Metilergometrin

Metilergometrin
(IUPAC) ime
	9,10-didehidro- N-[1-(hidroksimetil)- propil]- D-lisergamid
Klinički podaci
Robne marke	Metergin
AHFS/Drugs.com	Internacionalno ime leka
MedlinePlus	a601077
Identifikatori
CAS broj	113-42-8
ATC kod	G02AB01
PubChem	8226
ChemSpider	7933
UNII	W53L6FE61V
ChEMBL	CHEMBL1201356
Hemijski podaci
Formula	C20H25N3O2
Mol. masa	339,432 g/mol
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C20H25N3O2/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25)/t13-,14+,18-/m1/s1; Key: UNBRKDKAWYKMIV-QWQRMKEZSA-N
Sinonimi	Metiergobasin; Metilergobrevin; Metilergonovin
Fizički podaci
Tačka topljenja	172 °C (342 °F)
Rastvorljivost u voda	nije rastvoran mg/mL (20 °C)
Farmakokinetički podaci
Metabolizam	Liver
Poluvreme eliminacije	30–120 min
Izlučivanje	Mostly bile
Farmakoinformacioni podaci
Trudnoća	?
Pravni status	℞ Prescription only
Način primene	Oralno

Metilergometrin (metilergonovin, metilergobazin, metergin, d-lizerginska kiselina 1-butanol amid) je sintetički analog ergonovina, psihodeličnog alkaloida prisutnog u ergotu, i mnogih vrsta biljaka familije Convolvulaceae. On je član ergolinske familije i hemijski je sličan sa LSD-om, erginom, ergometrinom, i lizerginskom kiselinom. Usled njegovih oksitocičkih svojstava, on ima medicinsku primenu u akušerstvu.

Upotreba

Akušerska uporeba

Metilergometrin je konstriktor glatkih mišića koji uglavnom deluje na matericu. On se najčešće koristi za sprečavanje ili kontrolu ekscesivnog krvarenja nakon porođaja i abortusa. On se takođe koristi kao pomoćno sredstvo u izbacivanju zadržanih produkata začeća nakon nepotpunog spontanog abortusa, i za odstranjivanje plancente nakom porođaja. On je dostupan za oralnu upotrebu ili putem injekcija.^[5]^[6]^[7]

Migrena

Metilergometrin se poneka koristi za sprečavenje^[8] i akutni tretman^[9] migrene. On je aktivni metabolit metisergida.

Mehanizam dejstva

Metilergometrin je parcijalni agonist/antagonist serotonergičkih, dopaminergičkih i alfa-adrenergičkih receptora. Njegov specifični obrazac vezivanja i aktivacije za te receptore dovodi do visoko specifične kontrakcije glatkih mišića materice putem 5-HT_2A serotoninskih receptora,^[10] dok na krvne sudove deluje u manjoj meri od drugih ergot alkaloida.^[5]

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
↑ 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
↑ ^5,0 ^5,1 Jasek, W, ur. (2007) (German). Austria-Codex (62nd izd.). Vienna: Österreichischer Apothekerverlag. str. 5193–5. ISBN 978-3-85200-181-4.
↑ Mutschler, Ernst; Schäfer-Korting, Monika (2001) (German). Arzneimittelwirkungen (8 izd.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. str. 447. ISBN 3-8047-1763-2.
↑ Fachinformation des Arzneimittel-Kompendium der Schweiz: Methergin^{[mrtav link]}
↑ Koehler, PJ; Tfelt-Hansen PC (Nov 2008). „History of methysergide in migraine.”. Cephalalgia 28 (11). DOI:10.1111/j.1468-2982.2008.01648.x. PMID 18644039. Pristupljeno 2011-12-11.
↑ Niño-Maldonado, Alfredo; Gary Caballero-García, Wilfrido Mercado-Bochero, Fernando Rico-Villademoros, Elena P Calandre (November 2009). „Efficacy and tolerability of intravenous methylergonovine in migraine female patients attending the emergency department: a pilot open-label study”. Head Face Med 5 (21). DOI:10.1186/1746-160X-5-21. PMC 2780385. PMID 19895705.
↑ Heinz Pertz, Eckart Eich (1999). „Ergot alkaloids and their derivatives as ligands for serotoninergic, dopaminergic and adrenergic receptors”. u: Vladimír Křen,Ladislav Cvak. Ergot: the genus Claviceps. CRC Press. str. 411-440. ISBN 978-905702375-0.

Literatura

Jasek, W, ur. (2007) (German). Austria-Codex (62nd izd.). Vienna: Österreichischer Apothekerverlag. str. 5193–5. ISBN 978-3-85200-181-4.
Heinz Pertz, Eckart Eich (1999). „Ergot alkaloids and their derivatives as ligands for serotoninergic, dopaminergic and adrenergic receptors”. u: Vladimír Křen,Ladislav Cvak. Ergot: the genus Claviceps. CRC Press. str. 411-440. ISBN 978-905702375-0.

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] 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

[Austria-Codex-5] 5,0 ^5,1 Jasek, W, ur. (2007) (German). Austria-Codex (62nd izd.). Vienna: Österreichischer Apothekerverlag. str. 5193–5. ISBN 978-3-85200-181-4.

[6] Mutschler, Ernst; Schäfer-Korting, Monika (2001) (German). Arzneimittelwirkungen (8 izd.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. str. 447. ISBN 3-8047-1763-2.

[7] Fachinformation des Arzneimittel-Kompendium der Schweiz: Methergin^{[mrtav link]}

[8] Koehler, PJ; Tfelt-Hansen PC (Nov 2008). „History of methysergide in migraine.”. Cephalalgia 28 (11). DOI:10.1111/j.1468-2982.2008.01648.x. PMID 18644039. Pristupljeno 2011-12-11.

[9] Niño-Maldonado, Alfredo; Gary Caballero-García, Wilfrido Mercado-Bochero, Fernando Rico-Villademoros, Elena P Calandre (November 2009). „Efficacy and tolerability of intravenous methylergonovine in migraine female patients attending the emergency department: a pilot open-label study”. Head Face Med 5 (21). DOI:10.1186/1746-160X-5-21. PMC 2780385. PMID 19895705.

[10] Heinz Pertz, Eckart Eich (1999). „Ergot alkaloids and their derivatives as ligands for serotoninergic, dopaminergic and adrenergic receptors”. u: Vladimír Křen,Ladislav Cvak. Ergot: the genus Claviceps. CRC Press. str. 411-440. ISBN 978-905702375-0.

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