crisaborole 🐶 Veterinary Use | 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:

PropertyValueReference
S (Water solubility) 0.11 mg/mL Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Bocci G, Oprea TI, Benet LZ

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 2060.51 42.08 332 3577 3850 63481263
Burning sensation 684.75 42.08 214 3695 54193 63430920
Dermatitis atopic 283.75 42.08 74 3835 9650 63475463
Application site erythema 248.51 42.08 58 3851 4777 63480336
Drug ineffective 181.31 42.08 266 3643 1044499 62440614
Skin burning sensation 154.70 42.08 49 3860 12685 63472428
Eczema 146.85 42.08 60 3849 32231 63452882
Application site pruritus 129.14 42.08 33 3876 3951 63481162
Drug effective for unapproved indication 119.59 42.08 30 3879 3334 63481779
Application site swelling 106.72 42.08 20 3889 558 63484555
Pruritus 103.98 42.08 119 3790 361334 63123779
Off label use 101.95 42.08 162 3747 674300 62810813
Drug ineffective for unapproved indication 95.31 42.08 45 3864 34018 63451095
Condition aggravated 92.12 42.08 118 3791 402099 63083014
Skin irritation 84.18 42.08 29 3880 9712 63475401
Eyelid irritation 82.80 42.08 16 3893 527 63484586
Erythema 75.76 42.08 72 3837 175679 63309434
Product use in unapproved indication 72.72 42.08 71 3838 179009 63306104
Rash 68.80 42.08 123 3786 560748 62924365
Application site burn 64.59 42.08 14 3895 820 63484293
Eye irritation 55.27 42.08 27 3882 21944 63463169
Therapeutic product effect incomplete 51.47 42.08 50 3859 125006 63360107
Application site discolouration 48.28 42.08 11 3898 810 63484303
Dry skin 46.90 42.08 34 3875 56853 63428260
Application site irritation 44.68 42.08 12 3897 1738 63483375
Pain 44.42 42.08 122 3787 740506 62744607
Application site paraesthesia 44.28 42.08 7 3902 68 63485045
Application site exfoliation 43.01 42.08 9 3900 445 63484668

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 1121.75 106.77 171 1548 1737 34953475
Burning sensation 422.54 106.77 110 1609 18284 34936928
Drug ineffective 205.28 106.77 171 1548 456580 34498632
Dermatitis atopic 197.65 106.77 47 1672 5300 34949912
Application site erythema 171.40 106.77 36 1683 2300 34952912

FDA Adverse Event Reporting System (Geriatric)

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 2029.31 59.89 328 4008 4419 79735633
Burning sensation 627.15 59.89 198 4138 58434 79681618
Drug ineffective 367.78 59.89 363 3973 1080550 78659502
Application site erythema 340.18 59.89 74 4262 5036 79735016
Dermatitis atopic 290.35 59.89 74 4262 9982 79730070
Off label use 182.06 59.89 233 4103 906982 78833070
Application site pruritus 170.92 59.89 40 4296 3770 79736282
Condition aggravated 154.35 59.89 161 4175 500963 79239089
Eczema 153.81 59.89 64 4272 40754 79699298
Pruritus 143.78 59.89 139 4197 394509 79345543
Skin burning sensation 133.69 59.89 43 4293 13229 79726823
Drug ineffective for unapproved indication 133.55 59.89 62 4274 51176 79688876
Rash 114.28 59.89 148 4188 578210 79161842
Erythema 107.20 59.89 92 4244 223198 79516854
Skin irritation 95.39 59.89 32 4304 11208 79728844
Application site swelling 91.63 59.89 18 4318 735 79739317
Therapeutic product effect incomplete 90.43 59.89 69 4267 141576 79598476
Application site irritation 76.56 59.89 18 4318 1726 79738326
Application site discolouration 71.56 59.89 15 4321 849 79739203
Dry skin 71.35 59.89 45 4291 67950 79672102
Product use in unapproved indication 67.04 59.89 75 4261 250284 79489768
Application site burn 65.65 59.89 14 4322 861 79739191

FDA Adverse Event Reporting System (Pediatric)

None

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 agent
CHEBI has role CHEBI:50748 antipsoriatic drug
CHEBI has role CHEBI:68844 phosphodiesterase IV inhibitors

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

DiseaseRelationSNOMED_IDDOID
Atopic dermatitis indication 24079001 DOID:3310




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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 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
Beta-lactamase Enzyme IC50 6.17 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
10024 INN_ID
9151 IUPHAR_LIGAND_ID
248463 MMSL
32196 MMSL
017053 NDDF
724007009 SNOMEDCT_US
763593001 SNOMEDCT_US
1865953 RXNORM
C543085 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Staquis HUMAN PRESCRIPTION DRUG LABEL 1 0009-2211 OINTMENT 20 mg TOPICAL EXPORT ONLY 1 sections
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
Eucrisa HUMAN PRESCRIPTION DRUG LABEL 1 55724-211 OINTMENT 20 mg TOPICAL NDA 27 sections