Mirtazapin
Mirtazapin
(IUPAC ) ime
(±)-2-metil-1,2,3,4,10,14b-heksahidropirazino[2,1-a]pirido[2,3-c][2]benzazepin
Klinički podaci
Robne marke
Remeron, Avanza, Zispin
AHFS/Drugs.com
Monografija
MedlinePlus
a697009
Identifikatori
CAS broj
61337-67-5
ATC kod
N06 AX11
PubChem [ 1] [ 2]
4205
DrugBank
DB00370
ChemSpider [ 3]
4060
UNII
A051Q2099Q Y
KEGG [ 4]
D00563 Y
ChEBI
CHEBI:6950 Y
ChEMBL [ 5]
CHEMBL654 Y
Hemijski podaci
Formula
C 17 H 19 N 3
Mol. masa
265,35 g/mol
SMILES
eMolekuli & PubHem
InChI
InChI=1S/C17H19N3/c1-19-9-10-20-16(12-19)15-7-3-2-5-13(15)11-14-6-4-8-18-17(14)20/h2-8,16H,9-12H2,1H3 Y Key: RONZAEMNMFQXRA-UHFFFAOYSA-N Y
Sinonimi
6-Azamianserin, Org 3770
Fizički podaci
Gustina
1,22 g/cm³
Tačka topljenja
114–116 °C (237–241 °F)
Tačka ključanja
432 °C (810 °F)
Rastvorljivost u voda
Rastvoran u metanolu i hloroformu mg/mL (20 °C)
Farmakokinetički podaci
Bioraspoloživost
50%[ 6]
Vezivanje za proteine plazme
85%[ 6]
Metabolizam
Hepatički (CYP1A2 , CYP2D6 , i CYP3A4 )[ 6] [ 7]
Poluvreme eliminacije
20–40 sata[ 6]
Izlučivanje
Urin (75%)[ 6] Izmet (15%)[ 6]
Farmakoinformacioni podaci
Trudnoća
?
Pravni status
℞ Prescription only
Način primene
Oralno
Mirtazapin (Remeron , Avanza , Zispin ) je noradrenergički i specifični serotonergički antidepresiv (NaSSA) koji je razvila kompanija Organon International u Sjedinjenim Državama 1990 . godine. On se prvenstveno koristi za lečenje depresije . On isto takao nalazi primenu kao anksiolitik , hipnotik , antiemetik i stimulant apetita . On je strukturno sličan sa mianserinom, i klasifikuje se kao tetraciklični antidepresant (TeCA).
Medicinska upotreba
Mirtazapin se prvenstveno koristi za tretiranje kliničke depresije i drugih poremećaja raspoloženja.[ 8] [ 9]
On isto tako može da bude koristan u tretiranju sledećih oboljenja, mada nije odobren za te primene:
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
↑ 6,0 6,1 6,2 6,3 6,4 6,5 Timmer CJ, Sitsen JM, Delbressine LP (June 2000). „Clinical pharmacokinetics of mirtazapine” . Clinical Pharmacokinetics 38 (6): 461–74. DOI :10.2165/00003088-200038060-00001 . PMID 10885584 .
↑ 7,0 7,1 Anttila SA, Leinonen EV (2001). „A review of the pharmacological and clinical profile of mirtazapine”. CNS Drug Reviews 7 (3): 249–64. DOI :10.1111/j.1527-3458.2001.tb00198.x . PMID 11607047 .
↑ Gorman JM (1999). „Mirtazapine: clinical overview”. J Clin Psychiatry 60 Suppl 17 : 9–13; discussion 46–8. PMID 10446735 .
↑ Benjamin S, Doraiswamy PM (July 2011). „Review of the use of mirtazapine in the treatment of depression” . Expert Opinion on Pharmacotherapy 12 (10): 1623–32. DOI :10.1517/14656566.2011.585459 . PMID 21644844 .
↑ Goodnick PJ, Puig A, DeVane CL, Freund BV (July 1999). „Mirtazapine in major depression with comorbid generalized anxiety disorder” . J Clin Psychiatry 60 (7): 446–8. DOI :10.4088/JCP.v60n0705 . PMID 10453798 .
↑ 11,0 11,1 11,2 11,3 Croom KF, Perry CM, Plosker GL (2009). „Mirtazapine: a review of its use in major depression and other psychiatric disorders” . CNS Drugs 23 (5): 427–52. DOI :10.2165/00023210-200923050-00006 . PMID 19453203 .
↑ Muehlbacher M, Nickel MK, Nickel C, et al. (December 2005). „Mirtazapine treatment of social phobia in women: a randomized, double-blind, placebo-controlled study” . Journal of Clinical Psychopharmacology 25 (6): 580–3. DOI :10.1097/01.jcp.0000186871.04984.8d . PMID 16282842 . Arhivirano iz originala na datum 2015-11-27. Pristupljeno 2014-04-05 .
↑ Koran LM, Quirk T, Lorberbaum JP, Elliott M (October 2001). „Mirtazapine treatment of obsessive-compulsive disorder”. J Clin Psychopharmacol 21 (5): 537–9. DOI :10.1097/00004714-200110000-00016 . PMID 11593084 .
↑ Carpenter LL, Leon Z, Yasmin S, Price LH (June 1999). „Clinical experience with mirtazapine in the treatment of panic disorder”. Ann Clin Psychiatry 11 (2): 81–6. DOI :10.3109/10401239909147053 . PMID 10440525 .
↑ Carli V, Sarchiapone M, Camardese G, Romano L, DeRisio S (July 2002). „Mirtazapine in the treatment of panic disorder”. Arch. Gen. Psychiatry 59 (7): 661–2. DOI :10.1001/archpsyc.59.7.661 . PMID 12090820 .
↑ Hrdlicka M, Beranova I, Zamecnikova R, Urbanek T (April 2008). „Mirtazapine in the treatment of adolescent anorexia nervosa. Case-control study” . European Child & Adolescent Psychiatry 17 (3): 187–9. DOI :10.1007/s00787-007-0670-8 . PMID 18357426 .
↑ Hartmann PM (January 1999). „Mirtazapine: a newer antidepressant”. Am Fam Physician 59 (1): 159–61. PMID 9917581 .
↑ Jindal RD (2009). „Insomnia in patients with depression: some pathophysiological and treatment considerations” . CNS Drugs 23 (4): 309–29. PMID 19374460 .
↑ Nutt DJ (June 2002). „Tolerability and safety aspects of mirtazapine” . Human Psychopharmacology 17 Suppl 1 : S37–41. DOI :10.1002/hup.388 . PMID 12404669 .
↑ 20,0 20,1 Li TC, Shiah IS, Sun CJ, Tzang RF, Huang KC, Lee WK (June 2011). „Mirtazapine relieves post-electroconvulsive therapy headaches and nausea: a case series and review of the literature” . The Journal of ECT 27 (2): 165–7. DOI :10.1097/YCT.0b013e3181e63346 . PMID 21602639 . Arhivirano iz originala na datum 2013-05-09. Pristupljeno 2014-04-05 .
↑ Kast RE, Foley KF (July 2007). „Cancer chemotherapy and cachexia: mirtazapine and olanzapine are 5-HT3 antagonists with good antinausea effects”. Eur J Cancer Care (Engl) 16 (4): 351–4. DOI :10.1111/j.1365-2354.2006.00760.x . PMID 17587360 .
↑ Landowski J (2002). „[Mirtazapine--an antidepressant]” (Polish). Psychiatria Polska 36 (6 Suppl): 125–30. PMID 12647431 .
↑ Chinuck RS, Fortnum H, Baldwin DR (December 2007). „Appetite stimulants in cystic fibrosis: a systematic review” . Journal of Human Nutrition and Dietetics : the Official Journal of the British Dietetic Association 20 (6): 526–37. DOI :10.1111/j.1365-277X.2007.00824.x . PMID 18001374 .
↑ Davis MP, Khawam E, Pozuelo L, Lagman R (August 2002). „Management of symptoms associated with advanced cancer: olanzapine and mirtazapine. A World Health Organization project” . Expert Review of Anticancer Therapy 2 (4): 365–76. DOI :10.1586/14737140.2.4.365 . PMID 12647979 .
↑ Twycross R, Greaves MW, Handwerker H, et al. (January 2003). „Itch: scratching more than the surface” . QJM : Monthly Journal of the Association of Physicians 96 (1): 7–26. DOI :10.1093/qjmed/hcg002 . PMID 12509645 .
↑ Greaves MW (2005). „Itch in systemic disease: therapeutic options” . Dermatologic Therapy 18 (4): 323–7. DOI :10.1111/j.1529-8019.2005.00036.x . PMID 16297004 .
↑ Colombo B, Annovazzi PO, Comi G (October 2004). „Therapy of primary headaches: the role of antidepressants” . Neurological Sciences : Official Journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology 25 Suppl 3 : S171–5. DOI :10.1007/s10072-004-0280-x . PMID 15549531 .
↑ Tajti J, Almási J (June 2006). „[Effects of mirtazapine in patients with chronic tension-type headache. Literature review]” (Hungarian). Neuropsychopharmacologia Hungarica : a Magyar Pszichofarmakológiai Egyesület Lapja = Official Journal of the Hungarian Association of Psychopharmacology 8 (2): 67–72. PMID 17073214 .
Literatura
Stimmel GL, Dopheide JA, Stahl SM (1997). „Mirtazapine: an antidepressant with noradrenergic and specific serotonergic effects”. Pharmacotherapy 17 (1): 10–21. PMID 9017762 .
Anttila SA, Leinonen EV (2001). „A review of the pharmacological and clinical profile of mirtazapine”. CNS Drug Rev 7 (3): 249–64. DOI :10.1111/j.1527-3458.2001.tb00198.x . PMID 11607047 .
Vanjske veze
Serotoninski modulatori i stimulatori (SMS)
Neselektivni
MAOA -Selektivni
MAOB -Selektivni
Agonisti :
5-FNE •
6-FNE •
Amidefrin •
Anisodamin •
Anisodin •
Cirazolin •
Dipivefrin •
Dopamin •
Efedrin •
Epinefrin (Adrenalin) •
Etilefrin •
Etilnorepinefrin •
Indanidin •
Levonordefrin •
Metaraminol •
Metoksamin •
Metildopa •
Midodrin •
Nafazolin •
Norepinefrin (Noradrenalin) •
Oktopamin •
Oksimetazolin •
Fenilefrin •
Fenilpropanolamin •
Pseudoefedrin •
Sinefrin •
Tetrahidrozolin Antagonisti :
Abanohil •
Adimolol •
Ajmalicin •
Alfuzosin •
Amosulalol •
Arotinolol •
Atiprosin •
Benoksatian •
Buflomedil •
Bunazosin •
Karvedilol •
CI-926 •
Korinantin •
Dapiprazol •
DL-017 •
Domesticin •
Doksazosin •
Eugenodilol •
Fenspirid •
GYKI-12,743 •
GYKI-16,084 •
Indoramin •
Ketanserin •
L-765,314 •
Labetalol •
Mefendioksan •
Metazosin •
Monatepil •
Moksisilit (Timoksamin) •
Naftopidil •
Nantenin •
Neldazosin •
Nicergolin •
Niguldipin •
Pelanserin •
Fendioksan •
Fenoksibenzamin •
Fentolamin •
Piperoksan •
Prazosin •
Hinazosin •
Ritanserin •
RS-97,078 •
SGB-1,534 •
Silodosin •
SL-89.0591 •
Spiperon •
Talipeksol •
Tamsulosin •
Terazosin •
Tibalosin •
Tiodazosin •
Tipentosin •
Tolazolin •
Trimazosin •
Upidosin •
Urapidil •
Zolertin * Mnogi TCA , TeCA , antipsihotici , ergolini , i neki piperazini kao što su buspiron , trazodon , nefazodon , etoperidon , i mepiprazol takođe antagoniziraju α1 -adrenergičke receptore, što doprinosi njihovim nuspojavama.
Receptor
Agonisti :
2-Piridiletilamin •
Betahistin •
Histamin •
HTMT •
UR-AK49 Antagonisti :
1. generacija :
4-Metildifenhidramin •
Alimemazin •
Antazolin •
Azatadin •
Bamipin •
Benzatropin/Benztropin •
Bepotastin •
Bromazin •
Bromfeniramin •
Buklizin •
Kaptodiam •
Karbinoksamin •
Hlorciklizin •
Hloropiramin •
Hloroten •
Hlorfenamin •
Hlorfenoksamin •
Cinarizin •
Klemastin •
Klobenzepam •
Klocinizin •
Ciklizin •
Ciproheptadin •
Dacemazin •
Deptropin •
Deksbromfeniramin •
Dekshlorfeniramin •
Dimenhidrinat •
Dimetinden •
Difenhidramin •
Difenilpiralin •
Doksilamin •
Embramin •
Etodroksizin •
Etibenzatropin/Etilbenztropin •
Etimemazin •
Flunarizin •
Histapirodin •
Homohlorciklizin •
Hidroksietilprometazin •
Hidroksizin •
Izoprometazin •
Izotipendil •
Meklozin •
Mepiramin/Pirilamin •
Mehitazin •
Metafurilen •
Metapirilen •
Metdilazin •
Moksastin •
Niaprazin •
Orfenadrin •
Oksatomid •
Oksomemazin •
Fenindamin •
Feniramin •
Feniltoloksamin •
Pimetiksen •
Piperoksan •
Pipoksizin •
Prometazin •
Propiomazin •
Pirobutamin •
Talastin •
Tenalidin •
Tenildiamin •
Tiazinamijum •
Tonzilamin •
Tolpropamin •
Tripelenamin •
Triprolidin
2. generacija : Akrivastin • Alinastin • Astemizol • Azelastin • Bamirastin • Barmastin • Bepiastin • Bepotastin • Bilastin • Kabastinen • Karebastin • Ketirizin • Klemastin • Klemizol • Klobenztropin • Dorastin • Ebastin • Emedastin • Epinastin • Flezelastin • Ketotifen • Latrepirdin • Levokabastin • Linetastin • Loratadin • Mapinastin • Mebhidrolin • Mizolastin • Moksastin • Noberastin • Oktastin • Olopatadin • Perastin • Piklopastin • Rokastin • Rupatadin • Setastin • Talastin • Temelastin • Terfenadin • Zepastin
3. generacija : Desloratadin • Feksofenadin • Cetirizin • Levocetirizin
Negrupisani : Belarizin • Efletirizin • Elbanizin • Flotrenizin • Medrilamin • Napaktadin • Pibaksizin • Tagorizin • Trelnarizin • Trenizin • Vapitadin
Razni :
Triciklični antidepresanti (
amitriptilin , •
doksepin , •
trimipramin , itd) •
Tetraciklični antidepresanti (
mianserin , •
mirtazapin , itd) •
Tipični antipsihotici (
hlorpromazin , •
tioridazin , itd) •
Atipični antipsihotici (
klozapin , •
olanzapin , •
hetiapin , itd)
Transporter
Enzim
Drugi
Agonisti :
Azapironi :
Alnespiron •
Binospiron •
Buspiron •
Enilospiron •
Eptapiron •
Gepiron •
Ipsapiron •
Perospiron •
Revospiron •
Tandospiron •
Tiospiron •
Umespiron •
Zalospiron ;
Antidepresivi :
Etoperidon •
Nefazodon •
Trazodon ;
Antipsihotici :
Aripiprazol •
Asenapin •
Klozapin •
Kvetiapin •
Ziprasidon ;
Ergolini :
Dihidroergotamin •
Ergotamin •
Lisurid •
Metisergid •
LSD ;
Triptamini :
5-CT •
5-MeO-DMT •
5-MT •
Bufotenin •
DMT •
Indorenat •
Psilocin •
Psilocibin ;
Drugi :
8-OH-DPAT •
Adatanserin •
Bay R 1531 •
Befiradol •
BMY-14802 •
Kanabidiol •
Dimemebfe •
Ebalzotan •
Eltoprazin •
F-11,461 •
F-12,826 •
F-13,714 •
F-14,679 •
F-15,063 •
F-15,599 •
Flesinoksan •
Flibanserin •
Lesopitron •
Lu AA21004 •
LY-293,284 •
LY-301,317 •
MKC-242 •
NBUMP •
Osemozotan •
Oksaflozan •
Pardoprunoks •
Piklozotan •
Rauvolscin •
Repinotan •
Roksindol •
RU-24,969 •
S 14,506 •
S-14,671 •
S-15,535 •
Sarizotan •
SSR-181,507 •
Sunepitron •
U-92,016-A •
Urapidil •
Vilazodon •
Ksaliproden •
Johimbin Antagonisti :
Antipsihotici :
Iloperidon •
Risperidon •
Sertindol ;
Beta blokatori :
Alprenolol •
Cianopindolol •
Jodocianopindolol •
Oksprenolol •
Pindobind •
Pindolol •
Propranolol •
Tertatolol ;
Drugi :
AV965 •
BMY-7,378 •
CSP-2503 •
Dotarizin •
Flopropion •
GR-46611 •
Isamoltan •
Lekozotan •
Metitepin/Metiotepin •
MPPF •
NAN-190 •
PRX-00023 •
Robalzotan •
S-15535 •
SB-649,915 •
SDZ 216-525 •
Spiperon •
Spiramid •
Spiroksatrin •
UH-301 •
WAY-100,135 •
WAY-100,635 •
Ksilamidin Agonisti :
Lisergamidi :
Dihidroergotamin •
Metisergid ;
Triptani :
Almotriptan •
Avitriptan •
Eletriptan •
Frovatriptan •
Naratriptan •
Rizatriptan •
Sumatriptan •
Zolmitriptan ;
Triptamini :
5-CT •
5-Etil-DMT •
5-MT •
5-(Noniloksi)triptamin ;
Drugi :
CP-135,807 •
CP-286,601 •
GR-46611 •
L-694,247 •
L-772,405 •
PNU-109,291 •
PNU-142,633 Antagonisti :
Lisergamidi :
Metergolin ;
Drugi :
Alniditan •
BRL-15,572 •
Elzasonan •
GR-127,935 •
Ketanserin •
LY-310,762 •
LY-367,642 •
LY-456,219 •
LY-456,220 •
Metitepin/Metiotepin •
Ritanserin •
Johimbin •
Ziprasidon
Agonisti :
Fenetilamini :
2C-B •
2C-E •
2C-I •
2C-T-2 •
2C-T-7 •
2C-T-21 •
DOB •
DOC •
DOI •
DOM •
MDA •
MDMA •
Meskalin ;
Piperazini :
Aripiprazol •
mCPP •
TFMPP ;
Triptamini :
5-CT •
5-MeO-α-ET •
5-MeO-α-MT •
5-MeO-DET •
5-MeO-DiPT •
5-MeO-DMT •
5-MeO-DPT •
5-MT •
α-ET •
α-Metil-5-HT •
α-MT •
Bufotenin •
DET •
DiPT •
DMT •
DPT •
Psilocin •
Psilocibin ;
Drugi :
A-372,159 •
AL-38022A •
CP-809,101 •
Dimemebfe •
Lorkaserin •
Medifoksamin •
MK-212 •
Org 12,962 •
ORG-37,684 •
Oksaflozan •
PNU-22394 •
Ro60-0175 •
Ro60-0213 •
Vabicaserin •
WAY-629 •
WAY-161,503 •
YM-348 Antagonisti :
Atipični antipsihotici :
Klozapin •
Iloperidon •
Melperon •
Olanzapin •
Paliperidon •
Pimozid •
Hetiapin •
Risperidon •
Sertindol •
Ziprasidon •
Zotepin ;
Tipični antipsihotici :
Hlorpromazin •
Loksapin •
Pipamperon ;
Antidepresivi :
Agomelatin •
Amitriptilin •
Amoksapin •
Aptazapin •
Etoperidon •
Fluoksetin •
Mianserin •
Mirtazapin •
Nefazodon •
Nortriptilin •
Trazodon ;
Drugi :
Adatanserin •
Cinanserin •
Ciproheptadin •
Deramciklan •
Dotarizin •
Eltoprazin •
Esmirtazapin •
FR-260,010 •
Ketanserin •
Ketotifen •
Latrepirdin •
Lu AA24530 •
Metitepin/Metiotepin •
Metisergid •
Pizotifen •
Ritanserin •
RS-102,221 •
S-14,671 •
SB-200,646 •
SB-206,553 •
SB-221,284 •
SB-228,357 •
SB-242,084 •
SB-243,213 •
SDZ SER-082 •
Ksilamidin
Agonisti :
Lisergamidi :
Dihidroergotamin •
Ergotamin •
Lisurid •
LSD •
Mesulergin •
Metergolin •
Metisergid ;
Triptamini :
2-Metil-5-HT •
5-BT •
5-CT •
5-MT •
Bufotenin •
E-6801 •
E-6837 •
EMD-386,088 •
EMDT •
LY-586,713 •
N -Metil-5-HT •
Triptamin ;
Drugi :
WAY-181,187 •
WAY-208,466 Antagonisti :
Antidepresanti :
Amitriptilin •
Amoksapin •
Klomipramin •
Doksepin •
Mianserin •
Nortriptilin ;
Atipični antipsihotici :
Aripiprazol •
Asenapin •
Klozapin •
Fluperlapin •
Iloperidon •
Olanzapin •
Tiospiron ;
Tipični antipsihotici :
Hlorpromazin •
Loksapin ;
Drugi :
BGC20-760 •
BVT-5182 •
BVT-74316 •
EGIS-12,233 •
GW-742,457 •
Ketanserin •
Latrepirdin •
Lu AE58054 •
Metitepin/Metiotepin •
MS-245 •
PRX-07034 •
Ritanserin •
Ro04-6790 •
Ro 63-0563 •
SB-258,585 •
SB-271,046 •
SB-357,134 •
SB-399,885 •
SB-742,457 Agonisti :
Lisergamidi :
LSD ;
Triptamini :
5-CT •
5-MT •
Bufotenin ;
Drugi :
8-OH-DPAT •
AS-19 •
Bifeprunoks •
LP-12 •
LP-44 •
RU-24,969 •
Sarizotan Antagonisti :
Lisergamidi :
2-Bromo-LSD •
Bromokriptin •
Dihidroergotamin •
Ergotamin •
Mesulergin •
Metergolin •
Metisergid ;
Antidepresanti :
Amitriptilin •
Amoksapin •
Klomipramin •
Imipramin •
Maprotilin •
Mianserin ;
Atipični antipsihotici :
Amisulprid •
Aripiprazol •
Klozapin •
Olanzapin •
Risperidon •
Sertindol •
Tiospiron •
Ziprasidon •
Zotepin ;
Tipični antipsihotici :
Hlorpromazin •
Loksapin ;
Drugi :
Butaklamol •
EGIS-12,233 •
Ketanserin •
LY-215,840 •
Metitepin/Metiotepin •
Pimozid •
Ritanserin •
SB-258,719 •
SB-258,741 •
SB-269,970 •
SB-656,104 •
SB-656,104-A •
SB-691,673 •
SLV-313 •
SLV-314 •
Spiperon •
SSR-181,507