(2R,4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^{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

• ChemBase ID: 205
• Molecular Formular: C33H37N5O5
• Molecular Mass: 583.67738
• Monoisotopic Mass: 583.27946931
• SMILES: O1[C@]2(O)N([C@H](C(=O)N3[C@H]2CCC3)Cc2ccccc2)C(=O)[C@@]1(NC(=O)[C@@H]1C[C@H]2[C@H](N(C1)C)Cc1c3c2cccc3[nH]c1)C
• Canonical SMILES: CN1C[C@@H](C[C@H]2[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/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/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39)/t21-,23-,25-,26+,27+,32-,33+/m1/s1
• InChIKey: LUZRJRNZXALNLM-JGRZULCMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^{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
• IUPAC Traditional name: dihydroergotamine
• Brand Name: Agit; Angionorm; D.H.E.; D.H.E. 45; DET MS; DHE-45; Dergotamine; Diergo; Dihydergot; Dirgotarl; Endophleban; Ergomimet; Ergont; Ergotonin; Ikaran; Migranal; Morena; Orstanorm; Tonopres; Verladyn
• Synonyms: 9,10-dihydro-ergotamine; Dihidroergotamina [INN-Spanish]; Dihydroergotamine mesylate; Dihydroergotamine methanesulfonate; Dihydroergotamine monomethanesulfonate; Dihydroergotaminum [INN-Latin]; Dihydroergotamine

Database IDs

• CAS Number: 6190-39-2
• PubChem SID: 46507711; 160963668
• PubChem CID: 10531

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 3.04
• LOG S: -3.41
• Solubility (Water): 2.29e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2

DETAILS

DrugBank - DB00320

• Drug Groups: approved
• Description: A 9,10alpha-dihydro derivative of ergotamine. It is used as a vasoconstrictor, specifically for the therapy of migraine disorders. [PubChem]
• Indication: For the acute treatment of migraine headaches with or without aura and the acute treatment of cluster headache episodes.
• Pharmacology: Dihydroergotamine is indicated for the acute treatment of migraine headaches with or without aura and the acute treatment of cluster headache episodes. Dihydroergotamine binds with high affinity to 5-HT_1Da and 5-HT_1Db receptors. It also binds with high affinity to serotonin 5-HT_1A, 5-HT_2A, and 5-HT_2C receptors, noradrenaline a2A, a2B and a receptors, and dopamine D2L and D3 receptors. The therapeutic activity of Dihydroergotamine in migraine is generally attributed to the agonist effect at 5-HT_1D receptors.
• Toxicity: Side effects include abdominal pain, abnormal speech, coma, confusion, convulsions, hallucinations, increase and/or decrease in blood pressure, nausea, numbness, tingling, pain, and a bluish color of your fingersand toes, slowed breathing, vomiting
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Interpatient variable and may be dependent on the administration technique
• Half Life: 9 hours
• Protein Binding: 93% (to plasma proteins)
• Elimination: The major excretory route of dihydroergotamine is via the bile in the feces. ; Only 6%-7% of unchanged dihydroergotamine is excreted in the urine after intramuscular injection.
• Distribution: * 800 L
• Clearance: * 1.5 L/min
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com