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4-cyclohexyl-alpha-methylnaphthalene-1-acetic acid

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4-cyclohexyl-alpha-methylnaphthalene-1-acetic acid Basic information

Product Name:
4-cyclohexyl-alpha-methylnaphthalene-1-acetic acid
Synonyms:
  • 4-cyclohexyl-alpha-methylnaphthalene-1-acetic acid
  • Quadrisol
  • 2-(4-Cyclohexil-1-naphthyl)-propionic Acid
  • 4-Cyclohexyl-a-methyl-1-naphthaleneacetic Acid
  • CERM 10202
  • PM-150
  • 4-Cyclohexyl-α-methyl-1-naphthaleneacetic acid
  • 4-Cyclohexyl-α-Methyl-
CAS:
71109-09-6
MF:
C19H22O2
MW:
282.38
EINECS:
275-196-6
Product Categories:
  • Aromatics
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
71109-09-6.mol
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4-cyclohexyl-alpha-methylnaphthalene-1-acetic acid Chemical Properties

Melting point:
150°C
Boiling point:
465.9±14.0 °C(Predicted)
Density 
1.132±0.06 g/cm3(Predicted)
storage temp. 
-20°C Freezer
solubility 
DMF: 25 mg/ml; DMSO: 10 mg/ml; Ethanol: 10 mg/ml
form 
Solid
pka
4.90±0.30(Predicted)
color 
White to off-white
BRN 
5568831
Major Application
forensics and toxicology
pharmaceutical (small molecule)
InChI
1S/C19H22O2/c1-13(19(20)21)15-11-12-16(14-7-3-2-4-8-14)18-10-6-5-9-17(15)18/h5-6,9-14H,2-4,7-8H2,1H3,(H,20,21)
InChIKey
VZUGVMQFWFVFBX-UHFFFAOYSA-N
SMILES
CC(C(O)=O)c1ccc(C2CCCCC2)c3ccccc13
EPA Substance Registry System
1-Naphthaleneacetic acid, 4-cyclohexyl-.alpha.-methyl- (71109-09-6)
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Safety Information

WGK Germany 
3
Storage Class
11 - Combustible Solids
Hazard Classifications
Acute Tox. 4 Oral
Toxicity
LD50 orally in rat: 400 mg/kg (Godfroid)
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4-cyclohexyl-alpha-methylnaphthalene-1-acetic acid Usage And Synthesis

Chemical Properties

Crystalline Solid

Uses

Propionic acid type non-steroidal anti-inflammatory drug (NSAID).

Definition

ChEBI: A racemate composed of equal amounts of (R)- and (S)-vedaprofen. Used for control of pain and inflammation particularly associated with chronic musculoskeletal disorders and soft tissue trauma in dogs and horses and for tr atment of pain due to horse colic.

Biological Activity

Vedaprofen is a non-steroidal anti-inflammatory drug (NSAID) th at has been found to have antimicrobial activity. Vedaprofen is primarily used as a veterinary analgesic and anti-inflammatory for arthritis and pain. Its anti-inflammatory activity is due to cyclooxygenase inihbition, while its antimicrobial activity is less certain. Vedaprofen can kill B. subtilis by permeabilizing its membrane. Other studies have shown vedaprofen can target the Escherichia coli DNA polymerase III β subunit.

in vivo

Pharmacokinetic parameters of vedaprofen in dogs[3].

Intravenous dose (mg/kg)t1/2β (h)AUC0–48 h (h·ng/mL)AUC0–∞ (h·ng/mL)
0.516.8±2.28612±11359518±1223

Oral dose (mg/kg)t1/2β (h)Cmax (ng/mL)tmax (h)AUC0–48 h (h·ng/mL)AUC0–∞ (h·ng/mL)F0–∞ (%)
0.512.7±2.12739±2770.63±0.147090±13117650±134886±7

IC 50

COX-1

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