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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H21F2N7O
Molecular Weight 389.4031
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BREPOCITINIB

SMILES

Cn1cc(cn1)Nc2nccc(n2)N3C[C@]4([H])CC[C@]([H])(C3)N4C(=O)[C@]5([H])CC5(F)F

InChI

InChIKey=BUWBRTXGQRBBHG-MJBXVCDLSA-N
InChI=1S/C18H21F2N7O/c1-25-8-11(7-22-25)23-17-21-5-4-15(24-17)26-9-12-2-3-13(10-26)27(12)16(28)14-6-18(14,19)20/h4-5,7-8,12-14H,2-3,6,9-10H2,1H3,(H,21,23,24)/t12-,13+,14-/m0/s1

HIDE SMILES / InChI

Molecular Formula C18H21F2N7O
Molecular Weight 389.4031
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

PF-06700841 is an inhibitor of JAK1 and TYK2 kinases. PF-06700841 tosylate salt is potentially a treatment of systemic lupus erythematosus and plaque psoriasis.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2091 ng/mL
175 mg 1 times / day multiple, oral
dose: 175 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BREPOCITINIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
16180 ng × h/mL
175 mg 1 times / day multiple, oral
dose: 175 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BREPOCITINIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.5 h
175 mg 1 times / day multiple, oral
dose: 175 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BREPOCITINIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
PubMed

PubMed

TitleDatePubMed
The Safety, Tolerability, Pharmacokinetics, and Pharmacodynamics of a TYK2/JAK1 Inhibitor (PF-06700841) in Healthy Subjects and Patients With Plaque Psoriasis.
2018 Apr
Janus kinase inhibitors for the treatment of inflammatory bowel diseases: developments from phase I and phase II clinical trials.
2018 Jul
Dual Inhibition of TYK2 and JAK1 for the Treatment of Autoimmune Diseases: Discovery of (( S)-2,2-Difluorocyclopropyl)((1 R,5 S)-3-(2-((1-methyl-1 H-pyrazol-4-yl)amino)pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone (PF-06700841).
2018 Oct 11
Patents

Patents

Sample Use Guides

4 week induction with 30-60 mg PF-06700841 once daily, followed by 8 week chronic administration of 10-100 mg PF-06700841 once daily
Route of Administration: Oral
Test articles were prepared as 30 m stocks in DMSO. A 11-point 2.5 dilution series was created in DMSO with a top concentration of 5 mM. Further dilution was done by adding 4 μΙ of the above test article solutions into 96 μΙ of PBS with a top concentration of 200 μΜ. Human whole blood was collected from healthy donors via vein puncture into Vacutainer collection tubes containing sodium heparin (Catalog No. 366480; Becton Dickinson, Franklin Lakes, NJ). Blood was warmed to 37°C prior to use. Human whole blood was aliquoted in 96-well, deep-well, V-bottom plates and treated with compounds at 11 different concentrations (0.2% DMSO final) at 37°C for 60 minutes. This was followed by a challenge with IFNa for 15 minutes. Samples were treated with warm 1X Lyse/Fix buffer to terminate activation and further incubated at 37°C for 20 minutes to lyse red blood cells. Plates were centrifuged at 300 x g for 5 minutes, supernatant was aspirated, and cells were washed with 800 μΙ per well of staining buffer. The washed cell pellets were resuspended with 350 μΙ per well of pre-chilled 90% methanol, and incubated on ice for 30 minutes. After the removal of 90% methanol, cells were washed once with staining buffer. Cell pellets were resuspended in staining buffer containing anti-pSTAT3-AlexaFluor647, and incubated at room temperature in the dark overnight.
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:22:00 UTC 2021
Edited
by admin
on Sat Jun 26 15:22:00 UTC 2021
Record UNII
3X8387Q25N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BREPOCITINIB
INN   USAN  
Official Name English
BREPOCITINIB [WHO-DD]
Common Name English
(1S)-2,2-DIFLUOROCYCLOPROPYL)(3-(2-((1-METHYL-1H-PYRAZOL-4-YL)AMINO)PYRIMIDIN-4-YL)-3,8-DIAZABICYCLO(3.2.1)OCTAN-8-YL)METHANONE
Systematic Name English
PF-06700841
Code English
BREPOCITINIB [USAN]
Common Name English
BREPOCITINIB [INN]
Common Name English
METHANONE, ((1S)-2,2-DIFLUOROCYCLOPROPYL)(3-(2-((1-METHYL-1H-PYRAZOL-4-YL)AMINO)-4-PYRIMIDINYL)-3,8-DIAZABICYCLO(3.2.1)OCT-8-YL)-
Systematic Name English
Code System Code Type Description
PUBCHEM
118878093
Created by admin on Sat Jun 26 15:22:01 UTC 2021 , Edited by admin on Sat Jun 26 15:22:01 UTC 2021
PRIMARY
INN
11169
Created by admin on Sat Jun 26 15:22:01 UTC 2021 , Edited by admin on Sat Jun 26 15:22:01 UTC 2021
PRIMARY
FDA UNII
3X8387Q25N
Created by admin on Sat Jun 26 15:22:01 UTC 2021 , Edited by admin on Sat Jun 26 15:22:01 UTC 2021
PRIMARY
CAS
1883299-62-4
Created by admin on Sat Jun 26 15:22:01 UTC 2021 , Edited by admin on Sat Jun 26 15:22:01 UTC 2021
PRIMARY
DRUG BANK
DB15003
Created by admin on Sat Jun 26 15:22:01 UTC 2021 , Edited by admin on Sat Jun 26 15:22:01 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY