Identification
- Summary
Ergometrine is an ergot alkaloid used for the treatment of postpartum haemorrhage and post abortion hemorrhage in patients with uterine atony.
- Generic Name
- Ergometrine
- DrugBank Accession Number
- DB01253
- Background
An ergot alkaloid with uterine and vascular smooth muscle contractile properties.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Ergometrine (DB01253)
- Weight
- Average: 325.4048
Monoisotopic: 325.179026995 - Chemical Formula
- C19H23N3O2
- 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
- [8β(S)]-9,10-didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8-carboxamide
- 9,10-didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8β(S)-carboxamide
- 9,10-didehydro-N-(α-(hydroxymethyl)ethyl)-6-methylergoline-8-β-carboxamide
- D-lysergic acid 1-hydroxymethylethylamide
- D-lysergic acid-L-propanolamide
- Ergobasine
- Ergometrina
- Ergometrine
- Ergométrine
- Ergometrinum
- Ergonovine
- Ergotocine
- Margonovine
- N-(2-Hydroxy-1-methylethyl)-D-(+)-lysergamide
- N-(α-(hydroxymethyl)ethyl)-D-lysergamide
Pharmacology
- Indication
Used to treat postpartum haemorrhage and postabortion haemorrhage in patients with uterine atony.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Hemorrhage •••••••••••• Prophylaxis of Hemorrhage •••••••••••• Diagnostic agent Vasospastic angina ••• ••••• - Contraindications & Blackbox Warnings
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Ergonovine 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 action
Ergonovine 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.
Target Actions Organism AAlpha-1A adrenergic receptor agonistHumans - Absorption
Absorption is rapid and complete after oral or intramuscular administration.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic.
- Route of elimination
Thought to be eliminated by non-renal mechanisms (i.e. hepatic metabolism, excretion in feces)
- Half-life
t1/2 α=10 minutes; t1/2 β=2 hours
- Clearance
Not Available
- Adverse Effects
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The 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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Ergometrine is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Ergometrine can be increased when it is combined with Abametapir. Acebutolol The therapeutic efficacy of Ergometrine can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Ergometrine is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Ergometrine is combined with Acemetacin. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Ergonovine maleate YMH3D0ZJWV 129-51-1 YREISLCRUMOYAY-IIPCNOPRSA-N - International/Other Brands
- Ergotrate
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ergonovine Maleate Tablet 0.2 mg/1 Oral Pharmacist Pharmaceutical, LLC 2007-01-01 2009-12-31 US 
Ergonovine Maleate Injection Solution 0.25 mg / mL Intramuscular; Intravenous Mylan Pharmaceuticals 1995-12-31 Not applicable Canada 
Ergonovine Maleate Injection USP Solution .25 mg / mL Intramuscular; Intravenous Pfizer Canada Ulc 1981-12-31 2020-01-23 Canada Ergonovine Maleate Injection USP Solution 0.25 mg / mL Intramuscular; Intravenous Hikma Canada Limited 2016-02-19 Not applicable Canada Ergonovine Maleate Injection USP, 0.25mg/ml Solution 0.25 mg / mL Intramuscular; Intravenous Alveda Pharmaceuticals Inc 2010-06-01 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image SYNTOMETRINE INJECTION Ergonovine maleate (0.5 mg/ml) + Oxytocin (5 iu/ml) Injection Intramuscular; Intravenous PHARMACON PTE LTD 1989-05-07 Not applicable Singapore 
อาโทเยน Ergometrine (125 MCG) + Ergotamine (250 MCG) Tablet, sugar coated Oral บริษัท เอเชี่ยนยูเนี่ยนแล็บบอราตอรี่ จำกัด 1988-03-06 Not applicable Thailand 
ไกเนมิน Ergometrine (125 MCG) + Ergotamine (250 MCG) Tablet, sugar coated Oral บริษัท เภสัชกรรมศรีประสิทธิ์ จำกัด จำกัด 1983-12-23 Not applicable Thailand - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Ergonovine Maleate Ergonovine maleate (0.2 mg/1) Tablet Oral Pharmacist Pharmaceutical, LLC 2007-01-01 2009-12-31 US Ergotrate Maleate Ergonovine maleate (0.2 mg/1mL) Injection, solution Intramuscular Pharmacist Pharmaceutical, LLC 2006-01-01 2009-12-31 US
Categories
- ATC Codes
- G02AB03 — Ergometrine
- Drug Categories
- Adrenergic Agonists
- Adrenergic alpha-1 Receptor Agonists
- Adrenergic alpha-Agonists
- Agents producing tachycardia
- Agents that produce hypertension
- Alkaloids
- Antidepressive Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Ergolines
- Ergot Alkaloids and Derivatives
- Genito Urinary System and Sex Hormones
- Heterocyclic Compounds, Fused-Ring
- P-glycoprotein inhibitors
- Reproductive Control Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin Agents
- Serotonin Modulators
- Uterotonic agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Ergoline and derivatives
- Sub Class
- Lysergic acids and derivatives
- Direct Parent
- Lysergamides
- Alternative Parents
- Indoloquinolines / Benzoquinolines / Quinoline-3-carboxamides / Pyrroloquinolines / 3-alkylindoles / Isoindoles and derivatives / Aralkylamines / Benzenoids / Heteroaromatic compounds / Pyrroles show 9 more
- Substituents
- 3-alkylindole / Alcohol / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzoquinoline / Carbonyl group show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- tertiary amino compound, organic heterotetracyclic compound, monocarboxylic acid amide, secondary amino compound, ergot alkaloid, primary alcohol (CHEBI:4822) / Indole alkaloids (C07543)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- WH41D8433D
- CAS number
- 60-79-7
- InChI Key
- 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[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
- SMILES
- [H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N[C@@H](C)CO
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015383
- KEGG Drug
- D07905
- KEGG Compound
- C07543
- PubChem Compound
- 443884
- PubChem Substance
- 46506922
- ChemSpider
- 391970
- BindingDB
- 50390991
- 4021
- ChEBI
- 4822
- ChEMBL
- CHEMBL119443
- ZINC
- ZINC000053174604
- Therapeutic Targets Database
- DAP000227
- PharmGKB
- PA449487
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Ergonovine
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Prevention Bloodloss / Postpartum Haemorrhage (PPH) 1 4 Completed Treatment Anemia / Bleeding 1 4 Unknown Status Prevention Postpartum Haemorrhage (PPH) 1 4 Unknown Status Treatment Postpartum Haemorrhage (PPH) 1 3 Unknown Status Treatment Postpartum Haemorrhage (PPH) 2
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- A-S Medication Solutions LLC
- Bedford Labs
- Ben Venue Laboratories Inc.
- Bioniche Pharma
- Direct Dispensing Inc.
- Diversified Healthcare Services Inc.
- Laboratoires Sterop SA
- PD-Rx Pharmaceuticals Inc.
- Pharmaceutical Co. Jelfa SA
- Pharmacia Inc.
- Prometic Pharma Inc.
- Spectrum Pharmaceuticals
- Valesco Pharmaceuticals Inc.
- Dosage Forms
Form Route Strength Solution Parenteral 0.200 mg Tablet Oral 0.5 MG Injection, solution Intramuscular Tablet Oral 0.2 mg/1 Solution Intramuscular; Intravenous 0.25 mg / mL Solution Intramuscular; Intravenous .25 mg / mL Tablet Oral Tablet Oral 0.200 mg Injection, solution Intramuscular 0.2 mg/1mL Tablet Oral .2 mg / tab Solution Intramuscular 0.2 mg Injection Intramuscular; Intravenous Injection Intramuscular Tablet, sugar coated Oral - Prices
Unit description Cost Unit Ergonovine maleate 100% powder 676.9USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 162 °C PhysProp water solubility 2.68 mg/mL at 25 °C MEYLAN,WM et al. (1996) logP 0.9 Not Available pKa 6.8 MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 0.321 mg/mL ALOGPS logP 1.53 ALOGPS logP 1.07 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 15 Chemaxon pKa (Strongest Basic) 7.93 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 68.36 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 95.05 m3·mol-1 Chemaxon Polarizability 36.54 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9967 Blood Brain Barrier + 0.6971 Caco-2 permeable - 0.8957 P-glycoprotein substrate Substrate 0.8385 P-glycoprotein inhibitor I Non-inhibitor 0.8782 P-glycoprotein inhibitor II Non-inhibitor 0.8382 Renal organic cation transporter Non-inhibitor 0.7295 CYP450 2C9 substrate Non-substrate 0.8097 CYP450 2D6 substrate Non-substrate 0.9115 CYP450 3A4 substrate Substrate 0.6814 CYP450 1A2 substrate Non-inhibitor 0.7284 CYP450 2C9 inhibitor Non-inhibitor 0.9116 CYP450 2D6 inhibitor Inhibitor 0.8931 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.9228 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9236 Ames test Non AMES toxic 0.5743 Carcinogenicity Non-carcinogens 0.9353 Biodegradation Not ready biodegradable 0.8714 Rat acute toxicity 3.3967 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.954 hERG inhibition (predictor II) Inhibitor 0.5624
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0002-3931000000-4bdb2fafa3f7edc31959 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0049000000-2a50daaa8bca72031a8b Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00dl-0059000000-d3cdaf35ba1bcc493ff3 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0kmi-9068000000-2ef4ebfc86702ef45157 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0kk9-0096000000-2f4f9c8f04c65826f8ce Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00fr-0091000000-24a77496573e6e6a270d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-006x-8090000000-f221cc3e867a15f9d8b0 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 182.1421823 predictedDarkChem Lite v0.1.0 [M-H]- 190.9468823 predictedDarkChem Lite v0.1.0 [M-H]- 184.3264823 predictedDarkChem Lite v0.1.0 [M-H]- 181.54866 predictedDeepCCS 1.0 (2019) [M+H]+ 182.6024823 predictedDarkChem Lite v0.1.0 [M+H]+ 190.8638823 predictedDarkChem Lite v0.1.0 [M+H]+ 184.9824823 predictedDarkChem Lite v0.1.0 [M+H]+ 183.90666 predictedDeepCCS 1.0 (2019) [M+Na]+ 181.5932823 predictedDarkChem Lite v0.1.0 [M+Na]+ 191.7918823 predictedDarkChem Lite v0.1.0 [M+Na]+ 190.04214 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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) prot...
- Gene Name
- ADRA1A
- Uniprot ID
- P35348
- Uniprot Name
- Alpha-1A adrenergic receptor
- Molecular Weight
- 51486.005 Da
References
- 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. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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 react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
Transporters
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- 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. [Article]
- 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. [Article]
Drug created at April 04, 2007 22:45 / Updated at February 20, 2024 23:55