Naproxen etemesil - ≥99% , Cyclooxygenase inhibitor, CAS No.385800-16-8, Cyclooxygenase inhibitor

CAS: 385800-16-8 Cat. No.: N648535 Formula: C₁₇H₂₀O₅S Molecular Weight: 336.40 PubChem CID: 25170420

GRADE & PURITY ≥99%

Synonyms

2-methylsulfonylethyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate | 2-NAPHTHALENEACETIC ACID, 6-METHOXY-.ALPHA.-METHYL-, 2-(METHYLSULFONYL)ETHYL ESTER, (.ALPHA.S)- | HY-19675 | (S)-2-(methylsulfonyl)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate | UNII-2142

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Naproxen etemesil is a lipophilic, non-acidic, inactive proagent of naproxen that is hydrolysed to pharmacologically active Naproxen once absorbed. Naproxen is a COX-1 and COX-2 inhibitor with IC 50 s of 8.72 and 5.15 μM, respectively in cell assay.

In Vitro

Naproxen etemesil is a lipophilic, non-acidic, inactive prodrug of naproxen that is hydrolysed to pharmacologically active Naproxen once absorbed. Naproxen is a well known nonsteroidal anti-inflammatory drug. Naproxen is approximately equipotent inhibitor of COX-1 and COX-2 in intact cells with IC 50 s of 2.2 μg/mL and 1.3 μg/mL, respectively. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Naproxen exerts an anti-inflammatory and antifibrotic effect in mouse model of bleomycin-induced lung fibrosis. Naproxen also downregulates TGF-β levels and Smad3/4 complex formation. Naproxen is shown to inhibit the time-courses of pain, fever and PGE2 with similar potencies (IC 50 =27, 40, 13 μM). MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:IC50: 8.72 μM (COX-1), 5.15 μM (COX-2)

Specifications

Synonyms

2-methylsulfonylethyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate | 2-NAPHTHALENEACETIC ACID, 6-METHOXY-.ALPHA.-METHYL-, 2-(METHYLSULFONYL)ETHYL ESTER, (.ALPHA.S)- | HY-19675 | (S)-2-(methylsulfonyl)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate | UNII-2142

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Naproxen etemesil is a lipophilic, non-acidic, inactive proagent of naproxen that is hydrolysed to pharmacologically active Naproxen once absorbed. Naproxen is a COX-1 and COX-2 inhibitor with IC 50 s of 8.72 and 5.15 μM, respectively in cell assay.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Mechanism of action

Cyclooxygenase inhibitor

Purity

≥99%

Product Properties

ALogP

2.5

Names and Identifiers

Canonical Smiles

CC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)OCCS(=O)(=O)C

IUPAC Name

2-methylsulfonylethyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate

InChIKey

JGBUBSOKFSVXKS-LBPRGKRZSA-N

INCHI

1S/C17H20O5S/c1-12(17(18)22-8-9-23(3,19)20)13-4-5-15-11-16(21-2)7-6-14(15)10-13/h4-7,10-12H,8-9H2,1-3H3/t12-/m0/s1

Isomeric SMILES

C[C@@H](C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)OCCS(=O)(=O)C

Alternate CAS

385800-16-8

PubChem CID

25170420

Molecular Weight

336.40

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Naphthalenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Naphthalenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthalenes
• Alternative Parents: Anisoles Alkyl aryl ethers Sulfones Carboxylic acid esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Naphthalene - Anisole - Phenol ether - Alkyl aryl ether - Sulfonyl - Sulfone - Carboxylic acid ester - Monocarboxylic acid or derivatives - Ether - Carboxylic acid derivative - Organosulfur compound - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Organic oxygen compound - Organic oxide - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: DMSO : 100 mg/mL (297.27 mM; Need ultrasonic)
• Molecular Weight: 336.400 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 336.103 Da
• Monoisotopic Mass: 336.103 Da
• Topological Polar Surface Area: 78.100 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 496.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 385800-16-8, the molecular formula is C17H20O5S, and the molecular weight is 336.40 g/mol. InChIKey JGBUBSOKFSVXKS-LBPRGKRZSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.