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Carbetapentane

Carbetapentane structure

CAS No:
77-23-6
Formula:
C20H31NO3
Chemical Name:
Carbetapentane
Synonyms:
Cyclopentanecarboxylic acid,1-phenyl-,2-[2-(diethylamino)ethoxy]ethyl ester;Carbetapentane;2-(Diethylaminoethoxy)ethyl 1-phenyl-1-cyclopentanecarboxylate;2-(2-Diethylaminoethoxy)ethyl 1-phenylcyclopentanecarboxylate;Pentoxyverine;1-Phenylcyclopentane-1-carboxylic acid diethylaminoethoxyethyl ester;Atussil;Pentoxiverine
Categories:
Active Pharmaceutical Ingredients > Respiratory Drugs

Description

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

Carbetapentane Basic Attributes

Molecular Weight：

333.46504

Exact Mass：

333.46

EC Number：

201-014-1

UNII：

32C726X12W

DSSTox ID：

DTXSID9022734

ATC Code：

R - Respiratory system

HScode：

2921300090

Characteristics

PSA：

38.8

XLogP3：

3.29

Density：

1.0±0.1 g/cm3

Melting Point：

90-95

Boiling Point：

165-170 °C @ Press: 0.01 Torr

Flash Point：

217.2±24.6 °C

Refractive Index：

1.4990-1.5010

Water Solubility：

1 g/10 ml

Toxicity：

LD50 oral in rat: 150mg/kg

Collision Cross Section：

175.5 Å² [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]

Experimental Properties：

CRYSTALS; MP: 93 °C; FREELY SOL IN WATER, CHLOROFORM; SOL IN ALC, ACETONE, ETHYL ACETATE; PRACTICALLY INSOL IN ETHER, PETROLEUM ETHER, BENZENE /CITRATE/

Safety Information

wgk germany：

safety instructions：

S26-S36

Toxicity

Toxicity Summary：

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

Protein Binding：

No pharmacokinetic data available.

Drug Information

Drug Indication：

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

Therapeutic Uses：

Antitussive Agents|...DRUGS THAT HAVE BEEN USED AS CENTRALLY ACTING ANTITUSSIVES INCL...CARBETAPENTANE...

Drug Warnings：

OTHER DRUGS THAT HAVE BEEN USED AS...ANTITUSSIVES INCL...CARBETAPENTANE, CARAMIPHEN, & OXOLAMINE. ...IN GENERAL THEIR TOXICITY IS LOW, BUT CONTROLLED CLINICAL STUDIES ARE STILL INSUFFICIENT TO DETERMINE WHETHER THEY MERIT CONSIDERATION AS ALTERNATIVES TO MORE THOROUGHLY STUDIED AGENTS.|GENERALLY, ANY CENTRALLY ACTING ANTITUSSIVE SHOULD BE GIVEN CAUTIOUSLY WITH OTHER CENTRALLY ACTING AGENTS. /ANTITUSSIVES/

Pharmacology：

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.

MeSH：

Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally. (See all compounds classified as Antitussive Agents.)

Absorption：

In humans, maximum plasma concentrations are achieved 1.2 hours after oral dosing.|No pharmacokinetic data available.

Metabolism/Metabolites：

No pharmacokinetic data available.

Biological Half-Life：

The half-life is 2.3 hours following oral dosing.

Mechanism of Action：

While the mechanism of antitussive action of pentoxyverine is not fully understood, it is thought to be mediated via sigma-1 receptors expressed in the central nervous system. Pentoxyverine acts as an agonist at sigma receptors with the Ki of 75±28 nM, as demonstrated in a competitive binding assay. The function of sigma receptors on cough suppressant activities is unclear, however these receptors are highly expressed in the nucleus tractus solitarius (NTS) of the brainstem where the afferent fibres first synapse. NTS is located very close to the cough centre in the brainstem thus may function as a ‘gate' for the cough reflex and allow sigma-1 receptor agonists to modulate afferent activity prior to reaching the cough center. It is suggested that highly lipophilic sigma-1 agonists may penetrate the CNS following systemic administration. When administered as aerosols, sigma-1 receptor agonists may temporarily act in the periphery to modulate cough by acting activate sigma receptors expressed in the lungs. However there is limited evidence of peripheral localization of the sigma agonists following aerosol administration and the ruling out of systemic exposure. The local anesthesia action of pentoxyverine may occur through inhibition of voltage-gated Na(+) currents.|NUMBER OF DRUGS ARE KNOWN TO REDUCE COUGH AS RESULT OF THEIR CENTRAL ACTIONS, ALTHOUGH EXACT MECHANISMS ARE STILL NOT ENTIRELY CLEAR. /NONOPIOID ANTITUSSIVES/

Human Toxicity Excerpts：

DRYNESS OF MOUTH OR THROAT, FEELING OF TIGHTNESS IN CHEST, & SLIGHT DEGREE OF RESPIRATORY DEPRESSION...ALLERGIC DERMATITIS /ADVERSE EFFECT, ORAL/

MeSH Entry Terms：

2-(2-diethylaminoethoxy)ethyl 1-phenylcyclopentyl-1-carboxylate

Carbetapentane Use and Manufacturing

Methods of Manufacturing

MORREN, BRITISH PATENT 753,799 (1956).

Uses

It is a non-narcotic central antitussive. This product and pentovirine citrate, also known as cough biqing. This is a non-addictive antitussive drug. The antitussive effect is inferior to codeine. Duohe is used to treat acute, mild cough and whooping cough caused by upper respiratory tract infection, which can reduce bronchial secretion. The product has low toxicity.

Formulations：

CARBETAPENTANE CITRATE /PRC: WITH CITRATE 1:1, TOCLASE & TUCLASE/. SYRUP, 7.25 MG/5 ML. SYRUP 7.25 MG, WITH TERPIN HYDRATE 16.7 MG, & CHLOROFORM 2.5 MG/5 ML (TOCLASE EXPECTORANT).

Analytic Methods：

TLC: SUNSHINE, I, WW FIKE, & H LANDESMAN, J FORENSIC SCI 11, 428 (1966).|TLC. MINIMUM AMT DETECTED 20 UG.

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:333.5
XLogP3:3.8
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:11
Exact Mass:333.23039385
Monoisotopic Mass:333.23039385
Topological Polar Surface Area:38.8
Heavy Atom Count:24
Complexity:356
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Calcium chloride

Trichloroethylene