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SML0408

Sigma-Aldrich

Carboxyamidotriazole

≥98% (HPLC)

Synonym(s):

5-Amino-1-[[3,5-Dichloro-4-(4-chlorobenzoyl)phenyl]meth yl]-1H-1,2,3-triazole-4-carboxamide, CAI, L-651582

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About This Item

Empirical Formula (Hill Notation):
C17H12Cl3N5O2
CAS Number:
99519-84-3
Molecular Weight:
424.67
MDL number:
MFCD00866325
UNSPSC Code:
12352200
PubChem Substance ID:
329825403
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL (clear solution)

storage temp.

2-8°C

SMILES string

NC(=O)c1nnn(Cc2cc(Cl)c(c(Cl)c2)C(=O)c3ccc(Cl)cc3)c1N

InChI

1S/C17H12Cl3N5O2/c18-10-3-1-9(2-4-10)15(26)13-11(19)5-8(6-12(13)20)7-25-16(21)14(17(22)27)23-24-25/h1-6H,7,21H2,(H2,22,27)

InChI key

WNRZHQBJSXRYJK-UHFFFAOYSA-N

Biochem/physiol Actions

Carboxyamidotriazole (CAI) is a non-cytotoxic anticancer drug. It exhibits anti-inflammatory properties and reduces the release of proinflammatory cytokines. CAI prevents the proliferation and invasive behavior of a variety of human cancer cell types and endothelial cells in vitro and in vivo. It is used to treat several acute and chronic inflammation models, like adjuvant arthritis and inflammatory bowel diseases (IBD). CAI blocks tumor cell proliferation and stimulates cell apoptosis in vitro.
Carboxyamidotriazole (L-651582) is an orally active calcium channel blocker. Carboxyamidotriazole blocks intracellular and mitochondrial calcium entry and flux, resulting in inhibition of cell proliferation, calcium-release-activated calcium channel (CRAC) function, and maintenance of mitochondrial membrane potential.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

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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Fabienne Largey et al.
Neurology(R) neuroimmunology & neuroinflammation, 6(6) (2019-09-27)
To investigate the effects of natalizumab (NAT) treatment on intrathecally produced antiviral antibodies in MS. We performed a longitudinal, observational study analyzing both serum and CSF samples collected before and during NAT treatment for antibodies against measles, rubella, mumps, influenza
J Y Hu et al.
Science advances, 7(2) (2021-02-02)
Equilibrium condensation of solar gas is often invoked to explain the abundance of refractory elements in planets and meteorites. This is partly motivated, by the observation that the depletions in both the least and most refractory rare earth elements (REEs)
Alessandra Fiorio Pla et al.
Molecular cancer research : MCR, 6(4), 535-545 (2008-04-12)
Growth factor-induced intracellular calcium signals in endothelial cells regulate cytosolic and nuclear events involved in the angiogenic process. Among the intracellular messengers released after proangiogenic stimulation, arachidonic acid (AA) plays a key role and its effects are strictly related to
Jens Henrik Norum et al.
The FEBS journal, 272(9), 2304-2316 (2005-04-28)
We have previously reported the Ras-dependent activation of the mitogen-activated protein kinases p44 and p42, also termed extracellular signal-regulated kinases (ERK)1 and 2 (ERK1/2), mediated through Gs-coupled serotonin receptors transiently expressed in human embryonic kidney (HEK) 293 cells. Whereas Gi-
Lei Guo et al.
European journal of pharmacology, 746, 14-21 (2014-12-03)
Carboxyamidotriazole (CAI) is a non-cytotoxic anti-tumor drug, which also shows considerable anti-inflammatory effects in a variety of animal models of inflammation. The exact target and mechanism of CAI were not clearly understood yet. In the present study, we demonstrate that
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