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HomeProduct name listPentoxyverine

Pentoxyverine

  • CAS NO.:77-23-6
  • Empirical Formula: C20H31NO3
  • Molecular Weight: 333.46
  • MDL number: MFCD00209899
  • EINECS: 201-014-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-28 23:16:16
Pentoxyverine Structural

What is Pentoxyverine?

Absorption

In humans, maximum plasma concentrations are achieved 1.2 hours after oral dosing .

Toxicity

Acute oral LD50 is 810 mg/kg in rat and 230 mg/kg in mouse .

Originator

Asthma ,Nichiiko

The Uses of Pentoxyverine

Carbetapentane is an antitussive anticonvulsant sigma site agonist.

Indications

Indicated as a cough suppressant to relieve cough caused by the common cold, flu, bronchitis, and sinusitis .

Background

Pentoxyverine, also referred to as carbetapentane, is a non-opioid central acting antitussive with antimuscarinic, anticonvulsant , and local anesthetic properties. It is an active ingredient in over-the-counter cough suppressants in combination with guaifenesin and H1-receptor antagonists . Pentoxyverine acts on sigma-1 receptors, as well as kappa and mu-opioid receptors.
The FDA withdrew the use of all oral gel drug products containing pentoxyverine citrate. Other forms of pentoxyverine citrate continue to be marketed.

What are the applications of Application

Carbetapentane is an antitussive anticonvulsant sigma site agonist

Definition

ChEBI: 1-phenyl-1-cyclopentanecarboxylic acid 2-[2-(diethylamino)ethoxy]ethyl ester is a member of benzenes.

Manufacturing Process

1-Phenylcyclopentane carbonitrile was obtained by treatment of phenylacetonitrile with sodium amide and 1,4-dibrombutane.
1-Phenyl-1-cyclopentane carboxylic acid was produced in the result of reaction of 1-phenylcyclopentane carbonitrile with sulfuric acid.
1-Phenyl-1-cyclopentanecarbonyl chloride was obtained by treatment of 1phenyl-1-cyclopentane carboxylic acid with thionyl chloride.
A mixture of 0.5 mol of 1-phenyl-1-cyclopentanecarbonyl chloride and of 0.5 mol of 2-(2-diethylaminoethoxy)ethanol (herein-after referred to as the amino alcohol) in 300 ml of toluene is heated under reflux for 20 h. The mixture is thereafter made alkaline by means of an aqueous solution of caustic soda and decanted; the toluenic layer is washed with water and concentrated in vacuo. The residue is distilled under high vacuum. After two fractional distillations, the 2-(2-diethylaminoethoxy)ethyl 1-phenylcyclopentane-carboxylate is obtained, in 85% yield. Boiling point 164°C/0.1 mm. Hg.

brand name

Toclase (Pfizer).

Therapeutic Function

Antitussive

Pharmacokinetics

Pentoxyverine induces an antitussive action. In animal studies, intraperitoneal administration of pentoxyverine inhibited citric-acid-induced cough in guinea-pigs in vivo . Some mice and rat studies suggest that pentoxyverine may also exert anticonvulsant activities without inducing a protective effect from NMDA-induced lethality . Protective effects against maximal electroshock-induced seizures in a dose-related fashion was also observed following either intraperitoneal or oral administration . In hERG-transfected cells, pentoxyverine inhibited the outward current of the hERG ion channel with half-maximal inhibition concentrations (IC50) of 3.0 μM . In rats receiving intrathecal administration, pentoxyverine exhibited dose-dependent spinal blockade with a more sensory-selective action over motor blockade . It induced a spinal blockade with a more sensory/nociceptive-selective action over motor blockade compared to lidocaine .

Metabolism

No pharmacokinetic data available.

Properties of Pentoxyverine

Boiling point: 165-170 °C (1.33Pa)
Density  1.048±0.06 g/cm3(Predicted)
refractive index  1.4990-1.5010
storage temp.  Refrigerator
solubility  Dichloromethane (Slightly), Methanol (Slightly)
form  Oil
pka 9.69±0.25(Predicted)
color  Clear Very Dark Red to Brown
CAS DataBase Reference 77-23-6(CAS DataBase Reference)
NIST Chemistry Reference 1-Cyclopentanecarboxylate, 2-(diethylaminoethoxy)ethyl-1-phenyl-(77-23-6)

Safety information for Pentoxyverine

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Pentoxyverine

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