Identification

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Name
Upadacitinib
Accession Number
DB15091
Type
Small Molecule
Groups
Approved, Investigational
Description

Upadacitinib is an oral Janus kinase (JAK)1-selective inhibitor and a disease-modifying antirheumatic drug (DMARD) used in the treatment of rheumatoid arthritis to slow down disease progression. Rheumatoid arthritis is a chronic autoimmune inflammatory disease affecting the peripheral joints. It is characterized by synovial inflammation and hyperplasia, autoantibody production, cartilage damage and bone destruction, leading to co-morbidities.4 Despite a variety of therapeutic agents available for treatment, up to 40% of the patients do not respond to current therapies, including biological therapies.6 The etiology of the disease is mostly unknown; however, the role of JAK as a driver of immune-mediated conditions was discovered, leading to the use of JAK as therapeutic targets for rheumatoid arthritis.5 To reduce dose-related toxicity (as seen with some pan-JAK inhibitors) without significantly affecting efficacy, more selective JAK1 inhibitors, upadacitinib and filgotinib, were developed.4

The FDA approved Upadacitinib in August 2019 for the treatment of adults with moderately to severely active rheumatoid arthritis who have had an inadequate response or intolerance to methotrexate.9 In December 2019, it was additionally approved by the European Commission for the same indication in patients with inadequate response or intolerance to one or more DMARDs and can be used as monotherapy or in combination with methotrexate.10 Upadacitinib is marketed under the brand name RINVOQ™ for oral administration.9 It is currently being investigated in several clinical trials assessing its therapeutic effectiveness in other inflammatory diseases, such as psoriatic arthritis, ankylosing spondylitis, ulcerative colitis, and atopic dermatitis.4

Structure
Thumb
Synonyms
  • Upadacitinib
External IDs
ABT 494 / ABT-494
Product Ingredients
IngredientUNIICASInChI Key
Upadacitinib hemihydrateNEW4DV02U5Not AvailableGJMQTRCDSIQEFK-SCDRJROZSA-N
Upadacitinib tartrate7KCW9IQM021607431-21-9LATZVDXOTDYECD-UFTFXDLESA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
RinvoqTablet, extended release15 mg/1OralAbbVie Inc.2019-08-16Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories
UNII
4RA0KN46E0
CAS number
1310726-60-3
Weight
Average: 380.375
Monoisotopic: 380.157243745
Chemical Formula
C17H19F3N6O
InChI Key
WYQFJHHDOKWSHR-MNOVXSKESA-N
InChI
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
IUPAC Name
(3S,4R)-3-ethyl-4-{1,5,7,10-tetraazatricyclo[7.3.0.0^{2,6}]dodeca-2(6),3,7,9,11-pentaen-12-yl}-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide
SMILES
CC[C@@H]1CN(C[C@@H]1C1=CN=C2C=NC3=C(C=CN3)N12)C(=O)NCC(F)(F)F

Pharmacology

Indication

Upadacitinib is indicated for the treatment of adults with moderately to severely active rheumatoid arthritis who have had an inadequate response or intolerance to methotrexate.9

For patients who do not responded well or are intolerant to one or more disease-modifying anti-rheumatic drugs (DMARDs), upadacitinib may be used as monotherapy or in combination with methotrexate (MTX).10

Associated Conditions
Pharmacodynamics

Upadacitinib is a DMARD that works by inhibiting the Janus Kinases (JAKs), which are essential downstream cell signalling mediators of pro-inflammatory cytokines. It is believed that these pro-inflammatory cytokines play a role in many autoimmune inflammatory conditions, such as rheumatoid arthritis.6 In clinical trials, upadacitinib decreased the activity of pro-inflammatory interleukins, transiently increased the levels of lymphocytes, and insignificantly decreased the levels of immunoglobulins from the baseline.9

Mechanism of action

Rheumatoid arthritis (RA) is a chronic autoimmune inflammatory disease that involves the interplay of several mediators, including the immune cells (mainly T- and B-lymphocytes) and pro-inflammatory cytokines, such as the tumour necrosis factor (TNF), transforming growth factor (TGF), and interleukin 6 (IL-6).4 The Janus Kinase (JAK) family plays an essential role in the normal physiological functions (such as erythropoiesis), but also the signalling of pro-inflammatory cytokines that are implicated in many immune-mediated diseases.5 The JAK family consists of four isoforms (JAK1, JAK2, JAK3, and Tyrosine Kinase 2) that each interacts with different cytokine receptors and uniquely associates with the intracellular domains of Type I/II cytokine receptors.5 JAK1 is primarily involved in the signalling transduction pathways of IL-6, IFN and the common γ -chain cytokines, including IL-2 and IL-15.8 IL-6 has been closely studied in particular, as it is a major cytokine involved in B- and T-cell differentiation and the acute phase response in inflammation.7

Upon interaction of cytokines with their cytokine receptors, the JAKs mediate the JAK-STAT signal transduction pathway in response to receptor activation. JAKs are tyrosine kinases that cause phosphorylation of several proteins, including cytokine receptors and JAKs themselves. Phosphorylation of JAKs promotes the phosphorylation and activation of the signalling molecules called STATs, leading to their nuclear translocation, binding to DNA promoters, and target gene transcription. JAK1-mediated signalling pathways ultimately promote pro-inflammatory events, such as increased proliferation and survival of immune cells, T cell differentiation, and macrophage activation.5 Upadacitinib is a selective JAK1 inhibitor that has a negligible effect on JAK3, leading to an improved drug safety profile.4 Upadacitinib blocks the cellular processes that contribute to the inflammatory conditions in rheumatoid arthritis. In human leukocytes cellular assays, upadacitinib inhibited JAK1/3-induced phosphorylation of STAT3/5 mediated by IL-6/7.9

TargetActionsOrganism
ATyrosine-protein kinase JAK1
inhibitor
Humans
Additional Data Available
Adverse Effects

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

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Absorption

Upadacitinib displays a dose-proportional pharmacokinetic profile over the therapeutic dose range. Following oral administration, the median time to reach Cmax (Tmax) ranges from 2 to 4 hours. The steady-state plasma concentrations of upadacitinib are reached within 4 days following multiple once-daily administrations, with minimal accumulation.9 Food intake has no clinically relevant effect on the AUC, Cmax, and Cmin of upadacitinib from the extended-release formulation.3

Volume of distribution

The volume of distribution of upadacitinib in a patient with rheumatoid arthritis and a body weight of 74 kg is estimated to be 224 L following oral administration of an extended-release formula.11 In a pharmacokinetic study consisting of healthy volunteers receiving the extended-release formulation, the steady-state volume of distribution was 294 L.1 Upadacitinib partitions similarly between plasma and blood cellular components with a blood to plasma ratio of 1.0.9

Protein binding

Upadacitinib is 52% bound to human plasma proteins.9

Metabolism

Upadacitinib predominantly undergoes CYP3A4-mediated metabolism;9 however, upadacitinib is a nonsensitive substrate of CYP3A4.3 It is also metabolized by CYP2D6 to a lesser extent.9 In a human radio-labelled study, about 79% of the total plasma radioactivity accounted for the parent drug, and about 13% of the total plasma radioactivity accounted for the main metabolite produced from mono-oxidation, followed by glucuronidation.9 There are no known active metabolites of upadacitinib.11

Route of elimination

Following administration of a single radio-labelled dose from the immediate-release formulation, approximately 53% of the total dose was excreted in the feces where 38% of the excreted dose was an unchanged parent drug. About 43% of the total dose was excreted in the urine, where 24% of that dose was in the unchanged parent drug form.11 Approximately 34% of the total dose of upadacitinib dose was excreted as metabolites.9

Half life

The mean terminal elimination half-life of upadacitinib ranged from 8 to 14 hours following administration of the extended-release formulation.9,11 In clinical trials, approximately 90% of upadacitinib in the systemic circulation was eliminated within 24 hours of dosing.9

Clearance

The apparent oral clearance of upadacitinib in healthy volunteers receiving the extended-release formulation was 53.7 L/h.1

Toxicity

There is limited clinical information on the overdose from upacitinib: in clinical trials, once-daily administration of 60 mg in extended-release formulations were well tolerated. In case of an overdose, it is recommended that the patient is monitored for signs and symptoms of adverse reactions and treated with appropriate symptomatic treatment.9

The oral LD50 in rats is 14500 mg/kg.12

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
ApalutamideThe metabolism of Upadacitinib can be increased when combined with Apalutamide.
AtazanavirThe metabolism of Upadacitinib can be decreased when combined with Atazanavir.
BoceprevirThe metabolism of Upadacitinib can be decreased when combined with Boceprevir.
CarbamazepineThe metabolism of Upadacitinib can be increased when combined with Carbamazepine.
CenobamateThe serum concentration of Upadacitinib can be decreased when it is combined with Cenobamate.
ClarithromycinThe metabolism of Upadacitinib can be decreased when combined with Clarithromycin.
CobicistatThe metabolism of Upadacitinib can be decreased when combined with Cobicistat.
ConivaptanThe metabolism of Upadacitinib can be decreased when combined with Conivaptan.
CurcuminThe metabolism of Upadacitinib can be decreased when combined with Curcumin.
DanoprevirThe metabolism of Upadacitinib can be decreased when combined with Danoprevir.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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Food Interactions
Not Available

References

General References
  1. Klunder B, Mittapalli RK, Mohamed MF, Friedel A, Noertersheuser P, Othman AA: Population Pharmacokinetics of Upadacitinib Using the Immediate-Release and Extended-Release Formulations in Healthy Subjects and Subjects with Rheumatoid Arthritis: Analyses of Phase I-III Clinical Trials. Clin Pharmacokinet. 2019 Aug;58(8):1045-1058. doi: 10.1007/s40262-019-00739-3. [PubMed:30945116]
  2. Parmentier JM, Voss J, Graff C, Schwartz A, Argiriadi M, Friedman M, Camp HS, Padley RJ, George JS, Hyland D, Rosebraugh M, Wishart N, Olson L, Long AJ: In vitro and in vivo characterization of the JAK1 selectivity of upadacitinib (ABT-494). BMC Rheumatol. 2018 Aug 28;2:23. doi: 10.1186/s41927-018-0031-x. eCollection 2018. [PubMed:30886973]
  3. Mohamed MF, Zeng J, Marroum PJ, Song IH, Othman AA: Pharmacokinetics of Upadacitinib With the Clinical Regimens of the Extended-Release Formulation Utilized in Rheumatoid Arthritis Phase 3 Trials. Clin Pharmacol Drug Dev. 2019 Feb;8(2):208-216. doi: 10.1002/cpdd.462. Epub 2018 Apr 24. [PubMed:29688617]
  4. Biggioggero M, Becciolini A, Crotti C, Agape E, Favalli EG: Upadacitinib and filgotinib: the role of JAK1 selective inhibition in the treatment of rheumatoid arthritis. Drugs Context. 2019 Oct 24;8:212595. doi: 10.7573/dic.212595. eCollection 2019. [PubMed:31692920]
  5. Schwartz DM, Kanno Y, Villarino A, Ward M, Gadina M, O'Shea JJ: JAK inhibition as a therapeutic strategy for immune and inflammatory diseases. Nat Rev Drug Discov. 2017 Dec 28;17(1):78. doi: 10.1038/nrd.2017.267. [PubMed:29282366]
  6. Rivellese F, Lobasso A, Barbieri L, Liccardo B, de Paulis A, Rossi FW: Novel Therapeutic Approaches in Rheumatoid Arthritis: Role of Janus Kinases Inhibitors. Curr Med Chem. 2019;26(16):2823-2843. doi: 10.2174/0929867325666180209145243. [PubMed:29424301]
  7. Guschin D, Rogers N, Briscoe J, Witthuhn B, Watling D, Horn F, Pellegrini S, Yasukawa K, Heinrich P, Stark GR, et al.: A major role for the protein tyrosine kinase JAK1 in the JAK/STAT signal transduction pathway in response to interleukin-6. EMBO J. 1995 Apr 3;14(7):1421-9. [PubMed:7537214]
  8. Choy EH: Clinical significance of Janus Kinase inhibitor selectivity. Rheumatology (Oxford). 2019 Jun 1;58(6):953-962. doi: 10.1093/rheumatology/key339. [PubMed:30508136]
  9. RINVOQTM (upadacitinib) extended-release tablets, for oral use - FDA Label [Link]
  10. AbbVie Receives European Commission Approval of RINVOQ™ (upadacitinib) for the Treatment of Adults with Moderate to Severe Active Rheumatoid Arthritis [Link]
  11. Upadacitinib Summary Review - FDA [Link]
  12. Upadacitinib Safety Data Sheet - EZSolution [Link]
  13. Upadacitinib Clinical Pharmacology and Biopharmaceutics Review(s) - FDA [Link]
External Links
ChemSpider
44210449
ChEMBL
CHEMBL3622821
Wikipedia
Upadacitinib
AHFS Codes
  • 92:36.00 — Disease-modifying Antirheumatic Agents
FDA label
Download (495 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedOtherRheumatoid Arthritis1
1RecruitingTreatmentAtopic Dermatitis (AD)1
1RecruitingTreatmentJuvenile Idiopathic Arthritis (JIA)1
2Active Not RecruitingOtherAnkylosing Spondylitis (AS)1
2Active Not RecruitingTreatmentCrohn's Disease (CD)1
2Active Not RecruitingTreatmentRheumatoid Arthritis2
2CompletedTreatmentAtopic Dermatitis (AD)1
2CompletedTreatmentCrohn's Disease (CD)1
2CompletedTreatmentRheumatoid Arthritis2
2Enrolling by InvitationTreatmentRheumatoid Arthritis1
2RecruitingTreatmentSystemic Lupus Erythematosus (SLE)1
2, 3Active Not RecruitingTreatmentRheumatoid Arthritis1
3Active Not RecruitingTreatmentAtopic Dermatitis (AD)1
3Active Not RecruitingTreatmentPsoriatic Arthritis2
3Active Not RecruitingTreatmentRheumatoid Arthritis7
3Enrolling by InvitationTreatmentCrohn's Disease (CD)1
3Enrolling by InvitationTreatmentUlcerative Colitis1
3RecruitingTreatmentAtopic Dermatitis (AD)5
3RecruitingTreatmentCrohn's Disease (CD)2
3RecruitingTreatmentGiant Cell Arteritis (GCA)1
3RecruitingTreatmentSpondyloarthritis1
3RecruitingTreatmentTakayasu Arteritis (TAK)1
3RecruitingTreatmentUlcerative Colitis2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Tablet, extended releaseOral15 mg/1
Tablet, extended releaseOral15 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8962629No2015-02-242031-01-15Us
USRE47221No2019-02-052030-12-01Us
US9951080No2018-04-242036-10-17Us
US9963459No2018-05-082036-10-17Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)16-19MSDS
boiling point (°C)189MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.0707 mg/mLALOGPS
logP2.57ALOGPS
logP0.85ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)13.99ChemAxon
pKa (Strongest Basic)4.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area78.32 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity93.03 m3·mol-1ChemAxon
Polarizability36.09 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Ubiquitin protein ligase binding
Specific Function
Tyrosine kinase of the non-receptor type, involved in the IFN-alpha/beta/gamma signal pathway. Kinase partner for the interleukin (IL)-2 receptor.
Gene Name
JAK1
Uniprot ID
P23458
Uniprot Name
Tyrosine-protein kinase JAK1
Molecular Weight
133275.995 Da
References
  1. Biggioggero M, Becciolini A, Crotti C, Agape E, Favalli EG: Upadacitinib and filgotinib: the role of JAK1 selective inhibition in the treatment of rheumatoid arthritis. Drugs Context. 2019 Oct 24;8:212595. doi: 10.7573/dic.212595. eCollection 2019. [PubMed:31692920]
  2. Parmentier JM, Voss J, Graff C, Schwartz A, Argiriadi M, Friedman M, Camp HS, Padley RJ, George JS, Hyland D, Rosebraugh M, Wishart N, Olson L, Long AJ: In vitro and in vivo characterization of the JAK1 selectivity of upadacitinib (ABT-494). BMC Rheumatol. 2018 Aug 28;2:23. doi: 10.1186/s41927-018-0031-x. eCollection 2018. [PubMed:30886973]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Klunder B, Mittapalli RK, Mohamed MF, Friedel A, Noertersheuser P, Othman AA: Population Pharmacokinetics of Upadacitinib Using the Immediate-Release and Extended-Release Formulations in Healthy Subjects and Subjects with Rheumatoid Arthritis: Analyses of Phase I-III Clinical Trials. Clin Pharmacokinet. 2019 Aug;58(8):1045-1058. doi: 10.1007/s40262-019-00739-3. [PubMed:30945116]
  2. Mohamed MF, Zeng J, Marroum PJ, Song IH, Othman AA: Pharmacokinetics of Upadacitinib With the Clinical Regimens of the Extended-Release Formulation Utilized in Rheumatoid Arthritis Phase 3 Trials. Clin Pharmacol Drug Dev. 2019 Feb;8(2):208-216. doi: 10.1002/cpdd.462. Epub 2018 Apr 24. [PubMed:29688617]
  3. RINVOQTM (upadacitinib) extended-release tablets, for oral use - FDA Label [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Klunder B, Mittapalli RK, Mohamed MF, Friedel A, Noertersheuser P, Othman AA: Population Pharmacokinetics of Upadacitinib Using the Immediate-Release and Extended-Release Formulations in Healthy Subjects and Subjects with Rheumatoid Arthritis: Analyses of Phase I-III Clinical Trials. Clin Pharmacokinet. 2019 Aug;58(8):1045-1058. doi: 10.1007/s40262-019-00739-3. [PubMed:30945116]
  2. Mohamed MF, Zeng J, Marroum PJ, Song IH, Othman AA: Pharmacokinetics of Upadacitinib With the Clinical Regimens of the Extended-Release Formulation Utilized in Rheumatoid Arthritis Phase 3 Trials. Clin Pharmacol Drug Dev. 2019 Feb;8(2):208-216. doi: 10.1002/cpdd.462. Epub 2018 Apr 24. [PubMed:29688617]
  3. RINVOQTM (upadacitinib) extended-release tablets, for oral use - FDA Label [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
Curator comments
Upadacitinib is a weak inhibitor of P-gp, but no interactions are expected at therapeutic levels with 15 mg QD dosing regimen. Modulation of P- gp transporters is expected to have minor effect on upadacitinib exposures.
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Upadacitinib Clinical Pharmacology and Biopharmaceutics Review(s) - FDA [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
Curator comments
Upadacitinib is a weak inhibitor of BCRP, but no interactions are expected at therapeutic levels with 15 mg QD dosing regimen. Modulation of BCRP transporters is expected to have minor effect on upadacitinib exposures.
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Upadacitinib Clinical Pharmacology and Biopharmaceutics Review(s) - FDA [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Curator comments
Upadacitinib is a weak inhibitor of OATP1B1, but no interactions are expected at therapeutic levels with 15 mg QD dosing regimen.
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Upadacitinib Clinical Pharmacology and Biopharmaceutics Review(s) - FDA [Link]

Drug created on May 20, 2019 08:49 / Updated on February 20, 2020 17:09