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{{drugbox
{{Drugbox
| IUPAC_name       = 2-(2-diethylaminoethoxy)ethyl 1-phenylcyclopentane-1-carboxylate
| Verifiedfields = changed
| image             = Pentoxyverine skeletal.svg
| verifiedrevid = 461940880
| CAS_number        = 77-23-6
| IUPAC_name = 2-[2-(diethylamino)ethoxy]ethyl 1-phenylcyclopentanecarboxylate
| ATC_prefix        = R05
| image =Pentoxyverine skeletal.png
| ATC_suffix        = DB05
 
| PubChem          = 2562
<!--Clinical data-->
| DrugBank          =
| tradename =
| C = 20 | H = 31 | N = 1 | O = 3
| Drugs.com = {{drugs.com|international|pentoxyverine}}
| molecular_weight  = 333.465 g/mol
| MedlinePlus = a606008
| bioavailability  =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| protein_bound    =
| pregnancy_US = <!-- A / B            / C / D / X -->
| metabolism        =  
| pregnancy_category = No studies; contraindicated
| elimination_half-life =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| excretion        = [[Kidney|Renal]]
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| pregnancy_AU     = <!-- A / B1 / B2 / B3 / C / D / X -->
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| pregnancy_US     = <!-- A / B            / C / D / X -->
| legal_US = OTC
| pregnancy_category=
| legal_status =
| legal_AU         = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA         = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK         = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| legal_US         = OTC
| legal_status     =  
| routes_of_administration = Oral, rectal
| routes_of_administration = Oral, rectal
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = [[Hepatic]]
| elimination_half-life = 2.3 hours (oral), 3–3.5 hours (rectal)
| excretion = [[Kidney|Renal]]
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 77-23-6
| CAS_supplemental = <br />{{CAS|23142-01-0}} (dihydrogen [[citrate]])<br />{{CAS|1406-98-0}} ([[tannate]])
| ATC_prefix = R05
| ATC_suffix = DB05
| PubChem = 2562
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2464
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 32C726X12W
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08334
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 73234
<!--Chemical data-->
| C=20 | H=31 | N=1 | O=3
| molecular_weight = 333.465 g/mol
| smiles = O=C(OCCOCCN(CC)CC)C2(c1ccccc1)CCCC2
| InChI = 1/C20H31NO3/c1-3-21(4-2)14-15-23-16-17-24-19(22)20(12-8-9-13-20)18-10-6-5-7-11-18/h5-7,10-11H,3-4,8-9,12-17H2,1-2H3
| InChIKey = CFJMRBQWBDQYMK-UHFFFAOYAD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H31NO3/c1-3-21(4-2)14-15-23-16-17-24-19(22)20(12-8-9-13-20)18-10-6-5-7-11-18/h5-7,10-11H,3-4,8-9,12-17H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CFJMRBQWBDQYMK-UHFFFAOYSA-N
}}
}}
'''Pentoxyverine''' ([[International Nonproprietary Name|rINN]]) or '''carbetapentane''' is a [[cough medicine|cough suppressant]]. It is sold [[over-the-counter drug|over-the-counter]] in the [[United States]], usually in combination with other medications, especially [[decongestant]]s. It is commonly used for cough associated with illnesses like [[common cold]]. Certuss is one such product. It is a combination of [[guaifenesin]] and pentoxyverine.
__Notoc__
{{SI}}
{{CMG}}
==Overview==
 
'''Pentoxyverine''' ([[International Nonproprietary Name|rINN]]) or '''carbetapentane''' is an [[antitussive]] (cough suppressant) commonly used for cough associated with illnesses like [[common cold]]. It is sold [[over-the-counter drug|over-the-counter]] in the United States as '''Solotuss''',<ref name="Drugs.com">
{{cite web
| publisher = Drugs.com
| url = http://www.drugs.com/mtm/carbetapentane.html
| title = Carbetapentane
}}</ref> or in combination with other medications, especially [[decongestant]]s. One such product is ''Certuss'', a combination of [[guaifenesin]] and pentoxyverine.<ref>
{{cite web
| publisher = Drugs.com
| url = http://www.drugs.com/mtm/certuss.html
| title = Certuss
}}</ref>
 
The drug is available in the form of drops, [[suspension (chemistry)|suspension]]s and [[suppositories]].<ref name="Drugs.com" /><ref name="AustriaCodex">
{{cite book
| title    = Austria-Codex
| editor    = Jasek, W.
| publisher = Österreichischer Apothekerverlag
| location  = Vienna
| year      = 2008
| edition  = 63
| isbn      = 978-3-85200-188-3
| language  = German
}}</ref>
 
==Uses==
The drug is used for the treatment of dry cough associated with conditions such as common cold, [[bronchitis]] or [[sinusitis]]. Like [[codeine]] and other antitussives, it relieves the symptom, but does not heal the illness.<ref name="Drugs.com" /> No controlled [[clinical trial]]s regarding the efficiency of pentoyxverine are available.<ref name="Arzneistoff-Profile" />
 
[[Pharmacologist]]s use the substance as a selective [[agonist]] at the [[sigma-1 receptor]] in animal<ref name="Brown">
{{cite pmid | 14691051 }}</ref> and [[in vitro]] experiments.<ref>
{{cite pmid | 12445574 }}</ref><ref>
{{cite web
| url = http://www.chemicalbook.cn/ProductChemicalPropertiesCB2476609_EN.htm
| title = Carbetapentane Citrate CAS#: 23142-01-0
| publisher = Chemicalbook
}}</ref>
 
==Contraindications==
Pentoxyverine is contraindicated in persons with [[bronchial asthma]]<ref name="Arzneistoff-Profile">
{{cite book
| title        = Arzneistoff-Profile
| editor1-last = Dinnendahl | editor1-first = V.
| editor2-last = Fricke    | editor2-first = U.
| publisher    = Govi Pharmazeutischer Verlag
| location    = Eschborn, Germany
| date        = 2010
| edition      = 23
| volume      = 4
| isbn        = 978-3-7741-9846-3
| language    = German
}}</ref> or other kinds of [[respiratory insufficiency]] (breathing difficulties), as well as angle-closure [[glaucoma]]. No data are available for the use of pentoxyverine during pregnancy, [[lactation]], or children under two years of age, wherefore the drug must not be used under these circumstances.<ref name="AustriaCodex" />
 
Antitussive drugs are not useful in patients with extensive [[phlegm]] production because they prevent coughing up the phlegm.<ref name="Arzneistoff-Profile" />
 
==Adverse effects==
The most common side effects (seen in more than 1% of patients) are upper abdominal (belly) pain, diarrhoea, dry mouth, and nausea or vomiting. [[Allergic reaction]]s of the skin like itching, rashes, [[hives]] and [[angiooedema]] are rare. The same is true for [[anaphylactic shock]] and [[convulsion]]s.<ref name="AustriaCodex" /><ref>
{{cite book
| title        = Rote Liste
| editor1-first = H. | editor1-last = Dootz
| editor2-first = A. | editor2-last = Kuhlmann
| editor3-first = K. | editor3-last = Hoffmann
| at            = 24&nbsp;037
| edition      = 2005
| isbn          = 3-87193-306-6
| publisher    = Editio Cantor
| location      = Aulendorf
| language      = German
}}</ref>
==Overdose==
Overdosage leads to drowsiness, [[Psychomotor agitation|agitation]], nausea and [[anticholinergic]] effects like [[tachycardia]] (high heart rate), dry mouth, blurred vision, glaucoma, or [[urinary retention]].<ref name="Drugs.com" /><ref name="AustriaCodex" /> Especially in children, pentoxyverine can cause [[hypoventilation]],<ref name="Arzneistoff-Profile" /> but much more seldom than codeine and other [[opioid]] antitussives.
 
The treatment of overdosage aims at the symptoms; there are no specific [[antidote]]s available.<ref name="AustriaCodex" />
 
==Interactions==
No interactions have been described at usual doses. It is possible that pentoxyverine can increase the potency of sedative drugs like [[benzodiazepine]]s, some [[anticonvulsant]]s and [[antidepressant]]s, and alcohol. Likewise, some consumer informations warn patients from taking the drug in combination with or up to two weeks after [[monoamine oxidase inhibitor]]s, which are known to cause potentially fatal reactions in combination with the (chemically only distantly related) antitussive [[dextromethorphan]].<ref name="Drugs.com" /><ref name="AustriaCodex" /><ref name="Arzneistoff-Profile" />
 
==Mechanism of action==
Pentoxyverine suppresses the [[cough reflex]] in the [[central nervous system]],<ref name="Drugs.com" /> but the exact mechanism of action is not known with certainty. The drug acts as an [[Receptor antagonist | antagonist]] at [[muscarinic receptors]]<ref name="AustriaCodex" /> (subtype [[M1 receptor | M<sub>1</sub>]]) and as an agonist at [[sigma receptor]]s (subtype σ<sub>1</sub>).<ref name="Brown" /> Its [[anticholinergic]] properties can theoretically relax the [[pulmonary alveoli]] and reduce phlegm production. [[Antispasmodic|Spasmolytic]] and local anaesthetic properties have also been described.<ref name="Arzneistoff-Profile" /> The clinical relevance of these mechanisms is uncertain.
 
==Pharmacokinetics==
The substance is absorbed quickly from the gut and reaches its [[Cmax (pharmacology)|maximum plasma concentration]] (C<sub>max</sub>) after about two hours. If applied rectally, C<sub>max</sub> is reached after four hours. The [[bioavailability]] of the suppositories, measured as [[Area under the curve (pharmacokinetics)|area under the curve]] (AUC), is about twofold that of oral formulations, due to a [[first pass effect]] of over 50%. By far the most important metabolisation reaction is [[ester hydrolysis]], which accounts for 26.3% of the total clearance through the kidneys. Only 0.37% are cleared in form of the original substance.<ref name="AustriaCodex" /> The [[Biological half-life|plasma half life]] is 2.3 hours for oral formulations and three to 3.5 hours for suppositories.<ref>
{{cite book
| last1    = Steinhilber        | first1 = D.
| last2    = Schubert-Zsilavecz | first2 = M.
| last3    = Roth              | first3 = H. J.
| title    = Medizinische Chemie
| trans_title = Medical Chemistry
| year      = 2005
| publisher = Deutscher Apothekerverlag
| location  = Stuttgart
| language  = German
| isbn      = 3-7692-3483-9
| page      = 190
}}</ref> Pentoxyverine is also excreted into the [[breast milk]].<ref name="AustriaCodex" />
 
==Chemical properties==
Pentoxyverine dihydrogen [[citrate]], the salt that is commonly used for oral preparations, is a white to off-white, crystalline powder. It dissolves easily in water or [[chloroform]], but not in [[benzene]], [[diethyl ether]], or [[petroleum ether]], and melts at 90–95&nbsp;°C.<ref name="Arzneistoff-Profile" /> Other orally available salts are the [[hydrochloride]] and the [[tannate]];<ref>
{{cite web
| work = [[Monthly Index of Medical Specialities | MIMS]]
| url = http://www.mims.com/USA/drug/info/pentoxyverine?type=full&h=pentoxyverine
| title = Pentoxyverine Full Prescribing Information
}}</ref> suppositories contain the free base.<ref name="AustriaCodex" />
 
==References==
{{reflist|2}}


{{pharma-stub}}
{{Cough and cold preparations}}
{{Cough and cold preparations}}
{{Sigmaergics}}
[[Category:Antitussives]]
[[Category:Antitussives]]
{{WikiDoc Sources}}
[[Category:Carboxylate esters]]
[[Category:Ethers]]
[[Category:Drug]]
[[Category:Amines]]

Latest revision as of 17:24, 13 April 2015

Pentoxyverine
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa606008
Pregnancy
category
  • No studies; contraindicated
Routes of
administration		Oral, rectal
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismHepatic
Elimination half-life2.3 hours (oral), 3–3.5 hours (rectal)
ExcretionRenal
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC20H31NO3
Molar mass333.465 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Pentoxyverine (rINN) or carbetapentane is an antitussive (cough suppressant) commonly used for cough associated with illnesses like common cold. It is sold over-the-counter in the United States as Solotuss,[1] or in combination with other medications, especially decongestants. One such product is Certuss, a combination of guaifenesin and pentoxyverine.[2]

The drug is available in the form of drops, suspensions and suppositories.[1][3]

Uses

The drug is used for the treatment of dry cough associated with conditions such as common cold, bronchitis or sinusitis. Like codeine and other antitussives, it relieves the symptom, but does not heal the illness.[1] No controlled clinical trials regarding the efficiency of pentoyxverine are available.[4]

Pharmacologists use the substance as a selective agonist at the sigma-1 receptor in animal[5] and in vitro experiments.[6][7]

Contraindications

Pentoxyverine is contraindicated in persons with bronchial asthma[4] or other kinds of respiratory insufficiency (breathing difficulties), as well as angle-closure glaucoma. No data are available for the use of pentoxyverine during pregnancy, lactation, or children under two years of age, wherefore the drug must not be used under these circumstances.[3]

Antitussive drugs are not useful in patients with extensive phlegm production because they prevent coughing up the phlegm.[4]

Adverse effects

The most common side effects (seen in more than 1% of patients) are upper abdominal (belly) pain, diarrhoea, dry mouth, and nausea or vomiting. Allergic reactions of the skin like itching, rashes, hives and angiooedema are rare. The same is true for anaphylactic shock and convulsions.[3][8]

Overdose

Overdosage leads to drowsiness, agitation, nausea and anticholinergic effects like tachycardia (high heart rate), dry mouth, blurred vision, glaucoma, or urinary retention.[1][3] Especially in children, pentoxyverine can cause hypoventilation,[4] but much more seldom than codeine and other opioid antitussives.

The treatment of overdosage aims at the symptoms; there are no specific antidotes available.[3]

Interactions

No interactions have been described at usual doses. It is possible that pentoxyverine can increase the potency of sedative drugs like benzodiazepines, some anticonvulsants and antidepressants, and alcohol. Likewise, some consumer informations warn patients from taking the drug in combination with or up to two weeks after monoamine oxidase inhibitors, which are known to cause potentially fatal reactions in combination with the (chemically only distantly related) antitussive dextromethorphan.[1][3][4]

Mechanism of action

Pentoxyverine suppresses the cough reflex in the central nervous system,[1] but the exact mechanism of action is not known with certainty. The drug acts as an antagonist at muscarinic receptors[3] (subtype M1) and as an agonist at sigma receptors (subtype σ1).[5] Its anticholinergic properties can theoretically relax the pulmonary alveoli and reduce phlegm production. Spasmolytic and local anaesthetic properties have also been described.[4] The clinical relevance of these mechanisms is uncertain.

Pharmacokinetics

The substance is absorbed quickly from the gut and reaches its maximum plasma concentration (Cmax) after about two hours. If applied rectally, Cmax is reached after four hours. The bioavailability of the suppositories, measured as area under the curve (AUC), is about twofold that of oral formulations, due to a first pass effect of over 50%. By far the most important metabolisation reaction is ester hydrolysis, which accounts for 26.3% of the total clearance through the kidneys. Only 0.37% are cleared in form of the original substance.[3] The plasma half life is 2.3 hours for oral formulations and three to 3.5 hours for suppositories.[9] Pentoxyverine is also excreted into the breast milk.[3]

Chemical properties

Pentoxyverine dihydrogen citrate, the salt that is commonly used for oral preparations, is a white to off-white, crystalline powder. It dissolves easily in water or chloroform, but not in benzene, diethyl ether, or petroleum ether, and melts at 90–95 °C.[4] Other orally available salts are the hydrochloride and the tannate;[10] suppositories contain the free base.[3]

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 "Carbetapentane". Drugs.com.
  2. ↑ "Certuss". Drugs.com.
  3. ↑ 3.00 3.01 3.02 3.03 3.04 3.05 3.06 3.07 3.08 3.09 Jasek, W., ed. (2008). Austria-Codex (in German) (63 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 978-3-85200-188-3.
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 4.6 Dinnendahl, V.; Fricke, U., eds. (2010). Arzneistoff-Profile (in German). 4 (23 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.
  5. ↑ 5.0 5.1 PMID 14691051 (PMID 14691051)
    Citation will be completed automatically in a few minutes. Jump the queue or expand by hand
  6. ↑ PMID 12445574 (PMID 12445574)
    Citation will be completed automatically in a few minutes. Jump the queue or expand by hand
  7. ↑ "Carbetapentane Citrate CAS#: 23142-01-0". Chemicalbook.
  8. ↑ Dootz, H.; Kuhlmann, A.; Hoffmann, K. (eds.). Rote Liste (in German) (2005 ed.). Aulendorf: Editio Cantor. 24 037. ISBN 3-87193-306-6.
  9. ↑ Steinhilber, D.; Schubert-Zsilavecz, M.; Roth, H. J. (2005). Medizinische Chemie (in German). Stuttgart: Deutscher Apothekerverlag. p. 190. ISBN 3-7692-3483-9. Unknown parameter |trans_title= ignored (help)
  10. ↑ "Pentoxyverine Full Prescribing Information". MIMS.

Template:Cough and cold preparations Template:Sigmaergics

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