(3R,4S)-Tofacitinib

Alias: Tofacitinib Impurity A; (3R,4S)-Tofacitinib; 1092578-46-5; 3-((3R,4S)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile; B64WR5WNB7; Epitofacitinib, (3R,4S)-; CHEMBL457871; 3-[(3R,4S)-4-METHYL-3-[METHYL(7H-PYRROLO[2,3-D]PYRIMIDIN-4-YL)AMINO]PIPERIDIN-1-YL]-3-OXOPROPANENITRILE; (3R,4S)-(+)-Tofacitinib isomer;

Cat No.:V33937 Purity: ≥98%

COA Product Data Instructions for use SDS

(3R,4S)-Tofacitinib (Tofacitinib Impurity A) is a less active diastereomer/enantiomer of Tofacitinib (CP 690550;tasocitinib; Xeljanz), which is a JAK3 (Janus-Associated kinase) inhibitor and an FDA approved drug for the treatment of rheumatoid arthritis (RA), psoriatic arthritis, and ulcerative colitis.

(3R,4S)-Tofacitinib Chemical Structure CAS No.: 1092578-46-5
Product category: JAK

This product is for research use only, not for human use. We do not sell to patients.

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Other Forms of (3R,4S)-Tofacitinib:

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Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators

Product Description

(3R,4S)-Tofacitinib (Tofacitinib Impurity A) is a less active diastereomer/enantiomer of Tofacitinib (CP 690550; tasocitinib; Xeljanz), which is a JAK3 (Janus-Associated kinase) inhibitor and an FDA approved drug for the treatment of rheumatoid arthritis (RA), psoriatic arthritis, and ulcerative colitis.

Biological Activity I Assay Protocols (From Reference)

Targets	JAK3; less active diastereomer/enantiomer of Tofacitinib
ln Vitro	(3R,4S)-Tofacitinib is an impurity of Tofacitinib and is a less active diastereomer of Tofacitinib.
References	[1]. https://pubchem.ncbi.nlm.nih.gov/compound/25180101
Additional Infomation	(3r,4s)-Tofacitinib is a N-acylpiperidine.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula	C16H20N6O
Molecular Weight	312.3696
Exact Mass	312.169
Elemental Analysis	C, 61.52; H, 6.45; N, 26.90; O, 5.12
CAS #	1092578-46-5
Related CAS #	Tofacitinib;477600-75-2;Tofacitinib citrate;540737-29-9;(3S,4S)-Tofacitinib;1092578-47-6;(3S,4R)-Tofacitinib;1092578-48-7
PubChem CID	25180101
Appearance	White to off-white solid powder
Density	1.3±0.1 g/cm3
Boiling Point	585.8±50.0 °C at 760 mmHg
Flash Point	308.1±30.1 °C
Vapour Pressure	0.0±1.6 mmHg at 25°C
Index of Refraction	1.646
LogP	0.93
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Heavy Atom Count	23
Complexity	488
Defined Atom Stereocenter Count	2
SMILES	C[C@H]1CCN(C[C@@H]1N(C)C2=NC=NC3=C2C=CN3)C(=O)CC#N
InChi Key	UJLAWZDWDVHWOW-AAEUAGOBSA-N
InChi Code	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-/m0/s1
Chemical Name	3-[(3R,4S)-4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-3-oxopropanenitrile
Synonyms	Tofacitinib Impurity A; (3R,4S)-Tofacitinib; 1092578-46-5; 3-((3R,4S)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile; B64WR5WNB7; Epitofacitinib, (3R,4S)-; CHEMBL457871; 3-[(3R,4S)-4-METHYL-3-[METHYL(7H-PYRROLO[2,3-D]PYRIMIDIN-4-YL)AMINO]PIPERIDIN-1-YL]-3-OXOPROPANENITRILE; (3R,4S)-(+)-Tofacitinib isomer;
HS Tariff Code	2934.99.9001
Storage	Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)	DMSO : ~100 mg/mL (~320.13 mM)
Solubility (In Vivo)	Solubility in Formulation 1: ≥ 2.5 mg/mL (8.00 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.)

Solubility (In Vitro)

DMSO : ~100 mg/mL (~320.13 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (8.00 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.2013 mL	16.0067 mL	32.0133 mL
	5 mM	0.6403 mL	3.2013 mL	6.4027 mL
	10 mM	0.3201 mL	1.6007 mL	3.2013 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Mass

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Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

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Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

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Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.