Tofacitinib

C₁₆H₂₀N₆OCAS 477600-75-2312.38 g/mol

Open in Covalent MOL file

Amide Nitrile Tertiary amine

Properties

Molecular formula: C₁₆H₂₀N₆O
Molar mass: 312.38 g/mol
Exact mass: 312.1699 Da
pKa: 8.46 (cyano), 13.56 (secondary amine)
logP: 1.54Crippen estimate
Polar surface area: 88.9 Å²
H-bond donors / acceptors: 1 / 5
Rotatable bonds: 3
Stereocentres: R, Rin SMILES atom order

Hazards

Danger

H301 Toxic if swallowed25% of notifiers
H302 Harmful if swallowed25% of notifiers
H311 Toxic in contact with skin25% of notifiers
H315 Causes skin irritation25% of notifiers
H319 Causes serious eye irritation25% of notifiers
H331 Toxic if inhaled25% of notifiers
H335 May cause respiratory irritation25% of notifiers
H351 Suspected of causing cancer25% of notifiers
H360 May damage fertility or the unborn child50% of notifiers
H360Df May damage the unborn child; Suspected of damaging fertility25% of notifiers
H373 May causes damage to organs through prolonged or repeated exposure25% of notifiers

Aggregated from 4 ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Precautionary statements

P203, P260, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, P501

Identifiers

CAS number

477600-75-2

SMILES

C[C@@H]1CCN(C(=O)CC#N)C[C@@H]1N(C)c1ncnc2[nH]ccc12

InChIKey

UJLAWZDWDVHWOW-YPMHNXCESA-N

InChI

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

Weigh it out

Type any one amount. The others follow from the molar mass.

Names and synonyms

4 names

1-Piperidinepropanenitrile, 4-methyl-3-(methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-β-oxo-, (3R,4R)-
3-Piperidinamine, 1-(cyanoacetyl)-4-methyl-N-methyl-N-1H-pyrrolo[2,3-d]pyrimidin-4-yl-, (3R,4R)-
(3R,4R)-4-Methyl-3-(methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-β-oxo-1-piperidinepropanenitrile
CP 690550

Work with Tofacitinib

Predict the NMR spectrum1H and 13C shifts with multiplicities Make a solutionWhat to weigh for any molarity and volume Check drug-likenessLipinski, Veber and lead-likeness Isotope patternExact mass and the mass spectrum pattern

Stereoisomers, salts and isotopologues

The same compound in another form: other stereochemistry, a salt or hydrate, the free acid or base, or an isotope-labelled version.

(3S,4R)-4-Methyl-3-(methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-β-oxo-1-piperidinepropanenitrile1092578-48-7Diastereomer Epitofacitinib, (3R,4S)-1092578-46-5Diastereomer Tofacitinib citrate540737-29-9Salt

Similar compounds

N-Methyl-N-((3R,4R)-4-methyl-1-(phenylmethyl)-3-piperidinyl)-7H-pyrrolo(2,3-d)pyrimidin-4-amine477600-73-060 % similar N-Methyl-N-[(3R,4R)-4-methyl-3-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine477600-74-154 % similar Oclacitinib1208319-26-940 % similar Oclacitinib maleate1208319-27-038 % similar 2-(7H-Pyrrolo[2,3-D]pyrimidin-4-yl)isoindoline-1,3-dione741686-49-738 % similar Capivasertib1143532-39-132 % similar β-Oxo-1-pyrrolidinepropanenitrile14227-95-330 % similar

Tanimoto similarity of circular fingerprints over the whole catalogue.

All similar compounds

Elsewhere

PubChem CAS Common Chemistry NIST WebBook