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AB141110

Piroxicam, cyclooxygenase-1 (COX-1) inhibitor

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MW 331.3 Da, Purity >99%. Reversible, selective cyclooxygenase-1 (COX-1) inhibitor. Shows 8-fold greater activity against COX-1 than COX-2 (IC50 values are 0.76 and 8.99 μM for COX-1 and COX-2, respectively).

View Alternative Names

(R)-limonene 6-monooxygenase, (S)-limonene 6-monooxygenase, (S)-limonene 7-monooxygenase, AHR_HUMAN, Ah receptor, Aromatic hydrocarbon receptor, Aryl hydrocarbon receptor, Aryl hydrocarbon receptor precursor, BAZ2B_HUMAN, Bromodomain adjacent to zinc finger domain 2B, Bromodomain adjacent to zinc finger domain protein 2B, CP2C9_HUMAN, CP2D6_HUMAN, CPC12, CPC8, CPC9, CPCJ, CPD6, CYP2C, CYP2C10, CYP2D, CYP2D7AP, CYP2D7BP, CYP2D7P2, CYP2D8P2, CYP2DL1, CYPIIC9, CYPIID6, Cholesterol 25-hydroxylase, Class E basic helix-loop-helix protein 76, Cyclooxygenase, Cyclooxygenase 2b, Cyclooxygenase 3, included, Cyclooxygenase-1, Cyclooxygenase-2, Cytochrome P-450MP, Cytochrome P450 2C9, Cytochrome P450 2D6, Cytochrome P450 MP-4, Cytochrome P450 MP-8, Cytochrome P450 PB-1, Cytochrome P450 family 2 subfamily D member 6, Cytochrome P450 family 2 subfamily D polypeptide 6, Cytochrome P450, family 2, subfamily C, polypeptide 9, Cytochrome P450-DB1, DKFZp434H071, DKFZp762I0516, Debrisoquine 4-hydroxylase, EC 1.14.99.1, FLJ45644, FLJ55736, GRIPGHS, Glucocorticoid-regulated inflammatory Prostaglandin G/H synthase, Glucocorticoid-regulated inflammatory cyclooxygenase, HGNC:348, MGC149605, MGC45260, MGC88320, Macrophage activation-associated marker protein P71/73, Microsomal monooxygenase, OAT1, OTTHUMP00000020135, OTTHUMP00000033524, OTTHUMP00000162897, OTTHUMP00000162898, OTTHUMP00000236796, OTTHUMP00000236797, OTTHUMP00000236798, OTTHUMP00000236799, Organic anion transporter 1, Organic anion transporter 3, P450 DB1, P450 MP, P450 PB 1, P450C2C, P450C2D, P450IIC19, P450IIC9, PAH transporter, PAHT, PCOX1, PES-2, PGG/HS, PGH synthase 1, PGH synthase 2, PGH1_HUMAN, PGH2_HUMAN, PGHS-1, PGHS-2, PHS 1, PHS 2, PHS II, PTGHS, PTGS1, PTGS2, Para aminohippurate transporter, Partial COX1 proteins, included, Prostaglandin G/H synthase, Prostaglandin G/H synthase 1, Prostaglandin G/H synthase 2, Prostaglandin G/H synthase 2 precursor, Prostaglandin G/H synthase and cyclooxygenase, Prostaglandin H2 synthase 1, Prostaglandin H2 synthase 2, Prostaglandin-endoperoxide synthase 1, Prostaglandin-endoperoxide synthase 1 (prostaglandin G/H synthase and cyclooxygenase), Prostaglandin-endoperoxide synthase 2, ROAT1, Renal organic anion transporter 1, S-mephenytoin 4-hydroxylase, S22A6_HUMAN, S22A8_HUMAN, SLC22A8, Solute carrier family 22 (organic anion transporter) member 6, Solute carrier family 22 (organic anion transporter), member 8, Solute carrier family 22 member 6, Solute carrier family 22 member 8, TIS10, TIS10 protein, WALp4, Xenobiotic monooxygenase, bHLHe76, cytochrome P-450 S-mephenytoin 4-hydroxylase, fj02a10, flavoprotein-linked monooxygenase, hCox 2, hOAT1, hOAT3, hPAHT, hROAT1, hWALp4, prostaglandin-endoperoxide synthase 2 (prostaglandin G/H synthase and cyclooxygenase), ptgs2a, unp1239, wu:fj02a10

1 Images
Chemical Structure - Piroxicam, cyclooxygenase-1 (COX-1) inhibitor (AB141110)
  • Chemical Structure

Lab

Chemical Structure - Piroxicam, cyclooxygenase-1 (COX-1) inhibitor (AB141110)

2D chemical structure image of ab141110, Piroxicam, cyclooxygenase-1 (COX-1) inhibitor

Key facts

CAS number

36322-90-4

Purity

>99%

Form

Solid

form

Molecular weight

331.3 Da

Molecular formula

C<sub>1</sub><sub>5</sub>H<sub>1</sub><sub>3</sub>N<sub>3</sub>O<sub>4</sub>S

PubChem

54676228

Nature

Synthetic

Solubility

Soluble in DMSO to 100 mM

Biochemical name

Piroxicam

Biological description

Reversible, selective cyclooxygenase-1 (COX-1) inhibitor. Shows 8-fold greater activity against COX-1 than COX-2 (IC50 values are 0.76 and 8.99 μM for COX-1 and COX-2, respectively).

Canonical smiles

CN1C(=C(C2=CC=CC=C2S1(=O)=O)O)C(=O)NC3=CC=CC=N3

InChi

InChI=1S/C15H13N3O4S/c1-18-13(15(20)17-12-8-4-5-9-16-12)14(19)10-6-2-3-7-11(10)23(18,21)22/h2-9,19H,1H3,(H,16,17,20)

InChiKey

QYSPLQLAKJAUJT-UHFFFAOYSA-N

IUPAC Name

4-hydroxy-2-methyl-1,1-dioxo-N-pyridin-2-yl-1λ6,2-benzothiazine-3-carboxamide

Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
+4°C
Appropriate long-term storage conditions
+4°C
Storage information
The product can be stored for up to 12 months

Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

COX1 and COX2 also known as cyclooxygenase 1 and cyclooxygenase 2 are enzymes that perform vital functions in the conversion of arachidonic acid to prostaglandins. These prostaglandins mediate inflammation and pain signals among other physiological processes. COX1 has a mass of about 69 kDa while COX2 approximates a similar size. COX1 is expressed widely in many tissues maintaining gastrointestinal and renal physiology. In contrast COX2 is usually induced at sites of inflammation. COX1 vs COX2 selective inhibition plays an important role in therapeutic approaches to inflammation management using drugs such as piroxicam.
Biological function summary

COX1 and COX2 facilitate the production of signaling molecules in various physiological processes. They form a complex with other proteins as part of their enzymatic activity. For instance cytochrome P450 enzymes like CYP2D6 CYP2C9 and their relatives (Cytochrome P450 2C8 2C9 2C19 2C12) share a role in drug metabolism and detoxification. The aryl hydrocarbon receptor (AHR) also interacts with these enzymes influencing their expression under certain conditions. Notably these enzymes have distinct but sometimes overlapping functions that ensure regular metabolic and inflammatory responses.

Pathways

COX enzymes participate in the arachidonic acid metabolism pathway essential for producing prostaglandins and thromboxanes. This pathway also involves cytochrome P450 enzymes which contribute to the metabolism of lipids and xenobiotics. SLC22A6 known as OAT3 is involved in organic anion transport pathways that modulate drug excretion and disposition. These interconnected pathways establish a network through which cells maintain homeostasis and respond to environmental stimuli.

COX1 and COX2 are important players in inflammation-related diseases such as arthritis and cancer. Aberrant expression or regulation of COX2 has been linked to carcinogenesis particularly in colorectal cancer. COX1 and COX2 inhibitors like piroxicam reduce inflammation but may have side effects due to COX1 activity in protective gastric functions. The action of proteins like AHR and cytochrome P450 in these diseases influence metabolic responses and contribute to the pathological state. Understanding these connections aids in designing therapies that minimize adverse effects while targeting disease mechanisms.

Product protocols

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