Tofacitinib citrateProduct ingredient for Tofacitinib

Name
Tofacitinib citrate
Drug Entry
Tofacitinib

Tofacitinib is an inhibitor of Janus kinases, a group of intracellular enzymes involved in signalling pathways that affect hematopoiesis and immune cell function. It is approved by the FDA for treatment of moderate to severe rheumatoid arthritis that responds inadequately to methotrexate or in those who are intolerant to methotrexate. Besides rheumatoid arthritis, tofacitinib has also been studied in clinical trials for the prevention of organ transplant rejection, and is currently under investigation for the treatment of psoriasis. Known adverse effects include nausea and headache as well as more serious immunologic and hematological adverse effects. Tofacitinib is marketed under the brand name Xeljanz by Pfizer.

Accession Number
DBSALT000180
Structure
Synonyms
Tasocitinib monocitrate / Tofacitinib monocitrate
UNII
O1FF4DIV0D
CAS Number
540737-29-9
Weight
Average: 504.4931
Monoisotopic: 504.196861902
Chemical Formula
C22H28N6O8
InChI Key
SYIKUFDOYJFGBQ-YLAFAASESA-N
InChI
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
IUPAC Name
2-hydroxypropane-1,2,3-tricarboxylic acid; 3-[(3R,4R)-4-methyl-3-[methyl({7H-pyrrolo[2,3-d]pyrimidin-4-yl})amino]piperidin-1-yl]-3-oxopropanenitrile
SMILES
OC(=O)CC(O)(CC(O)=O)C(O)=O.C[C@@H]1CCN(C[C@@H]1N(C)C1=NC=NC2=C1C=CN2)C(=O)CC#N
KEGG Drug
D09783
PubChem Compound
10174505
ChemSpider
8350010
ChEBI
71197
ChEMBL
CHEMBL2103743
Wikipedia
Tofacitinib
Predicted Properties
PropertyValueSource
Water Solubility0.299 mg/mLALOGPS
logP1.58ALOGPS
logP1.24Chemaxon
logS-3ALOGPS
pKa (Strongest Acidic)9.15Chemaxon
pKa (Strongest Basic)6.44Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area88.91 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity87.8 m3·mol-1Chemaxon
Polarizability32.38 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon