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Key Documents

PZ0196

Sigma-Aldrich

Tenidap

≥97% (HPLC)

Synonym(s):

(3Z)-5-Chloro-2,3-dihydro-3-(hydroxy-2-thienylmethylene)-2-oxo-1H-indole-1-carboxamide, CP 66248

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About This Item

Empirical Formula (Hill Notation):
C14H9ClN2O3S
CAS Number:
120210-48-2
Molecular Weight:
320.75
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥97% (HPLC)

form

powder

color

faintly yellow to dark yellow

solubility

DMSO: 1 mg/mL, clear (warmed)

storage temp.

2-8°C

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/h1-6,19H,(H2,16,20)

InChI key

IZSFDUMVCVVWKW-UHFFFAOYSA-N

Biochem/physiol Actions

Tenidap is an anti-inflammatory and anti-rheumatic with a variety of activities. Tenidap preferentially inhibits COX-1 with an IC50 value of 30 nM, and also has some lesser inhibitory activity towards COX-2 and 5-lipoxygenase (IC50 values are 1.2 and > 30 μM for COX-2 and 5-lipoxygenase respectively). Tenidap is also a cytokine modulator, an opener of inward rectifying hKIR2.3 channels (EC50 = 402 nM) and has been shown to modulate cytoplasmic pH and inhibit anion transport in vitro.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Samuel Parry et al.
The Journal of general virology, 87(Pt 8), 2269-2278 (2006-07-19)
The human placenta is relatively resistant to Human immunodeficiency virus 1 (HIV-1), but obstetric complications associated with inflammatory processes, including chorioamnionitis and spontaneous preterm delivery, are associated with increased rates of vertical transmission. It was hypothesized that the pro-inflammatory mediator
Hiroko Matsumoto et al.
The Journal of pharmacology and experimental therapeutics, 300(2), 668-672 (2002-01-24)
The effect of tenidap [(+/-)-5-chloro-2,3-dihydro-3-(hydroxy-2-thienylmethylene)-2-oxo-1H-indole-1-carboxamide], a new anti-inflammatory agent, was investigated on DNA synthesis by means of [(3)H]thymidine incorporation, collagen synthesis by means of [(3)H]proline incorporation, cell proliferation, and intracellular pH in nicardipine-reactive human gingival fibroblasts. Tenidap significantly inhibited [(3)H]thymidine
M G Attur et al.
Osteoarthritis and cartilage, 6(4), 269-277 (1999-01-07)
To examine the effects of non-steroidal anti-inflammatory drugs (NSAIDS) on nitric oxide (NO) and prostaglandin E2 (PGE2) production in chondrocytes from three different species. We have estimated NO production by Griess method, and PGE2 by RIA from the supernatants of
P Lavigne et al.
Osteoarthritis and cartilage, 10(11), 898-904 (2002-11-19)
Introduction and goal Proinflammatory cytokines and prostaglandin E(2) (PGE(2)) play an important role in the pathophysiology of osteolysis and implant loosening. The aim of this study was to evaluate the role of pharmacological agents in the inhibition of Interleukin-1 (IL-1)
J C Fernandes et al.
The Journal of rheumatology, 25(5), 951-958 (1998-05-23)
To examine the effect of tenidap on the expression of collagenase- and interleukin 1beta (IL-1beta) genes in experimental canine osteoarthritis (OA). The anterior cruciate ligaments of the right stifle joints of experimental dogs were sectioned by a stab wound incision
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