2-[(1R)-1,8-diethyl-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl]acetic acid

• ChemBase ID: 44454
• Molecular Formular: C17H21NO3
• Molecular Mass: 287.35354
• Monoisotopic Mass: 287.15214354
• SMILES: c12[nH]c3c(c1CCO[C@@]2(CC(=O)O)CC)cccc3CC
• Canonical SMILES: CC[C@@]1(OCCc2c1[nH]c1c2cccc1CC)CC(=O)O
• InChI: InChI=1S/C17H21NO3/c1-3-11-6-5-7-12-13-8-9-21-17(4-2,10-14(19)20)16(13)18-15(11)12/h5-7,18H,3-4,8-10H2,1-2H3,(H,19,20)/t17-/m1/s1
• InChIKey: NNYBQONXHNTVIJ-QGZVFWFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R)-1,8-diethyl-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl]acetic acid
• IUPAC Traditional name: (-)-etodolac; [(1R)-1,8-diethyl-3H,4H,9H-pyrano[3,4-b]indol-1-yl]acetic acid
• Synonyms: 1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid; (1R)-1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic Acid; (-)-(R)-Etodolac; (-)-Etodolac; (-)-Etodolic Acid; R-Etodolac; RAK 593; SDX 101; (R)-(-)-Etodolac; Lodine; Lodine XL; Etodolac(Lodine)

Database IDs

• CAS Number: 87226-41-3; 41340-25-4
• MDL Number: MFCD00133313
• PubChem SID: 162049217
• PubChem CID: 667528

CALCULATED PROPERTIES

• Acid pKa: 4.726933
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.603543
• LogD (pH = 7.4): 0.82613367
• Log P: 3.4435265
• Molar Refractivity: 81.1573 cm^3
• Polarizability: 32.41477 Å^3
• Polar Surface Area: 62.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C
• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Target: COX COX

Product Information

• Purity: 95+%
• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1328

Research Area: Inflammation
Biological Activity:
Etodolac (Lodine) is a COX inhibitor with an IC50 of 53.5 nM. Etodolac (Lodine) belongs to a class of compounds called nonsteroidal anti-inflammatory agents (NSAIDs). Etodolac (Lodine) works by reducing the levels of prostaglandins, which are chemicals that are responsible for pain and the fever and tenderness that occur with inflammation. Etodolac (Lodine) blocks the enzyme that makes prostaglandins (cyclooxygenase), resulting in lower concentrations of prostaglandins. As a consequence, inflammation, pain and fever are reduced. [1][2]

Toronto Research Chemicals - E933090

The R-enantiomer of Etodolac (E933090). Anti-inflammatory; analgesic.

REFERENCES

• http://www.rxlist.com/lodine-drug.htm
• Boxenbaum, H., et al.: J. Pharmacokin. Biopharm., 10, 201 (1982)
• Iwatsubo, T., et al.: Biopharm. Drug Dispos., 17, 273 (1982)
• Obach, R., et al.: J. Pharmacol. Exp. Ther., 283, 46 (1982)