Tìm theo
Ergotamine
Các tên gọi khác (7 ) :
  • (5'alpha)-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione
  • 12'-Hydroxy-2'-methyl-5'alpha-(phenylmethyl)ergotaman-3',6',18-trione
  • Ergotamin
  • Ergotamina
  • Ergotamine
  • Ergotaminum
  • Gynergen
Thuốc Gốc
Small Molecule
CAS: 113-15-5
ATC: N02CA02
ĐG : Cypress Pharmaceutical Inc. , http://www.cypressrx.com
CTHH: C33H35N5O5
PTK: 581.6615
A vasoconstrictor found in ergot of Central Europe. It is an alpha-1 selective adrenergic agonist and is commonly used in the treatment of migraine disorders. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C33H35N5O5
Phân tử khối
581.6615
Monoisotopic mass
581.263819255
InChI
InChI=1S/C33H35N5O5/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/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1
InChI Key
InChIKey=XCGSFFUVFURLIX-VFGNJEKYSA-N
IUPAC Name
(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),2,9,12,14-pentaene-4-carboxamide
Traditional IUPAC Name
ergotamine
SMILES
[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)C4=C3)O[C@@]21O
Độ tan chảy
213.5 dec °C
Độ hòa tan
Slight
logP
2
logS
-3.4
pKa (strongest acidic)
9.7
pKa (Strongest Basic)
7.78
PSA
118.21 Å2
Refractivity
160.17 m3·mol-1
Polarizability
61.69 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 : Ergotamine is a vasoconstrictor and alpha adrenoreceptor antagonist. The pharmacological properties of ergotamine are extremely complex; some of its actions are unrelated to each other, and even mutually antagonistic. The drug has partial agonist and/or antagonist activity against tryptaminergic, dopaminergic and alpha adrenergic receptors depending upon their site, and it is a highly active uterine stimulant. It causes constriction of peripheral and cranial blood vessels and produces depression of central vasomotor centers. The pain of a migraine attack is believed to be due to greatly increased amplitude of pulsations in the cranial arteries, especially the meningeal branches of the external carotid artery. Ergotamine reduces extracranial blood flow, causes a decline in the amplitude of pulsation in the cranial arteries, and decreases hyperperfusion of the territory of the basilar artery. It does not reduce cerebral hemispheric blood flow.
Cơ Chế Tác Dụng : A vasoconstrictor found in ergot of Central Europe. It is an alpha-1 selective adrenergic agonist and is commonly used in the treatment of migraine disorders. [PubChem] Ergotamine acts on migraine by one of two proposed mechanisms: 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 :
The bioavailability of sublingually administered ergotamine has not been determined.
▧ Metabolism :
Hepatic. Ergotamine is metabolized by the liver by largely undefined pathways, and 90% of the metabolites are excreted in the bile.
▧ Half Life :
2 hours
Độc Tính : Signs of overexposure include irritation, nausea, vomiting, headache, diarrhea, thirst, coldness of skin, pruritus, weak pulse, numbness, tingling of extremities, and confusion.
Chỉ Định : For use as therapy to abort or prevent vascular headache, e.g., migraine, migraine variants, or so called "histaminic cephalalgia".
Tương Tác Thuốc :
  • Acebutolol Ischemia with risk of gangrene
  • Almotriptan Possible severe and prolonged vasoconstriction
  • Amprenavir Amprenavir may increase the effect and toxicity of ergotamine.
  • Amyl Nitrite Possible antagonism of action
  • Atazanavir Atazanavir may increase the effect and toxicity of ergotamine.
  • Atenolol Ischemia with risk of gangrene
  • Betaxolol Ischemia with risk of gangrene
  • Bevantolol Ischemia with risk of gangrene
  • Bisoprolol Ischemia with risk of gangrene
  • Carteolol Ischemia with risk of gangrene
  • Carvedilol Ischemia with risk of gangrene
  • Clarithromycin Risk of ergotism and severe ischemia with this association
  • Delavirdine The antiretroviral agent may increase the ergot derivative toxicity
  • Desvenlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
  • Efavirenz The antiretroviral agent may increase the ergot derivative toxicity
  • 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 ergotamine. 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
  • Lorcaserin Avoid all combinations with any ergot derivative such as ergotamine. The combination can increase the risk of developing serotonin syndrome and/or valvular heart disease.
  • Metoprolol Ischemia with risk of gangrene
  • Nadolol Ischemia with risk of gangrene
  • Naratriptan Possible severe and prolonged vasoconstriction.
  • 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, ergotamine.
  • Rizatriptan Possible severe and prolonged vasoconstriction
  • Saquinavir The protease inhibitor, saquinavir, may increase the effect and toxicity of the ergot derivative, ergotamine.
  • 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 Ergotamine. Concomitant therapy is contraindicated.
  • Timolol Ischemia with risk of gangrene
  • Tipranavir Tipranavir, co-administered with Ritonavir, may increase the plasma concentration of Ergotamine. 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 ergotamine 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, ergotamine, may result in additive vasoconstrictive effects. Concomitant use within 24 hours is contraindicated.
Liều Lượng & Cách Dùng : Tablet - Sublingual
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Ergotamine-caffeine tablet
    Giá bán buôn : USD >1.14
    Đơn vị tính : tablet
  • Biệt dược thương mại : Cafergot tablet
    Giá bán buôn : USD >1.89
    Đơn vị tính : tablet
  • Biệt dược thương mại : Migergot suppository
    Giá bán buôn : USD >7.39
    Đơn vị tính : suppository
  • Biệt dược thương mại : Ergomar 2 mg tablet sl
    Giá bán buôn : USD >8.97
    Đơn vị tính : tablet
  • Biệt dược thương mại : Ergotamine tartrate powder
    Giá bán buôn : USD >224.35
    Đơn vị tính : powder
Nhà Sản Xuất
  • Công ty : Recip
    Sản phẩm biệt dược : Anervan
  • Công ty : Ta Fong
    Sản phẩm biệt dược : Antimigraine
  • Công ty : Novartis
    Sản phẩm biệt dược : Cafergot
  • Công ty : Cazi
    Sản phẩm biệt dược : Enxak
  • Công ty : Gedeon Richter
    Sản phẩm biệt dược : Ergam
  • Sản phẩm biệt dược : Ergo-Kranit
  • Công ty : Rosedale
    Sản phẩm biệt dược : Ergomar
  • Sản phẩm biệt dược : Gynaemine
  • Công ty :
    Sản phẩm biệt dược : Wigrettes
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00696
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=8223
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507632
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07544
ChemSpider
http://www.chemspider.com/Chemical-Structure.7930.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0089-0762-21
PharmGKB
http://www.pharmgkb.org/drug/PA164747651
Wikipedia
http://en.wikipedia.org/wiki/Ergotamine
RxList
http://www.rxlist.com/cgi/generic2/ergotamine.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/caf1060.shtml
Drugs.com
http://www.drugs.com/cdi/ergotamine.html
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