Identification

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Name
Apremilast
Accession Number
DB05676
Type
Small Molecule
Groups
Approved, Investigational
Description

Apremilast, also known as Otezla, is a phosphodiesterase 4 (PDE4) inhibitor used to treat various types of symptoms resulting from certain inflammatory autoimmune diseases. It belongs to the same drug class as Roflumilast and Crisaborole.11,12 Initially approved in 2014, it is marketed by Celgene.14 In July 2019, apremilast was granted a new FDA approval for the treatment of oral ulcers associated with Behcet's disease, an autoimmune condition that causes recurrent skin, blood vessel, and central nervous system inflammation.4

Structure
Thumb
Synonyms
  • Apremilast
  • Aprémilast
  • Apremilastum
  • N-{2-[(1S)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide
External IDs
CC 10004 / CC-10004 / CC10004
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
OtezlaTablet, film coated30 mgOralCelgene Europe Bv2015-01-14Not applicableEu
OtezlaTablet, film coated30 mgOralCelgene Europe Bv2015-01-14Not applicableEu
OtezlaTablet30 mgOralCelgene2014-12-01Not applicableCanada
OtezlaTablet, film coated30.0 mg/1OralCelgene Corporation2014-04-03Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
OtezlaApremilast (10 mg) + Apremilast (20 mg) + Apremilast (30 mg)Kit; TabletOralCelgene2014-11-27Not applicableCanada
OtezlaApremilast (10.0 mg/1) + Apremilast (20.0 mg/1) + Apremilast (30.0 mg/1)KitOralCelgene Corporation2014-03-25Not applicableUs
OtezlaApremilast (10 mg) + Apremilast (20 mg) + Apremilast (30 mg)Kit; TabletOralCelgene2014-11-27Not applicableCanada
OtezlaApremilast (10.0 mg/1) + Apremilast (20.0 mg/1) + Apremilast (30.0 mg/1)KitOralCelgene Corporation2015-02-01Not applicableUs
OtezlaApremilast (10.0 mg/1) + Apremilast (20.0 mg/1) + Apremilast (30.0 mg/1)KitOralCelgene Corporation2014-03-25Not applicableUs
OtezlaApremilast (10 mg) + Apremilast (20 mg) + Apremilast (30 mg)Kit; TabletOralCelgene2014-11-27Not applicableCanada
OtezlaApremilast (10.0 mg/1) + Apremilast (20.0 mg/1) + Apremilast (30.0 mg/1)KitOralCelgene Corporation2015-02-01Not applicableUs
OtezlaApremilast (10.0 mg/1) + Apremilast (20.0 mg/1) + Apremilast (30.0 mg/1)KitOralCelgene Corporation2015-02-01Not applicableUs
OtezlaApremilast (10.0 mg/1) + Apremilast (20.0 mg/1) + Apremilast (30.0 mg/1)KitOralCelgene Corporation2014-03-25Not applicableUs
Categories
UNII
UP7QBP99PN
CAS number
608141-41-9
Weight
Average: 460.5
Monoisotopic: 460.130422295
Chemical Formula
C22H24N2O7S
InChI Key
IMOZEMNVLZVGJZ-QGZVFWFLSA-N
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
IUPAC Name
N-{2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}ethanimidic acid
SMILES
[H][C@](CS(C)(=O)=O)(N1C(=O)C2=C(C1=O)C(=CC=C2)N=C(C)O)C1=CC(OCC)=C(OC)C=C1

Pharmacology

Indication

Apremilast is indicated for the treating of active psoriatic arthritis in adults, for the treating of active moderate to severe psoriatic arthritis in patients who are eligible for phototherapy and systemic treatment. In addition, apremilast is now indicated for the treatment of oral ulcers associated with Behcet's disease in adults.14

Associated Conditions
Pharmacodynamics

Apremilast reduces but does not completely inhibit various inflammatory cytokines such as IL-1α, IL-6, IL-8, IL-10 MCP-1, MIP-1β, MMP-3, and TNF-α, relieving the symptoms of psoriasis and Behcet's disease, which are caused by an increase in these inflammatory mediators.6,13 This drug has also been proven to be effective in relieving the pain associated with oral ulcers in Behcet's disease.11

A note on depression and weight loss

Apremilast may cause unwanted weight loss and worsen depression, leading to suicidal thoughts or actions. It is advisable to monitor for symptoms of depression and seek medical attention if they occur, especially in patients with pre-existing depression. The need for apremilast should be carefully assessed along with the risk of worsening depression and suicide. If weight loss occurs, the degree of weight loss should be evaluated, and consideration should be made for the possible discontinuation of apremilast.14

Mechanism of action

The full mechanism of action of this drug is not fully established, however, it is known that apremilast is an inhibitor of phosphodiesterase 4 (PDE4), which mediates the activity of cyclic adenosine monophosphate (cAMP), a second messenger.5 The inhibition of PDE4 by apremilast leads to increased intracellular cAMP levels.14 An increase in cAMP results in the suppression of inflammation by decreasing the expression of TNF-α, IL-17, IL-23, and other inflammatory mediators. The above inflammatory mediators have been implicated in various psoriatic conditions as well as Behcet's disease, leading to their undesirable inflammatory symptoms such as mouth ulcers, skin lesions, and arthritis.6,13,14 Apremilast administration leads to a cascade which eventually decreases the levels of the above mediators, relieving inflammatory symptoms.

TargetActionsOrganism
APhosphodiesterase isozyme 4
antagonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

An oral dose of apremilast is well-absorbed and the absolute bioavailability is approximately 73%. Tmax is approximately 2.5 hours14 and Cmax has been reported to be approximately 584 ng/mL in one pharmacokinetic study.8 Food intake does not appear to affect apremilast absorption.14

Volume of distribution

The average apparent volume of distribution (Vd) is about 87 L, suggesting that apremilast is distributed in the extravascular compartment.13

Protein binding

The plasma protein binding of apremilast is about 68%.13

Metabolism

Apremilast is heavily metabolized by various pathways, which include oxidation, hydrolysis, in addition to conjugation. About 23 metabolites are produced from its metabolism.3 The CYP3A4 primarily mediates the oxidative metabolism of this drug, with smaller contributions from CYP1A2 and CYP2A6 enzymes.13 The main metabolite of apremilast, M12, is an inactive glucuronide conjugate form of the O-demethylated drug.13 Some other major metabolites, M14 and M16, are significantly less active in the inhibition of PDE4 and inflammatory mediators than their parent drug, apremilast. After an oral dose, unchanged apremilast (45%) and the inactive metabolite, O-desmethyl apremilast glucuronide (39%) are found in the plasma. 10 Minor metabolites M7 and M17 are active, but are only present in about 2% or less of apremilast concentrations, and likely not significant contributors to the actions of apremilast.10

Route of elimination

Only 3% and 7% of an apremilast dose are detected in the urine and feces as unchanged drug, respectively, indicating extensive metabolism and high absorption.13

Half life

The average elimination half-life of this drug ranges from 6-9 hours.7,14

Clearance

In healthy patients, the plasma clearance of apremilast is about 10 L/hour.13

Toxicity

The oral LD50 in mice was greater than 2000 mg/kg in mice. In rats, oral LD50 was 2000 mg/kg males and 300 mg/kg in females.16

Overdose information

In healthy subjects receiving a maximum dose of 100 mg (given as 50 mg twice daily) for about 5 days, no significant toxicity was observed. In cases of an overdose, supportive and symptomatic treatment should be administered. Contact the local poison control center for the most recent overdose management for apremilast.15

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Apremilast.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Apremilast.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Apremilast.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Apremilast.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be increased when combined with Apremilast.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be increased when combined with Apremilast.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be increased when combined with Apremilast.
8-azaguanineThe metabolism of 8-azaguanine can be increased when combined with Apremilast.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be increased when combined with Apremilast.
9-(N-methyl-L-isoleucine)-cyclosporin AThe risk or severity of adverse effects can be increased when Apremilast is combined with 9-(N-methyl-L-isoleucine)-cyclosporin A.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Molostvov G, Morris A, Rose P, Basu S, Muller G: 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. Br J Haematol. 2004 Feb;124(3):366-75. [PubMed:14717786]
  2. Abdulrahim H, Thistleton S, Adebajo AO, Shaw T, Edwards C, Wells A: Apremilast: a PDE4 inhibitor for the treatment of psoriatic arthritis. Expert Opin Pharmacother. 2015 May;16(7):1099-108. doi: 10.1517/14656566.2015.1034107. Epub 2015 Apr 11. [PubMed:25864487]
  3. Hoffmann M, Kumar G, Schafer P, Cedzik D, Capone L, Fong KL, Gu Z, Heller D, Feng H, Surapaneni S, Laskin O, Wu A: Disposition, metabolism and mass balance of [(14)C]apremilast following oral administration. Xenobiotica. 2011 Dec;41(12):1063-75. doi: 10.3109/00498254.2011.604745. Epub 2011 Aug 23. [PubMed:21859393]
  4. Suzuki Kurokawa M, Suzuki N: Behcet's disease. Clin Exp Med. 2004 Sep;4(1):10-20. [PubMed:15598081]
  5. Fertig BA, Baillie GS: PDE4-Mediated cAMP Signalling. J Cardiovasc Dev Dis. 2018 Jan 31;5(1). pii: jcdd5010008. doi: 10.3390/jcdd5010008. [PubMed:29385021]
  6. Tong B, Liu X, Xiao J, Su G: Immunopathogenesis of Behcet's Disease. Front Immunol. 2019 Mar 29;10:665. doi: 10.3389/fimmu.2019.00665. eCollection 2019. [PubMed:30984205]
  7. Young M, Roebuck HL: Apremilast, an oral phosphodiesterase 4 (PDE4) inhibitor: A novel treatment option for nurse practitioners treating patients with psoriatic disease. J Am Assoc Nurse Pract. 2016 Dec;28(12):683-695. doi: 10.1002/2327-6924.12428. Epub 2016 Nov 21. [PubMed:27869356]
  8. Liu Y, Zhou S, Nissel J, Wu A, Lau H, Palmisano M: The pharmacokinetic effect of coadministration of apremilast and methotrexate in individuals with rheumatoid arthritis and psoriatic arthritis. Clin Pharmacol Drug Dev. 2014 Nov;3(6):456-465. doi: 10.1002/cpdd.109. Epub 2014 May 8. [PubMed:26097790]
  9. Zerilli T, Ocheretyaner E: Apremilast (Otezla): A New Oral Treatment for Adults With Psoriasis and Psoriatic Arthritis. P T. 2015 Aug;40(8):495-500. [PubMed:26236137]
  10. Cada DJ, Ingram K, Baker DE: Apremilast. Hosp Pharm. 2014 Sep;49(8):752-62. doi: 10.1310/hpj4908-752. [PubMed:25477601]
  11. Afra TP, Razmi TM, Dogra S: Apremilast in Psoriasis and Beyond: Big Hopes on a Small Molecule. Indian Dermatol Online J. 2019 Jan-Feb;10(1):1-12. doi: 10.4103/idoj.IDOJ_437_18. [PubMed:30775293]
  12. FDA approvals, Otezla [Link]
  13. Otezla product information [Link]
  14. FDA label, Otezla [Link]
  15. Medsafe NZ [Link]
  16. EMA label, Otezla [Link]
External Links
KEGG Drug
D08860
PubChem Compound
11561674
PubChem Substance
310264858
ChemSpider
9736448
BindingDB
50248919
ChEBI
78540
ChEMBL
CHEMBL514800
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Apremilast
ATC Codes
L04AA32 — Apremilast
AHFS Codes
  • 92:36.00 — Disease-modifying Antirheumatic Agents
MSDS
Download (104 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentRecurrent Aphthous Stomatitis1
1CompletedNot AvailableHealthy Volunteers3
1CompletedBasic ScienceHealthy Volunteers1
1CompletedOtherHealthy Volunteers2
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentPharmacokinetics1
1, 2CompletedTreatmentDiscoid Lupus Erythematosus (DLE)1
1, 2RecruitingTreatmentPrurigo Nodularis1
1, 2TerminatedTreatmentUveitis1
2Active Not RecruitingTreatmentItching1
2Active Not RecruitingTreatmentVitiligo1
2CompletedOtherHidradenitis Suppurativa (HS)1
2CompletedTreatmentAllergic Contact Dermatitis / Atopic Dermatitis (AD)1
2CompletedTreatmentAnkylosing Spondylitis (AS)1
2CompletedTreatmentBehcet's Syndrome1
2CompletedTreatmentChronic Prostatitis With Chronic Pelvic Pain Syndrome / Prostatitis1
2CompletedTreatmentDermatitis, Atopic Dermatitis1
2CompletedTreatmentErosive Osteoarthritis of the Hand1
2CompletedTreatmentHidradenitis Suppurativa (HS)1
2CompletedTreatmentPapulopustular Rosacea (PPR) / Rosacea Subtype 1 (Erythematotelangiectatic)1
2CompletedTreatmentPrurigo Nodularis1
2CompletedTreatmentPsoriasis3
2CompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis) / Psoriasis-Type Psoriasis1
2CompletedTreatmentPsoriasis / Psoriasis Arthropatica / Psoriatic Arthritis1
2CompletedTreatmentPsoriasis / Psoriasis Vulgaris (Plaque Psoriasis)1
2CompletedTreatmentPsoriatic Arthritis1
2CompletedTreatmentRheumatoid Arthritis1
2CompletedTreatmentUlcerative Colitis1
2CompletedTreatmentVitiligo1
2CompletedTreatmentVulvodynia1
2Not Yet RecruitingTreatmentOral Lichen Planus1
2Not Yet RecruitingTreatmentPalmoplantaris Pustulosis1
2RecruitingOtherAlcohol Use Disorder (AUD)1
2RecruitingTreatmentDermatitis Eczema / Dermatitis, Eczematous / Nummular Dermatitis / Nummular Eczema1
2RecruitingTreatmentDermatomyositis, Adult Type1
2RecruitingTreatmentFemale Genital Disease / Lichen Planus of Vulva1
2RecruitingTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
2TerminatedTreatmentAcnes1
2TerminatedTreatmentRheumatoid Arthritis1
2Unknown StatusTreatmentLichen Planus (LP)1
2WithdrawnTreatmentAcute Gouty Arthritis1
2WithdrawnTreatmentChronic Plaque Psoriasis1
2WithdrawnTreatmentRheumatoid Arthritis1
3Active Not RecruitingTreatmentBehcet's Syndrome / Behçet's Syndrome1
3Active Not RecruitingTreatmentPsoriasis1
3CompletedTreatmentAnkylosing Spondyloarthritis1
3CompletedTreatmentPsoriasis1
3CompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)2
3CompletedTreatmentPsoriasis / Psoriatic Arthritis1
3CompletedTreatmentPsoriatic Arthritis5
3Not Yet RecruitingTreatmentArthritis; Psoriasis (Etiology)1
3RecruitingTreatmentPsoriasis4
3RecruitingTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
4CompletedTreatmentPalmo-plantar Psoriasis1
4CompletedTreatmentParapsoriasis1
4CompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)3
4Enrolling by InvitationTreatmentPsoriasis / Psoriasis Vulgaris (Plaque Psoriasis) / Psoriatic Nail1
4Not Yet RecruitingDiagnosticPsoriatic Arthritis1
4Not Yet RecruitingTreatmentChronic Hand Dermatitis1
4Not Yet RecruitingTreatmentPsoriasis of the scalp / Psoriasis Vulgaris (Plaque Psoriasis)1
4RecruitingTreatmentCardiovascular Disease (CVD) / Psoriasis1
4RecruitingTreatmentCentral Centrifugal Cicatricial Alopecia1
4RecruitingTreatmentFrontal Fibrosing Alopecia1
4RecruitingTreatmentPsoriasis6
4RecruitingTreatmentPsoriatic Arthritis2
4WithdrawnOtherModerate to Severe Plaque Psoriasis1
4WithdrawnTreatmentPsoriatic Arthritis1
Not AvailableActive Not RecruitingNot AvailablePsoriasis1
Not AvailableActive Not RecruitingNot AvailablePsoriatic Arthritis1
Not AvailableActive Not RecruitingTreatmentAlopecia Areata (AA)1
Not AvailableCompletedNot AvailableAtopic Dermatitis (AD)1
Not AvailableNo Longer AvailableNot AvailableBechet's Disease1
Not AvailableNot Yet RecruitingNot AvailablePsoriasis Vulgaris (Plaque Psoriasis)1
Not AvailableRecruitingNot AvailableNail Psoriasis1
Not AvailableRecruitingNot AvailablePsoriasis2
Not AvailableRecruitingNot AvailablePsoriasis / Psoriatic Arthritis2
Not AvailableRecruitingNot AvailablePsoriatic Arthritis2
Not AvailableTerminatedTreatmentDermatomyositis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
KitOral
Kit; tabletOral
TabletOral30 mg
Tablet, film coatedOral30 mg
Tablet, film coatedOral30.0 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8802717No2014-08-122023-03-19Us
US6962940No2005-11-082023-03-19Us
US6020358No2000-02-012018-10-30Us
US7208516No2007-04-242023-03-19Us
US7659302No2010-02-092023-03-19Us
US8455536No2013-06-042023-03-19Us
US9018243No2015-04-282023-03-19Us
US7427638No2008-09-232024-11-17Us
US7893101No2011-02-222023-12-09Us
US9872854No2018-01-232034-05-29Us
US9724330No2017-08-082023-03-19Us
US10092541No2018-10-092034-05-29Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)156.1http://www.guildlink.com.au/gc/ws/celgene/pi.cfm?product=cjpaprem
boiling point (°C)741.3±60.0 http://www.chemspider.com/Chemical-Structure.9736448.html
pKa12.58https://pubchem.ncbi.nlm.nih.gov/compound/Apremilast#section=Solubility
Predicted Properties
PropertyValueSource
Water Solubility0.0503 mg/mLALOGPS
logP1.79ALOGPS
logP1.39ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.83ChemAxon
pKa (Strongest Basic)-0.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area122.57 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity119.85 m3·mol-1ChemAxon
Polarizability46.71 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phthalimides. These are aromatic heterocyclic compounds containing a 1,3-dioxoisoindoline moiety. They are imide derivatives of phthalic anhydrides.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Isoindoles and derivatives
Sub Class
Isoindolines
Direct Parent
Phthalimides
Alternative Parents
Isoindoles / N-acetylarylamines / Anisoles / Methoxybenzenes / Phenoxy compounds / Alkyl aryl ethers / N-substituted carboxylic acid imides / Sulfones / Vinylogous amides / Acetamides
show 6 more
Substituents
Phthalimide / Isoindole / N-acetylarylamine / Phenol ether / N-arylamide / Methoxybenzene / Phenoxy compound / Anisole / Alkyl aryl ether / Benzenoid
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
aromatic ether, sulfone, phthalimides, N-acetylarylamine (CHEBI:78540)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Not Available
Specific Function
3',5'-cyclic-nucleotide phosphodiesterase activity
Gene Name
PDE4
Uniprot ID
Q86V67
Uniprot Name
Phosphodiesterase isozyme 4
Molecular Weight
11946.535 Da
References
  1. Baumer W, Hoppmann J, Rundfeldt C, Kietzmann M: Highly selective phosphodiesterase 4 inhibitors for the treatment of allergic skin diseases and psoriasis. Inflamm Allergy Drug Targets. 2007 Mar;6(1):17-26. [PubMed:17352685]
  2. Abdulrahim H, Thistleton S, Adebajo AO, Shaw T, Edwards C, Wells A: Apremilast: a PDE4 inhibitor for the treatment of psoriatic arthritis. Expert Opin Pharmacother. 2015 May;16(7):1099-108. doi: 10.1517/14656566.2015.1034107. Epub 2015 Apr 11. [PubMed:25864487]
  3. Afra TP, Razmi TM, Dogra S: Apremilast in Psoriasis and Beyond: Big Hopes on a Small Molecule. Indian Dermatol Online J. 2019 Jan-Feb;10(1):1-12. doi: 10.4103/idoj.IDOJ_437_18. [PubMed:30775293]
  4. FDA label, Otezla [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Hoffmann M, Kumar G, Schafer P, Cedzik D, Capone L, Fong KL, Gu Z, Heller D, Feng H, Surapaneni S, Laskin O, Wu A: Disposition, metabolism and mass balance of [(14)C]apremilast following oral administration. Xenobiotica. 2011 Dec;41(12):1063-75. doi: 10.3109/00498254.2011.604745. Epub 2011 Aug 23. [PubMed:21859393]
  2. Zerilli T, Ocheretyaner E: Apremilast (Otezla): A New Oral Treatment for Adults With Psoriasis and Psoriatic Arthritis. P T. 2015 Aug;40(8):495-500. [PubMed:26236137]
  3. Young M, Roebuck HL: Apremilast, an oral phosphodiesterase 4 (PDE4) inhibitor: A novel treatment option for nurse practitioners treating patients with psoriatic disease. J Am Assoc Nurse Pract. 2016 Dec;28(12):683-695. doi: 10.1002/2327-6924.12428. Epub 2016 Nov 21. [PubMed:27869356]
  4. FDA label, Otezla [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Zerilli T, Ocheretyaner E: Apremilast (Otezla): A New Oral Treatment for Adults With Psoriasis and Psoriatic Arthritis. P T. 2015 Aug;40(8):495-500. [PubMed:26236137]
  2. FDA label, Otezla [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Zerilli T, Ocheretyaner E: Apremilast (Otezla): A New Oral Treatment for Adults With Psoriasis and Psoriatic Arthritis. P T. 2015 Aug;40(8):495-500. [PubMed:26236137]
  2. FDA label, Otezla [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da

Drug created on November 18, 2007 11:26 / Updated on November 16, 2019 10:39