double-blind Study to Evaluate the Efficacy and Safety of Apremilast (CC-10004) in Subjects With Active Behçet's Disease
A Phase 3B, Open-label, Single-arm Study of the Efficacy and Safety of Apremilast, in Subjects With Plaque Psoriasis That is Not Adequately Controlled by Topical Therapy
A Phase 4 Study of Efficacy and Safety of Apremilast in Subjects With Moderate Plaque Psoriasis.
A Real-world Observational Study to Compare Effectiveness of Deucravacitinib Vs Apremilast in Adults With Plaque Psoriasis
A Study About How Well TAK-279 Works and Its Safety in Participants With Moderate-to-severe Plaque Psoriasis During 52 Weeks of Treatment
A Study About How Well TAK-279 Works and Its Safety in Participants With Moderate-to-severe Plaque Psoriasis During 60 Weeks of Treatment With a Withdrawal and Retreatment Period
A Study Evaluating the Efficacy and Tolerability of Oral Apremilast for the Treatment of Nail Psoriasis
A Study Examining the Medication Apremilast as Treatment for Chronic Itch
A Study in Healthy People to Compare 3 Different Formulations of Apremilast Tablets Taken With or Without Food
A Study in Patients With Moderate to Severe Plaque Psoriasis to Evaluate the Efficacy and Safety of ESK-001
A Study of Apremilast in Children With Oral Ulcers Associated With Behçet's Disease or Juvenile Psoriatic Arthritis
A Study of Apremilast in Pediatric Participants in Children With Mild to Moderate Plaque Psoriasis
A Study of LY2775240 in Healthy Participants
A Study of Safety, Tolerability and Pharmacokinetics of Apremilast (CC-10004) in Pediatric Subjects With Moderate to Severe Plaque Psoriasis
A Study of the Comparative Effectiveness of Deucravacitinib in Adults With Plaque Psoriasis in Japan (RePhlect)
A Study of the Efficacy and Safety of Apremilast (CC-10004) in Subjects With Moderate to Severe Plaque Psoriasis of the Scalp

Approved for (5)

Behcet disease
Immune system disorder
Palmoplantar pustulosis
Psoriasis
Psoriatic arthritis

In development for (23)

Acne Phase 2
Alcohol dependence Phase 2
Allergic contact dermatitis Phase 2
Ankylosing spondylitis Phase 3
Atopic eczema Phase 2
COVID-19 Phase 3
Dermatitis Phase 2
Dermatomyositis Phase 2
Discoid lupus erythematosus Phase 1
Erythema multiforme Phase 2
Gout Phase 2
Hidradenitis suppurativa Phase 2
Influenza Phase 3
Lichen planus Phase 2
Lichen planus, oral Phase 2
Pneumonia Phase 3
Prostatitis Phase 2
Prurigo nodularis Phase 2
Rheumatoid arthritis Phase 2
Rosacea Phase 2

Targets (4)

PDE4A Phosphodiesterase 4 inhibitor
PDE4B Phosphodiesterase 4 inhibitor
PDE4C Phosphodiesterase 4 inhibitor
PDE4D Phosphodiesterase 4 inhibitor

Apremilast

Development status

Names and chemistry

Brand names (4)

Other names (38)

Identifiers

Regulatory information

United States

European Union

Therapeutic areas

Other regulatory facts

Pharmacology

Drug classification

Administration routes

Mechanisms of action (8)

Open Targets mechanisms

DrugCentral mechanisms (4)

Investigated indications (30)

Open Targets indications (63)

Reported adverse events (14)

Trial references (84)

Dosing

Conditions of use (2)

Chemical properties

National Drug Codes

Evidence counts

Active assay types (2)

Pharmacologic actions

Biological measurements

Related records

Trials (148)

Approved for (5)

In development for (23)

Other linked conditions (1)

Targets (4)