U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C33H35N5O5
Molecular Weight 581.6615
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERGOTAMINE

SMILES

CN1C[C@@H](C=C2[C@H]1CC3=CNC4=C3C2=CC=C4)C(=O)N[C@]5(C)O[C@@]6(O)[C@@H]7CCCN7C(=O)[C@H](CC8=CC=CC=C8)N6C5=O

InChI

InChIKey=XCGSFFUVFURLIX-VFGNJEKYSA-N
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

HIDE SMILES / InChI

Description

The isolation and naming of ergotamine by Stoll occurred in 1925 but the complete elucidation of structure was not achieved until 1951, with synthesis following some 10 years later. Current sources of ergotamine include the isolation from field ergot and fermentation broth, as well as synthesis via coupling of (+)-lysergic acid with the appropriate synthetic peptidic moiety. Ergotamine was introduced into world commerce in 1921, and is currently marketed as its water soluble tartrate salt. Ergotamine is a partial agonist at various tryptaminergic receptors (including the serotonin receptor [5-HT2]) and at various α-adrenergic receptors in blood vessels and various smooth muscles. It is likely that the major activity of ergotamine and related alkaloids is one of agonism at the 5-HT1B/1D receptors, just as with the “triptan” antimigraine compounds. FDA-labeled indications for ergotamine tartrate are in the abortion or prevention of vascular headaches, such as migraine, migraine variant, cluster headache, and histaminic cephalalgia.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
A case of multiple arterial thromboses after oral contraceptives and ergotamine.
1967 Apr
Upper limb ischaemia due to ergotamine tartrate.
1970 Jul
[Severe generalized arteriospasm after a minimal therapeutic dose of ergotamine].
1972 Dec 14
[Severe arterial spasms after the use of Ergotamine].
1972 Feb 8
[Spasms of the main muscular arteries in the extremities following ingestion of ergotamine-containing drugs].
1973 Apr 20
Arterial spasm associated with oral ergotamine therapy.
1973 Dec
Ergotism. Unilateral brachial artery thrombosis secondary to ergotamine tartrate.
1973 Jun
[Acute ischemia of the lower limbs due to ergotamine-induced arteriospasm].
1973 Nov 30
[Chronic ergotamine poisoning after migraine treatment].
1974
Ergotamine-induced venous thrombosis.
1974 Apr
Ischaemic lateral popliteal nerve palsy due to ergot intoxication.
1974 Dec
Letter: Ergotamine-induced headaches.
1974 Jun 29
Letter: Rebound migraine.
1974 May 11
[Ergotamine as a cause of arterial insufficiency].
1974 Oct 10
[Letter: Coronary spasm following ergotamine medication].
1975 Sep 5
Peripheral vascular spasm due to ergotamine tartrate.
1977 Dec
[Alarming course of drug-induced ergotism following prolonged use of ergotamine tartatare].
1977 Feb 18
Myocardial ischaemia in migraine sufferers taking ergotamine.
1978 Jan
Adverse effects of ergotamine. Blood circulation disorders--increased headache.
1978 Jan 10
[Bilateral vascular papillitis following ergotamin medication (author's transl)].
1978 Nov
Angina pectoris and sudden death in the absence of atherosclerosis following ergotamine therapy for migraine.
1979 Jul
[Non-invasive method for recognition of coronary artery spasm: 201thallium sequential scintigraphy of the myocardium after ergotamine provocation (author's transl)].
1980 Apr 11
Reversal of ergotamine-induced arteriospasm by mechanical intra-arterial dilatation.
1980 Dec 13
Acute myocardial infarction induced by ergotamine tartrate: possible role of coronary arterial spasm.
1981 Jun
[A case report of acute myocardial infarction induced by ergotamine tartrate (author's transl)].
1981 Mar
Ergotamine abuse: results of ergotamine discontinuation, with special reference to the plasma concentrations.
1982 Dec
Arterial complications of migraine treatment with methysergide and parenteral ergotamine.
1982 Jul 24
Myocardial infarction following administration of sublingual ergotamine.
1982 Sep
[Myocardial infarct during ergotamine medication in a young man with normal coronary arteries].
1983 Apr 22
[Ergotamine-induced spasm of the extremities with dorsalis pedis gangrene].
1983 Jun 10
[Ergotism causing peripheral arterial occlusion in the hand].
1983 Mar
Severe vascular spasm due to erythromycin-ergotamine interaction.
1984 Jun
Screening for new compounds with antiherpes activity.
1984 Oct
Reversible cerebral arteriopathy associated with the administration of ergot derivatives.
1984 Sep
[Ergotism with cerebral complications. Case report and review of the literature].
1986 Apr 5
Ergotamine-induced peripheral ischaemia reversed by oral thymoxamine hydrochloride.
1986 Jan
Amelioration of ergotamine withdrawal symptoms with naproxen.
1987 Mar
[Myocardial infarct caused by an ergotamine tartrate-troleandomycin combination].
1988 Sep-Oct
St. Anthony's fire: a medieval disease in modern times: case history.
1989 Oct
[Generalized brain edema and cerebral infarct in ergotamine abuse: imaging by computerized tomography, magnetic resonance tomography and angiography].
1989 Sep
Mitral and aortic valve disease associated with ergotamine therapy for migraine. Report of two cases and review of literature.
1990 Jan
Two members of a distinct subfamily of 5-hydroxytryptamine receptors differentially expressed in rat brain.
1993 Apr 15
[Daily chronic headache in patients with migraine induced by abuse of ergotamine-analgesics: response due to a protocol of outpatient treatment].
1993 Aug-Sep
Ergotamine-induced fetal stress: review of side effects of ergot alkaloids during pregnancy.
1993 Sep
[Ergotamine-induced rectal lesions in asymptomatic patients].
1994
Variant angina complicating ergot therapy of migraine.
1994 Apr
Cloning and characterisation of the human 5-HT5A serotonin receptor.
1994 Dec 5
Ergot induced peripheral vascular insufficiency, non-interventional treatment.
1994 Mar
Ergotamine-induced headache can be sustained by sumatriptan daily intake.
1994 Oct
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013 Sep 5
Patents

Patents

Sample Use Guides

In Vivo Use Guide
MIGERGOT - ergotamine tartrate and caffeine rectal suppository. One suppository at start of attack; second suppository after 1 hour, if needed for full relief. Two suppositories is the maximum dose for an individual attack. Cafergot (Ergotamine tartrate 1 mg and Caffeine 100 mg Tablets) First attack: The first time Cafergot is taken, an initial dose of 2 Cafergot tablets orally, is recommended. If relief is not obtained within half an hour, a further tablet should be administered; this may be repeated at half-hourly intervals, but the maximum daily dose of 6 tablets should not be exceeded. Subsequent attacks: If the pain persists, take 1 tablet every half an hour up to the maximum daily dose of 6 tablets. The maximum weekly dose is 10 tablets. ERGOMAR SUBLINGUAL- ergotamine tartrate tablet For best results, dosage should start at the first sign of an attack. Early Administration Gives Maximum Effectiveness. At the first sign of an attack or to relieve symptoms after onset of an attack, one 2 mg tablet is placed under the tongue. Another tablet should be taken at half-hour intervals thereafter, if necessary, but dosage must not exceed three tablets in any 24hour period. Total weekly dosage should not exceed five tablets (10 mg) in any one week. Ergomar® Sublingual Tablets should not be used for chronic daily administration.
Route of Administration: rectal, oral, sublingual
In Vitro Use Guide
The bovine anterior pituitary cells were implanted on culture tubes using D-valine minimal essential medium with serum to suppress the overgrowth of fibroblasts and then maintained in L-valine Dulbecco's modified Eagle medium. (3H)-Uridine uptake by these cells was suppressed by ergotamine at a concentration varing from 1-10 uM
Name Type Language
ERGOTAMINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
ERGOTAMINE [HSDB]
Common Name English
ERGOTAMINE [VANDF]
Common Name English
ERGOTAMINE [WHO-DD]
Common Name English
ERGOTAMINE [MI]
Common Name English
ERGOTAMINE [INN]
Common Name English
NSC-95090
Code English
ERGOTAMAN-3',6',18-TRIONE, 12'-HYDROXY-2'-METHYL-5'-(PHENYLMETHYL)-, (5'.ALPHA.)-
Common Name English
Classification Tree Code System Code
NDF-RT N0000007621
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
NCI_THESAURUS C47794
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
NDF-RT N0000007621
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
WHO-ATC N02CA72
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
WHO-VATC QN02CA52
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
WHO-ATC N02CA02
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
LIVERTOX 363
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
NDF-RT N0000175766
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
WHO-ATC N02CA52
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
WHO-VATC QN02CA02
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
WHO-VATC QN02CA72
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
Code System Code Type Description
INN
391
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
PRIMARY
CAS
113-15-5
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
PRIMARY
NCI_THESAURUS
C61751
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
PRIMARY
EVMPD
SUB06598MIG
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
PRIMARY
IUPHAR
149
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
PRIMARY
DRUG BANK
DB00696
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
PRIMARY
MESH
D004878
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
PRIMARY
EPA CompTox
113-15-5
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
PRIMARY
LactMed
113-15-5
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
PRIMARY
RXCUI
4025
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
PRIMARY RxNorm
MERCK INDEX
M4988
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
PRIMARY Merck Index
PUBCHEM
8223
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
PRIMARY
HSDB
113-15-5
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
PRIMARY
WIKIPEDIA
ERGOTAMINE
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
PRIMARY
ECHA (EC/EINECS)
204-023-9
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
PRIMARY
ChEMBL
CHEMBL442
Created by admin on Tue Oct 22 00:45:23 UTC 2019 , Edited by admin on Tue Oct 22 00:45:23 UTC 2019
PRIMARY