crisaborole Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	5201	906673-24-3

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: staquis crisaborole AN2728 eucrisa	Crisaborole is a phosphodiesterase 4 (PDE-4) inhibitor. PDE-4 inhibition results in increased intracellular cyclic adenosine monophosphate (cAMP) levels. The specific mechanism(s) by which crisaborole exerts its therapeutic action for the treatment of atopic dermatitis is not well defined. Molecular weight: 251.05 Formula: C14H10BNO3 CLOGP: 2.63 LIPINSKI: 0 HAC: 4 HDO: 1 TPSA: 62.48 ALOGS: -4.03 ROTB: 2 Status: ONP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

staquis
crisaborole
AN2728
eucrisa

Crisaborole is a phosphodiesterase 4 (PDE-4) inhibitor. PDE-4 inhibition results in increased intracellular cyclic adenosine monophosphate (cAMP) levels. The specific mechanism(s) by which crisaborole exerts its therapeutic action for the treatment of atopic dermatitis is not well defined.

Molecular weight: 251.05
Formula: C14H10BNO3
CLOGP: 2.63
LIPINSKI: 0
HAC: 4
HDO: 1
TPSA: 62.48
ALOGS: -4.03
ROTB: 2

Status: ONP

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

Drug dosage:

None

ADMET properties:

None

Approvals:

Date	Agency	Company	Orphan
March 27, 2020	EMA	Pfizer Europe MA EEIG
Dec. 14, 2016	FDA	ANACOR PHARMS INC

FDA Adverse Event Reporting System (Female)

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
Application site pain	2144.54	95.96	332	2276	3851	53342607
Burning sensation	712.66	95.96	203	2405	47810	53298648
Application site erythema	253.60	95.96	57	2551	5034	53341424
Dermatitis atopic	169.66	95.96	39	2569	3795	53342663
Drug ineffective	165.50	95.96	199	2409	817046	52529412
Application site pruritus	140.56	95.96	34	2574	4115	53342343
Drug effective for unapproved indication	124.60	95.96	27	2581	2003	53344455
Skin burning sensation	118.38	95.96	37	2571	11573	53334885
Application site swelling	111.49	95.96	20	2588	554	53345904
Eczema	98.81	95.96	39	2569	24143	53322315

FDA Adverse Event Reporting System (Male)

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
Application site pain	1134.63	161.95	163	962	1611	32510790
Burning sensation	400.39	161.95	97	1028	17381	32495020
Application site erythema	171.92	161.95	34	1091	2309	32510092

Pharmacologic Action:

Source	Code	Description
ATC	D11AH06	DERMATOLOGICALS OTHER DERMATOLOGICAL PREPARATIONS OTHER DERMATOLOGICAL PREPARATIONS Agents for dermatitis, excluding corticosteroids
FDA MoA	N0000182960	Phosphodiesterase 4 Inhibitors
FDA EPC	N0000182961	Phosphodiesterase 4 Inhibitor
CHEBI has role	CHEBI:35475	non-steroidal anti-inflammatory drugs
CHEBI has role	CHEBI:50748	antipsoriatic agent
CHEBI has role	CHEBI:68844	PDE4 inhibitors

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Atopic dermatitis	indication	24079001	DOID:3310

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	7.8	acidic

Orange Book patent data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
2%	EUCRISA	ANACOR PHARMS INC	N207695	Dec. 14, 2016	RX	OINTMENT	TOPICAL	8501712	Feb. 16, 2027	METHOD OF TREATING MILD TO MODERATE ATOPIC DERMATITIS.
2%	EUCRISA	ANACOR PHARMS INC	N207695	Dec. 14, 2016	RX	OINTMENT	TOPICAL	9682092	Feb. 16, 2027	METHOD OF TREATING MILD TO MODERATE ATOPIC DERMATITIS.
2%	EUCRISA	ANACOR PHARMS INC	N207695	Dec. 14, 2016	RX	OINTMENT	TOPICAL	8168614	Jan. 20, 2030	METHOD OF TREATING MILD TO MODERATE ATOPIC DERMATITIS.

Orange Book exclusivity data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
2%	EUCRISA	ANACOR PHARMS INC	N207695	Dec. 14, 2016	RX	OINTMENT	TOPICAL	June 14, 2022	PEDIATRIC EXCLUSIVITY
2%	EUCRISA	ANACOR PHARMS INC	N207695	Dec. 14, 2016	RX	OINTMENT	TOPICAL	March 23, 2023	NEW PATIENT POPULATION
2%	EUCRISA	ANACOR PHARMS INC	N207695	Dec. 14, 2016	RX	OINTMENT	TOPICAL	Sept. 23, 2023	PEDIATRIC EXCLUSIVITY

Bioactivity Summary:

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	6.31	SCIENTIFIC LITERATURE	DRUG LABEL
Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A	Enzyme	P54750	PDE1A_HUMAN		IC50	5.21	CHEMBL
High affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A	Enzyme	Q13946	PDE7A_HUMAN		IC50	6.14	CHEMBL

External reference:

ID	Source
Q2R47HGR7P	UNII
4036360	VANDF
C4301781	UMLSCUI
CHEBI:134677	CHEBI
CHEMBL484785	ChEMBL_ID
44591583	PUBCHEM_CID
DB05219	DRUGBANK_ID
D10873	KEGG_DRUG
C543085	MESH_SUPPLEMENTAL_RECORD_UI
9151	IUPHAR_LIGAND_ID
10024	INN_ID
1865953	RXNORM
248463	MMSL
32196	MMSL
017053	NDDF
724007009	SNOMEDCT_US
763593001	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Staquis	HUMAN PRESCRIPTION DRUG LABEL	1	0009-2211	OINTMENT	20 mg	TOPICAL	EXPORT ONLY	1 sections
Eucrisa	HUMAN PRESCRIPTION DRUG LABEL	1	55724-211	OINTMENT	20 mg	TOPICAL	NDA	27 sections