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 8297
cAMP-specific 3',5'-cyclic phosphodiesterase 4B 5 Target ID: CHEMBL2366442 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=27050693	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atopic dermatitis 43 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207695s000lbl.pdf	Primary		Approved 8429	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	30000 mg/m² single, topical dose: 30000 mg/m² 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	30000 mg/m² single, topical dose: 30000 mg/m² 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	30000 mg/m² single, topical dose: 30000 mg/m² 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 Page: p. 120	unhealthy, 2-21 years n = 1021 Health Status: unhealthy Age Group: 2-21 years Sex: M+F Population Size: 1021 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf Page: p. 120	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 Page: p. 120

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 Page: p. 120	unhealthy, 2-21 years n = 1021 Health Status: unhealthy Age Group: 2-21 years Sex: M+F Population Size: 1021 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf Page: p. 120
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 Page: p. 120	unhealthy, 2-21 years n = 1021 Health Status: unhealthy Age Group: 2-21 years Sex: M+F Population Size: 1021 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf Page: p. 120
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 Page: p. 120	unhealthy, 2-21 years n = 1021 Health Status: unhealthy Age Group: 2-21 years Sex: M+F Population Size: 1021 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf Page: p. 120
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 Page: p. 120	unhealthy, 2-21 years n = 1021 Health Status: unhealthy Age Group: 2-21 years Sex: M+F Population Size: 1021 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf Page: p. 120
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 Page: p. 120	unhealthy, 2-21 years n = 1021 Health Status: unhealthy Age Group: 2-21 years Sex: M+F Population Size: 1021 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf Page: p. 120
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 Page: p. 120	unhealthy, 2-21 years n = 1021 Health Status: unhealthy Age Group: 2-21 years Sex: M+F Population Size: 1021 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000MedR.pdf Page: p. 120

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587 substrate 1737	inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2B6 810 CYP2C8 911 CYP2C19 1478 OCT2 647 OATP1B1 788 OAT1 599 OAT3 642 OATP1B3 706 P-gp 1461 BCRP 699	CYP1A2 1054 CYP1A1 349 CYP2B6 664 CYP2E1 667 OCT2 355 OATP1B3 350 OAT1 326 OAT3 339 OATP1B1 406 BCRP 561 P-gp 1537	CYP1A2 701 CYP2B6 547 CYP3A 129

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=72 Page: 72.0	no [IC50 >15 uM]	AN2728 1
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=72 Page: 72.0	no [IC50 >15 uM]	AN2728 1
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=72 Page: 72.0	no [IC50 >15 uM]	AN2728 1
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=72 Page: 72.0	no [IC50 >15 uM]	AN2728 1
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=72 Page: 72.0	no [IC50 >15 uM]	AN2728 1
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=72 Page: 72.0	no [IC50 >15 uM]	AN2728 1
CYP2C9 1819	inhibitor 3277 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 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no	AN7602 1
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no	AN8323 1
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no
CYP2B6 1001	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
CYP2B6 1001	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no	AN7602 1
CYP2B6 1001	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no	AN8323 1
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no	AN8323 1
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no	AN8323 1
CYP3A 298	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
CYP3A 298	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no	AN7602 1
CYP3A 298	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no	AN8323 1
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	no	AN8323 1
OATP1B1 803	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=89 Page: 89.0	no	AN8323 1
OCT2 648	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=89 Page: 89.0	no	AN8323 1
OAT1 603	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=89 Page: 89.0	weak [Inhibition 50 uM]	AN8323 1
OAT3 644	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=89 Page: 89.0	weak [Inhibition 50 uM]	AN8323 1
OATP1B3 715	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=89 Page: 89.0	weak [Inhibition 50 uM]	AN8323 1
CYP2C19 1553	inhibitor 3277 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 1553	inhibitor 3277 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 773	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=89 Page: 89.0	yes	AN8323 1
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	yes	AN8323 1
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	yes	AN8323 1
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	yes	AN8323 1
P-gp 1650	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=89 Page: 89.0	yes	AN8323 1
CYP2C9 1819	inhibitor 3277 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 350	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=88 Page: 88.0	no	AN8323 1
OCT2 355	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=88 Page: 88.0	no	AN8323 1
OAT1 326	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=88 Page: 88.0	weak	AN8323 1
OAT3 339	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=88 Page: 88.0	weak	AN8323 1
OATP1B1 406	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=88 Page: 88.0	weak	AN8323 1
BCRP 561	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=88 Page: 88.0	yes	AN8323 1
CYP1A1 349	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	yes
CYP1A2 1054	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	yes
CYP2B6 664	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	yes
CYP2E1 667	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	yes
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/207695Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	yes
P-gp 1537	substrate 3367 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 1647	inhibitor 1626 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
Discovery and structure-activity study of a novel benzoxaborole anti-inflammatory agent (AN2728) for the potential topical treatment of psoriasis and atopic dermatitis.	2009 Apr 15	19303290
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 Dec	26659931
Crisaborole Topical Ointment, 2% in Adults With Atopic Dermatitis: A Phase 2a, Vehicle-Controlled, Proof-of-Concept Study.	2015 Oct	26461821
Crisaborole Topical Ointment, 2%: A Nonsteroidal, Topical, Anti-Inflammatory Phosphodiesterase 4 Inhibitor in Clinical Development for the Treatment of Atopic Dermatitis.	2016 Apr	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 Feb	26885784
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 Jul	27193740
Crisaborole and its potential role in treating atopic dermatitis: overview of early clinical studies.	2016 Jul	27283509
Pharmacokinetic Profile, Safety, and Tolerability of Crisaborole Topical Ointment, 2% in Adolescents with Atopic Dermatitis: An Open-Label Phase 2a Study.	2016 Mar-Apr	26777394
Tolerability of Crisaborole Ointment for Application on Sensitive Skin Areas: A Randomized, Double-Blind, Vehicle-Controlled Study in Healthy Volunteers.	2016 Oct	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 Sep	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 Sep	27417017

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 `Fri Dec 15 20:24:41 GMT 2023` Edited by `admin` on `Fri Dec 15 20:24:41 GMT 2023`
Record UNII	Q2R47HGR7P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CRISABOROLE

Official 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 [INN]

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