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{{drugbox
{{Drugbox
| IUPAC_name       = 2-[(4-butylsulfanylphenyl)-phenyl-methyl]<Br>sulfanyl-''N'',''N''-dimethylethanamine
| Verifiedfields = changed
| image             = Captodiame.svg
| verifiedrevid = 447821290
| CAS_number        = 486-17-9
| IUPAC_name = 2-[(4-butylsulfanylphenyl)-phenyl-methyl]sulfanyl-''N'',''N''-dimethylethanamine
| ATC_prefix        = N05
| image = Captodiame.svg
| ATC_suffix        = BB02
 
| PubChem          = 10240
<!--Clinical data-->
| DrugBank          =
| tradename =   
| C=21|H=29|N=1|S=2
| Drugs.com = {{drugs.com|international|captodiame}}
| molecular_weight  = 359.594 g/mol
| legal_status = Rx-only
| bioavailability  =
| protein_bound    =
| metabolism        =
| elimination_half-life =
| excretion        = [[Kidney|Renal]]
| pregnancy_AU      =  <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US      =  <!-- A / B            / C / D / X -->
| pregnancy_category=   
| 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                  / Rx-only / Schedule I, II, III, IV, V -->
| legal_status      =
| routes_of_administration = Oral
| routes_of_administration = Oral
<!--Pharmacokinetic data-->
| excretion = [[Kidney|Renal]]
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 486-17-9
| ATC_prefix = N05
| ATC_suffix = BB02
| PubChem = 10240
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB09014
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9823
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = H93K9455DD
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07316
<!--Chemical data-->
| C=21 | H=29 | N=1 | S=2
| molecular_weight = 359.594 g/mol
| smiles = S(c1ccc(cc1)C(SCCN(C)C)c2ccccc2)CCCC
| InChI = 1/C21H29NS2/c1-4-5-16-23-20-13-11-19(12-14-20)21(24-17-15-22(2)3)18-9-7-6-8-10-18/h6-14,21H,4-5,15-17H2,1-3H3
| InChIKey = IZLPZXSZLLELBJ-UHFFFAOYAE
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C21H29NS2/c1-4-5-16-23-20-13-11-19(12-14-20)21(24-17-15-22(2)3)18-9-7-6-8-10-18/h6-14,21H,4-5,15-17H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IZLPZXSZLLELBJ-UHFFFAOYSA-N
}}
}}
'''Captodiame''' ([[International Nonproprietary Name|INN]], also known as '''captodiamine''') is an [[anxiolytic]]. It is a derivative of [[diphenhydramine]].<ref name=Mercier-Guyon/>
 
'''Captodiame''' ([[International Nonproprietary Name|INN]]), also known as '''captodiamine''', is an [[antihistamine]] sold under the trade names '''Covatine''', '''Covatix''', and '''Suvren''' which is used as a [[sedative]] and [[anxiolytic]]. It is a [[chemical derivative|derivative]] of [[diphenhydramine]].<ref name=Mercier-Guyon/>


A 2004 study suggested captodiame may be helpful in preventing [[benzodiazepine withdrawal syndrome]] in people discontinuing [[benzodiazepine]] treatment.<ref name=Mercier-Guyon>{{cite journal |author=Mercier-Guyon C, Chabannes JP, Saviuc P |title=The role of captodiamine in the withdrawal from long-term benzodiazepine treatment |journal=Curr Med Res Opin |volume=20 |issue=9 |pages=1347–55 |year=2004 |pmid=15383182 |doi=10.1185/030079904125004457}} [http://www.medscape.com/viewarticle/489359 Free full text with registration]</ref>
A 2004 study suggested captodiame may be helpful in preventing [[benzodiazepine withdrawal syndrome]] in people discontinuing [[benzodiazepine]] treatment.<ref name=Mercier-Guyon>{{cite journal |author=Mercier-Guyon C, Chabannes JP, Saviuc P |title=The role of captodiamine in the withdrawal from long-term benzodiazepine treatment |journal=Curr Med Res Opin |volume=20 |issue=9 |pages=1347–55 |year=2004 |pmid=15383182 |doi=10.1185/030079904125004457}} [http://www.medscape.com/viewarticle/489359 Free full text with registration]</ref>
In addition to its actions as an antihistamine, captodiamine has been found to act as a [[5-HT2C receptor|5-HT<sub>2C</sub> receptor]] [[receptor antagonist|antagonist]] and [[sigma-1 receptor|σ<sub>1</sub> receptor]] and [[D3 receptor|D<sub>3</sub> receptor]] [[agonist]].<ref name="pmid23863923">{{cite journal | author = Ring RM, Regan CM | title = Captodiamine, a putative antidepressant, enhances hypothalamic BDNF expression in vivo by synergistic 5-HT2c receptor antagonism and sigma-1 receptor agonism | journal = J. Psychopharmacol. (Oxford) | volume = 27 | issue = 10 | pages = 930–9 |date=October 2013  | pmid = 23863923 | doi = 10.1177/0269881113497614 | url = http://jop.sagepub.com/cgi/pmidlookup?view=long&pmid=23863923}}</ref> It produces [[antidepressant]]-like effects in rats.<ref name="pmid23863923" /> However, captodiamine is unique among antidepressant-like drugs in that it increases [[brain-derived neurotrophic factor]] (BDNF) levels in the [[hypothalamus]] but not in the [[frontal cortex]] or [[hippocampus]].<ref name="pmid23863923" /> This unique action may be related to its ability to attenuate [[Stress (psychology)|stress]]-induced [[anhedonia]] and [[corticotropin-releasing factor]] (CRF) signaling in the hypothalamus.<ref name="pmid23863923" />
==Synthesis==
The oxygen atom in these molecules can in many cases be dispensed with as well; substitution of sulfur for nitrogen affords a molecule whose salient biologic properties are those of a sedative and tranquilizer.
[[File:Captodiamine synthesis.png|thumb|center|700px|Captodiamine synthesis: Hubner Oluf Herman, Petersen Povl Viggo. {{US patent|2830088}} (1958).]]
[[Friedel-Crafts]] acylation of the n-butyl ether of thiophenol with [[benzoyl chloride]] gives the corresponding [[benzophenone]]. Reduction of the ketone with zinc/NaOH followed by treatment with HCl in ether affords the benzhydryl chloride. Displacement of the halogen with [[thiourea]] gives, by reaction of the last at its most nucleophilic center, the [[isothiouronium]] salt. Hydrolysis of the salt leads to the sulfur analog of a benzhydrol. Alkylation of the sodium salt of this last with ''N''-(2-chloroethyl)dimethylamine affords captodiamine.
==See also==
* [[Hydroxyzine]]
* [[Cyproheptadine]]


==References==
==References==
{{Reflist}}
{{Reflist|2}}




{{pharmacology-stub}}
{{Sedatives}}
{{Anxiolytics}}
{{Anxiolytics}}
{{Cholinergics}}
{{Dopaminergics}}
{{Histaminergics}}
{{Serotonergics}}
{{Sigmaergics}}


[[Category:5-HT2C antagonists]]
[[Category:Anticholinergics]]
[[Category:Antihistamines]]
[[Category:Anxiolytics]]
[[Category:Anxiolytics]]
[[Category:Dopamine agonists]]
[[Category:Sedatives]]
[[Category:Sigma agonists]]
[[Category:Thioethers]]
{{nervous-system-drug-stub}}

Revision as of 13:07, 13 April 2015

Captodiame
File:Captodiame.svg
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
ExcretionRenal
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
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
FormulaC21H29NS2
Molar mass359.594 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Captodiame (INN), also known as captodiamine, is an antihistamine sold under the trade names Covatine, Covatix, and Suvren which is used as a sedative and anxiolytic. It is a derivative of diphenhydramine.[1]

A 2004 study suggested captodiame may be helpful in preventing benzodiazepine withdrawal syndrome in people discontinuing benzodiazepine treatment.[1]

In addition to its actions as an antihistamine, captodiamine has been found to act as a 5-HT2C receptor antagonist and σ1 receptor and D3 receptor agonist.[2] It produces antidepressant-like effects in rats.[2] However, captodiamine is unique among antidepressant-like drugs in that it increases brain-derived neurotrophic factor (BDNF) levels in the hypothalamus but not in the frontal cortex or hippocampus.[2] This unique action may be related to its ability to attenuate stress-induced anhedonia and corticotropin-releasing factor (CRF) signaling in the hypothalamus.[2]

Synthesis

The oxygen atom in these molecules can in many cases be dispensed with as well; substitution of sulfur for nitrogen affords a molecule whose salient biologic properties are those of a sedative and tranquilizer.

File:Captodiamine synthesis.png
Captodiamine synthesis: Hubner Oluf Herman, Petersen Povl Viggo. U.S. Patent 2,830,088 (1958).

Friedel-Crafts acylation of the n-butyl ether of thiophenol with benzoyl chloride gives the corresponding benzophenone. Reduction of the ketone with zinc/NaOH followed by treatment with HCl in ether affords the benzhydryl chloride. Displacement of the halogen with thiourea gives, by reaction of the last at its most nucleophilic center, the isothiouronium salt. Hydrolysis of the salt leads to the sulfur analog of a benzhydrol. Alkylation of the sodium salt of this last with N-(2-chloroethyl)dimethylamine affords captodiamine.

See also

References

  1. ↑ 1.0 1.1 Mercier-Guyon C, Chabannes JP, Saviuc P (2004). "The role of captodiamine in the withdrawal from long-term benzodiazepine treatment". Curr Med Res Opin. 20 (9): 1347–55. doi:10.1185/030079904125004457. PMID 15383182. Free full text with registration
  2. ↑ 2.0 2.1 2.2 2.3 Ring RM, Regan CM (October 2013). "Captodiamine, a putative antidepressant, enhances hypothalamic BDNF expression in vivo by synergistic 5-HT2c receptor antagonism and sigma-1 receptor agonism". J. Psychopharmacol. (Oxford). 27 (10): 930–9. doi:10.1177/0269881113497614. PMID 23863923.


Template:Sedatives Template:Anxiolytics

Template:Sigmaergics


Template:Nervous-system-drug-stub

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