Structure via PubChem · Public domain (PubChem)
ergotamine
Sign in to saveAlso known as 12'-hydroxy-2'-methyl-5'alpha-(phenylmethyl)ergotaman-3',6',18-trione, (5'alpha)-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione, (5'α)-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'α-(phenylmethyl)ergotaman-3',6',18-trione
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.
Key facts
- Drug.StdInChI
- 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
- Drug.StdInChIKey
- XCGSFFUVFURLIX-VFGNJEKYSA-N
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 443732840
- Drug.image
- Ergotamine-skeletal.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200px
- Drug.image2
- Ergotamine ball-and-stick.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 250px
- Drug.tradename
- Ergomar, others
- Drug.DailyMedID
- Ergotamine
- Drug.pregnancy_AU
- C
- Drug.pregnancy_category
- US: Contraindicated
- Drug.routes_of_administration
- Oral
- Drug.ATC_prefix
- N02
- Drug.ATC_suffix
- CA02
via Wikipedia infobox
Chemical data
- Formula
- C33H35N5O5
- Molecular weight
- 581.7 g/mol
- IUPAC name
- (6aR,9R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
- 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
- InChIKey
- XCGSFFUVFURLIX-VFGNJEKYSA-N
- XLogP
- 2
- Polar surface area
- 118 Ų
- H-bond donors
- 3
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
13,523 papers- Ergotamine enhances circadian amplitude and diurnally mitigates nitroglycerin-induced mechanical hypersensitivity.The journal of headache and pain · 2025
- Ergotamine and nicergoline - facts and myths.Pharmacological reports : PR · 2015
- Ergotamine and dihydroergotamine: a review.Current pain and headache reports · 2003
- Ergotamine dependency--a review.Headache · 1987
- Ergotamine and dihydroergotamine: history, pharmacology, and efficacy.Headache · 2003
via PubMed
~6 min read
Encyclopedic overview
15 sectionsContents
- Medical uses
- Available forms
- Contraindications
- Side effects
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Natural occurrence
- Biosynthesis
- Society and culture
- Legal status
- United States
- See also
- References
- External links
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.
Excerpted from Wikipedia’s “ergotamine” article, available under the CC BY-SA 4.0 licence.