OCLACITINIB

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H23N5O2S
Molecular Weight	337.44
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNS(=O)(=O)C[C@H]1CC[C@@H](CC1)N(C)C2=C3C=CNC3=NC=N2

InChI

InChIKey=HJWLJNBZVZDLAQ-HAQNSBGRSA-N

InChI=1S/C15H23N5O2S/c1-16-23(21,22)9-11-3-5-12(6-4-11)20(2)15-13-7-8-17-14(13)18-10-19-15/h7-8,10-12,16H,3-6,9H2,1-2H3,(H,17,18,19)/t11-,12-

HIDE SMILES / InChI

Molecular Formula	C15H23N5O2S
Molecular Weight	337.44
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24495176
Curator's Comment: Description was created based on several sources, including http://www.fda.gov/downloads/AnimalV.../UCM363901.pdf

Oclacitinib (PF03394197) is a novel Janus kinase inhibitor with activity against cytokines involved in allergy. Oclacitinib inhibited JAK family members by 50% at concentrations (IC50 's) ranging from 10 to 99 nM and did not inhibit a panel of 38 non-JAK kinases (IC50 's > 1000 nm). Oclacitinib was most potent at inhibiting JAK1 (IC50 = 10 nm). Oclacitinib also inhibited the function of JAK1-dependent cytokines involved in allergy and inflammation (IL-2, IL-4, IL-6, and IL-13) as well as pruritus (IL-31) at IC50 's ranging from 36 to 249 nM. Oclacitinib as oclacitinib maleate is approved for control of pruritus associated with allergic dermatitis and control of atopic dermatitis in dogs at least 12 months of age.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Tyrosine-protein kinase JAK3 27 Target ID: CHEMBL2148 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24495176	Inhibitor 8297	99.0 nM [IC50]
Tyrosine-protein kinase JAK2 55 Target ID: CHEMBL2971 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24495176	Inhibitor 8297	18.0 nM [IC50]
Tyrosine-protein kinase JAK1 38 Target ID: CHEMBL2835 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24495176	Inhibitor 8297	10.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atopic dermatitis 43 Sources: http://www.fda.gov/downloads/AnimalV.../UCM363901.pdf	Primary		Approved 8429	APOQUEL Approved Use Control of pruritus associated with allergic dermatitis and control of atopic dermatitis in dogs at least 12 months of age. Launch Date 2013

PubMed

Title	Date	PubMed
Efficacy and safety of oclacitinib for the control of pruritus and associated skin lesions in dogs with canine allergic dermatitis.	2013 Oct	23829933
Oclacitinib (APOQUEL(®)) is a novel Janus kinase inhibitor with activity against cytokines involved in allergy.	2014 Aug	24495176

Patents

Sample Use Guides

In Vivo Use Guide

Dogs: Oclacitinib, administered orally at a dose of 0.4–0.6 mg/kg twice daily is safe and efficacious in controlling the pruritus associated with allergic dermatitis.

Route of Administration: Oral

In Vitro Use Guide

Oclacitinib inhibited JAK family members by 50% at concentrations (IC50 's) ranging from 10 to 99 nm

Substance Class	Chemical Created by `admin` on `Fri Dec 15 20:15:38 GMT 2023` Edited by `admin` on `Fri Dec 15 20:15:38 GMT 2023`
Record UNII	99GS5XTB51
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OCLACITINIB

Official Name

English

N-METHYL(TRANS-4-(METHYL(7H-PYRROLO(2,3-D)PYRIMIDIN-4-YL)AMINO)CYCLOHEXYL)METHANESULFONAMIDE

Systematic Name

English

OCLACITINIB [GREEN BOOK]

Common Name

English

CYCLOHEXANEMETHANESULFONAMIDE, N-METHYL-4-(METHYL-7H-PYRROLO(2,3-D)PYRIMIDIN-4-YLAMINO)-, TRANS-

Systematic Name

English

oclacitinib [INN]

Common Name

English

PF-03394197

Code

English

PF 03394197

Code

English

OCLACITINIB [USAN]

Common Name

English

OCLACITINIB [MI]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 520.1604