Ergotamine (BioDeep_00000003922)

human metabolite blood metabolite Chemicals and Drugs

代谢物信息卡片

化学式: C33H35N5O5 (581.263806)
中文名称: 麦角胺
谱图信息: 最多检出来源 Homo sapiens(blood) 1.8%

分子结构信息

SMILES: CC1(C(=O)N2C(C(=O)N3CCCC3C2(O1)O)CC4=CC=CC=C4)NC(=O)C5CN(C6CC7=CNC8=CC=CC(=C78)C6=C5)C
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)

描述信息

Ergotamine is only found in individuals that have used or taken this drug. It is 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-HT_1D 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-HT_1D receptors on sensory nerve endings of the trigeminal system results in the inhibition of pro-inflammatory neuropeptide release.
D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D017366 - Serotonin Receptor Agonists
N - Nervous system > N02 - Analgesics > N02C - Antimigraine preparations > N02CA - Ergot alkaloids
D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents > D000322 - Adrenergic Agonists
C78272 - Agent Affecting Nervous System > C47794 - Serotonin Agonist > C61751 - Ergotamine
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents
D002491 - Central Nervous System Agents > D000700 - Analgesics
D012102 - Reproductive Control Agents > D010120 - Oxytocics

同义名列表

33 个代谢物同义名

(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),2,9,12,14-pentaene-4-carboxamide; (5-alpha)-12-Hydroxy-2-methyl-5-(phenylmethyl)ergotaman-3,6,18-trione; (5alpha)-12-Hydroxy-2-methyl-5-(phenylmethyl)ergotoman-3,6,18-trione; 12-Hydroxy-2-methyl-5alpha-(phenylmethyl)ergotaman-3,6,18-trione; (5a)-12-Hydroxy-2-methyl-5-(phenylmethyl)ergotoman-3,6,18-trione; (5Α)-12-hydroxy-2-methyl-5-(phenylmethyl)ergotoman-3,6,18-trione; 12-Hydroxy-2-methyl-5α-(phenylmethyl)ergotaman-3,6,18-trione; 12-Hydroxy-2-methyl-5a-(phenylmethyl)ergotaman-3,6,18-trione; 5-Benzyl-12-hydroxy-2-methyl-3,6,18-trioxoergotaman; Sanofi winthrop brand OF ergotamine tartrate; Pfizer brand OF ergotamine tartrate; Krewel brand OF ergotamine tartrate; Lotus brand OF ergotamine tartrate; Ergotamine tartrate (2:1); Tartrate, ergotamine; Ergotamine Tartrate; mono, Ergodryl; Ergodryl mono; Ergotaminine; Ergo kranit; Cornutamine; Ergo-kranit; Ergotaminum; ErgoKranit; ergotamine; Ergo sanol; Ergotamina; Lingraine; Ergotamin; Gynergen; NSC95090; Ergostat; Ergomar

数据库引用编号

22 个数据库交叉引用编号

ChEBI: CHEBI:64318
KEGG: C07544
PubChem: 11954224
PubChem: 8223
PubChem: 3251
HMDB: HMDB0014834
Metlin: METLIN2571
DrugBank: DB00696
ChEMBL: CHEMBL1982133
ChEMBL: CHEMBL442
Wikipedia: Ergotamine
MeSH: Ergotamine
KNApSAcK: C00011222
chemspider: 7930
CAS: 1080650-16-3
CAS: 113-15-5
PMhub: MS000013628
PubChem: 9747
KNApSAcK: C00001724
PDB-CCD: ERM
3DMET: B05247
NIKKAJI: J2.889D

分类词条

Ergotamines, dihydroergotamines, and derivatives

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

9 个相关的物种来源信息

173841 - Cenchrus echinatus: 10.1021/NP50071A021
40602 - Claviceps fusiformis: 10.1128/AEM.01040-07
5111 - Claviceps purpurea:
98750 - Festuca ovina: 10.1016/S0021-9673(01)83714-6
4608 - Festuca pratensis: 10.1016/S0021-9673(01)83714-6
52153 - Festuca rubra:
9606 - Homo sapiens: -
4606 - Lolium arundinaceum:
375857 - Scolochloa festucacea:

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

文献列表

Priyanka Reddy, Joanne Hemsworth, Kathryn M Guthridge, Antony Vinh, Simone Vassiliadis, Vilnis Ezernieks, German C Spangenberg, Simone J Rochfort. Ergot alkaloid mycotoxins: physiological effects, metabolism and distribution of the residual toxin in mice. Scientific reports. 2020 06; 10(1):9714. doi: 10.1038/s41598-020-66358-2. [PMID: 32546814]
M D Combs, S H Edwards, J M Scherpenhuizen, E J Narayan, A E Kessell, J Ramsay, J Piltz, S R Raidal, J C Quinn. Treatment with potassium bromide mitigates ataxia and reduces tremor in lambs with perennial ryegrass toxicosis. New Zealand veterinary journal. 2019 Nov; 67(6):287-294. doi: 10.1080/00480169.2019.1637300. [PMID: 31248334]
Wiebke Rudolph, Daniela Remane, Dirk K Wissenbach, Frank T Peters. Comparative study on the metabolism of the ergot alkaloids ergocristine, ergocryptine, ergotamine, and ergovaline in equine and human S9 fractions and equine liver preparations. Xenobiotica; the fate of foreign compounds in biological systems. 2019 Oct; 49(10):1149-1157. doi: 10.1080/00498254.2018.1542187. [PMID: 30623698]
M D Combs, S H Edwards, J M Scherpenhuizen, E J Narayan, A E Kessell, J Piltz, S R Raidal, J Ramsay, J C Quinn. Development of a model for investigation of perennial ryegrass toxicosis in sheep. New Zealand veterinary journal. 2018 Nov; 66(6):281-289. doi: 10.1080/00480169.2018.1492986. [PMID: 29949720]
Matevž Likar, Marjana Grandič, Breda Jakovac Strajn, Katarina Kos, Franci Aco Celar. Links Between Genetic Groups, Host Specificity, and Ergot-Alkaloid Profiles within Claviceps purpurea (Fr.) Tul. on Slovenian Grasses. Plant disease. 2018 Jul; 102(7):1334-1340. doi: 10.1094/pdis-08-17-1179-re. [PMID: 30673578]
H K Sran, A Vathsala. Renal infarction due to ergotamine. QJM : monthly journal of the Association of Physicians. 2016 Nov; 109(11):749-750. doi: 10.1093/qjmed/hcw163. [PMID: 27654501]
Yukari Yaju, Yaeko Kataoka, Hiromi Eto, Shigeko Horiuchi, Rintaro Mori. Prophylactic interventions after delivery of placenta for reducing bleeding during the postnatal period. The Cochrane database of systematic reviews. 2013 Nov; ?(11):CD009328. doi: 10.1002/14651858.cd009328.pub2. [PMID: 24277681]
J E Dalziel, K E Dunstan, S C Finch. Combined effects of fungal alkaloids on intestinal motility in an in vitro rat model. Journal of animal science. 2013 Nov; 91(11):5177-82. doi: 10.2527/jas.2013-6449. [PMID: 23989880]
Maryam Pakfetrat, Akbar Rasekhi, Fatemeh Eftekhari, Nahid Hashemi, Jamshid Roozbeh, Simin Torabineghad, Leila Malekmakan. Ergotamine-induced acute tubulo-interstitial nephritis. Saudi journal of kidney diseases and transplantation : an official publication of the Saudi Center for Organ Transplantation, Saudi Arabia. 2013 Sep; 24(5):981-3. doi: 10.4103/1319-2442.118100. [PMID: 24029265]
Chien C Wang, Liliana P Fernández, María Roxana Gómez. Sensitive ergotamine determination in pharmaceuticals and biological samples using cloud point preconcentration and spectrofluorimetric detection. Analytica chimica acta. 2013 Mar; 768(?):90-5. doi: 10.1016/j.aca.2013.01.023. [PMID: 23473254]
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Maria Neve Ombra, Maria Musumeci, Jacques Simpore, Grazia Maria Palano, Salvatore Musumeci. beta-Endorphin concentration in colostrums of Burkinabe and Sicilian women. Nutrition (Burbank, Los Angeles County, Calif.). 2008 Jan; 24(1):31-6. doi: 10.1016/j.nut.2007.09.004. [PMID: 17981438]
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Kazuto Yasuda, Lu-Bin Lan, Dominique Sanglard, Katryn Furuya, John D Schuetz, Erin G Schuetz. Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. The Journal of pharmacology and experimental therapeutics. 2002 Oct; 303(1):323-32. doi: 10.1124/jpet.102.037549. [PMID: 12235267]
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Richard Browning, Frederick N Thompson. Endocrine and respiratory responses to ergotamine in Brahman and Hereford steers. Veterinary and human toxicology. 2002 Jun; 44(3):149-54. doi: . [PMID: 12046966]
Keiko Tsutsumi, Yasuko Obata, Tsuneji Nagai, Thorsteinn Loftsson, Kozo Takayama. Buccal absorption of ergotamine tartrate using the bioadhesive tablet system in guinea-pigs. International journal of pharmaceutics. 2002 May; 238(1-2):161-70. doi: 10.1016/s0378-5173(02)00070-4. [PMID: 11996820]
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