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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

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)

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Hui Song et al.
Frontiers in microbiology, 8, 1419-1419 (2017-08-12)
Codon usage bias plays an important role in shaping genomes and genes in unicellular species and multicellular species. Here, we first analyzed codon usage bias in seven
Andreia S P Sousa et al.
Scientific reports, 9(1), 3115-3115 (2019-03-01)
This study aims to: (1) to compare 2 methods of assessing the timing of medium latency responses (MLR), in regard to intrasession reliability and mean values, in subjects with and without chronic ankle instability (CAI), and (2) to analyze the
Lars P J Cruysberg et al.
Retina (Philadelphia, Pa.), 25(8), 1022-1031 (2005-12-13)
To evaluate the human transscleral diffusion and intravitreal delivery of carboxyamido-triazole (CAI) and 2-Methoxyestradiol (2ME2). The transscleral diffusion of two retinal antiangiogenic molecules, CAI and 2ME2, was measured in vitro to assess their potential transscleral delivery. Varying concentrations and different
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
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-
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