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roflumilast 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
phosphodiesterase IV (PDE IV) inhibitors	3531	162401-32-3

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: libertek roflumilast daxas daliresp BY217 B9302-107 BYK20869	Roflumilast and its active metabolite (roflumilast N-oxide) are selective inhibitors of phosphodiesterase 4 (PDE4). Roflumilast and roflumilast N-oxide inhibition of PDE4 (a major cyclic-3′,5′-adenosine monophosphate (cyclic AMP)-metabolizing enzyme in lung tissue) activity leads to accumulation of intracellular cyclic AMP. While the specific mechanism(s) by which DALIRESP exerts its therapeutic action in COPD patients is not well defined, it is thought to be related to the effects of increased intracellular cyclic AMP in lung cells. Molecular weight: 403.21 Formula: C17H14Cl2F2N2O3 CLOGP: 3.12 LIPINSKI: 0 HAC: 5 HDO: 1 TPSA: 60.45 ALOGS: -4.81 ROTB: 7 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

libertek
roflumilast
daxas
daliresp
BY217
B9302-107
BYK20869

Roflumilast and its active metabolite (roflumilast N-oxide) are selective inhibitors of phosphodiesterase 4 (PDE4). Roflumilast and roflumilast N-oxide inhibition of PDE4 (a major cyclic-3′,5′-adenosine monophosphate (cyclic AMP)-metabolizing enzyme in lung tissue) activity leads to accumulation of intracellular cyclic AMP. While the specific mechanism(s) by which DALIRESP exerts its therapeutic action in COPD patients is not well defined, it is thought to be related to the effects of increased intracellular cyclic AMP in lung cells.

Molecular weight: 403.21
Formula: C17H14Cl2F2N2O3
CLOGP: 3.12
LIPINSKI: 0
HAC: 5
HDO: 1
TPSA: 60.45
ALOGS: -4.81
ROTB: 7

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.50	mg	O

ADMET properties:

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Property	Value	Reference
CL (Clearance)	2.20 mL/min/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	15.10 hours	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	1.92 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.01 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Feb. 28, 2011	EMA
Feb. 28, 2011	FDA	ASTRAZENECA PHARMS

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Chronic obstructive pulmonary disease	186.81	24.13	89	4215	62597	63422121
Dyspnoea	118.63	24.13	181	4123	661132	62823586
Full blood count abnormal	94.22	24.13	45	4259	31672	63453046
Wheezing	87.14	24.13	63	4241	95532	63389186
Asthma	85.47	24.13	70	4234	127491	63357227
Pneumothorax spontaneous	80.09	24.13	17	4287	817	63483901
Emphysema	63.76	24.13	25	4279	10913	63473805
Adenocarcinoma	58.76	24.13	17	4287	2933	63481785
Sleep disorder due to a general medical condition	57.74	24.13	24	4280	12164	63472554
Hypercapnia	56.34	24.13	19	4285	5412	63479306

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Dyspnoea	186.05	28.20	220	3772	376562	34576377
Chronic obstructive pulmonary disease	166.64	28.20	90	3902	48828	34904111
Product prescribing error	88.70	28.20	46	3946	22881	34930058
Weight decreased	81.22	28.20	100	3892	176201	34776738
Asthma-chronic obstructive pulmonary disease overlap syndrome	54.56	28.20	15	3977	1272	34951667
Cough	50.30	28.20	73	3919	150067	34802872
Asthma	49.25	28.20	40	3952	42616	34910323
Nasal obstruction	48.58	28.20	12	3980	668	34952271
Sinus pain	47.78	28.20	12	3980	715	34952224
Wheezing	43.98	28.20	37	3955	41365	34911574

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Chronic obstructive pulmonary disease	281.44	26.24	138	6412	85281	79652557
Dyspnoea	255.51	26.24	330	6220	856695	78881143
Asthma	103.70	26.24	87	6463	135008	79602830
Product prescribing error	89.56	26.24	52	6498	44761	79693077
Wheezing	89.23	26.24	75	6475	116589	79621249
Full blood count abnormal	89.03	26.24	50	6500	40424	79697414
Weight decreased	88.23	26.24	126	6424	355072	79382766
Emphysema	77.40	26.24	34	6516	16266	79721572
Pneumothorax spontaneous	62.50	26.24	16	6534	1438	79736400
Sputum discoloured	59.33	26.24	31	6519	21712	79716126

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	R03DX07	RESPIRATORY SYSTEM DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES OTHER SYSTEMIC DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES Other systemic drugs for obstructive airway diseases
CHEBI has role	CHEBI:49167	anti-asthmatic drugs
CHEBI has role	CHEBI:68844	phosphodiesterase IV inhibitors
FDA EPC	N0000182961	Phosphodiesterase 4 Inhibitor
FDA MoA	N0000182960	Phosphodiesterase 4 Inhibitors

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID
Plaque psoriasis	indication	200965009
Severe chronic obstructive pulmonary disease	indication	313299006
COPD Associated with Chronic Bronchitis	indication
Suicidal thoughts	contraindication	6471006
Mood swings	contraindication	18963009
Depressive disorder	contraindication	35489007
Hepatic failure	contraindication	59927004
Weight loss	contraindication	89362005
Suicidal	contraindication	267073005

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	10.92	acidic
pKa2	2.32	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
0.3%	ZORYVE	ARCUTIS	N215985	July 29, 2022	RX	CREAM	TOPICAL	9907788	June 7, 2037	TOPICAL TREATMENT OF PLAQUE PSORIASIS, INCLUDING INTERTRIGINOUS AREAS, IN PATIENTS 12 YEARS OF AGE AND OLDER. (1)
0.3%	ZORYVE	ARCUTIS	N215985	July 29, 2022	RX	CREAM	TOPICAL	11129818	Aug. 25, 2037	TOPICAL TREATMENT OF PLAQUE PSORIASIS, INCLUDING INTERTRIGINOUS AREAS, IN PATIENTS 12 YEARS OF AGE AND OLDER. (1)
250MCG	DALIRESP	ASTRAZENECA	N022522	Jan. 23, 2018	RX	TABLET	ORAL	8536206	March 8, 2024	TREATMENT TO REDUCE THE RISK OF COPD EXACERBATIONS IN PATIENTS WITH SEVERE COPD ASSOCIATED WITH CHRONIC BRONCHITIS AND A HISTORY OF EXACERBATIONS
250MCG	DALIRESP	ASTRAZENECA	N022522	Jan. 23, 2018	RX	TABLET	ORAL	8604064	March 8, 2024	TREATMENT TO REDUCE THE RISK OF COPD EXACERBATIONS IN PATIENTS WITH SEVERE COPD ASSOCIATED WITH CHRONIC BRONCHITIS AND A HISTORY OF EXACERBATIONS
500MCG	DALIRESP	ASTRAZENECA	N022522	Feb. 28, 2011	RX	TABLET	ORAL	8536206	March 8, 2024	TREATMENT TO REDUCE THE RISK OF COPD EXACERBATIONS IN PATIENTS WITH SEVERE COPD ASSOCIATED WITH CHRONIC BRONCHITIS AND A HISTORY OF EXACERBATIONS
500MCG	DALIRESP	ASTRAZENECA	N022522	Feb. 28, 2011	RX	TABLET	ORAL	8604064	March 8, 2024	TREATMENT TO REDUCE THE RISK OF COPD EXACERBATIONS IN PATIENTS WITH SEVERE COPD ASSOCIATED WITH CHRONIC BRONCHITIS AND A HISTORY OF EXACERBATIONS

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
0.3%	ZORYVE	ARCUTIS	N215985	July 29, 2022	RX	CREAM	TOPICAL	July 29, 2025	NEW PRODUCT
250MCG	ROFLUMILAST	MSN	A208256	Sept. 7, 2022	RX	TABLET	ORAL	April 18, 2023	PATENT CHALLENGE
500MCG	ROFLUMILAST	HETERO LABS LTD III	A208213	Nov. 23, 2018	RX	TABLET	ORAL	April 17, 2023	PATENT CHALLENGE
500MCG	ROFLUMILAST	STRIDES PHARMA	A208247	March 30, 2020	RX	TABLET	ORAL	April 17, 2023	PATENT CHALLENGE
500MCG	ROFLUMILAST	MYLAN	A208257	July 13, 2018	RX	TABLET	ORAL	April 17, 2023	PATENT CHALLENGE

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Phosphodiesterase 4	Enzyme	P27815 Q07343 Q08493 Q08499	PDE4A_HUMAN PDE4B_HUMAN PDE4C_HUMAN PDE4D_HUMAN	INHIBITOR	IC50	9.10	CHEMBL	CHEMBL
cAMP-specific 3',5'-cyclic phosphodiesterase 4B	Enzyme	Q07343	PDE4B_HUMAN		IC50	9.40	CHEMBL
cAMP-specific 3',5'-cyclic phosphodiesterase 4A	Enzyme	P27815	PDE4A_HUMAN		IC50	9.46	CHEMBL
cAMP-specific 3',5'-cyclic phosphodiesterase 4D	Enzyme	Q08499	PDE4D_HUMAN		IC50	9.57	CHEMBL
Phosphodiesterase	Enzyme		Q8WQX9_9TRYP		Ki	5.50	CHEMBL

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External reference:

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ID	Source
ROF	PDB_CHEM_ID
013499	NDDF
0P6C6ZOP5U	UNII
1091836	RXNORM
180364	MMSL
27361	MMSL
358833	MMSL
4030722	VUID
4030722	VANDF
448971002	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Daliresp	HUMAN PRESCRIPTION DRUG LABEL	1	0310-0088	TABLET	250 ug	ORAL	NDA	27 sections
Daliresp	HUMAN PRESCRIPTION DRUG LABEL	1	0310-0088	TABLET	250 ug	ORAL	NDA	27 sections
Daliresp	HUMAN PRESCRIPTION DRUG LABEL	1	0310-0095	TABLET	500 ug	ORAL	NDA	27 sections
Daliresp	HUMAN PRESCRIPTION DRUG LABEL	1	0310-0095	TABLET	500 ug	ORAL	NDA	27 sections
Roflumilast	HUMAN PRESCRIPTION DRUG LABEL	1	0378-1905	TABLET	500 ug	ORAL	ANDA	30 sections
Roflumilast	HUMAN PRESCRIPTION DRUG LABEL	1	13668-476	TABLET	500 ug	ORAL	ANDA	26 sections
Roflumilast	HUMAN PRESCRIPTION DRUG LABEL	1	13668-476	TABLET	500 ug	ORAL	ANDA	26 sections
Roflumilast	HUMAN PRESCRIPTION DRUG LABEL	1	31722-623	TABLET	500 ug	ORAL	ANDA	27 sections
Roflumilast	HUMAN PRESCRIPTION DRUG LABEL	1	31722-623	TABLET	500 ug	ORAL	ANDA	27 sections
Roflumilast	HUMAN PRESCRIPTION DRUG LABEL	1	31722-676	TABLET	250 ug	ORAL	ANDA	27 sections

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