3/23/2021 Ergomar | C37H41N5O11 - PubChem

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COMPOUND SUMMARY

Ergomar
PubChem CID 5351539

Structure

2D

Find Similar Structures

Molecular Formula C37H41N5O11

NSC41869
Ergomar
Ergostat
Synonyms Rigetamin
ETIN
More...

Molecular Weight 731.7 g/mol

CID 3251 (Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-

Parent Compound

(phenylmethyl)-, (5'alpha)-)

CID 875 (Tartaric acid)

Component Compounds
CID 3251 (Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-

(phenylmethyl)-, (5'alpha)-)

Modify Create
Dates
2021-03-20 2006-02-02

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.

MeSH

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 1/18
3/23/2021 Ergomar | C37H41N5O11 - PubChem

1 Structures

1.1 2D Structure

Chemical Structure
Depiction

PubChem

1.2 3D Status
Conformer generation is disallowed since too many atoms, mixture or salt, too many undefined stereo centers

PubChem

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 2/18
3/23/2021 Ergomar | C37H41N5O11 - PubChem

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-(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
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

PubChem

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)
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

PubChem

2.1.3 InChI Key

NMTWKEWYQXZGCI-UHFFFAOYSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

PubChem

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
Computed by OEChem 2.1.5 (PubChem release 2019.06.18)

PubChem

2.2 Molecular Formula

C37H41N5O11
Computed by PubChem 2.1 (PubChem release 2019.06.18)

PubChem

2.3 Other Identifiers

2.3.1 CAS

379-79-3

DTP/NCI; EPA Chemicals under the TSCA

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 3/18
3/23/2021 Ergomar | C37H41N5O11 - PubChem

2.3.2 NSC Number

41869

DTP/NCI

2.4 Synonyms

2.4.1 MeSH Entry Terms

Cornutamine Mono, Ergodryl

Ergo Kranit Tartrate, Ergotamine
ergo sanol
Ergo-Kranit
Ergodryl Mono
Ergomar
Ergostat
Ergotamine
Ergotamine Tartrate
Ergotamine Tartrate (2:1)
Ergotaminine
Gynergen
Lingraine

MeSH

2.4.2 Depositor-Supplied Synonyms

NSC41869 MCULE-9244521233
Ergomar ST072185
Ergostat Ergotaman-3',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'.alpha.)-, [R-(R*,R*)]-2,3-dihydroxybu
Rigetamin Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5.alpha.)-, (2R,3R)-2,3-dihydroxybuta
ETIN N-(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
Ergotamine, bitartrate fg]quinoline-9-carboxamide;2,3-dihydroxybutanedioic acid

Ergotamine, tartrate (2:1) (salt) WLN: T C6656 1A P GN LM CUTT&&J G1 EVM- DT B565 CO EVN HVNTJ BQ D1 G1R &OVYQYQVO

Ergotamine, hemitartrate
SCHEMBL8046
ERGOTAMIME, HEMITARTRATE
NSC-41869
AKOS024283991

PubChem

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 4/18
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3 Chemical and Physical Properties

3.1 Computed Properties

Property Name Property Value Reference

Molecular Weight 731.7 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18)

Hydrogen Bond Donor Count 7 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Hydrogen Bond Acceptor Count 12 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Rotatable Bond Count 7 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Exact Mass 731.280257 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18)

Monoisotopic Mass 731.280257 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18)

Topological Polar Surface Area 233 Ų Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Heavy Atom Count 53 Computed by PubChem

Formal Charge 0 Computed by PubChem

Complexity 1350 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Isotope Atom Count 0 Computed by PubChem

Defined Atom Stereocenter Count 0 Computed by PubChem

Undefined Atom Stereocenter Count 8 Computed by PubChem

Defined Bond Stereocenter Count 0 Computed by PubChem

Undefined Bond Stereocenter Count 0 Computed by PubChem

Covalently-Bonded Unit Count 2 Computed by PubChem

Compound Is Canonicalized Yes Computed by PubChem (release 2019.01.04)

PubChem

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 5/18
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4 Related Records

4.1 Related Compounds with Annotation

PubChem

4.2 Parent Compound

CID 3251 (Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha)-)

PubChem

4.3 Component Compounds

CID 875 (Tartaric acid)

CID 3251 (Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha)-)

PubChem

4.4 Related Compounds

Same Connectivity 7 Records

Same Isotope 6 Records

Same Parent, Connectivity 71 Records

Same Parent, Isotope 69 Records

Same Parent, Exact 6 Records

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 6/18
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Mixtures, Components, and 2 Records
Neutralized Forms

Similar Compounds 258 Records

PubChem

4.5 Substances

4.5.1 Related Substances

Same 13 Records

PubChem

4.5.2 Substances by Category

PubChem

4.6 NCBI LinkOut

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 7/18
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NCBI

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 8/18
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5 Chemical Vendors

PubChem

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 9/18
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6 Drug and Medication Information

6.1 FDA Orange Book

FDA Drugs

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 10/18
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7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

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.)

MeSH

Vasoconstrictor Agents

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

MeSH

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.)

MeSH

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.)

MeSH

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.)

MeSH

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 11/18
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8 Use and Manufacturing

8.1 Use Classification

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

FDA Drugs

8.2 General Manufacturing Information

EPA TSCA Commercial Activity Status

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

ACTIVE
https://www.epa.gov/tsca-inventory

EPA Chemicals under the TSCA

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 12/18
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9 Literature

9.1 NLM Curated PubMed Citations

PubChem

9.2 Chemical Co-Occurrences in Literature

PubChem

9.3 Chemical-Gene Co-Occurrences in Literature

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 13/18
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PubChem

9.4 Chemical-Disease Co-Occurrences in Literature

PubChem

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 14/18
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10 Patents

10.1 Depositor-Supplied Patent Identifiers

PubChem

Link to all deposited patent identifiers

PubChem

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 15/18
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11 Biological Test Results

11.1 BioAssay Results

PubChem

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 16/18
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12 Classification

12.1 Ontologies

12.1.1 MeSH Tree

Medical Subject Headings (MeSH)

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 17/18
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13 Information Sources
FILTER BY SOURCE ALL SOURCES

1. DTP/NCI
LICENSE
Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute
as the source.
https://www.cancer.gov/policies/copyright-reuse

Cornutamin
https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=41869

2. EPA Chemicals under the TSCA

LICENSE
https://www.epa.gov/privacy/privacy-act-laws-policies-and-resources

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

https://www.epa.gov/chemicals-under-tsca

3. FDA Drugs
LICENSE
Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and
may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug
Administration as the source is appreciated but not required.
https://www.fda.gov/about-fda/about-website/website-policies#linking

https://www.fda.gov/Drugs/InformationOnDrugs/ucm129662.htm

4. MeSH
Ergotamine
https://www.ncbi.nlm.nih.gov/mesh/68004878
Analgesics, Non-Narcotic
https://www.ncbi.nlm.nih.gov/mesh/68018712

Vasoconstrictor Agents
https://www.ncbi.nlm.nih.gov/mesh/68014662

Adrenergic alpha-1 Receptor Agonists

https://www.ncbi.nlm.nih.gov/mesh/68058646

Oxytocics
https://www.ncbi.nlm.nih.gov/mesh/68010120

Serotonin Receptor Agonists

https://www.ncbi.nlm.nih.gov/mesh/68017366

5. PubChem
https://pubchem.ncbi.nlm.nih.gov

6. Medical Subject Headings (MeSH)

MeSH Tree
http://www.nlm.nih.gov/mesh/meshhome.html

7. NCBI
https://www.ncbi.nlm.nih.gov/projects/linkout

https://pubchem.ncbi.nlm.nih.gov/compound/5351539 18/18