Ergoloid mesylate

Common Name

Ergoloid mesylate Description

Ergoloid mesylate is only found in individuals that have used or taken this drug. It is a dihydrogenated ergot (Claviceps purpurea) derivative alkaloid used as a vasodilator agent. Ergoloid Mesylate is the only vasodilator that has shown mild benefits in the treatment of vascliar dementia.Ergoloid mesylates act centrally, decreasing vascliar tone and slowing the heart rate, and acts peripherally to block alpha-receptors. One other possible mechanism is the effect of ergoloid mesylates on neuronal cell metabolism, resliting in improved oxygen uptake and cerebral metabolism, thereby normalizing depressed neurotransmitter levels. Structure

Synonyms

Not Available Chemical Formlia

C30H41N5O8S Average Molecliar Weight

631.74 Monoisotopic Molecliar Weight

631.267584003 IUPAC Name

(2R,4R,7R)-N-[(1S,2S,4R,7S)-2-hydroxy-7-methyl-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene-4-carboxamide; methaneslifonic acid Traditional Name

(2R,4R,7R)-N-[(1S,2S,4R,7S)-2-hydroxy-4-isopropyl-7-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene-4-carboxamide; methaneslifonic acid CAS Registry Number

8067-24-1 SMILES

CS(O)(=O)=O.[H][C@@]12CCCN1C(=O)[C@H](C)N1C(=O)[C@](NC(=O)[C@H]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)[C@@]4([H])C3)(O[C@@]21O)C(C)C

InChI Identifier

InChI=1S/C29H37N5O5.CH4O3S/c1-15(2)28(27(37)34-16(3)26(36)33-10-6-9-23(33)29(34,38)39-28)31-25(35)18-11-20-19-7-5-8-21-24(19)17(13-30-21)12-22(20)32(4)14-18;1-5(2,3)4/h5,7-8,13,15-16,18,20,22-23,30,38H,6,9-12,14H2,1-4H3,(H,31,35);1H3,(H,2,3,4)/t16-,18+,20+,22+,23-,28+,29-;/m0./s1

InChI Key

FQHMMOGHDWAXDI-WUQHHHCFSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as ergopeptines. These are ergoline derivatives that contain a tripeptide structure attached to the basic ergoline ring in the same location as the amide group of the lysergic acid derivatives. Kingdom

Chemical entities Super Class

Organic compounds Class

Alkaloids and derivatives Sub Class

Ergoline and derivatives Direct Parent

Ergopeptines Alternative Parents

  • Hybrid peptides
  • Dipeptides
  • Lysergamides
  • Indoloquinolines
  • Benzoquinolines
  • Quinoline-3-carboxamides
  • Pyrroloquinolines
  • N-acyl-alpha amino acids and derivatives
  • 3-alkylindoles
  • Piperidinecarboxamides
  • Isoindoles and derivatives
  • Aralkylamines
  • N-alkylpiperazines
  • Oxazolidinones
  • Benzenoids
  • Pyrroles
  • Pyrrolidines
  • Tertiary carboxylic acid amides
  • Heteroaromatic compounds
  • Secondary carboxylic acid amides
  • Trialkylamines
  • Orthocarboxylic acid derivatives
  • Lactams
  • Azacyclic compounds
  • Oxacyclic compounds
  • Alkanolamines
  • Hydrocarbon derivatives
  • Organopnictogen compounds
  • Carbonyl compounds
  • Organic oxides
  • Substituents

  • Ergopeptine
  • Hybrid peptide
  • Alpha-dipeptide
  • Lysergic acid amide
  • Indoloquinoline
  • Benzoquinoline
  • Quinoline-3-carboxamide
  • N-acyl-alpha amino acid or derivatives
  • Pyrroloquinoline
  • Alpha-amino acid or derivatives
  • Quinoline
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Isoindole or derivatives
  • 3-piperidinecarboxamide
  • Piperidinecarboxamide
  • N-alkylpiperazine
  • Aralkylamine
  • Benzenoid
  • Piperidine
  • 1,4-diazinane
  • Piperazine
  • Oxazolidinone
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Pyrrole
  • Heteroaromatic compound
  • Oxazolidine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Tertiary aliphatic amine
  • Carboxamide group
  • Lactam
  • Amino acid or derivatives
  • Orthocarboxylic acid derivative
  • Alkanolamine
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
  • Molecliar Framework

    Not Available External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug
  • Biofunction

  • Adrenergic alpha-Antagonists
  • Nootropic Agents
  • Sympatholytics
  • Vasodilator Agents
  • Application

  • Pharmaceutical
  • Cellliar locations

  • Membrane
  • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP2.8Not Available

    Predicted Properties

    Property Value Source logP2.17ChemAxon pKa (Strongest Acidic)9.71ChemAxon pKa (Strongest Basic)8.39ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area118.21 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity143.66 m3·mol-1ChemAxon Polarizability57.99 Å3ChemAxon Number of Rings7ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane
  • Biofluid Locations

  • Blood
  • Urine
  • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01049

  • 21059682
  • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01049

  • 21059682
  • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01049 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    Not Available KEGG Compound ID

    C14055 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Ergoloid NuGOwiki Link

    HMDB15183 Metagene Link

    HMDB15183 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    34706

    Product: CP-640187 (hydrochloride)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585
    References
    1. Althaus M, Retzow A, Castell JV, Gomez-Lechon MJ, Amalou Z, Rose T, Appel K: In vitro identification of the cytochrome P450 isoform responsible for the metabolism of alpha-dihydroergocryptine. Xenobiotica. 2000 Nov;30(11):1033-45. [PubMed:11197065 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
    Gene Name:
    ADRA2A
    Uniprot ID:
    P08913
    Molecular weight:
    48956.3
    References
    1. Markstein R: Hydergine: interaction with the neurotransmitter systems in the central nervous system. J Pharmacol. 1985;16 Suppl 3:1-17. [PubMed:2869188 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
    Gene Name:
    HTR1A
    Uniprot ID:
    P08908
    Molecular weight:
    46106.3
    References
    1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
    3. Korneyev AY, Cincotta AH: Identification of hepatic, non-monoamine, dihydroergocryptine binding sites with significant gender differences. Life Sci. 1996;58(12):241-8. [PubMed:8786706 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
    Gene Name:
    ADRA1A
    Uniprot ID:
    P35348
    Molecular weight:
    51486.0
    References
    1. Markstein R: Hydergine: interaction with the neurotransmitter systems in the central nervous system. J Pharmacol. 1985;16 Suppl 3:1-17. [PubMed:2869188 ]

    Transporters

    General function:
    Involved in transporter activity
    Specific function:
    Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost
    Gene Name:
    SLCO2B1
    Uniprot ID:
    O94956
    Molecular weight:
    76697.9
    References
    1. Lu WJ, Huang JD, Lai ML: The effects of ergoloid mesylates and ginkgo biloba on the pharmacokinetics of ticlopidine. J Clin Pharmacol. 2006 Jun;46(6):628-34. [PubMed:16707409 ]

    PMID: 17892531