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

Stem definitionDrug idCAS RN
5201 906673-24-3

Description:

MoleculeDescription

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:

DateAgencyCompanyOrphan
March 27, 2020 EMA Pfizer Europe MA EEIG
Dec. 14, 2016 FDA ANACOR PHARMS INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients 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 termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients 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:

SourceCodeDescription
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)

DiseaseRelationSNOMED_IDDOID
Atopic dermatitis indication 24079001 DOID:3310

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.8 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent 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 strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
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:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Phosphodiesterase 4 Enzyme INHIBITOR IC50 6.31 SCIENTIFIC LITERATURE DRUG LABEL
Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A Enzyme IC50 5.21 CHEMBL
High affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A Enzyme IC50 6.14 CHEMBL

External reference:

IDSource
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:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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