Captodiame: Difference between revisions

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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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VisualWikitext

Latest 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]

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 1: / Line 1: @@
-{{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.png
-| 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
+<!--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/>
+              __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/>
 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" />
+==See also==
+* [[Hydroxyzine]]
+* [[Cyproheptadine]]
 ==References==
-{{Reflist}}
+{{Reflist|2}}
-{{pharmacology-stub}}
 {{Anxiolytics}}
+[[Category:Drug]]
+[[Category:Anticholinergics]]
+[[Category:Antihistamines]]
 [[Category:Anxiolytics]]
+[[Category:Dopamine agonists]]
+[[Category:Sedatives]]
+[[Category:Sigma agonists]]
+[[Category:Thioethers]]

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

Latest revision as of 13:09, 13 April 2015

Overview

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References

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