Description
Tofacitinib · CAS 477600-75-2 · C16H20N6O. UNII 87LA6FU830. LogP: 1.808.
Identification
| CAS Registry Number | 477600-75-2 |
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| PubChem CID | 9926791 |
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| Molecular formula | C16H20N6O |
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| IUPAC name | 3-[(3R,4R)-4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-3-oxopropanenitrile |
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| UNII (FDA) | 87LA6FU830 |
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Computed Descriptors
| Molecular Weight | 312.37 |
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| XLogP3 | 1.5 |
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| Hydrogen Bond Donor Count | 1 |
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| Hydrogen Bond Acceptor Count | 5 |
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| Rotatable Bond Count | 3 |
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| Exact Mass | 312.16985928 |
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| Monoisotopic Mass | 312.16985928 |
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| Topological Polar Surface Area | 88.9 |
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| Heavy Atom Count | 23 |
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| Formal Charge | 0 |
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Physical & Chemical Properties
Physical description & handling notes
- White crystalline solid. MP: 199-206 °C /Tofacitinib monocitrate/
- Stable under recommended storage conditions. /Tofacitinib citrate/
- Specific optical rotation: +10.4 deg at 25 °C/D (c = 0.64 in methanol)
- pKa1 = 8.46 (cyano); pKa2 = 13.56 (secondary amine)
- Oral: Tablets, film-coated, 5 mg (of tofacitinib), Xeljanz (Pfizer).
GHS Hazard Classification
| Reported hazard statements | H301 (25%), H302 (25%), H311 (25%), H315 (25%), H319 (25%), H331 (25%), H335 (25%), H351 (25%) |
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H301 (25%): Toxic if swallowed [Danger Acute toxicity, oral]
H302 (25%): Harmful if swallowed [Warning Acute toxicity, oral]
Documented Uses
- Preparation (unspecified stereo): T. A. Blumenkopf et al., World Intellectual Property Organization patent 0142246; eidem, United States of America patent 7265221 (2001, 2007 both to Pfizer).
- Tofacitinib is an oral, small molecule inhibitor of Janus kinases that is used to treat moderate-to-severe rheumatoid arthritis, psoriatic arthritis and inflammatory bowel disease. Tofacitinib is associated with transient and usually mild elevations in serum aminotransferase levels during therapy, but has yet to be linked to cases of clinically apparent acute liver injury.
- Breast Feeding; Lactation; Milk, Human; Antirheumatic Agents; Enzyme Inhibitors; Janus Kinase Inhibitors; JAK Inhibitors; Signal Transduction Inhibitors; Protein Kinase Inhibitors
- Xeljanz (tofacitinib) is indicated 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). /Included in US product label/
- /BOXED WARNING/ MALIGNANCIES. Lymphoma and other malignancies have been observed in patients treated with Xeljanz. Epstein Barr Virus-associated post-transplant lymphoproliferative disorder has been observed at an increased rate in renal transplant patients treated with Xeljanz and concomitant immunosuppressive medications
- Patients receiving tofacitinib are at increased risk of developing serious infections that may require hospitalization or result in death. Opportunistic infections caused by bacterial, mycobacterial, invasive fungal, viral, or other opportunistic organisms-including cryptococcosis, pneumocystosis, tuberculosis and other mycobacterial infections, esophageal candidiasis, multidermatomal herpes zoster, cytomegalovirus infection, and BK virus infection-have been reported in patients with rheumatoid arthritis receiving
Synonyms
Tofacitinib; 477600-75-2; Tasocitinib; 3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile; CP-690550; CP 690550; Cp-690 free base; tofacitinibum; 3-{(3R,4R)-4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl}-3-oxopropanenitrile; CP690550; 87LA6FU830; CP-690550 FREE BASE; CP-690,550 FREE BASE; CP690,550; CP-690-550; CHEBI:71200
Frequently Asked Questions
What are the CAS number and molecular formula of Tofacitinib?
CAS 477600-75-2; molecular formula C16H20N6O; molecular weight — g/mol.
What other names is Tofacitinib known by?
Tofacitinib, 477600-75-2, Tasocitinib, 3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile, CP-690550, CP 690550.
Is Tofacitinib classified as hazardous?
Hazard statements reported: H301, H302, H311, H315, H319.
What are the key physical properties of Tofacitinib?
LogP: 1.808.
Facts on this page are taken from PubChem (US National Library of Medicine) and Wikidata. Grade-specific data — assay, moisture, particle size, packaging, shelf life — is issued per batch on the COA and is not published here.
