Takinib
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MedKoo CAT#: 561836

CAS#: 1111556-37-6

Description: Takinib is a selective TAK1 inhibitor that induces apoptosis following TNF-α stimulation in cell models of rheumatoid arthritis and metastatic breast cancer. Takinib is an inhibitor of autophosphorylated and non-phosphorylated TAK1 that binds within the ATP-binding pocket and inhibits by slowing down the rate-limiting step of TAK1 activation.

Chemical Structure

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Takinib
CAS# 1111556-37-6
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 561836
Name: Takinib
CAS#: 1111556-37-6
Chemical Formula: C18H18N4O2
Exact Mass: 322.14
Molecular Weight: 322.360
Elemental Analysis: C, 67.07; H, 5.63; N, 17.38; O, 9.93

Price and Availability

Size Price Availability Quantity
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1250 Ready to ship
500mg USD 1950 Ready to ship
1g USD 2950 Ready to ship
2g USD 5250 Ready to ship
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Synonym: Takinib; EDHS-206; EDHS 206; EDHS206;

IUPAC/Chemical Name: 3-N-(1-Propylbenzimidazol-2-yl)benzene-1,3-dicarboxamide

InChi Key: UOZVVPXKJGOFIG-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H18N4O2/c1-2-10-22-15-9-4-3-8-14(15)20-18(22)21-17(24)13-7-5-6-12(11-13)16(19)23/h3-9,11H,2,10H2,1H3,(H2,19,23)(H,20,21,24)

SMILES Code: O=C(C1=CC=CC(C(NC2=NC3=CC=CC=C3N2CCC)=O)=C1)N

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Takinib is a potent and selective TAK1 inhibitor with an IC50 of 9.5 nM.
In vitro activity: MDA-MB-231 cells were serum-starved for 3h and pre-treated with 10μM Takinib for 2h. Stimulation of cells with TNFα was performed over a time-course of 60min and the phosphorylation status of IKK, p38, and p65 was determined via Western Blot (Fig. 5B). IKK and p65 are maximally phosphorylated at 15 minutes, which indicate activation of the NFkB pathway, while p38 phosphorylation peaks at 30 minutes. Takinib reduced phosphorylation of significantly but did not influence total protein levels. Dose-dependency studies were performed in Hela cells following 15 minutes of TNFα stimulation. Western Blot analysis demonstrated that Takinib inhibits phosphorylation of IKK, MAPK 8/9, and cJun in a dose-dependent manner (Fig. 5C). Additionally, we investigated cellular TAK1 autophosphorylation following 15min of TNFα stimulation. Thr184 phosphorylation was significantly reduced at low μM concentrations (Fig. S3A). Reference: Cell Chem Biol. 2017 Aug 17;24(8):1029-1039.e7. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/28820959/
In vivo activity: Takinib has an ability to reduce the clinical score in the CIA mouse model of rheumatoid arthritis (RA) (p < 0.001). TAK1 inhibition reduced inflammation (p < 0.01), cartilage damage (p < 0.01), pannus, bone resorption, and periosteal bone formation and periosteal bone width in all joints of treated mice compared to vehicle treated. Significant reduction of inflammation (p < 0.004) and cartilage damage (p < 0.004) were observed in the knees of diseased treated animals, with moderate reduction seen in the forepaws and hind paws. Furthermore, the pharmacokinetics of takinib show rapid plasma clearance (t½ = 21 min). In stimulated RA-FLS cells, takinib reduced GROα, G-CSF, and ICAM-1 pro-inflammatory cytokine signaling. Reference: Arthritis Res Ther. 2019 Dec 17;21(1):292. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/31847895/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.0 93.06

Preparing Stock Solutions

The following data is based on the product molecular weight 322.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol: 1. Totzke J, Gurbani D, Raphemot R, Hughes PF, Bodoor K, Carlson DA, Loiselle DR, Bera AK, Eibschutz LS, Perkins MM, Eubanks AL, Campbell PL, Fox DA, Westover KD, Haystead TAJ, Derbyshire ER. Takinib, a Selective TAK1 Inhibitor, Broadens the Therapeutic Efficacy of TNF-α Inhibition for Cancer and Autoimmune Disease. Cell Chem Biol. 2017 Aug 17;24(8):1029-1039.e7. doi: 10.1016/j.chembiol.2017.07.011. PMID: 28820959; PMCID: PMC5576570.
In vivo protocol: 1. Scarneo SA, Eibschutz LS, Bendele PJ, Yang KW, Totzke J, Hughes P, Fox DA, Haystead TAJ. Pharmacological inhibition of TAK1, with the selective inhibitor takinib, alleviates clinical manifestation of arthritis in CIA mice. Arthritis Res Ther. 2019 Dec 17;21(1):292. doi: 10.1186/s13075-019-2073-x. PMID: 31847895; PMCID: PMC6918687.

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1: Totzke J, Gurbani D, Raphemot R, Hughes PF, Bodoor K, Carlson DA, Loiselle DR, Bera AK, Eibschutz LS, Perkins MM, Eubanks AL, Campbell PL, Fox DA, Westover KD, Haystead TAJ, Derbyshire ER. Takinib, a Selective TAK1 Inhibitor, Broadens the Therapeutic Efficacy of TNF-α Inhibition for Cancer and Autoimmune Disease. Cell Chem Biol. 2017 Aug 17;24(8):1029-1039.e7. doi: 10.1016/j.chembiol.2017.07.011. PubMed PMID: 28820959; PubMed Central PMCID: PMC5576570.