Upadacitinib

ChemicalBook > CAS DataBase List > Upadacitinib

Introduction

Product Name: Upadacitinib
CAS No.: 1310726-60-3
Chemical Name: Upadacitinib
Synonyms: ABT-494;(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;upatinib;Upadacitinib (ABT-494);benzyl (4S)-3-(N-(ethoxycarbonyl)-N-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)glycyl)-4-ethylpyrrolidine-1-carboxylate;1-Pyrrolidinecarboxamide, 3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)-, (3S,4R)-;(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, Upadacitinib;CS-2730;Upadacitinb;Upadacitinib
CBNumber: CB53121345
Molecular Formula: C17H19F3N6O
Formula Weight: 380.37
MOL File: 1310726-60-3.mol

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Upadacitinib Property

Density: 1.56±0.1 g/cm3(Predicted)
storage temp.: Store at -20°C
solubility: DMSO:42.67(Max Conc. mg/mL);112.17(Max Conc. mM)
DMSO:PBS (pH 7.2) (1:1):0.5(Max Conc. mg/mL);1.31(Max Conc. mM)
DMF:30.0(Max Conc. mg/mL);78.87(Max Conc. mM)
Ethanol:76.0(Max Conc. mg/mL);199.8(Max Conc. mM)
form: A crystalline solid
pka: 11.89±0.60(Predicted)
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
InChIKey: WYQFJHHDOKWSHR-MNOVXSKESA-N
SMILES: N1(C(NCC(F)(F)F)=O)C[C@H](C2N3C4C=CNC=4N=CC3=NC=2)[C@H](CC)C1

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 29706
Product name: Upadacitinib
Packaging: 5mg
Price: $116
Updated: 2024/03/01

Cayman Chemical

Product number: 29706
Product name: Upadacitinib
Packaging: 25mg
Price: $381
Updated: 2024/03/01

Cayman Chemical

Product number: 29706
Product name: Upadacitinib
Packaging: 1mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 29706
Product name: Upadacitinib
Packaging: 10mg
Price: $169
Updated: 2024/03/01

TRC

Product number: U800075
Product name: Upadacitinib
Packaging: 1mg
Price: $300
Updated: 2021/12/16

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Upadacitinib Chemical Properties,Usage,Production

Introduction

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).
AS is an inflammatory, progressive autoimmune disease that affects the joints of the spine. As the disease progresses, calcium deposits form where ligaments attach to the bones that form the spine, leading to reduced flexibility of the back.

Description

Upadacitinib is a JAK1 inhibitor (IC₅₀ = 47 nM). It is selective for JAK1 over JAK3 and tyrosine kinase 2 (Tyk2; IC₅₀s = 2,304 and 4,690 nM, respectively), as well as a panel of 83 additional kinases at 1 μM, but does inhibit JAK2, Rho-associated kinase I (ROCK1), and ROCK2 (IC₅₀s = 120, 920, and 430 nM, respectively). Upadacitinib decreases cytokine-induced STAT phosphorylation in a variety of human cells with IC₅₀ values ranging from 1.6 to 649 nM. It reduces M. tuberculosis-induced paw swelling and bone erosion in a rat model of arthritis when administered at doses of 1, 3, and 10 mg/kg twice per day for 17 days. Formulations containing upadacitinib have been used in the treatment of rheumatoid arthritis.

Uses

Upadacitinib also known as ABT-494, is a potent and selective Janus kinase (JAK) 1 inhibitor being developed for the treatment of several autoimmune disorders, Janus kinase inhibitors for rheumatoid arthritis. It is used to treat moderate to severely active rheumatoid arthritis, active psoriatic arthritis, ankylosing spondylitis, non-radiographic axial spondyloarthritis (a type of arthritis in the spine) with objective signs of swelling, moderate to severe ulcerative colitis, and moderate to severe Crohn's disease in patients who have taken other medicines (eg, methotrexate) that did not work well. It is also used to treat moderate to severe atopic dermatitis (eczema) in patients who have taken other medicines that did not work well and whose condition is not well controlled with other treatments or in patients who cannot tolerate these treatments. It is also used to treatpsoriatic arthritis, axial SpA and Giant Cell Arteritis and Takayasu Arteritis.

brand name

Upadacitinib is marketed under the brand name RINVOQ for oral administration.

Biological Activity

Upadacitinib is a potent, orally active and selective Janus kinase 1 (JAK1) inhibitor (IC50=43 nM). Upadacitinib displays approximately 74 fold selective for JAK1 over JAK2 (200 nM) in cellular assays dependent on specific, relevant cytokines. Upadacitinib can be used for several autoimmune disorders research. In vivo, Upadacitinib inhibited paw swelling and bone destruction in a rat model of arthritis.

Mechanism of action

The Janus kinases (JAKs) are a family of cytoplasmic tyrosine kinases whose function is to transduce cytokine-mediated signals via the JAK-STAT pathway. There are four JAK subtypes, each of which has overlapping receptor responsibilities. Inhibitors of this enzyme family (jakinibs) have shown efficacy in treating certain inflammatory and autoimmune diseases such as rheumatoid arthritis and Crohn's disease. However, the first generation of these drugs, tofacitinib and ruxolitinib, lacked subtype selectivity, affecting JAK1/JAK3 and JAK1/JAK2 respectively. This has led to dose-limiting side effects in this otherwise promising class of drugs. Upadacitinib is a second generation Janus kinase inhibitor that is selective for the JAK1 subtype of this enzyme over the JAK2 (74-fold), JAK3 (58-fold) and tyrosine kinase 2 subtypes.

Clinical Use

Upadacitinib is indicated for the treatment of moderate to severe active rheumatoid arthritis in adults who have responded inadequately to, or who are intolerant to one or more disease-modifying antirheumatic drugs (DMARDs). Upadacitinib may be used as monotherapy or in combination with methotrexate.

Side effects

Common side effects are upper respiratory tract infections such as common cold and sinus infections (13.5% of patients in studies), nausea (3.5%), cough (2.2%), fever, and increased liver enzymes. Serious side effects include infections, including life-threatening ones, such as pneumonia, cellulitis, tuberculosis, as well as shingles and other herpes infections.

Synthesis

To a solution of (3S,4R)-3-ethyl-4-(3-tosyl-3H-imidazo[l,2-a]pyrrolo[2,3-e]pyrazin-8-yl)- N-(2,2,2-trifluoroethyl)pyrrolidine-l-carboxamide (10 g) in tetrahydrofurane (50 ml_), a 10% solution of sodium hydroxide in water (15 ml) was added and heated to 50??C. The reaction mixture was stirred for 5 hours and cooled to 25??C. A saturated solution of sodium chloride (100 ml_) was added to the reaction mixture and extracted with dichloromethane (100 ml). The organic phase was separated and washed with water (100 ml_). An 2.5 % aqueous solution of HCI (100 ml) was added and stirred for 30 minutes. The organic phase was removed and the resultant acid aqueous phase was extracted with dichloromethane (100 ml). The final aqueous phase was cooled down to 0/5 ??C and a 10% solution of NaOH was charged until pH 10/12. The resultant suspension was filtered and washed with water (2 x 50 ml_). The cake was drained and dried at 30/40??C under vacuum to give an almost white amorphous solid. Yield: 80%. 1 H NMR (400MHz, d-DMSO) 612.27 (s,1H), 8.58 (s,1H), 7.47-7.43 (m,2H), 7.00-6.94 (m,2H), 4.38 -4.33 (m,1H), 3.92-3.67 (m,5H), 3.33-3.25 (m,1 H), 2.59-2.54 (m,1 H), 1.14-1.08 (m,1 H), 0.86-0.78 (m, 1H), 0.65-0.62 (m, 3H).

storage

Store at -20°C

Upadacitinib Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Upadacitinib manufacturers

hebei hongtan Biotechnology Co., Ltd

Product: Upadacitinib 1310726-60-3
Price: US $30.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 2000kg
Release date: 2024-03-27

Sinoway Industrial co., ltd.

Product: Upadacitinib 1310726-60-3
Price: US $0.00-0.00/Kg/Bag
Min. Order: 1Kg/Bag
Purity: 0.99
Supply Ability: 20 tons
Release date: 2023-11-03

Anhui Dexinjia Biopharm Co., Ltd

Product: Upadacitinib 1310726-60-3
Price: US $300.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 200kg per month
Release date: 2023-04-02

1310726-60-3, UpadacitinibRelated Search:

Baricitinib Ibrutinib tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate [2-[(3R,4S)-4-ethyl-1-[(phenylmethoxy)carbonyl]-3-pyrrolidinyl]-2-oxoethyl]dimethyl-Sulfoxonium inner salt (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester AZD-9291 Nintedanib Ethanesulfonate Salt Olaparib Vandetanib 3-(1-Methyl-1H-pyrazol-4-yl)-5-oxo-N-(2-pyridinylmethyl)-5H-benzo[4,5]cyclohepta[1,2-b]pyridine-7-methanesulfonamide 2-[[(2E)-3-(2-NAPHTHALENYL)-1-OXO-2-BUTEN-1-YL]AMINO]BENZOIC ACID Q-VD-OPh hydrate N-(2-(4'-cyanobiphenyl-4-yl)propyl)propane-2-sulfonaMide H3B-6527 1-((2S,5R)-5-((7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-2-methylpiperidin-1-yl)prop-2-en-1-one Senexin B 1,3-Pyrrolidinedicarboxylic acid, 4-ethyl-, 3-ethyl 1-(phenylmethyl) ester 1,3-Pyrrolidinedicarboxylic acid, 4-ethyl-, 1-(phenylmethyl) ester

Upadacitinib

ABT-494

ABT-494(Upadacitinib) free base

Upadacitinib (ABT-494)

ABT-494 (Upadacitinib)

Upadacitinib (Rinvoq)

ABT-494; ABT494; ABT 494

CS-2730

(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, Upadacitinib

(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

1-Pyrrolidinecarboxamide, 3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)-, (3S,4R)-

benzyl (4S)-3-(N-(ethoxycarbonyl)-N-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)glycyl)-4-ethylpyrrolidine-1-carboxylate

Upacidatinib

upatinib

(3S,4R)-3-Ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)-1-pyrrolidinecarboxamide

(3S,4R)-3-ethyl-4-(1,5,7,10-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaen-12-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Upadacitinb

Upatinib anhydrous substance

Upadacitinib in Stock

1310726-60-3

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