Dihydroergotamine tartrateProduct ingredient for Dihydroergotamine

Name
Dihydroergotamine tartrate
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
DBSALT001066
Structure
Synonyms
Not Available
UNII
76F2R89O7X
CAS Number
5989-77-5
Weight
Average: 2484.842
Monoisotopic: 2483.134315159
Chemical Formula
C136H154N20O26
InChI Key
FXDJFTCVYTUARH-YZPGULDNSA-N
InChI
InChI=1S/4C33H37N5O5.C4H6O6/c4*1-32(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;5-1(3(7)8)2(6)4(9)10/h4*3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39);1-2,5-6H,(H,7,8)(H,9,10)/t4*21-,23-,25-,26+,27+,32-,33+;1-,2-/m11111/s1
IUPAC Name
(2R,3R)-2,3-dihydroxybutanedioic acid; tetrakis((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-carboximidic acid)
SMILES
[H][C@](O)(C(O)=O)[C@@]([H])(O)C(O)=O.[H][C@@]12CCCN1C(=O)[C@]([H])(CC1=CC=CC=C1)N1C(=O)[C@@](C)(O[C@@]21O)N=C(O)[C@@]1([H])CN(C)[C@]2([H])CC3=CNC4=CC=CC(=C34)[C@@]2([H])C1.[H][C@@]12CCCN1C(=O)[C@]([H])(CC1=CC=CC=C1)N1C(=O)[C@@](C)(O[C@@]21O)N=C(O)[C@@]1([H])CN(C)[C@]2([H])CC3=CNC4=CC=CC(=C34)[C@@]2([H])C1.[H][C@@]12CCCN1C(=O)[C@]([H])(CC1=CC=CC=C1)N1C(=O)[C@@](C)(O[C@@]21O)N=C(O)[C@@]1([H])CN(C)[C@]2([H])CC3=CNC4=CC=CC(=C34)[C@@]2([H])C1.[H][C@@]12CCCN1C(=O)[C@]([H])(CC1=CC=CC=C1)N1C(=O)[C@@](C)(O[C@@]21O)N=C(O)[C@@]1([H])CN(C)[C@]2([H])CC3=CNC4=CC=CC(=C34)[C@@]2([H])C1
ChemSpider
34986990
Predicted Properties
PropertyValueSource
Water Solubility0.0769 mg/mLALOGPS
logP2.98ALOGPS
logP1.04Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.71Chemaxon
pKa (Strongest Basic)8.68Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area121.7 Å2Chemaxon
Rotatable Bond Count19Chemaxon
Refractivity159.92 m3·mol-1Chemaxon
Polarizability64.17 Å3Chemaxon
Number of Rings32Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon