Ergotamine

Ergotamine
Clinical data
Trade names	Ergomar, others
Other names	2'-Methyl-5'α-benzyl-12'-hydroxy-3',6',18-trioxoergotaman; 9,10α-Dihydro-12'-hydroxy-2'-methyl-5'α-(phenylmethyl)ergotaman-3',6',18-trione
AHFS/Drugs.com	Monograph
License data	US DailyMed: Ergotamine;
Pregnancy; category	AU: C; US: Contraindicated;
Routes of; administration	Oral
ATC code	N02CA02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class D1 (Drug precursors); CA: Schedule VI; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	Intravenous: 100%, ; Intramuscular: 47%,; Oral: <1% (Enhanced by co-administration of caffeine)
Metabolism	Liver
Elimination half-life	2 hours
Excretion	90% Bile duct
Identifiers
	IUPAC name (6aR,9R)-N-((2R,5S,10aS,10bS)-5-Benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-2H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide;
CAS Number	113-15-5 ;
PubChem CID	8223;
IUPHAR/BPS	149;
DrugBank	DB00696 ;
ChemSpider	7930 ;
UNII	PR834Q503T;
KEGG	D07906 ;
ChEBI	CHEBI:64318 ;
ChEMBL	ChEMBL442 ;
PDB ligand	ERM (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID9043774 ;
ECHA InfoCard	100.003.658
Chemical and physical data
Formula	C33H35N5O5
Molar mass	581.673 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)CC4=CC=CC=C4)NC(=O)[C@H]5CN([C@@H]6CC7=CNC8=CC=CC(=C78)C6=C5)C;
	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 ;
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Ergotamine, sold under the brand name Ergomar among others, is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline. It is structurally similar to several neurotransmitters, and it acts as a vasoconstrictor. It is used for acute migraines, sometimes with caffeine as the combination ergotamine/caffeine.

The drug is a non-selective modulator or agonist of serotonin receptors and other receptors. It is peripherally selective and crosses into the brain in minimal amounts.

Medicinal use of ergot fungus began in the 16th century, for the induction of childbirth; but dosage uncertainty discouraged its use. It has been used to prevent post-partum hemorrhage (bleeding after childbirth). It was first isolated from the ergot fungus by Arthur Stoll, at Sandoz in 1918, and was marketed as Gynergen in 1921.