Crisaborole

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H10BNO3
Molecular Weight	251.045
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OB1OCC2=C1C=CC(OC3=CC=C(C=C3)C#N)=C2

InChI

InChIKey=USZAGAREISWJDP-UHFFFAOYSA-N

InChI=1S/C14H10BNO3/c16-8-10-1-3-12(4-2-10)19-13-5-6-14-11(7-13)9-18-15(14)17/h1-7,17H,9H2

HIDE SMILES / InChI

Molecular Formula	C14H10BNO3
Molecular Weight	251.045
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=19303290
Curator's Comment: Description was created using several sources including:| https://www.ncbi.nlm.nih.gov/pubmed/27335049 | https://www.ncbi.nlm.nih.gov/pubmed/27525671 | https://www.ncbi.nlm.nih.gov/pubmed/27417017 | https://www.ncbi.nlm.nih.gov/pubmed/?term=27050693

Crisaborole is a topically administered, boron-containing, anti-inflammatory compound that inhibits the phosphodiesterase-4 (PDE4) activity and thereby suppresses the cytokine release of TNFalpha, IL-12, IL-23 and other cytokines. PDE4 is an an enzyme that converts the intracellular second messenger 3'5'-cyclic adenosine monophosphate (cAMP) into the active metabolite adenosine monophosphate (AMP). By inhibiting PDE4 and thus increasing levels of cAMP, crisaborole controls inflammation. The use of boron chemistry enabled synthesis of a low-molecular-weight compound (251 daltons), thereby facilitating effective penetration of crisaborole through human skin. Crisaborole is in clinical development for the topical treatment of psoriasis and being pursued for the topical treatment of atopic dermatitis. Preliminary studies in children and adults demonstrated favorable efficacy and safety profiles. Crisaborole may represent an anti-inflammatory option that safely minimizes the symptoms and severity of AD and that can be used for both acute and long-term management.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
cAMP-specific 3',5'-cyclic phosphodiesterase 4A 3 Target ID: CHEMBL2366459 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=27050693	Inhibitor 8504
cAMP-specific 3',5'-cyclic phosphodiesterase 4B 6 Target ID: CHEMBL2366442 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=27050693	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atopic dermatitis 64 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207695s000lbl.pdf	Primary		Approved 8583	EUCRISA Approved Use EUCRISA is indicated for topical treatment of mild to moderate atopic dermatitis in patients 2 years of age and older. Launch Date 2016

C_max

Value	Dose	Co-administered	Analyte	Population
105 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26777394	3 mg/cm² single, topical dose: 3 mg/cm² route of administration: Topical experiment type: SINGLE co-administered:		CRISABOROLE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN
163.7 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31657024	435 mg single, topical dose: 435 mg route of administration: Topical experiment type: SINGLE co-administered:		CRISABOROLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
448 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26777394	3 mg/cm² single, topical dose: 3 mg/cm² route of administration: Topical experiment type: SINGLE co-administered:		CRISABOROLE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN
1171 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31657024	435 mg single, topical dose: 435 mg route of administration: Topical experiment type: SINGLE co-administered:		CRISABOROLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
7.17 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26777394	3 mg/cm² single, topical dose: 3 mg/cm² route of administration: Topical experiment type: SINGLE co-administered:		CRISABOROLE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
3% DRUG LABEL https://nctr-crs.fda.gov/fdalabel/services/spl/set-ids/609b77de-1ca3-4783-b8f5-01a9c0f1d77d/spl-doc?hl=crisaborole			CRISABOROLE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
2 % 2 times / day steady, topical Recommended Dose: 2 %, 2 times / day Route: topical Route: steady Dose: 2 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf	unhealthy, 2-21 years Health Status: unhealthy Age Group: 2-21 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf	Disc. AE: Application site pain, Impetigo... Other AEs: Application site rash... AEs leading to discontinuation/dose reduction: Application site pain (moderate\|severe, 3 patients) Impetigo (moderate, 1 patient) Application site urticaria (mild\|moderate, 2 patients) Dermatitis atopic (severe, 1 patient) Application site irritation (mild, 1 patient) Other AEs: Application site rash (moderate, 1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf

AEs

AE	Significance	Dose	Population
Application site irritation	mild, 1 patient Disc. AE	2 % 2 times / day steady, topical Recommended Dose: 2 %, 2 times / day Route: topical Route: steady Dose: 2 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf	unhealthy, 2-21 years Health Status: unhealthy Age Group: 2-21 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf
Application site urticaria	mild\|moderate, 2 patients Disc. AE	2 % 2 times / day steady, topical Recommended Dose: 2 %, 2 times / day Route: topical Route: steady Dose: 2 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf	unhealthy, 2-21 years Health Status: unhealthy Age Group: 2-21 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf
Application site rash	moderate, 1 patient	2 % 2 times / day steady, topical Recommended Dose: 2 %, 2 times / day Route: topical Route: steady Dose: 2 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf	unhealthy, 2-21 years Health Status: unhealthy Age Group: 2-21 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf
Impetigo	moderate, 1 patient Disc. AE	2 % 2 times / day steady, topical Recommended Dose: 2 %, 2 times / day Route: topical Route: steady Dose: 2 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf	unhealthy, 2-21 years Health Status: unhealthy Age Group: 2-21 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf
Application site pain	moderate\|severe, 3 patients Disc. AE	2 % 2 times / day steady, topical Recommended Dose: 2 %, 2 times / day Route: topical Route: steady Dose: 2 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf	unhealthy, 2-21 years Health Status: unhealthy Age Group: 2-21 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf
Dermatitis atopic	severe, 1 patient Disc. AE	2 % 2 times / day steady, topical Recommended Dose: 2 %, 2 times / day Route: topical Route: steady Dose: 2 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf	unhealthy, 2-21 years Health Status: unhealthy Age Group: 2-21 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 substrate 1946	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 OCT2 779 OATP1B1 1079 OAT1 725 OAT3 747 OATP1B3 961 P-gp 1741 BCRP 910	CYP1A2 1197 CYP1A1 389 CYP2B6 776 CYP2E1 729 OCT2 434 OATP1B3 435 OAT1 395 OAT3 391 OATP1B1 503 BCRP 697 P-gp 2052	CYP1A2 832 CYP2B6 669 CYP3A 142

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=72 Page: 72.0	no [IC50 >15 uM]	AN2728 1
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=72 Page: 72.0	no [IC50 >15 uM]	AN2728 1
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=72 Page: 72.0	no [IC50 >15 uM]	AN2728 1
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=72 Page: 72.0	no [IC50 >15 uM]	AN2728 1
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=72 Page: 72.0	no [IC50 >15 uM]	AN2728 1
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=72 Page: 72.0	no [IC50 >15 uM]	AN2728 1
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no [Ki 8.96 uM]		no (co-administration study) Comment: The most sensitive enzyme, CYP2C9, was further investigated for drug interaction potential in a clinical trial (AN2728-PK-101) using 25 mg oral dose of warfarin as a CYP2C9 substrate. The results of this clinical trial showed there was no drug interaction potential. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no	AN7602 1
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no	AN8323 1
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no	AN7602 1
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no	AN8323 1
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no	AN8323 1
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no	AN8323 1
CYP3A 317	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
CYP3A 317	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no	AN7602 1
CYP3A 317	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no	AN8323 1
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no	AN8323 1
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=89 Page: 89.0	no	AN8323 1
OCT2 782	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=89 Page: 89.0	no	AN8323 1
OAT1 730	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=89 Page: 89.0	weak [Inhibition 50 uM]	AN8323 1
OAT3 749	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=89 Page: 89.0	weak [Inhibition 50 uM]	AN8323 1
OATP1B3 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=89 Page: 89.0	weak [Inhibition 50 uM]	AN8323 1
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=72 Page: 72.0	yes [IC50 25.3 uM]	AN2728 1
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	yes [Ki 22.3 uM]		no (co-administration study) Comment: To address the potential for crisaborole to inhibit CYP2C19 following clinical application of Crisaborole Ointment, 2%, the exposure of crisaborole, as determined in the maximal use PK trial (AN2728-AD-102) conducted in pediatric subjects with AD, was considered for the calculation of I/Ki. In this study, after topical administration of Crisaborole Ointment, 2% at a dose of 3 mg/cm2 applied to treatable BSA (mean %BSA = 48.7%), the mean ±SD plasma Cmax on Day 8 was 0.506 ± 0.781 μM (127± 196 ng/mL). Hence the ratios of [I]/ Ki for competitive inhibition (0.506/8.96 or 0.056) and metabolismbased inhibition (0.506/22.3 or 0.023) would be <0.1 and the corresponding R values would be < 1.1 which indicates that the probability of crisaborole to inhibit CYP2C19 under conditions of clinical use is low. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=89 Page: 89.0	yes	AN8323 1
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	yes	AN8323 1
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	yes	AN8323 1
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	yes	AN8323 1
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=89 Page: 89.0	yes	AN8323 1
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	yes	AN8323 1	no (co-administration study) Comment: The most sensitive enzyme, CYP2C9, was further investigated for drug interaction potential in a clinical trial (AN2728-PK-101) using 25 mg oral dose of warfarin as a CYP2C9 substrate. The results of this clinical trial showed there was no drug interaction potential. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0

Drug as victim

Target	Modality	Activity	Metabolite
OATP1B3 435	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=88 Page: 88.0	no	AN8323 1
OCT2 434	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=88 Page: 88.0	no	AN8323 1
OAT1 395	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=88 Page: 88.0	weak	AN8323 1
OAT3 391	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=88 Page: 88.0	weak	AN8323 1
OATP1B1 503	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=88 Page: 88.0	weak	AN8323 1
BCRP 697	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=88 Page: 88.0	yes	AN8323 1
CYP1A1 389	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	yes
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	yes
CYP2B6 776	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	yes
CYP2E1 729	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	yes
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	yes
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=88 Page: 88.0	yes	AN8323 1

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:134677	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:134677
ChemicalBook	CB42518350	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB42518350
MolPort	MolPort-023-332-548	https://www.molport.com/shop/molecule-link/MolPort-023-332-548
ZINC	ZINC000169748244	http://zinc15.docking.org/substances/ZINC000169748244

PubMed

Title	Date	PubMed
Tolerability of Crisaborole Ointment for Application on Sensitive Skin Areas: A Randomized, Double-Blind, Vehicle-Controlled Study in Healthy Volunteers.	2016-10	27335049
Treatment of Skin Inflammation with Benzoxaborole Phosphodiesterase Inhibitors: Selectivity, Cellular Activity, and Effect on Cytokines Associated with Skin Inflammation and Skin Architecture Changes.	2016-09	27353073
Efficacy and safety of crisaborole ointment, a novel, nonsteroidal phosphodiesterase 4 (PDE4) inhibitor for the topical treatment of atopic dermatitis (AD) in children and adults.	2016-09	27417017
Crisaborole Topical Ointment, 2% in Patients Ages 2 to 17 Years with Atopic Dermatitis: A Phase 1b, Open-Label, Maximal-Use Systemic Exposure Study.	2016-07	27193740
Crisaborole and its potential role in treating atopic dermatitis: overview of early clinical studies.	2016-07	27283509
Assessing the New and Emerging Treatments for Atopic Dermatitis.	2016-06	27525671
Crisaborole Topical Ointment, 2%: A Nonsteroidal, Topical, Anti-Inflammatory Phosphodiesterase 4 Inhibitor in Clinical Development for the Treatment of Atopic Dermatitis.	2016-04	27050693
Post Hoc Analyses of the Effect of Crisaborole Topical Ointment, 2% on Atopic Dermatitis: Associated Pruritus from Phase 1 and 2 Clinical Studies.	2016-02	26885784
Pharmacokinetic Profile, Safety, and Tolerability of Crisaborole Topical Ointment, 2% in Adolescents with Atopic Dermatitis: An Open-Label Phase 2a Study.	2016-01-19	26777394
A Phase 2, Randomized, Controlled, Dose-Ranging Study Evaluating Crisaborole Topical Ointment, 0.5% and 2% in Adolescents With Mild to Moderate Atopic Dermatitis.	2015-12	26659931
Crisaborole Topical Ointment, 2% in Adults With Atopic Dermatitis: A Phase 2a, Vehicle-Controlled, Proof-of-Concept Study.	2015-10	26461821
Discovery and structure-activity study of a novel benzoxaborole anti-inflammatory agent (AN2728) for the potential topical treatment of psoriasis and atopic dermatitis.	2009-04-15	19303290

Patents

Sample Use Guides

In Vivo Use Guide

2% AN2728 applied twice daily for up to 28 days in children, adolescents, and adults (ages 2 years and older) with atopic dermatitis

Route of Administration: Topical

In Vitro Use Guide

In vitro experiments showed that crisaborole inhibits cytokine production from peripheral blood mononuclear cells in a pattern similar to other PDE4 inhibitors and distinct from corticosteroids.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:09:33 GMT 2025` Edited by `admin` on `Mon Mar 31 20:09:33 GMT 2025`
Record UNII	Q2R47HGR7P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Crisaborole

Official Name

English

crisaborole [INN]

Preferred Name

English

AN-2728

Code

English

EUCRISA

Brand Name

English

BENZONITRILE, 4-((1,3-DIHYDRO-1-HYDROXY-2,1-BENZOXABOROL-5-YL)OXY)-

Systematic Name

English

CRISABOROLE [MI]

Common Name

English

CRISABOROLE [ORANGE BOOK]

Common Name

English

AN2728

Code

English

4-((1-HYDROXY-1,3-DIHYDROBENZO(C)(1,2)OXABOROL-6-YL)OXY)BENZONITRILE

Systematic Name

English

CRISABOROLE [USAN]

Common Name

English

Crisaborole [WHO-DD]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000182961