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Identification
NameErgonovine
Accession NumberDB01253
TypeSmall Molecule
GroupsApproved
Description

An ergot alkaloid with uterine and vascular smooth muscle contractile properties. [PubChem]

Structure
Thumb
Synonyms
(6AR,9R)-7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid ((S)-2-hydroxy-1-methyl-ethyl)-amide
[8beta(S)]-9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8-carboxamide
9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8beta(S)-carboxamide
9,10-Didehydro-N-(alpha-(hydroxymethyl)ethyl)-6-methylergoline-8-beta-carboxamide
D-Lysergic acid 1-hydroxymethylethylamide
D-Lysergic acid-L-propanolamide
Ergobasine
Ergometrina
Ergometrine
Ergometrinum
Ergonovine
Ergotrate maleate
N-(2-Hydroxy-1-methylethyl)-D(+)-lysergamide
N-(alpha-(Hydroxymethyl)ethyl)-D-lysergamide
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ergonovine Maleate Injectionsolution0.25 mgintramuscular; intravenousMylan Pharmaceuticals Ulc1995-12-31Not applicableCanada
Ergonovine Maleate Injectionsolution0.25 mgintramuscular; intravenousAlveda Pharmaceuticals Inc2016-02-19Not applicableCanada
Ergonovine Maleate Injectionsolution.25 mgintramuscular; intravenousHospira Healthcare Corporation1981-12-31Not applicableCanada
Ergonovine Maleate Injection USP, 0.25mg/mlsolution0.25 mgintramuscular; intravenousAlveda Pharmaceuticals Inc2010-06-01Not applicableCanada
Ergotrate Maleate Tablet 1572 0.2mgtablet.2 mgoralEli Lilly Canada Inc1939-12-311998-08-04Canada
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
ErgotrateNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Ergonovine maleate
ThumbNot applicableDBSALT001151
Categories
UNIIWH41D8433D
CAS number60-79-7
WeightAverage: 325.4048
Monoisotopic: 325.179026995
Chemical FormulaC19H23N3O2
InChI KeyInChIKey=WVVSZNPYNCNODU-XTQGRXLLSA-N
InChI
InChI=1S/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11-,13+,17+/m0/s1
IUPAC Name
(4R,7R)-N-[(2S)-1-hydroxypropan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
SMILES
[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[[email protected]](CN2C)C(=O)N[C@@H](C)CO
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassErgoline and derivatives
Sub ClassLysergic acids and derivatives
Direct ParentLysergamides
Alternative Parents
Substituents
  • Lysergic acid amide
  • Indoloquinoline
  • Benzoquinoline
  • Quinoline-3-carboxamide
  • Pyrroloquinoline
  • Quinoline
  • Isoindole or derivatives
  • Indole or derivatives
  • Indole
  • Aralkylamine
  • Tetrahydropyridine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationUsed to treat postpartum haemorrhage and postabortion haemorrhage in patients with uterine atony.
PharmacodynamicsErgonovine belongs to the group of medicines known as ergot alkaloids. These medicines are usually given to stop excessive bleeding that sometimes occurs after abortion or a baby is delivered. They work by causing the muscle of the uterus to contract.
Mechanism of actionErgonovine directly stimulates the uterine muscle to increase force and frequency of contractions. With usual doses, these contractions precede periods of relaxation; with larger doses, basal uterine tone is elevated and these relaxation periods will be decreased. Contraction of the uterine wall around bleeding vessels at the placental site produces hemostasis. Ergonovine also induces cervical contractions. The sensitivity of the uterus to the oxytocic effect is much greater toward the end of pregnancy. The oxytocic actions of ergonovine are greater than its vascular effects. Ergonovine, like other ergot alkaloids, produces arterial vasoconstriction by stimulation of alpha-adrenergic and serotonin receptors and inhibition of endothelial-derived relaxation factor release. It is a less potent vasoconstrictor than ergotamine. As a diagnostic aid (coronary vasospasm), ergonovine causes vasoconstriction of coronary arteries.
Related Articles
AbsorptionAbsorption is rapid and complete after oral or intramuscular administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationThought to be eliminated by non-renal mechanisms (i.e. hepatic metabolism, excretion in feces)
Half lifet1/2 α=10 minutes; t1/2 β=2 hours
ClearanceNot Available
ToxicityThe principal symptoms of overdose are convulsions and gangrene. Other symptoms include bradycardia, confusion, diarrhoea, dizziness, dyspnoea, drowsiness, fast and/or weak pulse, miosis, hypercoagulability, loss of consciousness, nausea and vomiting, numbness and coldness of the extremities, pain in the chest, peripheral vasoconstriction, respiratory depression, rise or fall in blood pressure, severe cramping of the uterus, tachycardia, tingling, and unusual thirst.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9967
Blood Brain Barrier+0.6971
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.8385
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.7295
CYP450 2C9 substrateNon-substrate0.8097
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.6814
CYP450 1A2 substrateNon-inhibitor0.7284
CYP450 2C9 inhibitorNon-inhibitor0.9116
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9228
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9236
Ames testNon AMES toxic0.5743
CarcinogenicityNon-carcinogens0.9353
BiodegradationNot ready biodegradable0.8714
Rat acute toxicity3.3967 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.954
hERG inhibition (predictor II)Inhibitor0.5624
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Solutionintramuscular; intravenous.25 mg
Solutionintramuscular; intravenous0.25 mg
Tabletoral.2 mg
Prices
Unit descriptionCostUnit
Ergonovine maleate 100% powder676.9USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point162 °CPhysProp
water solubility2.68 mg/mL at 25 °CMEYLAN,WM et al. (1996)
logP0.9Not Available
pKa6.8MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.321 mg/mLALOGPS
logP1.53ALOGPS
logP1.07ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)15ChemAxon
pKa (Strongest Basic)7.93ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area68.36 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.05 m3·mol-1ChemAxon
Polarizability36.54 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesG02AB03
AHFS Codes
  • 76:00.00
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcepromazineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Acepromazine.
AcetophenazineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Acetophenazine.
AmisulprideThe risk or severity of adverse effects can be increased when Ergonovine is combined with Amisulpride.
AprepitantThe serum concentration of Ergonovine can be increased when it is combined with Aprepitant.
AripiprazoleThe risk or severity of adverse effects can be increased when Ergonovine is combined with Aripiprazole.
BatimastatThe serum concentration of Ergonovine can be increased when it is combined with Batimastat.
BenzquinamideThe risk or severity of adverse effects can be increased when Ergonovine is combined with Benzquinamide.
BoceprevirThe serum concentration of Ergonovine can be increased when it is combined with Boceprevir.
CarphenazineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Carphenazine.
ChlormezanoneThe risk or severity of adverse effects can be increased when Ergonovine is combined with Chlormezanone.
ChlorpromazineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Chlorpromazine.
ChlorprothixeneThe risk or severity of adverse effects can be increased when Ergonovine is combined with Chlorprothixene.
ClarithromycinThe serum concentration of Ergonovine can be increased when it is combined with Clarithromycin.
ClozapineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Clozapine.
ConivaptanThe serum concentration of Ergonovine can be increased when it is combined with Conivaptan.
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Ergonovine.
DasatinibThe serum concentration of Ergonovine can be increased when it is combined with Dasatinib.
DipivefrinErgonovine may increase the hypertensive activities of Dipivefrin.
DroperidolThe risk or severity of adverse effects can be increased when Ergonovine is combined with Droperidol.
EletriptanErgonovine may increase the vasoconstricting activities of Eletriptan.
FencamfamineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Fencamfamine.
FluconazoleThe metabolism of Ergonovine can be decreased when combined with Fluconazole.
FlupentixolThe risk or severity of adverse effects can be increased when Ergonovine is combined with Flupentixol.
FluphenazineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Fluphenazine.
FluspirileneThe risk or severity of adverse effects can be increased when Ergonovine is combined with Fluspirilene.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Ergonovine.
FosaprepitantThe serum concentration of Ergonovine can be increased when it is combined with Fosaprepitant.
Fusidic AcidThe serum concentration of Ergonovine can be increased when it is combined with Fusidic Acid.
GranisetronGranisetron may increase the serotonergic activities of Ergonovine.
HaloperidolThe risk or severity of adverse effects can be increased when Ergonovine is combined with Haloperidol.
IdelalisibThe serum concentration of Ergonovine can be increased when it is combined with Idelalisib.
IsoflurophateThe serum concentration of Ergonovine can be increased when it is combined with Isoflurophate.
ItraconazoleThe serum concentration of Ergonovine can be increased when it is combined with Itraconazole.
IvacaftorThe serum concentration of Ergonovine can be increased when it is combined with Ivacaftor.
KetoconazoleThe serum concentration of Ergonovine can be increased when it is combined with Ketoconazole.
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Ergonovine.
LoxapineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Loxapine.
LuliconazoleThe serum concentration of Ergonovine can be increased when it is combined with Luliconazole.
MesoridazineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Mesoridazine.
MethotrimeprazineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Methotrimeprazine.
MetoclopramideThe risk or severity of adverse effects can be increased when Ergonovine is combined with Metoclopramide.
MidodrineErgonovine may increase the hypertensive activities of Midodrine.
MifepristoneThe serum concentration of Ergonovine can be increased when it is combined with Mifepristone.
MolindoneThe risk or severity of adverse effects can be increased when Ergonovine is combined with Molindone.
NadololNadolol may increase the vasoconstricting activities of Ergonovine.
NelfinavirThe metabolism of Ergonovine can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Ergonovine can be increased when it is combined with Netupitant.
NitroglycerinErgonovine may decrease the vasodilatory activities of Nitroglycerin.
OlanzapineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Olanzapine.
OndansetronThe risk or severity of adverse effects can be increased when Ergonovine is combined with Ondansetron.
PalbociclibThe serum concentration of Ergonovine can be increased when it is combined with Palbociclib.
PaliperidoneThe risk or severity of adverse effects can be increased when Ergonovine is combined with Paliperidone.
PerphenazineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Perphenazine.
PimozideThe risk or severity of adverse effects can be increased when Ergonovine is combined with Pimozide.
PiperacetazineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Piperacetazine.
PosaconazoleThe serum concentration of Ergonovine can be increased when it is combined with Posaconazole.
ProchlorperazineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Prochlorperazine.
PromazineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Promazine.
QuetiapineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Quetiapine.
RemoxiprideThe risk or severity of adverse effects can be increased when Ergonovine is combined with Remoxipride.
ReserpineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Reserpine.
RisperidoneThe risk or severity of adverse effects can be increased when Ergonovine is combined with Risperidone.
SertindoleThe risk or severity of adverse effects can be increased when Ergonovine is combined with Sertindole.
SimeprevirThe serum concentration of Ergonovine can be increased when it is combined with Simeprevir.
StiripentolThe serum concentration of Ergonovine can be increased when it is combined with Stiripentol.
SulpirideThe risk or severity of adverse effects can be increased when Ergonovine is combined with Sulpiride.
Tedizolid PhosphateTedizolid Phosphate may increase the serotonergic activities of Ergonovine.
TelaprevirThe serum concentration of Ergonovine can be increased when it is combined with Telaprevir.
ThioridazineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Thioridazine.
ThiothixeneThe risk or severity of adverse effects can be increased when Ergonovine is combined with Thiothixene.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Ergonovine.
TrifluoperazineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Trifluoperazine.
TriflupromazineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Triflupromazine.
VoriconazoleThe serum concentration of Ergonovine can be increased when it is combined with Voriconazole.
ZiprasidoneThe risk or severity of adverse effects can be increased when Ergonovine is combined with Ziprasidone.
ZuclopenthixolThe risk or severity of adverse effects can be increased when Ergonovine is combined with Zuclopenthixol.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein heterodimerization activity
Specific Function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular Weight:
51486.005 Da
References
  1. Gibson A, Carvajal A: Agonist profile of ergometrine (ergonovine) on a population of postsynaptic alpha-adrenoceptors. J Pharm Pharmacol. 1988 Feb;40(2):137-9. [PubMed:2897449 ]
  2. Zhu F, Han B, Kumar P, Liu X, Ma X, Wei X, Huang L, Guo Y, Han L, Zheng C, Chen Y: Update of TTD: Therapeutic Target Database. Nucleic Acids Res. 2010 Jan;38(Database issue):D787-91. doi: 10.1093/nar/gkp1014. Epub 2009 Nov 20. [PubMed:19933260 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Moubarak AS, Rosenkrans CF Jr, Johnson ZB: Modulation of cytochrome P450 metabolism by ergonovine and dihydroergotamine. Vet Hum Toxicol. 2003 Feb;45(1):6-9. [PubMed:12583687 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. [PubMed:11961113 ]
  2. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. [PubMed:12235267 ]
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Drug created on April 04, 2007 16:45 / Updated on September 16, 2015 12:21