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I8280

Sigma-Aldrich

Indomethacin

meets USP testing specifications

Synonym(s):

1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetic acid

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About This Item

Empirical Formula (Hill Notation):
C19H16ClNO4
CAS Number:
53-86-1
Molecular Weight:
357.79
Beilstein:
497341
EC Number:
200-186-5
MDL number:
MFCD00057095
UNSPSC Code:
12352101
PubChem Substance ID:
24896136
NACRES:
NA.21

Agency

USP/NF
meets USP testing specifications

Quality Level

200

Assay

98.0-102.0%

form

powder

Mode of action

enzyme | inhibits

SMILES string

COc1ccc2n(c(C)c(CC(O)=O)c2c1)C(=O)c3ccc(Cl)cc3

InChI

1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)

InChI key

CGIGDMFJXJATDK-UHFFFAOYSA-N

Gene Information

human ... ALB(213) , ALOX5(240) , ELA2(1991) , GPR44(11251) , IL1A(3552) , PLA2G1B(5319) , PTGDR(5729) , PTGS1(5742) , PTGS2(5743)
mouse ... Alox5(11689) , Ptgdr(19214) , Ptger1(19216) , Ptger2(19217) , Ptger3(19218) , Ptger4(19219) , Ptgs1(19224) , Ptgs2(19225)
rat ... Alox5(25290) , Ptgs1(24693) , Ptgs2(29527)

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Biochem/physiol Actions

Cyclooxygenase (COX) inhibitor that is relatively selective for COX-1.
Used as a non-selective inhibitor of cyclooxygenases, COX1 and COX2, leading to reduced prostaglandin biosynthesis from arachidonic acid.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Precautionary Statements

P264 - P301 + P310

Hazard Classifications

Acute Tox. 1 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Amal M Youssef et al.
Bioorganic & medicinal chemistry, 18(5), 2019-2028 (2010-02-09)
Novel pyrazolyl-2,4-thiazolidinediones were prepared via the reaction of appropriate pyrazolecarboxaldehydes with 2,4-thiazolidinediones and substituted benzyl-2,4-thiazolidinediones. The resultant compounds were first evaluated for their anti-inflammatory and neuroprotective properties in vitro. The active compounds were further studied in vivo by using the
Dongfei Liu et al.
Journal of controlled release : official journal of the Controlled Release Society, 170(2), 268-278 (2013-06-13)
Nanoparticulate drug delivery systems offer remarkable opportunities for clinical treatment. However, there are several challenges when they are employed to deliver multiple cargos/payloads, particularly concerning the synchronous delivery of small molecular weight drugs and relatively larger peptides. Since porous silicon
Christel A S Bergström et al.
Journal of medicinal chemistry, 50(23), 5858-5862 (2007-10-13)
We determined the intrinsic aqueous solubility of 15 poorly soluble drugs with solubilities ranging from 2.9 nM to 1.1 microM. We then analyzed the data from a physicochemical perspective, using experimentally determined solid-state properties and easily interpretable two-dimensional molecular descriptors
Marsel Lino et al.
Molecular metabolism, 39, 101006-101006 (2020-05-04)
Discoidin domain receptor 1 (DDR1) is a collagen binding receptor tyrosine kinase implicated in atherosclerosis, fibrosis, and cancer. Our previous research showed that DDR1 could regulate smooth muscle cell trans-differentiation, fibrosis and calcification in the vascular system in cardiometabolic disease.
Zhangjian Huang et al.
Journal of medicinal chemistry, 54(5), 1356-1364 (2011-02-02)
The carboxylic acid group of the anti-inflammatory (AI) drugs indo-methacin, (S)-naproxen and ibuprofen was covalently linked via a two-carbon ethyl spacer to a sulfohydroxamic acid moiety (CH(2)CH(2)SO(2)NHOH) to furnish a group of hybrid ester prodrugs that release nitric oxide (NO)
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