CAS 6190-39-2|CAS 11032-41-0|(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}]...

General Information

Structure

Molecular Formula

C₃₄H₄₁N₅O₈S

Molecular Mass

679.78304

Exact Mass

679.2675843

Charge

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

Canonic 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

Isomeric 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

Calculated Properties

JChem

Acid pKa

9.712761

H Acceptors

H Donor

LogD (pH = 5.5)

0.07567159

LogD (pH = 7.4)

1.835023

Log P

2.7116222

Molar Refractivity

159.3948

Polarizability

62.858227

Polar Surface Area

118.21

Rotatable Bonds

Lipinski's Rule of Five

false

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

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[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene-4-carboxamide; methanesulfonic acid (4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),9,12(16),13-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[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]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[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene-4-carboxamide; methanesulfonic acid

Synonyms

DihydroergotoxineEndophlebanOrstanorm9,10-Dihydroergotamine Monomethanesulfonate (Salt)双氢麦角胺甲磺酸盐VerladynIkaranMorena(5'α,10α)-9,10-Dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotaman-3',6',18-trione MethanesulfonateErgomimetDihytamineErgotoninErgontDihydro Ergotamine MesylateSeglorMigranalDirgotarlDihydroergotamine methanesulfonate salt(+)-Dihydroergotamine MesylateTonopres

Names and Identifiers

Registration numbers

PubChem SID

4650513624277913160964605

PubChem CID

EC Number

CAS Number

MDL Number

Registration numbers

Properties

Physical Property

Solubility

methanol: soluble21 mg/mL

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble5.45 mg/mL

H2O: insoluble

Apperance

white powder

Pharmacology Properties

Gene Information

human ... DRD2(1813)

Product Information

Certificate of Analysis

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Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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.

TRC

D449080

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

Molecule Details

References

PubChem Literature

From Data Sources

• McCarthy, B.G., et al.: Headache, 29, 420 (1986)

• Ziegler, D., et al.: Neurology, 44, 447 (1986)

• de Marees, et al.: Eur. J. Clin. Pharmacol., 30, 685 (1986)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

IUPAC name

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[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]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[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene-4-carboxamide; methanesulfonic acid

Synonyms