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Ergotamine Tartrate

Synopsis, Chemistry

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TABLET;ORAL - 100MG;1MG, SUPPOSITORY;RECTAL - 100MG;2MG

TABLET;ORAL - 100MG;1MG
SUPPOSITORY;RECTAL - 100MG;2MG

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Also known as: Ergotamine tartrate, Ergotamine bitartrate, 379-79-3, Schembl8045, Akos015897172, Ac-14836

Molecular Formula

C₃₇H₄₁N₅O₁₁

Molecular Weight

731.7 g/mol

InChI Key

NMTWKEWYQXZGCI-DDLCCZDQSA-N

A vasoconstrictor found in ergot of Central Europe. It is a serotonin agonist that has been used as an oxytocic agent and in the treatment of MIGRAINE DISORDERS.

1 2D Structure

Ergotamine Tartrate

2 Identification

2.1 Computed Descriptors

2.1.1 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;2,3-dihydroxybutanedioic acid

2.1.2 InChI

InChI=1S/C33H35N5O5.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39);1-2,5-6H,(H,7,8)(H,9,10)/t21-,25-,26+,27+,32-,33+;/m1./s1

2.1.3 InChI Key

NMTWKEWYQXZGCI-DDLCCZDQSA-N

2.1.4 Canonical SMILES

CC1(C(=O)N2C(C(=O)N3CCCC3C2(O1)O)CC4=CC=CC=C4)NC(=O)C5CN(C6CC7=CNC8=CC=CC(=C78)C6=C5)C.C(C(C(=O)O)O)(C(=O)O)O

2.1.5 Isomeric 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.C(C(C(=O)O)O)(C(=O)O)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Cornutamine

2. Ergo Kranit

3. Ergo Sanol

4. Ergo-kranit

5. Ergodryl Mono

6. Ergomar

7. Ergostat

8. Ergotamine

9. Ergotamine Tartrate

10. Ergotamine Tartrate (2:1)

11. Ergotaminine

12. Gynergen

13. Lingraine

14. Mono, Ergodryl

15. Tartrate, Ergotamine

2.2.2 Depositor-Supplied Synonyms

1. Ergotamine Tartrate

2. Ergotamine Bitartrate

3. 379-79-3

4. Schembl8045

5. Akos015897172

6. Ac-14836

2.3 Create Date

2007-05-07

3 Chemical and Physical Properties

Molecular Formula	C₃₇H₄₁N₅O₁₁
Molecular Weight	731.7 g/mol
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	7
Exact Mass	731.28025714 g/mol
Monoisotopic Mass	731.28025714 g/mol
Topological Polar Surface Area	233 Å²
Heavy Atom Count	53
Formal Charge	0
Complexity	1350
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Ergomar
PubMed Health	Ergotamine Tartrate (By mouth)
Drug Classes	Antimigraine
Active Ingredient	Ergotamine tartrate
Dosage Form	Tablet
Route	Sublingual
Strength	2mg
Market Status	Prescription
Company	Rosedale Therapeutic

2 of 2
Drug Name	Ergomar
PubMed Health	Ergotamine Tartrate (By mouth)
Drug Classes	Antimigraine
Active Ingredient	Ergotamine tartrate
Dosage Form	Tablet
Route	Sublingual
Strength	2mg
Market Status	Prescription
Company	Rosedale Therapeutic

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Adrenergic alpha-1 Receptor Agonists

Compounds that bind to and activate ADRENERGIC ALPHA-1 RECEPTORS. (See all compounds classified as Adrenergic alpha-1 Receptor Agonists.)

Analgesics, Non-Narcotic

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.)

Oxytocics

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) (See all compounds classified as Oxytocics.)

Serotonin Receptor Agonists

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. (See all compounds classified as Serotonin Receptor Agonists.)

Vasoconstrictor Agents

Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Ergotamines [CS]; Ergotamine Derivative [EPC]