Roflumilast

Identification

Summary

Roflumilast is a selective phosphodiesterase-4 inhibitor indicated to decrease the risk of exacerbations in patients with severe chronic obstructive pulmonary disease (COPD) and to treat plaque psoriasis.

Brand Names

Daliresp, Zoryve

Generic Name

Roflumilast

DrugBank Accession Number

DB01656

Background

Roflumilast is a highly selective phosphodiesterase-4 (PDE4) inhibitor.⁷ PDE4 is a major cyclic-3',5′-adenosinemonophosphate (cyclic AMP, cAMP)-metabolizing enzyme ⁹ expressed on nearly all immune and pro-inflammatory cells, in addition to structural cells like those of the smooth muscle or epithelium.⁷ The resultant increase in intracellular cAMP induced by roflumilast's inhibition of PDE4 is thought to mediate its disease-modifying effects, although its precise mechanism of action has yet to be elucidated.^9,7

The oral formulation of roflumilast is indicated to manage chronic obstructive pulmonary disease.¹³ It was first approved by the EMA in July 2010, and by the FDA in January 2018.⁹ Roflumilast topical cream is indicated to treat plaque psoriasis. The cream formulation was first approved by the FDA in July 2022 ¹⁰ and by Health Canada in April 2023.¹² On December 15, 2023, the FDA approved a new topical foam formulation of roflumilast for the treatment of seborrheic dermatitis in patients aged 9 years and older.¹⁵

Type

Small Molecule

Groups

Approved

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Roflumilast (DB01656)

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Weight

Average: 403.207
Monoisotopic: 402.034954148

Chemical Formula

C₁₇H₁₄Cl₂F₂N₂O₃

Synonyms

• Roflumilast
• Roflumilastum

External IDs

• B-9302-107
• B9302-107
• BY-217
• BY217
• BYK-20869
• BYK20869

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Pharmacology

Indication

Oral roflumilast is indicated to reduce the risk of COPD exacerbations in patients with severe COPD associated with chronic bronchitis and a history of exacerbations.^9,12,13

Topical cream roflumilast is indicated to treat plaque psoriasis, including intertriginous areas, in patients 12 years of age and older, while topical foam roflumilast is indicated to treat seborrheic dermatitis in adult and pediatric patients 9 years of age and older..^10,12,14

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Prevention of	Exacerbation of copd		••••••••••••		••••••• •• •••••••••••• •• ••••• •••••• ••••••• ••••••••••• ••••••••• •••••••	••••••
Treatment of	Psoriasis vulgaris (plaque psoriasis)		••••••••••••			•••••
Treatment of	Seborrheic dermatitis		••••••••••••	•••••• •••••••••		•••••••• ••••

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Pharmacodynamics

Roflumilast and its active metabolite, roflumilast N-oxide, increase cyclic adenosine-3′, 5′-monophosphate (cAMP) in affected cells by inhibiting PDE4. They are highly selective for PDE4 and are effectively inactive against PDEs 1, 2, 3, 5, and 7.⁷

Mechanism of action

Roflumilast and its active metabolite (roflumilast N-oxide) are inhibitors of PDE4. Roflumilast and roflumilast N-oxide inhibition of PDE4 (a major cyclic 3′,5′-adenosine monophosphate (cyclic AMP) metabolizing enzyme) activity leads to accumulation of intracellular cyclic AMP. The specific mechanism(s) by which roflumilast exerts its therapeutic action is not well defined.¹⁴

Target	Actions	Organism
AcAMP-specific 3',5'-cyclic phosphodiesterase 4 (PDE4)	inhibitor	Humans

Absorption

After a 500mcg dose, the bioavailability of roflumilast is about 80%.⁹ In the fasted state, maximum plasma concentrations are reached in 0.5 to 2 hours, while in the fed state, Cmax is reduced by 40%, Tmax is increased by one hour, and total absorption is unchanged.⁹

Applied topically, the mean systemic exposure for roflumilast and its N-oxide metabolite in adults was 72.7 ± 53.1 and 628 ± 648 h∙ng/mL, respectively.¹⁰ The mean systemic exposure for roflumilast and its N-oxide metabolite in adolescents was 25.1 ± 24.0 and 140 ± 179 h∙ng/mL, respectively.¹⁰

Volume of distribution

Following a single oral dose of 500 mcg, the volume of distribution of roflumilast is approximately 2.9 L/kg.⁹

Protein binding

Plasma protein binding of roflumilast and its N-oxide metabolite is approximately 99% and 97%, respectively.⁹

Metabolism

Roflumilast is metabolized to roflumilast N-oxide, the active metabolite of roflumilast in humans, by CYP3A4 and CYP1A2.⁹ The N-oxide metabolite is less potent than its parent drug in regards to PDE4 inhibition, but its plasma AUC is approximately 10-fold greater.⁹

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• Roflumilast
  • Roflumilast N-oxide

Route of elimination

Roflumilast is excreted 70% in the urine as roflumilast N-oxide.⁸

Half-life

Following oral administration, the plasma half-lives of roflumilast and roflumilast N-oxide are 17 hours and 30 hours, respectively.⁹

Clearance

Plasma clearance of roflumilast following short-term intravenous infusion is approximately 9.6 L/h.⁹

Adverse Effects

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Toxicity

There are no data regarding overdosage with orally administered roflumilast. Phase I studies in which roflumilast was administered at single doses up to 5000 mcg showed an increase in the incidence of headache, gastrointestinal disorders, dizziness, palpitations, lightheadedness, clamminess, and arterial hypotension.⁹ In the event of an overdose, administer support medical care as soon as possible. Hemodialysis is unlikely to be of benefit given the extensive protein binding of roflumilast.⁹

Pathways

Not Available

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Interactions

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	Abacavir may decrease the excretion rate of Roflumilast which could result in a higher serum level.
Abametapir	The serum concentration of Roflumilast can be increased when it is combined with Abametapir.
Abatacept	Roflumilast may increase the immunosuppressive activities of Abatacept.
Abemaciclib	The metabolism of Abemaciclib can be decreased when combined with Roflumilast.
Abiraterone	The serum concentration of Roflumilast can be increased when it is combined with Abiraterone.

Food Interactions

• Take with or without food. Administering roflumilast with a high-fat meal reduced and delayed the Cmax and Tmax, respectively, but did not impact the AUC of roflumilast or its active metabolite (roflumilast N‐oxide).

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Product Images

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Daliresp	Tablet	500 ug/1	Oral	Cardinal Health	2011-02-28	2016-07-31
Daliresp	Tablet	500 ug/1	Oral	Allergan	2011-02-28	2016-07-31
Daliresp	Tablet	250 ug/1	Oral	AstraZeneca Pharmaceuticals LP	2015-07-01	Not applicable
Daliresp	Tablet	500 ug/1	Oral	AstraZeneca Pharmaceuticals LP	2015-07-01	Not applicable
Daxas	Tablet, film coated	500 μg	Oral	Astra Zeneca Ab	2016-09-08	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Roflumilast	Tablet	250 ug/1	Oral	Novadoz Pharmaceuticals Llc	2022-09-07	Not applicable
Roflumilast	Tablet	250 ug/1	Oral	Zydus Pharmaceuticals USA Inc.	2023-05-18	Not applicable
Roflumilast	Tablet	500 ug/1	Oral	Torrent Pharmaceuticals Limited	2022-10-19	Not applicable
Roflumilast	Tablet	250 ug/1	Oral	Camber Pharmaceuticals, Inc.	2023-04-18	Not applicable
Roflumilast	Tablet	500 ug/1	Oral	Micro Labs Limited	2022-10-19	Not applicable

Categories

ATC Codes

R03DX07 — Roflumilast

• R03DX — Other systemic drugs for obstructive airway diseases
• R03D — OTHER SYSTEMIC DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
• R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
• R — RESPIRATORY SYSTEM

Drug Categories

• Acids, Carbocyclic
• Agents to Treat Airway Disease
• Amides
• Amines
• Benzene Derivatives
• Benzoates
• Cycloparaffins
• Cytochrome P-450 CYP1A2 Substrates
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A4 Substrates (strength unknown)
• Cytochrome P-450 Substrates
• Drugs for Obstructive Airway Diseases
• Drugs that are Mainly Renally Excreted
• Phosphodiesterase 4 Inhibitors
• Phosphodiesterase Inhibitors
• Pyridines

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzamides

Alternative Parents

Benzoyl derivatives / Phenol ethers / Phenoxy compounds / Polyhalopyridines / Alkyl aryl ethers / Aryl chlorides / Heteroaromatic compounds / Secondary carboxylic acid amides / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organofluorides / Organochlorides / Organic oxides / Hydrocarbon derivatives / Alkyl fluorides

show 6 more

Substituents

Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzamide / Benzoyl / Carboxamide group / Carboxylic acid derivative / Ether / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organochloride / Organofluoride / Organohalogen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Phenol ether / Phenoxy compound / Polyhalopyridine / Pyridine / Secondary carboxylic acid amide

show 19 more

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound, aromatic ether, benzamides, cyclopropanes, chloropyridine (CHEBI:47657)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

0P6C6ZOP5U

CAS number

162401-32-3

InChI Key

MNDBXUUTURYVHR-UHFFFAOYSA-N

InChI

InChI=1S/C17H14Cl2F2N2O3/c18-11-6-22-7-12(19)15(11)23-16(24)10-3-4-13(26-17(20)21)14(5-10)25-8-9-1-2-9/h3-7,9,17H,1-2,8H2,(H,22,23,24)

IUPAC Name

3-(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide

SMILES

FC(F)OC1=C(OCC2CC2)C=C(C=C1)C(=O)NC1=C(Cl)C=NC=C1Cl

References

Synthesis Reference

王朝阳, 马静君, 郭培良, 黄耀宗, 王利春, 沈芃, 梁隆, & 程志鹏. (2015, March 25). Method for synthesizing roflumilast. CN103012256B.

General References

1. Meyers JA, Taverna J, Chaves J, Makkinje A, Lerner A: Phosphodiesterase 4 inhibitors augment levels of glucocorticoid receptor in B cell chronic lymphocytic leukemia but not in normal circulating hematopoietic cells. Clin Cancer Res. 2007 Aug 15;13(16):4920-7. [Article]
2. Sanz MJ, Cortijo J, Taha MA, Cerda-Nicolas M, Schatton E, Burgbacher B, Klar J, Tenor H, Schudt C, Issekutz AC, Hatzelmann A, Morcillo EJ: Roflumilast inhibits leukocyte-endothelial cell interactions, expression of adhesion molecules and microvascular permeability. Br J Pharmacol. 2007 Oct;152(4):481-92. Epub 2007 Aug 20. [Article]
3. Barone FC, Barton ME, White RF, Legos JJ, Kikkawa H, Shimamura M, Kuratani K, Kinoshita M: Inhibition of phosphodiesterase type 4 decreases stress-induced defecation in rats and mice. Pharmacology. 2008;81(1):11-7. Epub 2007 Aug 28. [Article]
4. Chong J, Poole P, Leung B, Black PN: Phosphodiesterase 4 inhibitors for chronic obstructive pulmonary disease. Cochrane Database Syst Rev. 2011 May 11;(5):CD002309. doi: 10.1002/14651858.CD002309.pub3. [Article]
5. Grootendorst DC, Gauw SA, Verhoosel RM, Sterk PJ, Hospers JJ, Bredenbroker D, Bethke TD, Hiemstra PS, Rabe KF: Reduction in sputum neutrophil and eosinophil numbers by the PDE4 inhibitor roflumilast in patients with COPD. Thorax. 2007 Dec;62(12):1081-7. Epub 2007 Jun 15. [Article]
6. Thappali SR, Varanasi KV, Veeraraghavan S, Vakkalanka SK, Mukkanti K: Simultaneous quantitation of IC87114, roflumilast and its active metabolite roflumilast N-oxide in plasma by LC-MS/MS: application for a pharmacokinetic study. J Mass Spectrom. 2012 Dec;47(12):1612-9. doi: 10.1002/jms.3103. [Article]
7. Giembycz MA, Field SK: Roflumilast: first phosphodiesterase 4 inhibitor approved for treatment of COPD. Drug Des Devel Ther. 2010 Jul 21;4:147-58. doi: 10.2147/dddt.s7667. [Article]
8. Baye J: Roflumilast (daliresp): a novel phosphodiesterase-4 inhibitor for the treatment of severe chronic obstructive pulmonary disease. P T. 2012 Mar;37(3):149-61. [Article]
9. FDA Approved Drug Products: Daliresp (roflumilast) tablets for oral use [Link]
10. FDA Approved Drug Products: Zoryve (roflumilast) cream for topical use [Link]
11. Arcutis Biotherapeutics: FDA Approves Arcutis’ ZORYVE™ (Roflumilast) Cream 0.3% For the Treatment of Plaque Psoriasis in Individuals Age 12 and Older [Link]
12. Health Canada Approved Drug Products: ZORYVE (Roflumilast) Topical Cream [Link]
13. EMA Approved Drug Products: DAXAS (roflumilast) Oral Tablets [Link]
14. FDA Approved Drug Products: ZORYVE® (roflumilast) topical foam, 0.3% (Dec 2023) [Link]
15. FDA Approves Arcutis’ ZORYVE® (roflumilast) Topical Foam, 0.3% for the Treatment of Seborrheic Dermatitis in Individuals Aged 9 Years and Older [Link]

External Links

Human Metabolome Database

HMDB0257288

KEGG Drug

D05744

PubChem Compound

449193

PubChem Substance

175426853

ChemSpider

395793

BindingDB

14774

RxNav

1091836

ChEBI

47657

ChEMBL

CHEMBL193240

ZINC

ZINC000000592419

PharmGKB

PA165948052

PDBe Ligand

ROF

Drugs.com

Drugs.com Drug Page

Wikipedia

Roflumilast

PDB Entries

1xmu / 1xoq / 3g4l

FDA label

Download (255 KB)

MSDS

Download (569 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Chronic Obstructive Pulmonary Disease (COPD)	2
4	Completed	Treatment	Chronic Bronchitis / Chronic Obstructive Pulmonary Disease (COPD) / Emphysema	1
4	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	2
4	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD) / Exacerbation of COPD / Lung Disorder / Respiratory Disorders	1
4	Completed	Treatment	Chronic Obstructive Pulmonary Disease and Allied Conditions	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet	Oral
Tablet	Oral	250 ug/1
Tablet	Oral	500 ug/1
Tablet	Oral	250 MCG
Tablet	Oral	250 ?g
Tablet	Oral	500 mcg
Tablet, film coated	Oral	500 μg
Tablet, film coated	Oral	500 mcg
Tablet	Oral	500.000 mcg
Tablet, film coated	Oral
Powder, for solution	Oral
Aerosol, foam	Topical	3 mg/1g
Cream	Topical	0.3 % w/w
Cream	Topical	3 mg/1g
Tablet, film coated	Oral	0.5 mg

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US8536206	No	2013-09-17	2024-03-08
US8604064	No	2013-12-10	2024-03-08
US5712298	No	1998-01-27	2020-01-27
US8618142	No	2013-12-31	2024-03-08
US8431154	No	2013-04-30	2023-02-19
US9468598	No	2016-10-18	2023-02-19
US9907788	No	2018-03-06	2037-06-07
US11129818	No	2021-09-28	2037-08-25
US10940142	No	2021-03-09	2037-06-07
US9884050	No	2018-02-06	2037-06-07
US11793796	No	2017-06-07	2037-06-07
US11819496	No	2017-06-07	2037-06-07
US11707454	No	2021-12-03	2041-12-03

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	158	Giembycz MA, Field SK: Roflumilast: first phosphodiesterase 4 inhibitor approved for treatment of COPD. Drug Des Devel Ther. 2010 Jul 21;4:147-58. doi: 10.2147/dddt.s7667.
water solubility	Sparingly soluble	Giembycz MA, Field SK: Roflumilast: first phosphodiesterase 4 inhibitor approved for treatment of COPD. Drug Des Devel Ther. 2010 Jul 21;4:147-58. doi: 10.2147/dddt.s7667.
pKa	8.74	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0062 mg/mL	ALOGPS
logP	4.47	ALOGPS
logP	4.45	Chemaxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.3	Chemaxon
pKa (Strongest Basic)	2.4	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	60.45 Å2	Chemaxon
Rotatable Bond Count	7	Chemaxon
Refractivity	93.92 m3·mol-1	Chemaxon
Polarizability	35.9 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9874
Caco-2 permeable	+	0.5235
P-glycoprotein substrate	Non-substrate	0.7295
P-glycoprotein inhibitor I	Non-inhibitor	0.5775
P-glycoprotein inhibitor II	Non-inhibitor	0.622
Renal organic cation transporter	Non-inhibitor	0.8057
CYP450 2C9 substrate	Non-substrate	0.8082
CYP450 2D6 substrate	Non-substrate	0.7705
CYP450 3A4 substrate	Substrate	0.5821
CYP450 1A2 substrate	Inhibitor	0.7732
CYP450 2C9 inhibitor	Inhibitor	0.5686
CYP450 2D6 inhibitor	Non-inhibitor	0.7204
CYP450 2C19 inhibitor	Inhibitor	0.7813
CYP450 3A4 inhibitor	Inhibitor	0.6242
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.8602
Ames test	Non AMES toxic	0.5216
Carcinogenicity	Non-carcinogens	0.8843
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	2.3522 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9704
hERG inhibition (predictor II)	Non-inhibitor	0.6336

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (81 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0f76-0950700000-9d3dc26457cb82e9e2af
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0udi-3000900000-fe5b82c045d7273cc5e7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-0009200000-b1fdd1ea5aa48bb404ba
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0udi-0002900000-f5ccf2c1a4d5e3e416ed
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-1091100000-b898c803614b421abc1b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0f7c-1933100000-f7b9aadf353ee8636b5b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000x-4192000000-4c114fdcda50865ba703
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	176.61873	predicted	DeepCCS 1.0 (2019)
[M+H]+	178.97672	predicted	DeepCCS 1.0 (2019)
[M+Na]+	186.01021	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. cAMP-specific 3',5'-cyclic phosphodiesterase 4 (PDE4) (Protein Group)

Kind

Protein group

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

General Function

Metal ion binding

Specific Function

Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.

---

Components:

Name	UniProt ID
cAMP-specific 3',5'-cyclic phosphodiesterase 4A	P27815
cAMP-specific 3',5'-cyclic phosphodiesterase 4B	Q07343
cAMP-specific 3',5'-cyclic phosphodiesterase 4C	Q08493
cAMP-specific 3',5'-cyclic phosphodiesterase 4D	Q08499

References

1. Giembycz MA, Field SK: Roflumilast: first phosphodiesterase 4 inhibitor approved for treatment of COPD. Drug Des Devel Ther. 2010 Jul 21;4:147-58. doi: 10.2147/dddt.s7667. [Article]
2. FDA Approved Drug Products: Daliresp (roflumilast) tablets for oral use [Link]
3. FDA Approved Drug Products: Zoryve (roflumilast) cream for topical use [Link]

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55