Captodiame: Difference between revisions

	WikiDoc Resources for Captodiame
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Most recent articles on Captodiame Most cited articles on Captodiame Review articles on Captodiame Articles on Captodiame in N Eng J Med, Lancet, BMJ
Media
Powerpoint slides on Captodiame Images of Captodiame Photos of Captodiame Podcasts & MP3s on Captodiame Videos on Captodiame
Evidence Based Medicine
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Clinical Trials
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Guidelines / Policies / Govt
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Captodiame
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	N05BB02 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Excretion	Renal
Identifiers
	IUPAC name 2-[(4-butylsulfanylphenyl)-phenyl-methyl]sulfanyl-N,N-dimethylethanamine;
CAS Number	486-17-9 ;
PubChem CID	10240;
DrugBank	DB09014 ;
ChemSpider	9823 ;
UNII	H93K9455DD;
KEGG	D07316 ;
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
Formula	C21H29NS2
Molar mass	359.594 g/mol
3D model (JSmol)	Interactive image;
	SMILES S(c1ccc(cc1)C(SCCN(C)C)c2ccccc2)CCCC;
	InChI InChI=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 ; Key:IZLPZXSZLLELBJ-UHFFFAOYSA-N ;
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Revision as of 13:09, 13 April 2015

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

Overview

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-HT_2C 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.

References

↑ ^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
↑ ^2.0 ^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:Anxiolytics

[Mercier-Guyon-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

[pmid23863923-2] 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.

[1]

[2]

@@ Line 3: / Line 3: @@
 | verifiedrevid = 447821290
 | IUPAC_name = 2-[(4-butylsulfanylphenyl)-phenyl-methyl]sulfanyl-''N'',''N''-dimethylethanamine
-| image = Captodiame.svg
+| image = Captodiame.png
 <!--Clinical data-->
@@ Line 40: / Line 40: @@
 | StdInChIKey = IZLPZXSZLLELBJ-UHFFFAOYSA-N
 }}
+              __NOTOC__
+{{SI}}
+{{CMG}}
+==Overview==
 '''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/>
@@ Line 60: / Line 64: @@
-{{Sedatives}}
 {{Anxiolytics}}
-{{Cholinergics}}
-{{Dopaminergics}}
-{{Histaminergics}}
-{{Serotonergics}}
-{{Sigmaergics}}
-[[Category:5-HT2C antagonists]]
+[[Category:Drug]]
 [[Category:Anticholinergics]]
 [[Category:Antihistamines]]
@@ Line 76: / Line 76: @@
 [[Category:Sigma agonists]]
 [[Category:Thioethers]]
-{{nervous-system-drug-stub}}

Captodiame: Difference between revisions

Revision as of 13:09, 13 April 2015

Overview

Synthesis

See also

References

Navigation menu

Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	N05BB02 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Excretion	Renal
Identifiers
IUPAC name 2-[(4-butylsulfanylphenyl)-phenyl-methyl]sulfanyl-N,N-dimethylethanamine
CAS Number	486-17-9^Y
PubChem CID	10240
DrugBank	DB09014^N
ChemSpider	9823^Y
UNII	H93K9455DD
KEGG	D07316^Y
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
Formula	C₂₁H₂₉NS₂
Molar mass	359.594 g/mol
3D model (JSmol)	Interactive image
SMILES S(c1ccc(cc1)C(SCCN(C)C)c2ccccc2)CCCC
InChI InChI=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^Y Key:IZLPZXSZLLELBJ-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Captodiame: Difference between revisions

Revision as of 13:09, 13 April 2015

Overview

Synthesis

See also

References

Navigation menu

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