Tìm theo
Dihydroergotamine
Các tên gọi khác (9 ) :
  • (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
  • 5'-Benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman
  • 9,10-dihydro-12'-Hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione
  • 9,10-dihydroergotamine
  • Dihidroergotamina
  • Dihydroergotamin
  • Dihydroergotamine
  • Dihydroergotaminum
  • Diidroergotamina
Thuốc điều trị đau nửa đầu
Thuốc Gốc
Small Molecule
CAS: 6190-39-2
ATC: N02CA01
ĐG : Bedford Labs , http://www.bedfordlabs.com
CTHH: C33H37N5O5
PTK: 583.6774
A 9,10alpha-dihydro derivative of ergotamine. It is used as a vasoconstrictor, specifically for the therapy of migraine disorders. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
Phân tử khối
583.6774
Monoisotopic mass
583.279469319
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
InChI Key
InChIKey=LUZRJRNZXALNLM-JGRZULCMSA-N
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
Traditional IUPAC Name
dihydroergotamine
SMILES
[H][[email protected]@]12CCCN1C(=O)[[email protected]](CC1=CC=CC=C1)N1C(=O)[[email protected]](C)(NC(=O)[[email protected]]3CN(C)[[email protected]]4([H])CC5=CNC6=CC=CC(=C56)[[email protected]@]4([H])C3)O[[email protected]@]21O
Độ hòa tan
2.29e-01 g/l
logP
2
logS
-3.4
pKa (strongest acidic)
9.71
pKa (Strongest Basic)
8.39
PSA
118.21 Å2
Refractivity
159.39 m3·mol-1
Polarizability
63.3 Å3
Rotatable Bond Count
4
H Bond Acceptor Count
6
H Bond Donor Count
3
Physiological Charge
1
Number of Rings
8
Bioavailability
1
Dược Lực Học : 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-HT1Da and 5-HT1Db receptors. It also binds with high affinity to serotonin 5-HT1A, 5-HT2A, and 5-HT2C 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-HT1D receptors.
Cơ Chế Tác Dụng : A 9,10alpha-dihydro derivative of ergotamine. It is used as a vasoconstrictor, specifically for the therapy of migraine disorders. [PubChem] Two theories have been proposed to explain the efficacy of 5-HT1D receptor agonists in migraine: 1) activation of 5-HT1D receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leads to vasoconstriction, which correlates with the relief of migraine headache and 2) activation of 5-HT1D receptors on sensory nerve endings of the trigeminal system results in the inhibition of pro-inflammatory neuropeptide release.
Dược Động Học :
▧ Absorption :
Interpatient variable and may be dependent on the administration technique
▧ Volume of Distribution :
* 800 L
▧ Protein binding :
93% (to plasma proteins)
▧ Metabolism :
Hepatic
▧ Route of 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.
▧ Half Life :
9 hours
▧ Clearance :
* 1.5 L/min
Độc Tính : 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
Chỉ Định : For the acute treatment of migraine headaches with or without aura and the acute treatment of cluster headache episodes.
Tương Tác Thuốc :
  • Acebutolol Ischemia with risk of gangrene
  • Almotriptan Possible severe and prolonged vasoconstriction
  • Amprenavir Amprenavir may increase the serum concentration of dihydroergotamine. Concomitant therapy is contraindicated.
  • Amyl Nitrite Possible antagonism of action
  • Atazanavir Atazanavir may increase the therapeutic and adverse effects of dihydroergotamine.
  • Atenolol Ischemia with risk of gangrene
  • Betaxolol Ischemia with risk of gangrene
  • Bevantolol Ischemia with risk of gangrene
  • Bisoprolol Ischemia with risk of gangrene
  • Boceprevir Boceprevir increases levels by affecting CYP3A4 metabolism. Concomitant therapy is contraindicated.
  • Carteolol Ischemia with risk of gangrene
  • Carvedilol Ischemia with risk of gangrene
  • Clarithromycin Risk of ergotism and severe ischemia with this association
  • Delavirdine Delavirdine, a strong CYP3A4 inhibitor, may increase the serum concentration of dihydroergotamine by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of dihydroergotamine if delavirdine is initiated, discontinued or dose changed.
  • Desvenlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Efavirenz Efavirenze may increase the adverse/toxic effects of dihydroergotamine. Concomitant therapy is contraindicated.
  • Eletriptan Possible severe and prolonged vasoconstriction
  • Erythrityl Tetranitrate Possible antagonism of action
  • Erythromycin Possible ergotism and severe ischemia with this combination
  • Esmolol Ischemia with risk of gangrene
  • Fluconazole Possible ergotism and severe ischemia with this combination
  • Fluoxetine Possible ergotism and severe ischemia with this combination
  • Fluvoxamine Possible ergotism and severe ischemia with this combination
  • Fosamprenavir Amprenavir increases the effect and toxicity of ergot derivative
  • Frovatriptan Possible severe and prolonged vasoconstriction
  • Indinavir Indinavir may increase the serum concentration of dihydroergotamine. Concomitant therapy is contraindicated.
  • Isosorbide Dinitrate Possible antagonism of action
  • Isosorbide Mononitrate Possible antagonism of action
  • Itraconazole Possible ergotism and severe ischemia with this combination
  • Josamycin Possible ergotism and severe ischemia with this combination
  • Ketoconazole Possible ergotism and severe ischemia with this combination
  • Labetalol Ischemia with risk of gangrene
  • Metoprolol Ischemia with risk of gangrene
  • Nadolol Ischemia with risk of gangrene.
  • Naratriptan Naratriptan, a serotonin 5-HT1D receptor agonists, may increase the vasoconstricting effect of dihydroergotamine. Concomitant use of these two agents within 24 hours is contraindicated.
  • Nefazodone Possible ergotism and severe ischemia with this combination
  • Nelfinavir Nelfinavir increases the effect and toxicity of ergot derivative
  • Nitroglycerin Possible antagonism of action
  • Oxprenolol Ischemia with risk of gangrene
  • Penbutolol Ischemia with risk of gangrene
  • Pentaerythritol Tetranitrate Possible antagonism of action
  • Pindolol Ischemia with risk of gangrene
  • Posaconazole Contraindicated co-administration
  • Practolol Ischemia with risk of gangrene
  • Propranolol Ischemia with risk of gangrene
  • Ritonavir The protease inhibitor, ritonavir, may increase the effect and toxicity of the ergot derivative, dihydroergotamine.
  • Rizatriptan Possible severe and prolonged vasoconstriction
  • Saquinavir The protease inhibitor, saquinavir, may increase the effect and toxicity of the ergot derivative, dihydroergotamine.
  • Sibutramine Possible serotoninergic syndrome with this combination
  • Sotalol Ischemia with risk of gangrene
  • Sumatriptan Possible severe and prolonged vasoconstriction
  • Telaprevir Telaprevir increases levels by affecting CYP3A4 metabolism. Concomitant therapy is contraindicated.
  • Telithromycin Telithromycin may reduce clearance of Dihydroergotamine. Concomitant therapy is contraindicated.
  • Timolol Ischemia with risk of gangrene
  • Tipranavir Tipranavir, co-administered with Ritonavir, may increase the plasma concentration of Dihydroergotamine. Concomitant therapy is contraindicated.
  • Tramadol Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Tranylcypromine Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
  • Trazodone Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Trimipramine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Troleandomycin Possible ergotism and severe ischemia with this combination
  • Venlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of dihydroergotamine by decreasing its metabolism. Concomitant therapy is contraindicated.
  • Zileuton Possible ergotism and severe ischemia with this combination
  • Zolmitriptan Concomitant use of the serotonin 5-HT1D receptor agonist, zolmitriptan, and the ergot derivative, dihydroergotamine, may result in additive vasoconstrictive effects. Concomitant use within 24 hours is contraindicated.
Liều Lượng & Cách Dùng : Liquid - Intravenous
Liquid - Nasal
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Valeant
    Sản phẩm biệt dược : D.H.E. 45
  • Công ty : Sandoz
    Sản phẩm biệt dược : Dihydergot
  • Công ty : Sigmapharm
    Sản phẩm biệt dược : Ergont
  • Công ty :
    Sản phẩm biệt dược : Ergotonin
  • Công ty : Pierre Fabre
    Sản phẩm biệt dược : Ikaran
  • Công ty : Valeant
    Sản phẩm biệt dược : Migranal
  • Công ty : Amdipharm
    Sản phẩm biệt dược : Orstanorm
  • Công ty : Verla
    Sản phẩm biệt dược : Verladyn
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