Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00683)
Name
Tofacitinib
Synonyms    Click to Show/Hide the Synonyms of This API
Tofacitinib; Tasocitinib; 477600-75-2; 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; racemic-tofacitinib; 1259404-17-5; rac-Tofacitinib; CP-690,550; Tofacitinib (CP-690550,Tasocitinib); UNII-87LA6FU830; 3-{(3R,4R)-4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl}-3-oxopropanenitrile; CHEMBL221959; 3-((3R,4R)-rel-4-Methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile; CHEBI:71200; 87LA6FU830; 477600-75-2 (free base); MFCD11035919; CP690550; 3-((3R,4R)-4-Methyl-3-(methyl(7H-pyrrolo(2,3-d)pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile; 3-[(3R*,4R*)-4-Methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-3-oxopropanenitrile; 3-[(3R,4R)-4-methyl-3-[methyl({7H-pyrrolo[2,3-d]pyrimidin-4-yl})amino]piperidin-1-yl]-3-oxopropanenitrile; 3-[(3R,4R)-4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-3-oxopropanenitrile; 3-{(3R,4R)-4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-3-oxo-propionitrile; Tofacitinib [USAN:INN]; C16H20N6O; tofacitinibum; Tofacitinib (USAN); PubChem16767; 1-Piperidinepropanenitrile, 4-methyl-3-(methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-beta-oxo-, (3R,4R)-; cc-396; SCHEMBL322753; GTPL5677; QCR-53; HSDB 8311; DTXSID90197271; EX-A205; BCPP000274; CP-690550 FREE BASE; AOB87470; ZINC3818808; CP-690,550 FREE BASE; ABP000824; ANW-51607; BDBM50193995; CP-690; NSC782351; NSC800953; AKOS005145814; AKOS005258733; AC-8193; BCP9000550; CA10005; CCG-264998; CS-0050; DB08895; GS-6106; NSC-782351; NSC-800953; PB20522; SB20004; SB20005; NCGC00229511-02; NCGC00229511-04; NCGC00229511-10; NCGC00244463-01; Tofacitinib (CP-690550, Tasocitinib); CP690550(Tasocitinib)/CP-690550; HY-40354; AB0007916; CP690,550; CP-690-550; CP- 690 550; D09970; Q-9324; AB01565786_02; 600M752; AR-270/43507983; J-524314; Q3530324; BRD-K31283835-001-01-9; BRD-K31283835-048-04-4; 3-((3R,4R)-4-Methyl(7H-Pyrrolo[2,3-D]Pyrimidin-4-Yi)Amino)Piperidin-1-Yl-3-Oxopropaneni; (3R,4R)-3-{4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-3-oxo-propionitrile; (3R,4R)-4-methyl-3-(methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-beta-oxo-1-piperidine propanenitrile; 3-[(3R,4R)-4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-1-piperidyl]-3-oxo-propanenitrile; 3-{(3R,4R)-4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]piperidin-1-yl}-3-oxo-propionitrile; 3-{(3R,4R)-4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin4-yl)-amino]-piperidin-1-yl}-3-oxo-propionitrile; 3-{4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-1-piperidinyl}-3-oxopropanenitrile; 3-Piperidinamine, 1-(cyanoacetyl)-4-methyl-N-methyl-N-1H-pyrrolo(2,3-d)pyrimidin-4-yl-, (3R,4R)-
Clinical Status
Approved
Disease Indication Rheumatoid arthritis ICD-11: FA20 [1]
PubChem CID
9926791
Formula
C16H20N6O
Canonical SMILES
C[C@@H]1CCN(C[C@@H]1N(C)C2=NC=NC3=C2C=CN3)C(=O)CC#N
InChI
1S/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+/m1/s1
InChIKey
UJLAWZDWDVHWOW-YPMHNXCESA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=9926791"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 312.37 Topological Polar Surface Area 88.9
XlogP 1.5 Complexity 488
Heavy Atom Count 23 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Full List of Drug Formulations (DFMs) Containing This API
          Tofacitinib Citrate eq 10mg base tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Croscarmellose Sodium; Fd&C Blue 1/Brilliant Blue Fcf Aluminum Lake; Fd&C Blue 2/Indigo Carmine Aluminum Lake; Hpmc 2910/Hypromellose 6Cp; Lactose Monohydrate; Macrogol/Peg3350; Magnesium Stearate; Microcrystalline Cellulose; Titanium Dioxide; Triacetin
                   Dosage Form Tablet
                   Company Pf Prism Cv
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Food blue 1 aluminum lake DIG Info Leukemia MT4 cells (IC50 = 1288.25 nM) [3]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
Polyethylene glycol 3350 DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
          Tofacitinib Citrate eq 22mg base extended release tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Cellulose Acetate; Copovidone; Fd&C Blue 2 Aluminum Lake; Hydroxyethyl Cellulose; Hydroxypropyl Cellulose; Hpmc 2910/Hypromellose; Magnesium Stearate; Red Iron Oxide; Sorbitol; Titanium Dioxide; Triacetin; Yellow Iron Oxide; Printing Ink Contains Ammonium Hydroxide; Ferrosoferric Oxide/Black Iron Oxide; Propylene Glycol; Shellac Glaze
                   Dosage Form Extended Release Tablet
                   Company Pfizer
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [6]
Hydroxypropyl cellulose DIG Info Mephenytoin 4-hydroxylase (EC50 = 89.5 uM) [4]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
          Tofacitinib Citrate eq 11mg base extended release tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Cellulose Acetate; Copovidone; Hydroxyethyl Cellulose; Hydroxypropyl Cellulose; Hpmc 2910/Hypromellose; Magnesium Stearate; Red Iron Oxide; Sorbitol; Titanium Dioxide; Triacetin; Printing Ink Contains Ammonium Hydroxide; Ferrosoferric Oxide/Black Iron; Propylene Glycol; Shellac Glaze
                   Dosage Form Extended Release Tablet
                   Company Pfizer
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [6]
Hydroxypropyl cellulose DIG Info Mephenytoin 4-hydroxylase (EC50 = 89.5 uM) [4]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
          Tofacitinib Citrate eq 5mg base tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Croscarmellose Sodium; Hpmc 2910/Hypromellose 6Cp; Lactose Monohydrate; Macrogol/Peg3350; Magnesium Stearate; Microcrystalline Cellulose; Titanium Dioxide; Triacetin
                   Dosage Form Tablet
                   Company Pf Prism Cv
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
Polyethylene glycol 3350 DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
          Tofacitinib Citrate eq 1mg base/ml solution Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Grape Flavor (Natural); Hydrochloric Acid; Lactic Acid; Purified Water; Sodium Benzoate; Sucralose; Xylitol
                   Dosage Form Solution
                   Company Pfizer
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sucralose DIG Info Carbonic anhydrase II (Ki = 300 nM) [7]
Sodium benzoate DIG Info Carbonic anhydrase II (Ki = 30000 nM) [8]
Hydrochloric acid DIG Info Carbonic anhydrase V (Ki = 156 nM) [9]
Lactic acid DIG Info Fetal lung MRC5 cells (IC50 = 23930 nM) [10]
          Tofacitinib 5 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Titanium dioxide; Triacetin; Croscarmellose sodium; Polyethylene glycol 3350; Hypromellose 2910 (6 mpa.s); Microcrystalline cellulose
                   Dosage Form Oral Tablet
                   Company Pfizer Laboratories; U.S. Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
Polyethylene glycol 3350 DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
          Tofacitinib 11 mg tablet Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Sorbitol; Ammonia; Ferric oxide red; Ferrosoferric oxide; Propylene glycol; Titanium dioxide; Triacetin; Cellulose acetate; Copovidone; Hydroxyethyl cellulose (140 mpa.s at 5%); Hydroxypropyl cellulose (1200000 mw); Hypromellose 2910 (6 mpa.s); Shellac
                   Dosage Form 24 HR Extended Release Oral Tablet
                   Company U.S. Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Sorbitol; Ammonia; Ferric oxide red; Ferrosoferric oxide; Propylene glycol; Titanium dioxide; Triacetin; Cellulose acetate; Copovidone k25-31; Hydroxyethyl cellulose (140 mpa.s at 5%); Hydroxypropyl cellulose (1200000 mw); Hypromellose 2910 (6 mpa.s); Shellac
                   Dosage Form 24 HR Extended Release Oral Tablet
                   Company Pfizer Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
References
1 FDA label for approved tofacitinib from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Synthesis and structure-activity relationship studies of CD4 down-modulating cyclotriazadisulfonamide (CADA) analogues. J Med Chem. 2006 Feb 23; 49(4):1291-312.
4 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
5 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
6 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
7 Sweet Binders: Carbonic Anhydrase IX in Complex with Sucralose. ACS Med Chem Lett. 2018 May 10; 9(7):657-661.
8 Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1; 15(3):573-8.
9 Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions. Bioorg Med Chem Lett. 2004 Nov 1; 14(21):5435-9.
10 Design, synthesis and biological studies of a library of NK1-Receptor Ligands Based on a 5-arylthiosubstituted 2-amino-4,6-diaryl-3-cyano-4H-pyran core: Switch from antagonist to agonist effect by chemical modification. Eur J Med Chem. 2017 Sep 29; 138:644-660.

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