Ergotamine

Ergotamine

Clinical data
Trade names	Cafergot, Ergomar
AHFS/Drugs.com	Monograph
Pregnancy category	US: X (Contraindicated)
Routes of administration
ATC code	N02CA02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: Schedule VI UK: POM (Prescription only) US: Rx Only; DEA controlled precursor
Pharmacokinetic data
Bioavailability	Intravenous: 100%, Intramuscular: 47%, Oral: <1% (Enhanced by co-administration of caffeine )
Metabolism	Hepatic
Biological 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 Y
PubChem (CID)	8223
IUPHAR/BPS	149
DrugBank	DB00696 Y
ChemSpider	7930 Y
UNII	PR834Q503T Y
KEGG	D07906 Y
ChEBI	CHEBI:64318 N
ChEMBL	CHEMBL442 Y
ECHA InfoCard	100.003.658
Chemical and physical data
Formula	C33H35N5O5
Molar mass	581.66 g/mol
3D model (Jmol)	Interactive image
SMILES O=C3N1CCC[C@H]1[C@]2(O)O[C@](C(=O)N2[C@H]3Cc4ccccc4)(NC(=O)[C@@H]8/C=C7/c5cccc6c5c(cn6)C[C@H]7N(C)C8)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 Y Key:XCGSFFUVFURLIX-VFGNJEKYSA-N Y
NY (what is this?)

Ergotamine 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.

The mechanism of action of ergotamine is complex. The molecule shares structural similarity with neurotransmitters such as serotonin, dopamine, and epinephrine and can thus bind to several receptors acting as an agonist. The anti-migraine effect is due to constriction of the intracranial extracerebral blood vessels through the 5-HT_1B receptor, and by inhibiting trigeminal neurotransmission by 5-HT_1D receptors. Ergotamine also has effects on the dopamine and norepinephrine receptors. Its side effects are due mainly to its action at the D2 dopamine and 5-HT_1A receptors.