ERM

Ergotamine

Created:	2013-01-23
Last modified:	2013-03-13

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6 entries where ERM is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	78
Chiral Atom Count	6
Bond Count	85
Aromatic Bond Count	16

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Chemical Component Summary
Name	Ergotamine
Systematic Name (OpenEye OEToolkits)	n/a
Formula	C₃₃ H₃₅ N₅ O₅
Molecular Weight	581.661
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=C6N7C(C(=O)N1CCCC1C7(O)OC6(NC(=O)C5C=C4c2cccc3c2c(cn3)CC4N(C)C5)C)Cc8ccccc8
SMILES	CACTVS	3.370	CN1C[CH](C=C2[CH]1Cc3c[nH]c4cccc2c34)C(=O)N[C]5(C)O[C]6(O)[CH]7CCCN7C(=O)[CH](Cc8ccccc8)N6C5=O
SMILES	OpenEye OEToolkits	1.7.6	CC1(C(=O)N2C(C(=O)N3CCCC3C2(O1)O)Cc4ccccc4)NC(=O)C5CN(C6Cc7c[nH]c8c7c(ccc8)C6=C5)C
Canonical SMILES	CACTVS	3.370	CN1C[C@@H](C=C2[C@H]1Cc3c[nH]c4cccc2c34)C(=O)N[C@]5(C)O[C@@]6(O)[C@@H]7CCCN7C(=O)[C@H](Cc8ccccc8)N6C5=O
Canonical SMILES	OpenEye OEToolkits	1.7.6	C[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)Cc4ccccc4)NC(=O)[C@H]5CN([C@@H]6Cc7c[nH]c8c7c(ccc8)C6=C5)C
InChI	InChI	1.03	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
InChIKey	InChI	1.03	XCGSFFUVFURLIX-VFGNJEKYSA-N

Drug Info: DrugBank

DrugBank ID	DB00696
Name	Ergotamine
Groups	approved
Description	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.
Synonyms	Ergotamine tartrate 12'-Hydroxy-2'-methyl-5'alpha-(phenylmethyl)ergotaman-3',6',18-trione Ergotamin Ergotaminum 12'-hydroxy-2'-methyl-5'α-(phenylmethyl)ergotaman-3',6',18-trione (5'α)-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione Ergotamine Ergotamina
Brand Names	Cafergot Pb Tab Cafergot Ergotamine Tartrate, Caffeine Cafergot Pb Sup Ergomar Sublingual Migergot Ergotamine Tartrate and Caffeine Ergodryl Cap Megral Tabs Bellergal Tab Medihaler-Ergotamine Truemed Group LLC Wigraine Suppositories Bellergal Spacetabs Wigraine Tab Gravergol Capsules Ergotamine Cafergot Sup Ergomar Cafergot Tab Ercaf Ergomar Slt 2mg
Indication	For use as therapy to abort or prevent vascular headache, e.g., migraine, migraine variants, or so called "histaminic cephalalgia".
Categories	Adrenergic Agents Adrenergic alpha-1 Receptor Antagonists Adrenergic alpha-Antagonists Adrenergic Antagonists Agents that produce hypertension Alkaloids Analgesics Analgesics, Non-Narcotic Antidepressive Agents Antimigraine Preparations Cardiovascular Agents Central Nervous System Agents Central Nervous System Depressants Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A4 Inhibitors (strong) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Ergot Alkaloids and Derivatives Ergotamine Derivative Ergotamines Heterocyclic Compounds, Fused-Ring Narrow Therapeutic Index Drugs Nervous System Neurotransmitter Agents P-glycoprotein inhibitors Peripheral Nervous System Agents Reproductive Control Agents Sensory System Agents Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome Serotonin 5-HT1 Receptor Agonists Serotonin 5-HT2 Receptor Agonists Serotonin Agents Serotonin Modulators Serotonin Receptor Agonists Sympatholytic (Adrenergic Blocking) Agents Uterotonic agents Vasoconstrictor Agents
ATC-Code	N02CA02 N02CA52 N02CA72
CAS number	113-15-5

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
5-hydroxytryptamine receptor 1D	MSPLNQSAEGLPQEASNRSLNATETSEAWDPRTLQALKISLAVVLSVITL...	unknown	agonist
5-hydroxytryptamine receptor 1B	MEEPGAQCAPPPPAGSETWVPQANLSSAPSQNCSAKDYIYQDSISLPWKV...	unknown	agonist
5-hydroxytryptamine receptor 2A	MDILCEENTSLSSTTNSLMQLNDDTRLYSNDFNSGEANTSDAFNWTVDSE...	unknown	agonist
Alpha-1A adrenergic receptor	MVFLSGNASDSSNCTQPPAPVNISKAILLGVILGGLILFGVLGNILVILS...	unknown	partial agonist
Alpha-1B adrenergic receptor	MNPDLDTGHNTSAPAHWGELKNANFTGPNQTSSNSTLPQLDITRAISVGL...	unknown	partial agonist
Alpha-1D adrenergic receptor	MTFRDLLSVSFEGPRPDSSAGGSSAGGGGGSAGGAAPSEGPAVGGVPGGA...	unknown	partial agonist
Dopamine D2 receptor	MDPLNLSWYDDDLERQNWSRPFNGSDGKADRPHYNYYATLLTLLIAVIVF...	unknown	agonist
Alpha-2A adrenergic receptor	MGSLQPDAGNASWNGTEAPGGGARATPYSLQVTLTLVCLAGLLMLLTVFG...	unknown	partial agonist
D(1) dopamine receptor	MRTLNTSAMDGTGLVVERDFSVRILTACFLSLLILSTLLGNTLVCAAVIR...	unknown	agonist
5-hydroxytryptamine receptor 1A	MDVLSPGQGNNTTSPPAPFETGGNTTGISDVTVSYQVITSLLLGTLIFCA...	unknown	agonist
5-hydroxytryptamine receptor 1F	MDFLNSSDQNLTSEELLNRMPSKILVSLTLSGLALMTTTINSLVIAAIIV...	unknown	agonist
5-hydroxytryptamine receptor 2C	MVNLRNAVHSFLVHLIGLLVWQCDISVSPVAAIVTDIFNTSDGGRFKFPD...	unknown	agonist
5-hydroxytryptamine receptor 2B	MALSYRVSELQSTIPEHILQSTFVHVISSNWSGLQTESIPEEMKQIVEEQ...	unknown
Alpha-2C adrenergic receptor	MASPALAAALAVAAAAGPNASGAGERGSGGVANASGASWGPPRGQYSAGA...	unknown
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682