N-[2-hydroxy-7-(2-methylbutan-2-yl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraene-4-carboxamide

• ChemBase ID: 921
• Molecular Formular: C33H45N5O5
• Molecular Mass: 591.7409
• Monoisotopic Mass: 591.34206957
• SMILES: O1C2(O)N(C(C(CC)(C)C)C(=O)N3C2CCC3)C(=O)C1(NC(=O)C1CC2C(N(C1)C)Cc1c3c2cccc3[nH]c1)C(C)C
• Canonical SMILES: CCC(C1C(=O)N2CCCC2C2(N1C(=O)C(O2)(NC(=O)C1CN(C)C2C(C1)c1cccc3c1c(C2)c[nH]3)C(C)C)O)(C)C
• InChI: InChI=1S/C33H45N5O5/c1-7-31(4,5)27-29(40)37-13-9-12-25(37)33(42)38(27)30(41)32(43-33,18(2)3)35-28(39)20-14-22-21-10-8-11-23-26(21)19(16-34-23)15-24(22)36(6)17-20/h8,10-11,16,18,20,22,24-25,27,34,42H,7,9,12-15,17H2,1-6H3,(H,35,39)
• InChIKey: YLXBZBPHTNJZQE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[2-hydroxy-7-(2-methylbutan-2-yl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraene-4-carboxamide
• IUPAC Traditional name: CO-dergocrine mesylate
• Brand Name: Hydrogenated Ergot Alkaloids; Ischelium; Redergin; Trigot; Alkergot; Circanol; Co-Dergocrine Mesylate; Deapril-ST; Dihydroergotoxin Mesilat; Dihydroergotoxin Mesylate; Dihydroergotoxin Methanesulfonate; Dihydroergotoxine Mesilate; Dihydroergotoxine Mesylate; Dihydroergotoxine Methanesulfonate; Dihydroergotoxine Methanesulphonate; Ergoloid Mesylates [Usan]; Gerimal; Hydergin; Hydergine; Hydergine LC
• Synonyms: Ergoloid mesylate

Database IDs

• CAS Number: 8067-24-1
• PubChem SID: 160964384
• PubChem CID: 592735

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.71327
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.2456039
• LogD (pH = 7.4): 3.0049589
• Log P: 3.881663
• Molar Refractivity: 161.6557 cm^3
• Polarizability: 64.315636 Å^3
• Polar Surface Area: 118.21 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.82
• LOG S: -3.66
• Solubility (Water): 1.31e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.8

DETAILS

DrugBank - DB01049

• Drug Groups: approved
• Description: Ergoloid mesylate 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 vascular dementia.
• Indication: For use as an adjunct therapy for patients with dementia
• Pharmacology: Ergoloid Mesylate may increase cerebral metabolism and blood flow. The role of this medication in the therapy of dementia is controversial. A recent controlled study in patients with Alzheimer's disease found that there was no advantage to the use of ergoloid mesylates compared to placebo, suggesting that ergoloid mesylates may lower scores on some cognitive and behavioral rating scales. Further study is needed to determine the risk-benefit profile of ergoloid mesylates in the treatment of dementia.
• Toxicity: Symptoms of overdose include dyspnea, hypotension or hypertension, rapid weak pulse, delirium, nausea, vomiting, and bradycardia.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Rapidly but incompletely (approximately 25%) absorbed from the gastrointestinal tract. Approximately 50% of the absorbed dose is eliminated by first-pass metabolism.
• Half Life: 3.5 hours
• Protein Binding: 98-99%
• External Links: Wikipedia