Dihydroergotamine mesylateProduct ingredient for Dihydroergotamine

Name
Dihydroergotamine mesylate
Drug Entry
Dihydroergotamine

A 9,10alpha-dihydro derivative of ergotamine. It is used as a vasoconstrictor, specifically for the therapy of migraine disorders.

Accession Number
DBSALT000997
Structure
Thumb
Synonyms
9,10-dihydroergotamine mesylate / 9,10-dihydroergotamine methanesulfonate / Dihydroergotamine mesilate / Dihydroergotamine methanesulfonate / Dihydroergotamine monomethanesulfonate
UNII
81AXN7R2QT
CAS Number
6190-39-2
Weight
Average: 679.79
Monoisotopic: 679.267584474
Chemical Formula
C34H41N5O8S
InChI Key
ADYPXRFPBQGGAH-UMYZUSPBSA-N
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
IUPAC Name
(2R,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
SMILES
CS(O)(=O)=O.[H][C@@]12CCCN1C(=O)[C@H](CC1=CC=CC=C1)N1C(=O)[C@](C)(NC(=O)[C@H]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)[C@@]4([H])C3)O[C@@]21O
External Links
KEGG Drug
D02211
ChemSpider
64311
ChEBI
59756
ChEMBL
CHEMBL1200517
Wikipedia
Dihydroergotamine
Predicted Properties
PropertyValueSource
Water Solubility0.229 mg/mLALOGPS
logP3.04ALOGPS
logP2.71ChemAxon
logS-3.4ALOGPS
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 Count4ChemAxon
Refractivity159.39 m3·mol-1ChemAxon
Polarizability63.48 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon