Tofacitinib citrate
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MedKoo CAT#: 100951

CAS#: 540737-29-9 (citrate)

Description: Tofacitinib, also known as tasocitinib, CP-690550, is a Janus kinase (JAK) inhibitor. Tofacitinib modulates the signaling pathway at the point of JAKs, preventing the phosphorylation and activation of STATs. JAK enzymes transmit cytokine signaling through pairing of JAKs (e.g., JAK1/JAK3, JAK1/JAK2, JAK1/TyK2, JAK2/JAK2). Tofacitinib inhibited the in vitro activities of JAK1/JAK2, JAK1/JAK3, and JAK2/JAK2 combinations with IC50 of 406, 56, and 1377 nM, respectively. Tofacitinib citrate was approved for for the treatment of adult patients with moderately to severely active rheumatoid arthritis who have had an inadequate response or intolerance to methotrexate. It may be used as monotherapy or in combination with methotrexate or other nonbiologic disease-modifying antirheumatic drugs (DMARDs).


Price and Availability

Size
Price

100mg
USD 90
1g
USD 450
10g
USD 2850
Size
Price

200mg
USD 150
2g
USD 850
20g
USD 4250
Size
Price

500mg
USD 250
5g
USD 1750
50g
USD 7650

Tofacitinib citrate, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100951
Name: Tofacitinib citrate
CAS#: 540737-29-9 (citrate)
Chemical Formula: C22H28N6O8
Exact Mass:
Molecular Weight: 504.5
Elemental Analysis: C, 52.38; H, 5.59; N, 16.66; O, 25.37


Related CAS #: 540737-29-9 (citrate)   477600-75-2 (free base)    

Synonym: Tofacitinib citrate; CP690550; CP-690550; CP 690550; CP-690550-10; CP-690,550-10; CP-690550 citrate; Tofacitinib; tasocitinib. Trade name Xeljanz.

IUPAC/Chemical Name: 1-Piperidinepropanenitrile, 4-methyl-3-(methyl-7H-pyrrolo(2,3-d)pyrimidin-4-ylamino)- beta-oxo-, (3R,4R)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

InChi Key: SYIKUFDOYJFGBQ-YLAFAASESA-N

InChi Code: InChI=1S/C16H20N6O.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h4,7,10-11,13H,3,5,8-9H2,1-2H3,(H,18,19,20);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t11-,13+;/m1./s1

SMILES Code: N#CCC(N1C[C@H](N(C)C2=C3C(NC=C3)=NC=N2)[C@H](C)CC1)=O.O=C(CC(C(O)=O)(O)CC(O)=O)O


Technical Data

Appearance:
White to off-white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Curtis JR, Zhang R, Krishnaswami S, Anisfeld A, Chen Y, Strengholt S, Chen C, Geier J. Use of a risk characterisation approach to contextualise the safety profile of new rheumatoid arthritis treatments: a case study using tofacitinib. Clin Rheumatol. 2017 Mar;36(3):683-688. doi: 10.1007/s10067-016-3359-x. PubMed PMID: 27470086; PubMed Central PMCID: PMC5323490.

2: Papp KA, Krueger JG, Feldman SR, Langley RG, Thaci D, Torii H, Tyring S, Wolk R, Gardner A, Mebus C, Tan H, Luo Y, Gupta P, Mallbris L, Tatulych S. Tofacitinib, an oral Janus kinase inhibitor, for the treatment of chronic plaque psoriasis: Long-term efficacy and safety results from 2 randomized phase-III studies and 1 open-label long-term extension study. J Am Acad Dermatol. 2016 May;74(5):841-50. doi: 10.1016/j.jaad.2016.01.013. PubMed PMID: 26899199.

3: Krueger J, Clark JD, Suárez-Fariñas M, Fuentes-Duculan J, Cueto I, Wang CQ, Tan H, Wolk R, Rottinghaus ST, Whitley MZ, Valdez H, von Schack D, O'Neil SP, Reddy PS, Tatulych S; A3921147 Study Investigators.. Tofacitinib attenuates pathologic immune pathways in patients with psoriasis: A randomized phase 2 study. J Allergy Clin Immunol. 2016 Apr;137(4):1079-90. doi: 10.1016/j.jaci.2015.12.1318. PubMed PMID: 27059729.

4: Lee YH, Bae SC, Song GG. Comparative efficacy and safety of tofacitinib, with or without methotrexate, in patients with active rheumatoid arthritis: a Bayesian network meta-analysis of randomized controlled trials. Rheumatol Int. 2015 Dec;35(12):1965-74. doi: 10.1007/s00296-015-3291-4. PubMed PMID: 25994093.

5: Fukuyama T, Tschernig T, Qi Y, Volmer DA, Bäumer W. Aggression behaviour induced by oral administration of the Janus-kinase inhibitor tofacitinib, but not oclacitinib, under stressful conditions. Eur J Pharmacol. 2015 Oct 5;764:278-82. doi: 10.1016/j.ejphar.2015.06.060. PubMed PMID: 26164790.

6: Lee MY, Park SK, Park SY, Byun JH, Lee SM, Ko SK, Lee EK. Cost-effectiveness of Tofacitinib in the Treatment of Moderate to Severe Rheumatoid Arthritis in South Korea. Clin Ther. 2015 Aug;37(8):1662-76.e2. doi: 10.1016/j.clinthera.2015.07.001. PubMed PMID: 26243076.

7: Tanaka Y, Takeuchi T, Yamanaka H, Nakamura H, Toyoizumi S, Zwillich S. Efficacy and safety of tofacitinib as monotherapy in Japanese patients with active rheumatoid arthritis: a 12-week, randomized, phase 2 study. Mod Rheumatol. 2015 Jul;25(4):514-21. doi: 10.3109/14397595.2014.995875. PubMed PMID: 25496464; PubMed Central PMCID: PMC4819568.

8: Koizumi H, Arito M, Endo W, Kurokawa MS, Okamoto K, Omoteyama K, Suematsu N, Beppu M, Kato T. Effects of tofacitinib on nucleic acid metabolism in human articular chondrocytes. Mod Rheumatol. 2015 Jul;25(4):522-7. doi: 10.3109/14397595.2014.995874. PubMed PMID: 25496463.

9: Wallenstein GV, Kanik KS, Wilkinson B, Cohen S, Cutolo M, Fleishmann R, Genovese MC, Gomez Reino J, Gruben D, Kremer J, Krishnaswami S, Lee EB, Pascual-Ramos V, Strand V, Zwillich SH. Effects of the oral Janus kinase inhibitor tofacitinib on patient-reported outcomes in patients with active rheumatoid arthritis: results of two Phase 2 randomised controlled trials. Clin Exp Rheumatol. 2016 May-Jun;34(3):430-42. PubMed PMID: 27156561.

10: Curtis JR, Lee EB, Kaplan IV, Kwok K, Geier J, Benda B, Soma K, Wang L, Riese R. Tofacitinib, an oral Janus kinase inhibitor: analysis of malignancies across the rheumatoid arthritis clinical development programme. Ann Rheum Dis. 2016 May;75(5):831-41. doi: 10.1136/annrheumdis-2014-205847. PubMed PMID: 25902789; PubMed Central PMCID: PMC4853586.

11: Winthrop KL, Silverfield J, Racewicz A, Neal J, Lee EB, Hrycaj P, Gomez-Reino J, Soma K, Mebus C, Wilkinson B, Hodge J, Fan H, Wang T, Bingham CO 3rd. The effect of tofacitinib on pneumococcal and influenza vaccine responses in rheumatoid arthritis. Ann Rheum Dis. 2016 Apr;75(4):687-95. doi: 10.1136/annrheumdis-2014-207191. PubMed PMID: 25795907; PubMed Central PMCID: PMC4819610.

12: Rizzi M, Lorenzetti R, Fischer K, Staniek J, Janowska I, Troilo A, Strohmeier V, Erlacher M, Kunze M, Bannert B, Kyburz D, Voll RE, Venhoff N, Thiel J. Impact of tofacitinib treatment on human B-cells in vitro and in vivo. J Autoimmun. 2017 Feb;77:55-66. doi: 10.1016/j.jaut.2016.10.005. PubMed PMID: 27793425.

13: Fleischmann R, Mease PJ, Schwartzman S, Hwang LJ, Soma K, Connell CA, Takiya L, Bananis E. Efficacy of tofacitinib in patients with rheumatoid arthritis stratified by background methotrexate dose group. Clin Rheumatol. 2017 Jan;36(1):15-24. doi: 10.1007/s10067-016-3436-1. PubMed PMID: 27734232; PubMed Central PMCID: PMC5216063.

14: Yamanaka H, Tanaka Y, Takeuchi T, Sugiyama N, Yuasa H, Toyoizumi S, Morishima Y, Hirose T, Zwillich S. Tofacitinib, an oral Janus kinase inhibitor, as monotherapy or with background methotrexate, in Japanese patients with rheumatoid arthritis: an open-label, long-term extension study. Arthritis Res Ther. 2016 Jan 28;18:34. doi: 10.1186/s13075-016-0932-2. PubMed PMID: 26818974; PubMed Central PMCID: PMC4730592.

15: Vieira MC, Zwillich SH, Jansen JP, Smiechowski B, Spurden D, Wallenstein GV. Tofacitinib Versus Biologic Treatments in Patients With Active Rheumatoid Arthritis Who Have Had an Inadequate Response to Tumor Necrosis Factor Inhibitors: Results From a Network Meta-analysis. Clin Ther. 2016 Dec;38(12):2628-2641.e5. doi: 10.1016/j.clinthera.2016.11.004. PubMed PMID: 27889300.

16: Charles-Schoeman C, Wicker P, Gonzalez-Gay MA, Boy M, Zuckerman A, Soma K, Geier J, Kwok K, Riese R. Cardiovascular safety findings in patients with rheumatoid arthritis treated with tofacitinib, an oral Janus kinase inhibitor. Semin Arthritis Rheum. 2016 Dec;46(3):261-271. doi: 10.1016/j.semarthrit.2016.05.014. PubMed PMID: 27443588.

17: Strand V, Ahadieh S, French J, Geier J, Krishnaswami S, Menon S, Checchio T, Tensfeldt TG, Hoffman E, Riese R, Boy M, Gómez-Reino JJ. Systematic review and meta-analysis of serious infections with tofacitinib and biologic disease-modifying antirheumatic drug treatment in rheumatoid arthritis clinical trials. Arthritis Res Ther. 2015 Dec 15;17:362. doi: 10.1186/s13075-015-0880-2. Review. PubMed PMID: 26669566; PubMed Central PMCID: PMC4704538.

18: Strand V, Kremer J, Wallenstein G, Kanik KS, Connell C, Gruben D, Zwillich SH, Fleischmann R. Effects of tofacitinib monotherapy on patient-reported outcomes in a randomized phase 3 study of patients with active rheumatoid arthritis and inadequate responses to DMARDs. Arthritis Res Ther. 2015 Nov 4;17:307. doi: 10.1186/s13075-015-0825-9. PubMed PMID: 26530039; PubMed Central PMCID: PMC4632359.

19: Feldman SR, Thaçi D, Gooderham M, Augustin M, de la Cruz C, Mallbris L, Buonanno M, Tatulych S, Kaur M, Lan S, Valdez H, Mamolo C. Tofacitinib improves pruritus and health-related quality of life up to 52 weeks: Results from 2 randomized phase III trials in patients with moderate to severe plaque psoriasis. J Am Acad Dermatol. 2016 Dec;75(6):1162-1170.e3. doi: 10.1016/j.jaad.2016.07.040. PubMed PMID: 27692733.

20: Wu JJ, Strober BE, Hansen PR, Ahlehoff O, Egeberg A, Qureshi AA, Robertson D, Valdez H, Tan H, Wolk R. Effects of tofacitinib on cardiovascular risk factors and cardiovascular outcomes based on phase III and long-term extension data in patients with plaque psoriasis. J Am Acad Dermatol. 2016 Nov;75(5):897-905. doi: 10.1016/j.jaad.2016.06.012. PubMed PMID: 27498960.