 Home > Encyclopedia > Dihydroergotamine

Dihydroergotamine

Dihydroergotamine structure

CAS No:
511-12-6
Formula:
C33H37N5O5
Chemical Name:
Dihydroergotamine
Synonyms:
Ergotaman-3′,6′,18-trione,9,10-dihydro-12′-hydroxy-2′-methyl-5′-(phenylmethyl)-,(5′α,10α)-;Ergotamine,9,10-dihydro-;Indolo[4,3-fg]quinoline,ergotaman-3′,6′,18-trione deriv.;8H-Oxazolo[3,2-a]pyrrolo[2,1-c]pyrazine,ergotaman-3′,6′,18-trione deriv.;(5′α,10α)-9,10-Dihydro-12′-hydroxy-2′-methyl-5′-(phenylmethyl)ergotaman-3′,6′,18-trione;Dihydroergotamine;DHE;9,10-Dihydroergotamine;MAP 0004;Levadex;98302-70-6;409-63-2;1381-00-6;5965-22-0;6016-53-1;7762-45-0;11019-70-8;17680-45-4;26913-96-2;29087-32-9;47842-41-1
Categories:
Active Pharmaceutical Ingredients > Circulatory System Drugs

Description

ChEBI: Ergotamine in which a single bond replaces the double bond between positions 9 and 10. A semisynthetic ergot alkaloid with weaker oxytocic and vasoconstrictor properties than ergotamine, it is used (as the methanesulfonic or tartaric acid salts) for the tr atment of migraine and orthostatic hypotension.

Solid

Dihydroergotamine is ergotamine in which a single bond replaces the double bond between positions 9 and 10. A semisynthetic ergot alkaloid with weaker oxytocic and vasoconstrictor properties than ergotamine, it is used (as the methanesulfonic or tartaric acid salts) for the treatment of migraine and orthostatic hypotension. It has a role as a serotonergic agonist, a non-narcotic analgesic, a vasoconstrictor agent, a dopamine agonist and a sympatholytic agent. It is an ergot alkaloid and a semisynthetic derivative.|A 9,10alpha-dihydro derivative of ergotamine. It is used as a vasoconstrictor, specifically for the therapy of migraine disorders.|Dihydroergotamine is an Ergotamine Derivative.|A 9,10alpha-dihydro derivative of ERGOTAMINE. It is used as a vasoconstrictor, specifically for the therapy of MIGRAINE DISORDERS.

Dihydroergotamine Basic Attributes

Molecular Weight：

583.68

Exact Mass：

583.68

EC Number：

208-123-3

UNII：

436O5HM03C

DSSTox ID：

DTXSID6045614

ATC Code：

N - Nervous system

Characteristics

PSA：

118

XLogP3：

Appearance：

Solid

Density：

1.45g/cm3

Melting Point：

239 °C

Boiling Point：

899.5ºC at 760mmHg

Flash Point：

497.8ºC

Refractive Index：

1.727

Water Solubility：

2.29e-01 g/L

Specific rotation：

D20 -64°; 20546 -79° (c = 0.5 in pyridine)

Safety Information

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501

Hazard Statements：

H302

Toxicity

Toxicity Summary：

Side effects include abdominal pain, abnormal speech, coma, confusion, convulsions, hallucinations, increase and/or decrease in blood pressure, nausea, numbness, tingling, pain, and a bluish color of your fingersand toes, slowed breathing, vomiting

Protein Binding：

93% (to plasma proteins)

Drug Information

Drug Indication：

For the acute treatment of migraine headaches with or without aura and the acute treatment of cluster headache episodes.|FDA Label

Pharmacology：

Dihydroergotamine is indicated for the acute treatment of migraine headaches with or without aura and the acute treatment of cluster headache episodes. Dihydroergotamine binds with high affinity to 5-HT_1Da and 5-HT_1Db receptors. It also binds with high affinity to serotonin 5-HT_1A, 5-HT_2A, and 5-HT_2C receptors, noradrenaline a2A, a2B and a receptors, and dopamine D2L and D3 receptors. The therapeutic activity of Dihydroergotamine in migraine is generally attributed to the agonist effect at 5-HT_1D receptors.

MeSH：

A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS. (See all compounds classified as Analgesics, Non-Narcotic.)|Drugs that bind to and activate dopamine receptors. (See all compounds classified as Dopamine Agonists.)|Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)

Absorption：

Interpatient variable and may be dependent on the administration technique|The major excretory route of dihydroergotamine is via the bile in the feces. Only 6%-7% of unchanged dihydroergotamine is excreted in the urine after intramuscular injection.|800 L|1.5 L/min

Metabolism/Metabolites：

Hepatic

Biological Half-Life：

9 hours

Mechanism of Action：

Two theories have been proposed to explain the efficacy of 5-HT_1D receptor agonists in migraine: 1) activation of 5-HT_1D receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leads to vasoconstriction, which correlates with the relief of migraine headache and 2) activation of 5-HT_1D receptors on sensory nerve endings of the trigeminal system results in the inhibition of pro-inflammatory neuropeptide release.

MeSH Entry Terms：

Agit

Dihydroergotamine Use and Manufacturing

Uses

Anti-adrenergic.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals

Computed Properties

Molecular Weight:583.7
XLogP3:2.4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:583.27946930
Monoisotopic Mass:583.27946930
Topological Polar Surface Area:118
Heavy Atom Count:43
Complexity:1160
Defined Atom Stereocenter Count:7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes