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Ergotamine Tartrate

HCID 9787
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Grundinformationen

CAS
379-79-3
Standard-SMILES
CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](Cc4ccccc4)N3C2=O)C=C2c3cccc4[nH]cc(c34)C[C@H]21.CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](Cc4ccccc4)N3C2=O)C=C2c3cccc4[nH]cc(c34)C[C@H]21.O=C(O)[C@H](O)[C@@H](O)C(=O)O
InChIKey
CJMJLDQKTOJACI-BGQAIRJTSA-N
Summenformel
C70H76N10O16
Durchschnittliche Molmasse
1.313,4 g/mol
Monoisotopische Masse
1.312,54407637

Überblick

Ergotamine Tartrate can cause developmental toxicity according to state or federal government labeling requirements.

Namen und Bezeichner

Bevorzugter Name
Ergotamine Tartrate
IUPAC
bis((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);(2R,3R)-2,3-dihydroxybutanedioic acid

Namen und Synonyme

ergotamine tartrateErgotamine D-tartrate379-79-3LingraineWigrettesErgostatGotamine tartrateMedihaler ergotamineErgotamine bitartrateExmigraFemerginLingran
Weitere Namen anzeigen
SecagynSecupanErgateNeo-ergotinRigetaminDTXSID3025253MRU5XH3B48Ergotamini tartras

Datenbank-Bezeichner

CAS
379-79-3
PubChem CID
9787
DTXSID
DTXSID3025253
ChEMBL
CHEMBL2448612
UNII
MRU5XH3B48
EC Number
206-835-9

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
351 Ų
H-Brücken-Donoren
10
H-Brücken-Akzeptoren
18
Frei drehbare Bindungen
11
Schwere Atome
96
Formalladung
0
Komplexität
1.350

Experimentelle und physikochemische Eigenschaften

Chemical ClassesTeratogens
Solubilityless than 1 mg/mL at 68 °F (NTP, 1992)
Human Drugs · 3 Einträge

Breast Feeding; Lactation; Milk, Human; Adrenergic Alpha-Agonists; Analgesics, Non-Narcotic; Ergot Alkaloids; Vasoconstrictor Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point397 °F decomposes (EPA, 1998)
Physical DescriptionPowder or liquid forms available as drugs. Used in obstetrics and in the treatment of migraine headaches. (EPA, 1998)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H301 (86%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P261, P262, P264, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P316, P318, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 50 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 3 Einträge

Hazard Traits - Developmental Toxicity

Ergotamine tartrate: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'.alpha.)-, [R-(R*,R*)]-2,3-dihydroxybutanedioate (2:1) (salt): Environment tier I assessment
DOT LabelPoison
Fire HazardsWhen heated to decomposition, it emits toxic fumes of nitrogen oxides. Protect from light and heat (EPA, 1998)
Health HazardsHigh oral toxicity and a convulsant in humans.People with liver damage are at a greater risk. (EPA, 1998)
Reactive GroupAmides and Imides

Chemie und Industrie

Pharmakologische Informationen

Metabolism/MetabolitesErgotamine is metabolized by the liver by largely undefined pathways, and 90% of the metabolites are excreted in the bile. (A1497) Half Life: 2 hours
FDA Pharmacological Classification · 2 Einträge

ERGOTAMINE TARTRATE

Ergotamines [CS]; Ergotamine Derivative [EPC]

MeSH Pharmacological Classification · 5 Einträge

Drugs that stimulate contraction of the myometrium. They are used to induce LABOR, OBSTETRIC at term, to prevent or control postpartum or postabortion hemorrhage, and to assess fetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (ABORTIFACIENTS). Oxytocics used clinically include the neurohypophyseal hormone OXYTOCIN and certain prostaglandins and ergot alkaloids. (From AMA Drug Evaluations, 1994, p1157)

Drugs used to cause constriction of the blood vessels.

Endogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS.

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.

Compounds that bind to and activate ADRENERGIC ALPHA-1 RECEPTORS.

Verwendung und Herstellung

Uses · 1 Eintrag

For use as therapy to abort or prevent vascular headache, e.g., migraine, migraine variants, or so called "histaminic cephalalgia". Ergotamine is a secondary metabolite (natural product) and principal alkaloid of the ergot fungus, Claviceps purpurea, and related fungi in the family Clavicipitaceae. It is used medicinally for treatment of acute migraine attacks (sometimes in combination with caffeine), and to induce childbirth and prevent post-partum haemorrhage. (L1927)

General Manufacturing InformationErgotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5.alpha.)-, (2R,3R)-2,3-dihydroxybutanedioate (2:1): ACTIVE

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Reactivity Profile
ERGOTAMINE TARTRATE is sensitive to prolonged exposure to heat and light. (NTP, 1992). When heated to decomposition, it emits toxic fumes of nitrogen oxides. Protect from light and heat [EPA, 1998].
Air and Water ReactionsInsoluble in water.
Hazard Classes and Categories · 2 Einträge

Acute Tox. 3 (86%)

Teratogens

Sicherheit und Schutzausrüstung

Fire FightingFires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First AidWarning: Effects may be delayed. Caution is advised. Vital signs should be monitored closely.
Nonfire Spill Response · 1 Eintrag

(Non-Specific -- Alkaloid, n.o.s.) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Do not touch spilled material; stop leak if you can do so without risk. Use water vapor to reduce vapors. Absorb spills with sand or other noncombustible absorbent material.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Protective Action Criteria (PAC) · 3 Einträge

0.91 [mg/m3]

10 [mg/m3]

32 [mg/m3]

Personal Protective Equipment (PPE) · 1 Eintrag

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

Toxikologische Informationen

Treatment · 1 Eintrag

Treatment consists of removal of the offending drug. Maintenance of adequate pulmonary ventilation, correction of hypotension, and control of convulsions and blood pressure are important considerations. Treatment of peripheral vasospasm should consist of warmth, but not heat, and protection of the ischemic limbs. Vasodilators may be beneficial but caution must be exercised to avoid aggravating an already existent hypotension. (L1733)

Health Effects · 1 Eintrag

Vasoconstrictive complications of a serious nature may occur at times. These include ischemia, cyanosis, absence of pulse, cold extremities, gangrene, precordial distress and pain, EKG changes and muscle pains. Although these effects occur most commonly with long-term therapy at relatively high doses, they have also been reported with short-term or normal doses. Other cardiovascular adverse effects include transient tachycardia or bradycardia and hypertension. Ingestion of ergoline alkaloids is also known to cause the disease ergotism. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. (A1497, L1452, A2913)

Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) The bioavailability of sublingually administered ergotamine has not been determined.
Toxicity Summary · 1 Eintrag

Ergoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Variables relating to these effects are influenced by the agent, dosage, species, tissue, physiological, and endocrinological state, and experimental conditions. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. This can result in a number of different effects, including vasoconstriction, convulsions, and hallucinations. Ergometrine is also known to have a non-receptor specific oxytocic activity. Ergotamine acts on migraine by one of two proposed mechanisms: 1) activation of 5-HT1D receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leading to vasoconstriction, which correlates with the relief of migraine headache, and 2) activation of 5-HT1D receptors on sensory nerve endings of the trigeminal system, resulting in the inhibition of pro-inflammatory neuropeptide release. (A2914, A2915, A2916)

Signs and Symptoms · 1 Eintrag

Signs of ergotamine overexposure include irritation, nausea, vomiting, headache, diarrhea, thirst, coldness of skin, pruritus, weak pulse, numbness, tingling of extremities, and confusion. Convulsive ergotism can cause painful seizures and spasms, diarrhea, paresthesias, itching, headaches, nausea and vomiting. Usually the gastrointestinal effects precede the central nervous system effects. As well as seizures there can be hallucinations and mental effects including mania or psychosis. Gangrenous ergotism causes dry gangrene as a result of vasoconstriction induced in the more poorly vascularized distal structures, such as the fingers and toes. Symptoms include desquamation, weak periphery pulse, loss of peripheral sensation, edema and ultimately the death and loss of affected tissues. (A1497, L1733, L1920)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Toxicity DataLD50: 62 mg/kg (Intravenous, Rat) (T178)