Ergotamine

Ergotamine
Clinical data
Trade names	Cafergot (with caffeine), 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
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 DEA controlled precursor;
Pharmacokinetic data
Bioavailability	Intravenous: 100%, ; Intramuscular: 47%,; Oral: <1% (Enhanced by co-administration of caffeine)
Metabolism	Hepatic
Elimination half-life	2 hours
Excretion	90% biliary
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 names Cafergot (with caffeine) and Ergomar among others, is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline. It possesses structural similarity to several neurotransmitters, and has biological activity as a vasoconstrictor.

It is used medicinally for treatment of acute migraine attacks (sometimes in combination with caffeine). Medicinal usage of ergot fungus began in the 16th century to induce childbirth, yet dosage uncertainties discouraged the 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 marketed as Gynergen in 1921.

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