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Tofacitinib

Tofacitinib Structure
Tofacitinib structure
CAS No.
477600-75-2
Chemical Name:
Tofacitinib
Synonyms
3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile;Tofactinib;Tasocitinib;Tofacitinib base;Tofacitinib (CP-690550,Tasocitinib);CS-344;CP 690550;Tofatinib;ofacitinib;Tofacitinb
CBNumber:
CB0970901
Molecular Formula:
C16H20N6O
Molecular Weight:
312.38
MDL Number:
MFCD11035919
MOL File:
477600-75-2.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-08-05 19:35:02
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Tofacitinib Properties

Density 1.3
storage temp. -20°C
solubility Soluble in DMSO (up to 100 mg/ml) or in Ethanol (up to 100 mg/ml).
form Pale powder.
pka 6.04±0.60(Predicted)
color Off-white
Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
InChI InChI=1/C16H20N6O/c1-11-5-8-22(14(23)3-6-17)9-13(11)21(2)16-12-4-7-18-15(12)19-10-20-16/h4,7,10-11,13H,3,5,8-9H2,1-2H3,(H,18,19,20)/t11-,13+/s3
InChIKey UJLAWZDWDVHWOW-BCFRMRSDNA-N
SMILES N([C@@H]1[C@@H](CCN(C(=O)CC#N)C1)C)(C1N=CN=C2NC=CC=12)C |&1:1,2,r|
CAS DataBase Reference 477600-75-2
FDA UNII 87LA6FU830
NCI Drug Dictionary tofacitinib
ATC code L04AA29

SAFETY

Risk and Safety Statements

Symbol(GHS)  Environment (GHS09)
GHS09
Signal word  Warning
Hazard statements  H410
Precautionary statements  P501-P273-P391
HS Code  29335990
Hazardous Substances Data 477600-75-2(Hazardous Substances Data)

Tofacitinib price

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Usbiological C7905-90 Tofacitinib ≥99%(HPLC,TLC) 936487-63-7 25mg $215 2026-06-03 Buy
Usbiological C7905-90 Tofacitinib ≥99%(HPLC,TLC) 936487-63-7 50mg $319 2026-06-03 Buy
Usbiological C7905-90 Tofacitinib ≥99%(HPLC,TLC) 936487-63-7 100mg $458 2026-06-03 Buy
Biosynth FT32555 Tofacitinib 477600-75-2 100mg $183 2026-06-04 Buy
Biosynth FT32555 Tofacitinib 477600-75-2 250mg $297.5 2026-06-04 Buy
Product number Packaging Price Buy
C7905-90 25mg $215 Buy
C7905-90 50mg $319 Buy
C7905-90 100mg $458 Buy
FT32555 100mg $183 Buy
FT32555 250mg $297.5 Buy

Tofacitinib Chemical Properties, Uses, Production

Description

In November 2012, the US FDA approved tofacitinib (also referred to as CP-690550) for the treatment of adult patients with moderate to severely active rheumatoid arthritis (RA) who have had an inadequate response or intolerance to methotrexate. Tofacitinib is the first small molecule kinase inhibitor approved for the treatment of RA. Tofacitinib is an inhibitor of the four subtypes of Janus kinase (JAK): JAK1, JAK2, JAK3, and Tyk2. The JAKs are intracellular, nonreceptor tyrosine kinases that play important roles in the signal transduction pathway of many cytokines (e.g., interleukins 2, 4, 7, 9, 15, and 21) and are involved in the propagation of inflammation in RA. Tofacitinib acts by inhibiting the phosphorylation and activation of signal transducers and activators of transcription (STATs), thereby suppressing the production of inflammatory mediators in joint tissue. At the enzyme level, tofacitinib inhibits JAKs 1, 2, 3, and Tyk2 with IC50s of 3.2, 4.1, 1.6, and 34 nM, respectively. At the cellular level, tofacitinib inhibits the in vitro activities of JAK1/JAK2, JAK1/JAK3, and JAK2/JAK2 combinations with IC50s of 406, 56, and 1377 nM, respectively.

Chemical Properties

Light Pink to Pale Orange Solid

Originator

Pfizer (United States)

Characteristics

Class: non-receptor tyrosine kinase
Treatment: RA, PA, JIA, UC
Oral bioavailability = 74%
Elimination half-life = 3.2 h
Protein binding = 40%

History

Tofacitinib (brand name: Xeljanz) is an oral JAK inhibitor developed by Pfizer Inc. It was first approved by the FDA on 6 November 2012 for the treatment of rheumatoid arthritis. Subsequently, Pfizer expanded its indications, securing approval for active psoriatic arthritis (December 2017), moderate to severe active ulcerative colitis (May 2018), and active polyarticular juvenile idiopathic arthritis (September 2020). Until December 2021, Xeljanz (tofacitinib) gained further FDA approval for treating active ankylosing spondylitis.

Uses

CP-690550 is a pyrrolo[2,3-d]pyrimidine derivative, as Janus kinase inhibitor for treatment of rheumatoid arthritis

Definition

ChEBI: A pyrrolopyrimidine that is pyrrolo[2,3-d]pyrimidine substituted at position 4 by an N-methyl,N-(1-cyanoacetyl-4-methylpiperidin-3-yl)amino moiety. Used as its citrate salt to treat moderately to severely ctive rheumatoid arthritis.

Indications

The JAK family includes four isoforms, JAK1, JAK2, JAK3, and tyrosine kinase (TYK2). Ruxolitinib (Jakafi(R), Incyte Corp.) was the first approved JAK inhibitor, which inhibits both JAK1 and JAK2, used for the treatment of different types of myelofibrosis. Tofacitinib (Xeljanz(R), Pfizer) was approved by FDA as a JAK3-selective inhibitor for the treatment of rheumatoid arthritis and is one of the only two FDA-approved kinase inhibitors for non-oncological indications.

brand name

Xeljanz

Pharmacokinetics

Tofacitinib has good solubility (>4 mg/mL in water for the crystalline citrate salt), which contributes to its excellent oral bioavailability (74%) in healthy volunteers. However, tofacitinib exhibits relatively short elimination half-life of 3.2 hours, and its protein binding is very low (approximately 40%, predominantly to albumin). Tofacitinib undergoes major hepatic clearance (70% of total clearance) and minor renal clearance (30%). The metabolism of tofacitinib proceeds primarily in the liver by CYP3A4 (major) and CYP2C19 (minor), resulting in oxidation of the pyrrolopyrimidine and piperidine rings, oxidation of the piperidine ring side-chain, N-demethylation, and glucuronidation. As opposed to the longer half-life of biologics, small-molecule JAK inhibitors such as tofacitinib typically display much shorter half-lives with once or twice-daily dosing regimens, which may be inconvenient to some patients. However, the shorter half-life ensures faster recovery to the full ability to fight infections which may occur with any immune suppressing medication.

Clinical Use

Tofacitinib was approved for treating rheumatoid arthritis in 2012, joint pain and swelling, psoriatic arthritis in 2017, and ulcerative colitis in 2018. However, severe side effects observed during clinical studies prevented the FDA from approving more efficacious doses for the treatment of rheumatoid arthritis (RA). Tofacitinib also carries a black box warning for an increased risk of pulmonary embolism and death associated with the 10 mg BID dose.

Synthesis

Commercially available aminopyridine 171 was reacted with dimethyl dicarbonate in the presence of potassium t-butoxide to give the methyl carbamate 172 in 87% yield. Hydrogenation of this carbamate 172 in the presence of 20 wt% of 5% Rh/C (JM type C101023-5) in acetic acid followed by reductive amination with benzaldehyde and sodium triacetoxy borohydride furnished the cis-benzyl protected piperidine 173 in 73% yield. Reduction of the methyl carbamate within 173 with lithium aluminum hydride (LAH) in THF gave the corresponding methyl amino piperidine which was isolated as the dihydrochloride salt 174 in 87% yield. Enantiomeric resolution of the methyl amino piperidine was achieved by freebasing the di-hydrochloride salt 174 with sodium hydroxide and then conversion to the di-toluol-L-tartaric acid salt followed by crystallization to give 175 in 42% yield and 98.6% ee. The enantioenriched tartrate salt 175 was then directly reacted with dichloride 176 (obtained from reaction of commercial 7H-pyrrolo[2,3-d]pyrimidine-2,4-diol (178) with phosphorous oxychloride) in the presence of potassium carbonate in water to give the coupled product 177 in essentially quantitative yield. Hydrogenation of intermediate 177 with DeGussaˉs catalyst triggered concomitant debenzylation and chloride removal, and this was followed by installation of the cyanoacetate group and subsequent treatment with citric acid to provide tofacitinib citrate (XXVII) in 90% yield.

Synthesis_477600-75-2

Background

Tofacitinib is a cell permeable Janus kinase inhibitor with demonstrated preference to inhibiting JAK1 and JAK3. Tofacitinib inhibits JAK isoforms 1, 2, and 3 with IC50 values of 6.1, 12, and 8.0 nM, respectively; the reported IC50 value relative to Tyk2 is 176 nM. Research studies show that tofacitinib primarily blocks γc cytokine receptors and inhibits cytokine production, which suggests that tofacitinib blocks cytokine action during both innate and adaptive responses. The overall effect of tofacitinib is to reduce inflammatory responses through selective inhibition of JAK family members.

References

[1] JIAN-KANG JIANG. Examining the Chirality, Conformation and Selective Kinase Inhibition of 3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile (CP-690,550)[J]. Journal of Medicinal Chemistry, 2008, 51 24: 8012-8018. DOI:10.1021/jm801142b
[2] MAURIZIO CUTOLO  Marianna M. Clinical utility of the oral JAK inhibitor tofacitinib in the treatment of rheumatoid arthritis.[J]. Journal of Inflammation Research, 2013, 6: 129-137. DOI:10.2147/jir.s35901
[3] M.N. MARTINA . Inhibition of JAK3 and PKC via Immunosuppressive Drugs Tofacitinib and Sotrastaurin Inhibits Proliferation of Human B Lymphocytes In Vitro[J]. Transplantation proceedings, 2016, 48 9: Pages 3046-3052. DOI:10.1016/j.transproceed.2016.07.052
[4] ANNIE MOISAN. White-to-brown metabolic conversion of human adipocytes by JAK inhibition[J]. Nature Cell Biology, 2014, 17 1: 57-67. DOI:10.1038/ncb3075
[5] MARTIN E DOWTY. Preclinical to clinical translation of tofacitinib, a Janus kinase inhibitor, in rheumatoid arthritis.[J]. Journal of Pharmacology and Experimental Therapeutics, 2014, 348 1: 165-173. DOI:10.1124/jpet.113.209304

Tofacitinib Preparation Products And Raw materials

Raw materials

Preparation Products

Tofacitinib Suppliers

Global Suppliers ( 510)
Supplier Tel Email Country ProdList Advantage
Shanghai Boc Chemical Co.,Ltd 021-34975603-808 18721111801 sales@bocpharma.com China 991 64
Zhuhai Yourun Co., Ltd. 0756-6811852 15876689832 zhyrpharm_sales03@126.com China 290 55
Shanghai Mixiu Chemical Co., Ltd. 18101936766 eileen@shmychem.com China 349 55
Junyu Chemexpress Co., Ltd. 0731-88036271 13723890100 info@csjyyy.com China 29 58
Hebei Chenguang Tianrun Pharma Co., Ltd. 0310-2816865 15175172220 hbcgtr@126.com China 13 58
Hangzhou Runyan Medical Technology Co., LTD 571-13989459766 18112526015 sales@runyanpharma.com China 496 58
Shanghai Boyle Chemical Co., Ltd. sales@boylechem.com China 2915 55
J & K SCIENTIFIC LTD. 18210857532 18210857532 jkinfo@jkchemical.com China 96815 76
Chembest Research Laboratories Limited 021-20908456 sales@BioChemBest.com China 5996 61
Beijing HwrkChemical Technology Co., Ltd 89508211 18501085097 sales.bj@hwrkchemical.com China 9407 55
Supplier Advantage
Shanghai Boc Chemical Co.,Ltd 64
Zhuhai Yourun Co., Ltd. 55
Shanghai Mixiu Chemical Co., Ltd. 55
Junyu Chemexpress Co., Ltd. 58
Hebei Chenguang Tianrun Pharma Co., Ltd. 58
Hangzhou Runyan Medical Technology Co., LTD 58
Shanghai Boyle Chemical Co., Ltd. 55
J & K SCIENTIFIC LTD. 76
Chembest Research Laboratories Limited 61
Beijing HwrkChemical Technology Co., Ltd 55

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View Latest Price from Tofacitinib manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile pictures 2026-09-14 3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile
477600-75-2
 0.99 RongNa Biotechnology Co.,Ltd
Tofacitinib. pictures 2026-09-14 Tofacitinib.
477600-75-2
 1g More Than 99% 100kg/Month BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Tofacitinib pictures 2026-09-02 Tofacitinib
477600-75-2
 $5.00 1KG 99% Henan Fengda Chemical Co., Ltd
  • Tofacitinib. pictures
  • Tofacitinib.
    477600-75-2
  • $0.00
  • More Than 99%
  • BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
  • Tofacitinib pictures
  • Tofacitinib
    477600-75-2
  • $5.00
  • 99%
  • Henan Fengda Chemical Co., Ltd

Tofacitinib Spectrum

Tofacitinib(477600-75-2)MSTofacitinib(477600-75-2)1HNMR

477600-75-2 (Tofacitinib) Related Search:

N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Tofacitinib citrate N-((3R,4R)-1-benzyl-4-Methylpiperidin-3-yl)-N-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine N-((3R,4R)-1-benzyl-4-Methylpiperidin-3-yl)-2-chloro-N-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine 2-Pentenoic acid, 3-amino-2-cyano-5-[(3R,4R)-4-methyl-3-(methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-1-piperidinyl]-5-oxo-, butyl ester
7H-Pyrrolo[2,3-d]pyrimidine-7-propanenitrile, 4-[[(3R,4R)-1-(2-cyanoacetyl)-4-methyl-3-piperidinyl]methylamino]-β-oxo- Nilotinib hydrochloride anhydrous Axitinib Cabozantinib Palbociclib
Trametinib Dacomitinib (PF299804) Lenvatinib AZD 1480 Pictilisib
Sunitinib Malate Ibrutinib Olverembatinib

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CP 690550 3-Piperidinamine, 1-(cyanoacetyl)-4-methyl-N-methyl-N-1H-pyrrolo(2,3-D)pyrimidin-4-yl-, (3R,4R)- CP-690550(Tasocitinib,CP690550) CP 690550(Tasocitinib) 3-((3R,4R)-4-Methyl-3-(Me... Tasocitinib (CP 690550) 1-Piperidinepropanenitrile, 4-Methyl-3-(Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-ylaMino)-beta-oxo-, (3R,4R)- Tofacitinib CP-690550 Tofacitinib 3-((3R,4R)-4-Methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropa Tofaimpurity Tofacitinib citrate, ≥98% (HPLC) CP 690550 - Tasocitinib | Tofacitinib 3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile, Tofacitinib 3-{(3R,4R)-4-Methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-1-piperidinyl}-3-oxopropanenitrile CS-344 CP690550 (Tofacitinib, Tasocitinib was stopped use) Tofacitinib ?Tasocitinib TOFACITINIB;TASOCITINIB;CP-690550;CP690550 Tofacitinib (CP-690550,Tasocitinib) 3-((3R,4R)-4-Methyl-3-(Methyl(7H-pyrrolo[2,3-d]pyriMidin-4-yl)aMino)-2-oxopiperidin-1-yl)propanenitrile Tropsch iMatinib CP 690550 3-((3R,4R)-4-Methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile (3R,4R)-4-methyl-3-(methyl-1H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-β-oxo-1-piperidinepropanenitrile Tofacitinib,CP-690550 Tofacitinib, >=98% 3-[4(R)-Methyl-3(R)-[N-methyl-N-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]- 3-oxopropanenitrile (3R,4R)-4-methyl-3-(methyl-1H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-β-oxo-2-piperidinepropanenitrile 3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile(CP-690550) ofacitinib Tofacitinib USP/EP/BP CP-690550 DISCONTINUED Tofacitinib 13C D2 15N Tofacitinib 13C3Q: What is Tofacitinib 13C3 Q: What is the CAS Number of Tofacitinib 13C3 Q: What is the storage condition of Tofacitinib 13C3 Q: What are the applications of Tofacitinib 13C3 Tofacitinib D3Q: What is Tofacitinib D3 Q: What is the CAS Number of Tofacitinib D3 1-Piperidinepropanenitrile, 4-methyl-3-(methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-β-oxo-, (3R,4R)- Tofatinib Tofacitinb Dapagliflozin Impurity 148 Tofacitinib, Janus kinase (JAK) inhibitor Tofacitinib, 10 mM in DMSO CAS:477600-75-2 Tofacitinib base, 98.0-102.0% Tofacitinib（477600-75-2） 3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile Tasocitinib Tofacitinib base Tofactinib 477600-75-2 Inhibitors Inhibitor API 477600-75-2 LFQ