Dihydroergotamine mesylateProduct ingredient for Dihydroergotamine
- Name
- Dihydroergotamine mesylate
- Drug Entry
- Dihydroergotamine
A 9,10alpha-dihydro derivative of ergotamine. Dihydroergotamine is used as an abortive therapy for migraines.10 Its use has largely been supplanted by triptans in current therapy due to the class's greater selectivity and more favourable side effect profile.
Recent improvements have been made in the design of intranasal delivery devices allowing for greater delivery of dihydroergotamine solution to the vasculature-rich upper nasal cavity.7 The recently approved Precision Olfactory Delivery technology developed by Impel Neuropharma technology has correlated with an increase of 3-fold in Cmax and 4-fold in AUC despite the solution formulated at 75% of the strength of the existing intranasal product.
- Accession Number
- DBSALT000997
- Structure
Structure for Dihydroergotamine mesylate (DBSALT000997)
- 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
Property Value Source Water Solubility 0.229 mg/mL ALOGPS logP 3.04 ALOGPS logP 2.71 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 9.71 Chemaxon pKa (Strongest Basic) 8.39 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 118.21 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 159.39 m3·mol-1 Chemaxon Polarizability 63.48 Å3 Chemaxon Number of Rings 8 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon