(4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-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; methanesulfonic acid

• ChemBase ID: 1142
• Molecular Formular: C34H41N5O8S
• Molecular Mass: 679.78304
• Monoisotopic Mass: 679.2675843
• SMILES: S(=O)(=O)(O)C.O1[C@]2(O)N([C@H](C(=O)N3[C@H]2CCC3)Cc2ccccc2)C(=O)[C@@]1(NC(=O)[C@@H]1CC2[C@H](N(C1)C)Cc1c3c2cccc3[nH]c1)C
• Canonical SMILES: CS(=O)(=O)O.CN1C[C@@H](CC2[C@H]1Cc1c[nH]c3c1c2ccc3)C(=O)N[C@]1(C)O[C@@]2(N(C1=O)[C@@H](Cc1ccccc1)C(=O)N1[C@H]2CCC1)O
• InChI: InChI=1S/C33H37N5O5.CH4O3S/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;1-5(2,3)4/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39);1H3,(H,2,3,4)/t21-,23?,25-,26+,27+,32-,33+;/m1./s1
• InChIKey: ADYPXRFPBQGGAH-WVVAGBSPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-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; methanesulfonic acid; (4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^2,^6]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),9,12(16),13-tetraene-4-carboxamide; methanesulfonic acid; (4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^2,^6]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraene-4-carboxamide; methanesulfonic acid
• IUPAC Traditional name: (4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-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 mesylate; (4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^2,^6]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),9,12(16),13-tetraene-4-carboxamide; methanesulfonic acid; (4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^2,^6]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraene-4-carboxamide; methanesulfonic acid
• Synonyms: Dihydroergotoxine; Dihydroergotamine methanesulfonate salt; (5'α,10α)-9,10-Dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotaman-3',6',18-trione Methanesulfonate; 9,10-Dihydroergotamine Monomethanesulfonate (Salt); (+)-Dihydroergotamine Mesylate; Dihytamine; Dirgotarl; Endophleban; Ergomimet; Ergont; Ergotonin; Ikaran; Migranal; Morena; Orstanorm; Seglor; Tonopres; Verladyn; Dihydro Ergotamine Mesylate; 双氢麦角胺 甲磺酸盐

Database IDs

• CAS Number: 11032-41-0; 6190-39-2
• EC Number: 228-235-6
• MDL Number: MFCD00058615
• PubChem SID: 46505136; 24277913; 160964605
• PubChem CID: 6420006

CALCULATED PROPERTIES

• Acid pKa: 9.712761
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.07567159
• LogD (pH = 7.4): 1.835023
• Log P: 2.7116222
• Molar Refractivity: 159.3948 cm^3
• Polarizability: 62.858227 Å^3
• Polar Surface Area: 118.21 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble5.45 mg/mL; H2O: insoluble; methanol: soluble21 mg/mL
• Apperance: white powder

Safety Information

• RTECS: KE7920000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... DRD2(1813)

DETAILS

DrugBank - DB01287

• Drug Groups: approved
• Description: Dihydroergotoxine is a cerebral vasodilator. Dihydroergotoxine is a mixture of three different ergotamantriones: dihydroergocornine, dihydroergocristine, and dihydroergocryptine. It has been proposed to be a neuroprotective agent. The mechanism of its therapeutic actions is not clear.
• Indication: For potential use in the treatment of Alzheimer's disease.
• Pharmacology: The drug may compensate for neurotransmitter deficits and can in different circumstances, compensate for hyperactivity in the same neurotransmitter pathways. The drug can counteract and prevent disturbances between monoaminergic and other transmitter systems in the CNS.

Sigma Aldrich - D2763

Biochem/physiol Actions
Agonist at vascular serotonin receptors; partial agonist at α-adrenergic and dopamine D2 receptors; vasoconstrictor.

Toronto Research Chemicals - D449080

α-Androgenic blocker with selective venoconstrictor properties. Also binds to serotonin 5HT1-receptors. Antimigraine.

REFERENCES

• de Marees, et al.: Eur. J. Clin. Pharmacol., 30, 685 (1986)
• McCarthy, B.G., et al.: Headache, 29, 420 (1986)
• Ziegler, D., et al.: Neurology, 44, 447 (1986)