Tenidap | CP-66248 | CAS#120210-48-2 | 100599-27-7 | COX/5-LOX inhibitor

MedKoo Cat#: 326635 | Name: Tenidap

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tenidap, also known as CP-66248, is a COX/5-LOX inhibitor and cytokine-modulating anti-inflammatory drug candidate that was under development by Pfizer as a promising potential treatment for rheumatoid arthritis, but Pfizer halted development after marketing approval was rejected by the FDA in 1996 due to liver and kidney toxicity, which was attributed to metabolites of the drug with a thiophene moiety that caused oxidative damage.

Chemical Structure

Tenidap

CAS#120210-48-2

Theoretical Analysis

MedKoo Cat#: 326635

Name: Tenidap

CAS#: 120210-48-2

Chemical Formula: C14H9ClN2O3S

Exact Mass: 320.0022

Molecular Weight: 320.75

Elemental Analysis: C, 52.43; H, 2.83; Cl, 11.05; N, 8.73; O, 14.96; S, 10.00

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 400.00
10mg	USD 650.00

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

120210-48-2 100599-27-7

Synonym

CP-66,248; CP 66,248; CP66,248; CP-66248; CP 66248; CP66248; Tenidap

IUPAC/Chemical Name

(3Z)-5-Chloro-2,3-dihydro-3-(hydroxy-2-thienylmethylene)-2-oxo-1H-indole-1-carboxamide

InChi Key

LXIKEPCNDFVJKC-QXMHVHEDSA-N

InChi Code

InChI=1S/C14H9ClN2O3S/c15-7-3-4-9-8(6-7)11(13(19)17(9)14(16)20)12(18)10-2-1-5-21-10/h1-6,18H,(H2,16,20)/b12-11-

SMILES Code

O=C(N1C(/C(C2=C1C=CC(Cl)=C2)=C(O)/C3=CC=CS3)=O)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, not in water

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 320.75 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.

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

1: Thangaraju P, Balan AK, Velmurugan H, Venkatesan S, Yella SST. Leprosy Reactions: Clinical Pharmacologist Perspective with Repurposed Medications. Infect Disord Drug Targets. 2023;23(2):e070922208607. doi: 10.2174/1871526522666220907125114. PMID: 36082854. 2: Bhat RM, Vaidya TP. What is New in the Pathogenesis and Management of Erythema Nodosum Leprosum. Indian Dermatol Online J. 2020 Jul 13;11(4):482-492. doi: 10.4103/idoj.IDOJ_561_19. PMID: 32832433; PMCID: PMC7413435. 3: Sreedharan R, Rajeshwaran P, Panyam PKR, Yadav S, Nagaraja CM, Gandhi T. Acylation of oxindoles using methyl/phenyl esters via the mixed Claisen condensation - an access to 3-alkylideneoxindoles. Org Biomol Chem. 2020 May 27;18(20):3843-3847. doi: 10.1039/d0ob00789g. PMID: 32400832. 4: Wu X, Chen Z, Sun W, Wang G, Zhang L, Zhang Y, Zang K, Wang Y. Activation of Kir2.3 Channels by Tenidap Suppresses Epileptiform Burst Discharges in Cultured Hippocampal Neurons. CNS Neurol Disord Drug Targets. 2019;18(8):621-630. doi: 10.2174/1871527318666190807122623. PMID: 31389319. 5: Zhang L, Sun W, Xu L, Wang Y, Zhu G, Wu X, Wang Y, Hong Z. The anticonvulsant and neuroprotective effects of kir2.3 activation in PTZ-induced seizures and the kainic acid model of TLE. Epilepsy Res. 2019 Oct;156:106167. doi: 10.1016/j.eplepsyres.2019.106167. Epub 2019 Jul 15. PMID: 31336325. 6: Rahman T, Uddin G, Choudhary MI. Short Communication: Discovery and molecular docking simulation of 7-hydroxy-6-methoxy-2H-chromen-2-one as a LOX Inhibitor. Pak J Pharm Sci. 2019 Jan;32(1):217-220. PMID: 30772812. 7: Bernardinelli E, Costa R, Nofziger C, Paulmichl M, Dossena S. Effect of Known Inhibitors of Ion Transport on Pendrin (SLC26A4) Activity in a Human Kidney Cell Line. Cell Physiol Biochem. 2016;38(5):1984-98. doi: 10.1159/000445559. Epub 2016 May 9. PMID: 27161422. 8: Chen G, Jiang L, Dong L, Wang Z, Xu F, Ding T, Fu L, Fang Q, Liu Z, Shan X, Liang G. Synthesis and biological evaluation of novel indole-2-one and 7-aza-2-oxindole derivatives as anti-inflammatory agents. Drug Des Devel Ther. 2014 Oct 13;8:1869-92. doi: 10.2147/DDDT.S65997. PMID: 25378906; PMCID: PMC4207570. 9: Lian Z, Friis SD, Skrydstrup T. Palladium-catalyzed carbonylative α-arylation of 2-oxindoles with (hetero)aryl bromides: efficient and complementary approach to 3-acyl-2-oxindoles. Angew Chem Int Ed Engl. 2014 Sep 1;53(36):9582-6. doi: 10.1002/anie.201404217. Epub 2014 Jul 9. PMID: 25044569. 10: Tang XH, Wu XY, Xu L, Fang YX, Wang JH, Zhu GX, Hong Z. Tenidap is neuroprotective in a pilocarpine rat model of temporal lobe epilepsy. Chin Med J (Engl). 2013;126(10):1900-5. PMID: 23673107. 11: Xu L, Hao Y, Wu X, Yu P, Zhu G, Hong Z. Tenidap, an agonist of the inwardly rectifying K+ channel Kir2.3, delays the onset of cortical epileptiform activity in a model of chronic temporal lobe epilepsy. Neurol Res. 2013 Jul;35(6):561-7. doi: 10.1179/1743132813Y.0000000157. Epub 2013 Feb 7. PMID: 23561319. 12: Bulur N, Crutzen R, Malaisse WJ, Sener A, Beauwens R, Golstein P. Interaction between cAMP, volume‑regulated anion channels and the Na+‑HCO3‑‑cotransporter, NBCe1, in the regulation of nutrient‑ and hypotonicity‑induced insulin release from isolated rat pancreatic islets and tumoral insulin‑producing BRIN‑BD11 cells. Mol Med Rep. 2013 May;7(5):1666-72. doi: 10.3892/mmr.2013.1346. Epub 2013 Feb 28. PMID: 23450392. 13: Mucsi Z, Porcs-Makkay M, Simig G, Csizmadia IG, Volk B. Application of the systems chemistry approach on the ammonolysis of 1-ethoxycarbonyl- and 1-phenoxycarbonyl-3-(2-thienyl)oxindoles. A method to predict reactivity. J Org Chem. 2012 Sep 7;77(17):7282-90. doi: 10.1021/jo300715d. Epub 2012 Aug 27. PMID: 22901033. 14: Parker MD, Qin X, Williamson RC, Toye AM, Boron WF. HCO(3)(-)-independent conductance with a mutant Na(+)/HCO(3)(-) cotransporter (SLC4A4) in a case of proximal renal tubular acidosis with hypokalaemic paralysis. J Physiol. 2012 Apr 15;590(8):2009-34. doi: 10.1113/jphysiol.2011.224733. Epub 2012 Feb 13. PMID: 22331414; PMCID: PMC3573318. 15: Chávez JC, Hernández-González EO, Wertheimer E, Visconti PE, Darszon A, Treviño CL. Participation of the Cl-/HCO(3)- exchangers SLC26A3 and SLC26A6, the Cl- channel CFTR, and the regulatory factor SLC9A3R1 in mouse sperm capacitation. Biol Reprod. 2012 Jan 19;86(1):1-14. doi: 10.1095/biolreprod.111.094037. PMID: 21976599; PMCID: PMC3313665. 16: Lai Y, Ma L, Huang W, Yu X, Zhang Y, Ji H, Tian J. Synthesis and biological evaluation of 3-[4-(amino/methylsulfonyl)phenyl]methylene-indolin-2-one derivatives as novel COX-1/2 and 5-LOX inhibitors. Bioorg Med Chem Lett. 2010 Dec 15;20(24):7349-53. doi: 10.1016/j.bmcl.2010.10.056. Epub 2010 Oct 20. PMID: 21055929. 17: Best L, Brown PD, Sener A, Malaisse WJ. Opposing effects of tenidap on the volume-regulated anion channel and K(ATP) channel activity in rat pancreatic beta-cells. Eur J Pharmacol. 2010 Mar 10;629(1-3):159-63. doi: 10.1016/j.ejphar.2009.12.013. Epub 2009 Dec 24. PMID: 20035738. 18: Perry C, Baker OJ, Reyland ME, Grichtchenko II. PKC{alpha}{beta}{gamma}- and PKC{delta}-dependent endocytosis of NBCe1-A and NBCe1-B in salivary parotid acinar cells. Am J Physiol Cell Physiol. 2009 Dec;297(6):C1409-23. doi: 10.1152/ajpcell.00028.2009. Epub 2009 Sep 25. PMID: 19783762; PMCID: PMC2793054. 19: Bulur N, Virreira M, Soyfoo MS, Louchami K, Delporte C, Perret J, Beauwens R, Malaisse WJ, Sener A. Expression of the electrogenic Na+-HCO3--cotransporter NBCe1 in tumoral insulin-producing BRIN-BD11 cells. Cell Physiol Biochem. 2009;24(3-4):187-92. doi: 10.1159/000233257. Epub 2009 Aug 3. PMID: 19710533. 20: Sussman CR, Zhao J, Plata C, Lu J, Daly C, Angle N, DiPiero J, Drummond IA, Liang JO, Boron WF, Romero MF, Chang MH. Cloning, localization, and functional expression of the electrogenic Na+ bicarbonate cotransporter (NBCe1) from zebrafish. Am J Physiol Cell Physiol. 2009 Oct;297(4):C865-75. doi: 10.1152/ajpcell.00679.2008. Epub 2009 Jul 22. PMID: 19625604; PMCID: PMC2770747.