Doksepin

smeša *cis*- i *trans*-izomera
(IUPAC) ime
	(E,Z)-3-(dibenzo[b,e]oksepin-11(6H)-iliden)-N,N-dimetilpropan-1-amin
Klinički podaci
Robne marke	Sinequan, Zonalon
AHFS/Drugs.com	Monografija
MedlinePlus	a682390
Identifikatori
CAS broj	1668-19-5
ATC kod	N06AA12
PubChem	3158
DrugBank	DB01142
ChemSpider	3046
UNII	5ASJ6HUZ7D
KEGG	D07875
ChEBI	CHEBI:4710
ChEMBL	CHEMBL101740
Hemijski podaci
Formula	C19H21NO
Mol. masa	279,376 g/mol
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C19H21NO/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3 ; Key: ODQWQRRAPPTVAG-UHFFFAOYSA-N
Farmakokinetički podaci
Bioraspoloživost	Apsolutna: 25%; sa glavnim metabolitom desmetildoksepinom: 31%
Metabolizam	Hepatički
Poluvreme eliminacije	Doksepin 17 sati, glavni metabolit desmetildoksepin 51 sata
Izlučivanje	Renalno
Farmakoinformacioni podaci
Trudnoća	C(AU)
Pravni status	℞ Prescription only
Način primene	Oralno, intramuskularno, IV

Doksepin je psihotropni agens sa svojstvima tricikličnog antidepresanta i anksiolitika. On je u prodaju pod nizom imena, kao što su Aponal, Adapin, Doksal, Deptran, Sinquan i Sinequan (Pfizer). U obliku doksepin hidrohlorida, on je aktivni sastojak u kremama (Zonalon i Ksepin) za tretmant dermatološkog svraba. Doksepin se takođe koristi za tratmant održavanja sna (Silenor).

Medicinska upotreba

Doksepin se koristi za tretiranje depresije, anksioznih poremećaja, i kao secudarni tretman za hronične idiopatske urtikarije.^[6]

Niska doza doksepina (3 do 6 mg) je odobrena od strane FDA za upotrebu u tretmanu insomnije.^[7]^[8]

Farmakologija

Doksepin inhibira preuzimaje serotonina i norepinefrina. Njegov uticaj na preuzimaje dopamina je zanemarljiv. Doksepin je takođe antagonist više receptora:

Ekstremno jak: H₁, H₂ (K_i = 0.7 nM)
Jak: 5-HT₂, α₁-adrenergički, mACh
Umeren: 5-HT₁ (lokalno anestetičko dejstvo)

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ „Doxepin”. The American Society of Health-System Pharmacists. Pristupljeno 3. 4. 2011.
↑ „Phase 3 Data Show New Insomnia Drug, Silenor(R), Effective Without Side Effects”. Medical News Today. 12. 04. 2006.. Pristupljeno 01. 02. 2008.
↑ Hajak G, Rodenbeck A, Voderholzer U i dr.. (2001). „Doxepin in the treatment of primary insomnia: a placebo-controlled, double-blind, polysomnographic study”. J Clin Psychiatry 62 (6): 453–63. DOI:10.4088/JCP.v62n0609. PMID 11465523.

Vanjske veze

	Portal Medicina
	Portal Hemija

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[5] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[AHFS-6] „Doxepin”. The American Society of Health-System Pharmacists. Pristupljeno 3. 4. 2011.

[7] „Phase 3 Data Show New Insomnia Drug, Silenor(R), Effective Without Side Effects”. Medical News Today. 12. 04. 2006.. Pristupljeno 01. 02. 2008.

[pmid11465523-8] Hajak G, Rodenbeck A, Voderholzer U i dr.. (2001). „Doxepin in the treatment of primary insomnia: a placebo-controlled, double-blind, polysomnographic study”. J Clin Psychiatry 62 (6): 453–63. DOI:10.4088/JCP.v62n0609. PMID 11465523.

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