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Ergotamine, sold under the brand name Ergomar among others, is an and part of the family of ; it is structurally and biochemically closely related to .

(2025). 9783887630751, Taylor & Francis. .
It is structurally similar to several , and it acts as a . It is used for acute , sometimes with as the combination ergotamine/caffeine.

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

use of ergot fungus began in the 16th century, for the induction of ; but dosage uncertainty discouraged its use. It has been used to prevent (bleeding after childbirth). It was first isolated from the by , at in 1918, and was marketed as Gynergen in 1921.A. J. Giannini, A. E. Slaby. Drugs of Abuse. Oradell, New Jersey: Medical Economics Books, 1989.


Medical uses
Ergotamine is as therapy to abort or prevent vascular headache.


Available forms
Ergotamine is available as a and as a tablet, sometimes in with .


Contraindications
Contraindications include: , Buerger's syndrome, coronary artery disease, hepatic disease, pregnancy, , Raynaud's syndrome, and renal disease. It's also contraindicated if patient is taking macrolide antibiotics (e.g., ), certain HIV protease inhibitors (e.g., , , ), certain azole antifungals (e.g., , , ) , , or a 5-HT1 receptor agonist (e.g., ).


Side effects
Side effects of ergotamine include nausea and vomiting. At higher doses, it can cause raised arterial , (including coronary vasospasm) and or . Severe vasoconstriction may cause symptoms of intermittent claudication.


Pharmacology

Pharmacodynamics
Ergotamine interacts with serotonin, adrenergic, and dopamine receptors. It is an of serotonin receptors including the 5-HT1 and 5-HT2 subtypes. Ergotamine is an agonist of the serotonin 5-HT2B receptor and has been associated with cardiac valvulopathy. Despite acting as a potent serotonin 5-HT2A receptor agonist, ergotamine is said to be non- similarly to .
(2025). 9780128002124
This has been posited to be due to functional selectivity at the serotonin 5-HT2A receptor. However, ergotamine is also peripherally selective, which may instead account for its lack of psychedelic effects.

+ ! Site ! Affinity (Ki/IC50 nM) ! Efficacy (Emax %) ! Action
5-HT1A0.17–0.3?Full agonist
5-HT1B0.3–4.7?Agonist
5-HT1D0.3–6.0?Agonist
5-HT1E19–840?Agonist
5-HT1F170–171?Agonist
5-HT2A0.64–0.97?Full agonist
5-HT2B1.3–45?Partial agonist
5-HT2C1.9–9.8?Partial agonist
5-HT3>10,000
5-HT465??
5-HT5A14?Agonist
5-HT5B3.2–16??
5-HT612??
5-HT71,291?Agonist
α1A15–>10,000
α1B12–>10,000
α1D???
α2A106??
α2B88??
α2C>10,000
β1>10,000
β2>10,000
D1>10,000
D24.0–>10,000Agonist
D33.2–>10,000
D412–>10,000
D5170??
H1>10,000
H2>10,000
M1862??
M2911??
M3>10,000
M4>10,000
M5>10,000
Notes: All receptors are human except 5-HT5A (mouse/rat) and 5-HT5B (mouse/rat—no human counterpart). No affinity for H1 or H2, cannabinoid CB1, , glutamate, or nicotinic acetylcholine receptors, nor the monoamine transporters (all >10,000 nM).


Pharmacokinetics
The of ergotamine is around 2% orally, 6% rectally, and 100% by intramuscular or intravenous injection. The low oral and rectal bioavailability is due to low gastrointestinal absorption and high first-pass metabolism.

However, ergotamine does not readily cross the blood–brain barrier and hence is peripherally selective.

(2025). 9783030105600
This is due to it being an avid substrate for and breast cancer resistance protein (BCRP). Only minimal amounts of the drug (~1%) cross into the .


Natural occurrence

Biosynthesis
Ergotamine is a secondary metabolite () and the principal alkaloid produced by the ergot fungus, Claviceps purpurea, and related fungi in the family . Its biosynthesis in these fungi requires the L- and dimethylallyl pyrophosphate. These precursor compounds are the substrates for the enzyme, tryptophan dimethylallyltransferase, catalyzing the first step in ergot alkaloid biosynthesis, i.e., the of L-tryptophan. Further reactions, involving methyltransferase and enzymes, yield the , . Lysergic acid (LA) is the substrate of lysergyl peptide synthetase, a nonribosomal peptide synthetase, which links LA to the amino acids, L-, L-, and L-. Enzyme-catalyzed or spontaneous cyclizations, oxygenations/, and at selected residues precede, and give rise to, formation of ergotamine.
(2025). 9780124695634


Society and culture

Legal status
Ergotamine is a List I regulated chemical in the United States.


External links
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