Ergotamin

Ergotamin
(IUPAC) ime
	(6aR,9R)-N-((2R,5S,10aS,10bS)- 5-benzil-10b-hidroksi-2-metil- 3,6-dioksooktahidro-2H-oksazolo[3,2-a] pirolo[2,1-c]pirazin-2-il) -7-metil-4,6,6a,7,8,9-heksahidroindolo[4,3-fg] hinolin-9-karboksamid
Klinički podaci
Robne marke	Ergomar
AHFS/Drugs.com	Monografija
Identifikatori
CAS broj	113-15-5
ATC kod	N02CA02
PubChem	8223
DrugBank	DB00696
ChemSpider	7930
UNII	PR834Q503T
KEGG	D07906
ChEBI	CHEBI:64318
ChEMBL	CHEMBL442
Hemijski podaci
Formula	C33H35N5O5
Mol. masa	581,66 g/mol
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1 ; Key: XCGSFFUVFURLIX-VFGNJEKYSA-N
Farmakokinetički podaci
Bioraspoloživost	Intravenozno: 100%,; Intramuskularno: 47%,; Oralno: <1% (Pojačan koadministracijom kafeina)
Metabolizam	Hepatički
Poluvreme eliminacije	2 sata
Izlučivanje	90% bilijarno
Farmakoinformacioni podaci
Trudnoća	X(US)
Pravni status	Samo na recept (S4) (AU) POM (UK) ℞-only (SAD)
Način primene	Oralno

Ergotamin je ergopeptin i član ergot familije alkaloida. On je strukturno i biohemijski blisko srodan sa ergolinom. On je isto tako strukturno sličan sa nakoliko neurotransmitera, i biološki deluje kao vazokonstriktor.

On se koristi za tretiranje akutnih napada migrene (nekad u kombinaciji sa kofeinom). Medicinska primena ergot gljivica je počela u 16. veku za indukovanje porođaja, mada je neizvesnost u pogledu adekvatnog doziranja otežavale upotrebu. On je korišten za sprečavanje krvarenja nakon porođaja. Artur Stol iz kompanije Sandoz ga je privi izolovao iz ergot gljivica 1918, i lek ušao je u prodaju pod imenom Ginergen 1921.^[9]

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 Sanders SW, Haering N, Mosberg H, Jaeger H. Pharmacokinetics of ergotamine in healthy volunteers following oral and rectal dosing. Eur J Clin Pharmacol 1983; 30: 331–4.
↑ ^7,0 ^7,1 ^7,2 ^7,3 Tfelt-Hansen P, Johnson ES. Ergotamine. In: Olesen J, Tfelt-Hansen P, Welch KM, editors. The headaches. New York: Raven Press; 1993. p. 313–22.
↑ Ibraheem JJ, Paalzow L, Tfelt-Hansen P. Low bioavailability of ergotamine tartrate after oral and rectal administration in migraine sufferers. Br J Clin Pharmacol 1983; 16: 695–9.
↑ AJ Giannini, AE Slaby. Drugs of Abuse. Oradell, NJ, Medical Economics Books, 1989.

Povezano

[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

[kinetics1-6] 6,0 ^6,1 Sanders SW, Haering N, Mosberg H, Jaeger H. Pharmacokinetics of ergotamine in healthy volunteers following oral and rectal dosing. Eur J Clin Pharmacol 1983; 30: 331–4.

[kinetics2-7] 7,0 ^7,1 ^7,2 ^7,3 Tfelt-Hansen P, Johnson ES. Ergotamine. In: Olesen J, Tfelt-Hansen P, Welch KM, editors. The headaches. New York: Raven Press; 1993. p. 313–22.

[8] Ibraheem JJ, Paalzow L, Tfelt-Hansen P. Low bioavailability of ergotamine tartrate after oral and rectal administration in migraine sufferers. Br J Clin Pharmacol 1983; 16: 695–9.

[9] AJ Giannini, AE Slaby. Drugs of Abuse. Oradell, NJ, Medical Economics Books, 1989.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]