H8D

(8beta)-N-[(2S)-1-hydroxybutan-2-yl]-6-methyl-9,10-didehydroergoline-8-carboxamide

Created:	2018-06-15
Last modified:	2020-06-05

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2 entries where H8D is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	50
Chiral Atom Count	3
Bond Count	53
Aromatic Bond Count	10

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Chemical Component Summary
Name	(8beta)-N-[(2S)-1-hydroxybutan-2-yl]-6-methyl-9,10-didehydroergoline-8-carboxamide
Synonyms	methylergonovine
Systematic Name (OpenEye OEToolkits)	(6~{a}~{R},9~{R})-7-methyl-~{N}-[(2~{S})-1-oxidanylbutan-2-yl]-6,6~{a},8,9-tetrahydro-4~{H}-indolo[4,3-fg]quinoline-9-carboxamide
Formula	C₂₀ H₂₅ N₃ O₂
Molecular Weight	339.431
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	c3ccc2C=1C(N(C)CC(C(NC(CO)CC)=O)C=1)Cc4c2c3nc4
SMILES	CACTVS	3.385	CC[CH](CO)NC(=O)[CH]1CN(C)[CH]2Cc3c[nH]c4cccc(C2=C1)c34
SMILES	OpenEye OEToolkits	2.0.6	CCC(CO)NC(=O)C1CN(C2Cc3c[nH]c4c3c(ccc4)C2=C1)C
Canonical SMILES	CACTVS	3.385	CC[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2Cc3c[nH]c4cccc(C2=C1)c34
Canonical SMILES	OpenEye OEToolkits	2.0.6	CC[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2Cc3c[nH]c4c3c(ccc4)C2=C1)C
InChI	InChI	1.03	InChI=1S/C20H25N3O2/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25)/t13-,14+,18-/m1/s1
InChIKey	InChI	1.03	UNBRKDKAWYKMIV-QWQRMKEZSA-N

Drug Info: DrugBank

DrugBank ID	DB00353
Name	Methylergometrine
Groups	approved
Description	A homolog of ergonovine containing one more CH2 group. (Merck Index, 11th ed)
Synonyms	Metilergometrina Methylergometrine maleate Methylergobasin Methylergometrinum Methylergometrine Méthylergométrine Methylergometrine tartrate Methylergonovine 9,10-Didehydro-N-[1-(hydroxymethyl)-propyl]-D-lysergamide Ergotyl Methylergometrin Metilergometrinio D-lysergic acid 1-butanolamide
Brand Names	Methergine Methylergonovine Maleate
Indication	For the prevention and control of excessive bleeding following vaginal childbirth
Categories	Agents that produce hypertension Alkaloids 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 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Dopamine Antagonists Ergolines Ergonovine Ergot Alkaloids and Derivatives Genito Urinary System and Sex Hormones Heterocyclic Compounds, Fused-Ring Reproductive Control Agents Uterotonic agents
ATC-Code	G02AC01 G02AB01
CAS number	113-42-8

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Dopamine D1 receptor	MRTLNTSAMDGTGLVVERDFSVRILTACFLSLLILSTLLGNTLVCAAVIR...	unknown	antagonist
5-hydroxytryptamine receptor 2B	MALSYRVSELQSTIPEHILQSTFVHVISSNWSGLQTESIPEEMKQIVEEQ...	unknown
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor

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