U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19F3N6O
Molecular Weight 380.3676
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of UPADACITINIB

SMILES

CC[C@@H]1CN(C[C@@H]1C2=CN=C3C=NC4=C(C=CN4)N23)C(=O)NCC(F)(F)F

InChI

InChIKey=WYQFJHHDOKWSHR-MNOVXSKESA-N
InChI=1S/C17H19F3N6O/c1-2-10-7-25(16(27)24-9-17(18,19)20)8-11(10)13-5-22-14-6-23-15-12(26(13)14)3-4-21-15/h3-6,10-11,21H,2,7-9H2,1H3,(H,24,27)/t10-,11+/m1/s1

HIDE SMILES / InChI
Molecular Formula C17H19F3N6O
Molecular Weight 380.3676
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Upadacitinib (ABT-494) is a Janus kinase 1 (JAK1) inhibitor currently being developed by AbbVie for the treatment of rheumatoid arthritis (RA), Crohn’s disease, ulcerative colitis, atopic dermatitis, and psoriatic arthritis. It is also being investigated as a potential treatment for people with active ankylosing spondylitis (AS). Currently, upadacitinib is being evaluatedin six global phase III studies in RA and twophase III studies in psoriatic arthritis (PsA), inaddition to phase II studies in Crohn’s disease and atopicdermatitis and a combined phase II/III study inulcerative colitis. Upadacitinib is a potent and selective Janus kinase (JAK) 1 inhibitor with an IC50 of 43 nM.

Originator

Approval Year

2019
334
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 43.0 nM [IC50]
Inhibitor
8297
 200.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
RINVOQ

Approved Use

RINVOQ is a Janus kinase (JAK) inhibitor indicated for the treatment of adults with moderately to severely active rheumatoid arthritis who have had an inadequate response or intolerance to methotrexate.

Launch Date

2019
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
63.7 ng/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/29688617
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
UPADACITINIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
491 ng × h/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/29688617
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
UPADACITINIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
18.1 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/29688617
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
UPADACITINIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
48%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211675s000lbl.pdf
UPADACITINIB plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
30 mg 1 times / day steady, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
unhealthy, 39.9 years (range: 18-75 years)
n = 42
Health Status: unhealthy
Condition: Moderate-to-Severe Atopic Dermatitis
Age Group: 39.9 years (range: 18-75 years)
Sex: M+F
Population Size: 42
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
Other AEs: Anemia, Neutropenia...
Other AEs:
Anemia (2.4%)
Neutropenia (4.8%)
Atopic dermatitis (9.5%)
Acne (14%)
Headache (9.5%)
Nasopharyngitis (7.1%)
CPK increased (9.5%)
Nausea (7.1%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
15 mg 1 times / day steady, oral
Recommended
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211675s000lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: serious infection
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211675s000lbl.pdf
Other AEs: Adverse event...
Other AEs:
Adverse event (grade 5)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211675s000lbl.pdf
15 mg 1 times / day steady, oral
Recommended
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
unhealthy, adult
n = 1035
Health Status: unhealthy
Condition: rheumatoid arthritis
Age Group: adult
Population Size: 1035
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
Disc. AE: Anemia, Vertigo...
AEs leading to
discontinuation/dose reduction:
Anemia (2 patients)
Vertigo (2 patients)
Bronchitis (2 patients)
ALT increased (2 patients)
Aspartate aminotransferase increased (3 patients)
Increased serum creatinine (2 patients)
Headache (2 patients)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
AEs

AEs

AESignificanceDosePopulation
Acne 14%
30 mg 1 times / day steady, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
unhealthy, 39.9 years (range: 18-75 years)
n = 42
Health Status: unhealthy
Condition: Moderate-to-Severe Atopic Dermatitis
Age Group: 39.9 years (range: 18-75 years)
Sex: M+F
Population Size: 42
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
Anemia 2.4%
30 mg 1 times / day steady, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
unhealthy, 39.9 years (range: 18-75 years)
n = 42
Health Status: unhealthy
Condition: Moderate-to-Severe Atopic Dermatitis
Age Group: 39.9 years (range: 18-75 years)
Sex: M+F
Population Size: 42
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
Neutropenia 4.8%
30 mg 1 times / day steady, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
unhealthy, 39.9 years (range: 18-75 years)
n = 42
Health Status: unhealthy
Condition: Moderate-to-Severe Atopic Dermatitis
Age Group: 39.9 years (range: 18-75 years)
Sex: M+F
Population Size: 42
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
Nasopharyngitis 7.1%
30 mg 1 times / day steady, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
unhealthy, 39.9 years (range: 18-75 years)
n = 42
Health Status: unhealthy
Condition: Moderate-to-Severe Atopic Dermatitis
Age Group: 39.9 years (range: 18-75 years)
Sex: M+F
Population Size: 42
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
Nausea 7.1%
30 mg 1 times / day steady, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
unhealthy, 39.9 years (range: 18-75 years)
n = 42
Health Status: unhealthy
Condition: Moderate-to-Severe Atopic Dermatitis
Age Group: 39.9 years (range: 18-75 years)
Sex: M+F
Population Size: 42
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
Atopic dermatitis 9.5%
30 mg 1 times / day steady, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
unhealthy, 39.9 years (range: 18-75 years)
n = 42
Health Status: unhealthy
Condition: Moderate-to-Severe Atopic Dermatitis
Age Group: 39.9 years (range: 18-75 years)
Sex: M+F
Population Size: 42
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
CPK increased 9.5%
30 mg 1 times / day steady, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
unhealthy, 39.9 years (range: 18-75 years)
n = 42
Health Status: unhealthy
Condition: Moderate-to-Severe Atopic Dermatitis
Age Group: 39.9 years (range: 18-75 years)
Sex: M+F
Population Size: 42
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
Headache 9.5%
30 mg 1 times / day steady, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
unhealthy, 39.9 years (range: 18-75 years)
n = 42
Health Status: unhealthy
Condition: Moderate-to-Severe Atopic Dermatitis
Age Group: 39.9 years (range: 18-75 years)
Sex: M+F
Population Size: 42
Sources:
https://pubmed.ncbi.nlm.nih.gov/31786154
Adverse event grade 5
15 mg 1 times / day steady, oral
Recommended
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211675s000lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: serious infection
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211675s000lbl.pdf
ALT increased 2 patients
Disc. AE
15 mg 1 times / day steady, oral
Recommended
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
unhealthy, adult
n = 1035
Health Status: unhealthy
Condition: rheumatoid arthritis
Age Group: adult
Population Size: 1035
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
Anemia 2 patients
Disc. AE
15 mg 1 times / day steady, oral
Recommended
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
unhealthy, adult
n = 1035
Health Status: unhealthy
Condition: rheumatoid arthritis
Age Group: adult
Population Size: 1035
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
Bronchitis 2 patients
Disc. AE
15 mg 1 times / day steady, oral
Recommended
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
unhealthy, adult
n = 1035
Health Status: unhealthy
Condition: rheumatoid arthritis
Age Group: adult
Population Size: 1035
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
Headache 2 patients
Disc. AE
15 mg 1 times / day steady, oral
Recommended
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
unhealthy, adult
n = 1035
Health Status: unhealthy
Condition: rheumatoid arthritis
Age Group: adult
Population Size: 1035
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
Increased serum creatinine 2 patients
Disc. AE
15 mg 1 times / day steady, oral
Recommended
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
unhealthy, adult
n = 1035
Health Status: unhealthy
Condition: rheumatoid arthritis
Age Group: adult
Population Size: 1035
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
Vertigo 2 patients
Disc. AE
15 mg 1 times / day steady, oral
Recommended
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
unhealthy, adult
n = 1035
Health Status: unhealthy
Condition: rheumatoid arthritis
Age Group: adult
Population Size: 1035
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
Aspartate aminotransferase increased 3 patients
Disc. AE
15 mg 1 times / day steady, oral
Recommended
Dose: 15 mg, 1 times / day
Route: oral
Route: steady
Dose: 15 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
unhealthy, adult
n = 1035
Health Status: unhealthy
Condition: rheumatoid arthritis
Age Group: adult
Population Size: 1035
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211675Orig1s000MedR.pdf
Page: p. 165
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737

inhibitor
1587
inhibitor
1767
substrate
1217

inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2B6
810

CYP2C19
1478

P-gp
1461

BCRP
699

BSEP
402

OATP1B1
788

OATP1B3
706

OCT1
512

OCT2
647

OAT1
599

OAT3
642

MATE1
306

MATE2
263
CYP3A5
395

P-gp
1537

BCRP
561

OATP1B1
406

OATP1B3
350

OCT1
327
CYP1A2
701

CYP2B6
547

CYP3A
129
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1692
 minor
CYP3A4
1925
 no [IC50 181 uM]
weak (co-administration study)
Comment: Clinically no meaningful effect on midazolam (sensitive CYP3A4 substrate), Coadministration of Upadacitinib (30 mg QD extended-release) decreased Cmax by 16% and AUCinf by 26%., IC50=181 mcM (midazolam) and 212 mcM (teststerone), Upadacitinib caused no detectable time-dependent inhibition of any isoform tested upto a concentration of 50 µM.
Page: 11, 18, 19, 23, 77-85
CYP2C9
1819
 no [IC50 40.3 uM]
no (co-administration study)
Comment: Clinically no meaningful effect on S-warffarin (sensitive CYP2C9 substrate), Coadministration of Upadacitinib (30 mg QD extended-release) increased Cmax by 7% and AUCinf by 11%., Upadacitinib caused no detectable time-dependent inhibition of any isoform tested up to a concentration of 50 µM.
Page: 11, 18, 19, 23, 77-85
CYP2C19
1553
 no [IC50 >250 uM]
no (co-administration study)
Comment: Clinically no meaningful effect on omeprazole (sensitive CYP2C19 substrate), Coadministration of Upadacitinib (30 mg QD extended-release) increased AUCinf Ratio (5-OH OME to OME metabolic ratio) by 9%., Upadacitinib caused no detectable time-dependent inhibition of any isoform tested up to a concentration of 50 µM.
Page: 11, 18, 19, 23, 77-85
CYP2D6
1891
 no [IC50 >250 uM]
no (co-administration study)
Comment: Clinically no meaningful effect on dextromethorphan (sensitive CYP2D6 substrate), Coadministration of Upadacitinib (30 mg QD extended-release) increased Cmax by 9% and AUCinf by 7%., Upadacitinib caused no detectable time-dependent inhibition of any isoform tested up to a concentration of 50 µM.
Page: 11, 18, 19, 23, 77-85
CYP1A2
1692
 no [IC50 >250 uM]
weak (co-administration study)
Comment: Clinically no meaningful effect on caffeine (sensitive CYP1A2 substrate), Coadministration of Upadacitinib (30 mg QD extended-release) increased Cmax by 13% and AUCinf by 22%., Upadacitinib caused no detectable time-dependent inhibition of any isoform tested up to a concentration of 50 µM.
Page: 11, 18, 19, 23, 77-85
CYP2B6
1001
 no [IC50 >250 uM]
weak (co-administration study)
Comment: Clinically no meaningful effect on bupropion (CYP2B6 substrate), Coadministration of Upadacitinib (30 mg QD extended-release) decreased Cmax by 13.2% and AUCinf by 7.6%., Upadacitinib caused no detectable time-dependent inhibition of any isoform tested up to a concentration of 50 µM.
Page: 11, 18, 19, 23, 87-89
MATE1
308
 unlikely [IC50 10 uM]
MATE2
263
 unlikely [IC50 10 uM]
BCRP
773
 unlikely [IC50 120 uM]
BSEP
403
 unlikely [IC50 220 uM]
OAT3
644
 unlikely [IC50 35 uM]
OATP1B1
803
 unlikely [IC50 48 uM]
P-gp
1650
 unlikely [IC50 510 uM]
OAT1
603
 unlikely [IC50 >30 uM]
OATP1B3
715
 unlikely [IC50 >30 uM]
OCT1
543
 unlikely [IC50 >30 uM]
OCT2
648
 unlikely [IC50 >30 uM]
CYP2B6
1001
 yes
CYP3A
298
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1737
 major
yes (co-administration study)
Comment: When upadacitinib was co-administered with ketoconazole (a strong CYP3A4 inhibitor, 400 mg QD x 6 days), upadacitinib exposure increased by 75% for AUC0-inf and 70% for Cmax. Upadacitinib should be used with caution if patients receive chronic treatment with strong CYP3A4 inhibitors. When upadacitinib was co-administered with rifampin (a strong CYP3A4 inducer, 600 mg QD x 9 days), upadacitinib exposure decreased by 61% for AUC0-inf and 51% for Cmax. Upadacitinib is not recommended to be co-administered with strong CYP3A4 inducers.
Page: 5, 10, 17, 18, 23, 70-72
CYP2D6
1217
 minor
CYP3A5
395
 minor
OATP1B3
350
 no
OCT1
327
 no
OATP1B1
406
 no
no (co-administration study)
Comment: OATP1B inhibitor (rifampin, 600 mg SD) do not have clinically meaningful effect on upadacitinib PK (increased Cmax by 14% and AUCinf by 7%).
Page: 11, 18, 23
BCRP
561
 yes
P-gp
1537
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
AA Blocks
AA01E0RQ
https://www.aablocks.com/goods/Goods/detail?id=AA01E0RQ
Aaron Chemicals
AR01E1JI
http://www.aaronchem.com/1310726-60-3
Achemtek
0102-032615
http://achemtek.com/1310726-60-3-2
Acorn PharmaTech
ACN-052823
http://www.acornpharmatech.com/
Ambeed
A165008
https://www.ambeed.com/products/1310726-60-3.html
BioChemPartner
BCP19011
http://www.biochempartner.com/1310726-60-3-BCP19011
CSNpharm
CSN18721
https://www.csnpharm.com/products/upadacitinib.html
Chem Scene
CS-6150
http://www.chemscene.com/1310726-60-3.html
ChemFish Tokyo co.,ltd
58557659
http://www.chemfish.co.jp/index.php?id=2929&project=product
Chemspace
CSSB00103150878
https://chem-space.com/CSSB00103150878
DC Chemicals
DC10431
http://www.dcchemicals.com/product_show-Upadacitinib.html
Excenen
EX-A1628
http://www.excenen.com/searchresultlist.php?id=1310726-60-3
Hairui
UPXF018
http://www.hairuichem.com/en/product/1310726-60-3.html
Lab Network
LN03250514
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN03250514
MedChem Express
HY-19569
https://www.medchemexpress.com/Upadacitinib.html
Selleck Chemicals
S8162
http://www.selleckchem.com/products/upadacitinib.html
Smolecule
S546407
http://www.smolecule.com/products/s546407
Synblock Inc
SB19218
http://www.synblock.com/product/1310726-60-3.html
THE BioTek
bt-285013
https://www.thebiotek.com/product/inhibitors/bt-285013
abcr GmbH
AB514878
http://www.abcr.com/shop/en/AB514878
eNovation Chemicals
Y0975799
https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0975799
iChemical
EBD4040026
http://www.ichemical.com/products/1310726-60-3.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
PubMed

PubMed

TitleDatePubMed
Population Pharmacokinetics of Upadacitinib in Healthy Subjects and Subjects with Rheumatoid Arthritis: Analyses of Phase I and II Clinical Trials.
2018 Aug
Patents

Patents

8426411
4
US20110311474
4

Sample Use Guides

In Vivo Use Guide
The recommended dose of RINVOQ (Upadacitinib) is 15 mg once daily.
Route of Administration: Oral
In Vitro Use Guide
Upadacitinib is a potent and selective Janus kinase (JAK) 1 inhibitor with an IC50 of 43 nM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:54:18 GMT 2023
Edited
by admin
on Sat Dec 16 08:54:18 GMT 2023
Record UNII
4RA0KN46E0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
UPADACITINIB
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
ABBV-599 COMPONENT UPADACITINIB
Common Name English
UPADACITINIB [ORANGE BOOK]
Common Name English
(3S,4R)-3-ETHYL-4-(3H-IMIDAZO(1,2-A)PYRROLO(2,3-E)PYRAZIN- 8-YL)-N-(2,2,2-TRIFLUOROETHYL)PYRROLIDINE-1-CARBOXAMIDE TYROSINE KINASE INHIBITOR
Common Name English
UPADACITINIB [MI]
Common Name English
UPADACITINIB [USAN]
Common Name English
(3S,4R)-3-ETHYL-4-(3H-IMIDAZO(1,2-A)PYRROLO(2,3-E)PYRAZIN-8-YL)-N-(2,2,2-TRIFLUOROETHYL)-1-PYRROLIDINECARBOXAMIDE
Systematic Name English
ABT-494
Code English
UPADACITINIB COMPONENT OF ABBV-599
Common Name English
Upadacitinib [WHO-DD]
Common Name English
1-PYRROLIDINECARBOXAMIDE, 3-ETHYL-4-(3H-IMIDAZO(1,2-A)PYRROLO(2,3-E)PYRAZIN-8-YL)-N-(2,2,2-TRIFLUOROETHYL)-, (3S,4R)-
Systematic Name English
UPADACITINIB ANHYDROUS
Common Name English
upadacitinib [INN]
Common Name English
REL-(-)-(3S,4R)-3-ETHYL-4-(3H-IMIDAZO(1,2-A)PYRROLO(2,3-E)PYRAZIN-8-YL)-N-(2,2,2-TRIFLUOROETHYL)PYRROLIDINE-1-CARBOXAMIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1967
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
FDA ORPHAN DRUG 522916
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
FDA ORPHAN DRUG 524116
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
FDA ORPHAN DRUG 575517
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
Code System Code Type Description
USAN
CD-19
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
PRIMARY
RXCUI
2196092
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
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INN
10209
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
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WIKIPEDIA
Upadacitinib
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
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SMS_ID
100000173002
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
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DRUG CENTRAL
5346
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
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FDA UNII
4RA0KN46E0
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
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PUBCHEM
58557659
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
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DRUG BANK
DB15091
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
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DAILYMED
4RA0KN46E0
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
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NCI_THESAURUS
C152802
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
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MERCK INDEX
m12178
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
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CAS
1310726-60-3
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
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LACTMED
Upadacitinib
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
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EPA CompTox
DTXSID901027919
Created by admin on Sat Dec 16 08:54:19 GMT 2023 , Edited by admin on Sat Dec 16 08:54:19 GMT 2023
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Related Record Type Details
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> SUBSTRATE
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
MAJOR
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
CYTOCHROME P450 2C9
METABOLIC ENZYME -> INHIBITOR
In the direct inhibition assays, upadacitinib inhibited CYP2C9 with an IC50 value of 40.3 μM
IC50
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
MINOR
Structure of UPADACITINIB HEMIHYDRATE
SOLVATE->ANHYDROUS
Structure of UPADACITINIB
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
Structure of UPADACITINIB TARTRATE ANHYDROUS
SALT/SOLVATE -> PARENT
Structure of UPADACITINIB TARTRATE
SALT/SOLVATE -> PARENT
TYROSINE-PROTEIN KINASE JAK1
TARGET -> INHIBITOR
Structure of UPADACITINIB HEMIHYDRATE
SALT/SOLVATE -> PARENT
Structure of UPADACITINIB
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Related Record Type Details
Structure of 5-((3R,4S)-4-ETHYL-1-(2,2,2-TRIFLUOROETHYLCARBAMOYL)PYRROLIDIN-3-YL)-1H-IMIDAZOLE-2-CARBOXAMIDE
METABOLITE INACTIVE -> PARENT
URINE
Structure of (3S,4R)-3-ETHYL-4-(3H-IMIDAZO(1,2-A)PYRROLO(2,3-E)PYRAZIN-8-YL)-N-(2,2,2-TRIFLUORO-1-HYDROXYETHYL)PYRROLIDINE-1-CARBOXAMIDE
METABOLITE -> PARENT
TRACE
FECAL; URINE
Structure of 5-((3R,4S)-4-ETHYL-1-(2,2,2-TRIFLUOROETHYLCARBAMOYL)PYRROLIDIN-3-YL)-1H-IMIDAZOLE-2-CARBOXAMIDE
METABOLITE INACTIVE -> PARENT
FECAL
Structure of 5-((3R,4S)-4-ETHYL-1-(2,2,2-TRIFLUOROETHYLCARBAMOYL)PYRROLIDIN-3-YL)-1H-IMIDAZOLE-2-CARBOXAMIDE
METABOLITE INACTIVE -> PARENT
PLASMA
Related Record Type Details
Structure of UPADACITINIB
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC STEADY-STATE

blood to plasma ratio PHARMACOKINETIC
Tmax PHARMACOKINETIC FASTED CONDITION

ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC FOLLOWING THE ADMINISTRATION OF ER FORMULATION

Tmax PHARMACOKINETIC ORAL ADMINISTRATION

FED CONDITION

NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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