Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H23N3O2.C4H4O4 |
Molecular Weight | 441.477 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C/C(O)=O.C[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2CC3=CNC4=C3C(=CC=C4)C2=C1
InChI
InChIKey=YREISLCRUMOYAY-IIPCNOPRSA-N
InChI=1S/C19H23N3O2.C4H4O4/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;5-3(6)1-2-4(7)8/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24);1-2H,(H,5,6)(H,7,8)/b;2-1-/t11-,13+,17+;/m0./s1
Molecular Formula | C4H4O4 |
Molecular Weight | 116.0722 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Molecular Formula | C19H23N3O2 |
Molecular Weight | 325.4048 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Ergonovine (also known as ergometrine) is the active water soluble component of ergot of rye. Ergonovine is being used as a maleate salt to prevent or treate postpartum haemorrhage and postabortion haemorrhage. Ergonovine stimulates alpha-adrenergic and serotonin receptors, thus activating contractions of uterine and vascular smooth muscle. Ergonovine may have depressant effect on CNS system as it binds to dopamine receptors.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095203 |
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Target ID: CHEMBL2096904 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | ERGOMETRINE Approved UseErgometrine is administered after the delivery of the placenta for the purpose of contracting the uterus in order to prevent or treat postpartum haemorrhage and postabortion haemorrhage due to uterine atony. |
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Preventing | ERGOMETRINE Approved UseErgometrine is administered after the delivery of the placenta for the purpose of contracting the uterus in order to prevent or treat postpartum haemorrhage and postabortion haemorrhage due to uterine atony. |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.07 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8161717/ |
0.2 mg single, oral dose: 0.2 mg route of administration: Oral experiment type: SINGLE co-administered: |
ERGONOVINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.11 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8161717/ |
0.2 mg single, oral dose: 0.2 mg route of administration: Oral experiment type: SINGLE co-administered: |
ERGONOVINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
1.69 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8161717/ |
0.075 mg single, intravenous dose: 0.075 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ERGONOVINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8161717/ |
0.2 mg single, oral dose: 0.2 mg route of administration: Oral experiment type: SINGLE co-administered: |
ERGONOVINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
2.06 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8161717/ |
0.075 mg single, intravenous dose: 0.075 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ERGONOVINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
500 ug single, intramuscular Recommended Dose: 500 ug Route: intramuscular Route: single Dose: 500 ug Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Vasoconstriction, Acute pulmonary oedema... Other AEs: Vasoconstriction Sources: Acute pulmonary oedema (rare) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Vasoconstriction | 500 ug single, intramuscular Recommended Dose: 500 ug Route: intramuscular Route: single Dose: 500 ug Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Acute pulmonary oedema | rare | 500 ug single, intramuscular Recommended Dose: 500 ug Route: intramuscular Route: single Dose: 500 ug Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
inconclusive [IC50 19.9526 uM] | ||||
no [IC50 >10 uM] | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
weak [Ki 100 uM] | ||||
yes [Inhibition 10 uM] | ||||
yes [Inhibition 10 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
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The cardiovascular effects of oxytocic drugs. | 1972 Aug |
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[Acute myocardial infarction probably induced by the oral administration of bromocriptine: a case report]. | 1989 Jun |
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The effect of varying concentrations of ergometrine maleate on the pituitary prolactin of the lizard, Uromastix hardwickii. | 2003 Jul |
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The influence of ergot-contaminated feed on growth and slaughtering performance, nutrient digestibility and carry over of ergot alkaloids in growing-finishing pigs. | 2005 Dec |
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Ergometrine. | 2005 Jan |
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A randomised trial of carbetocin versus syntometrine in the management of the third stage of labour. | 2006 Dec |
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Oral misoprostol in the third stage of labor. | 2006 Jan |
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Comparison of flow characteristics and vascular reactivity of radial artery and long saphenous vein grafts [NCT00139399]. | 2006 Mar 3 |
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Successful management of uterine incision hemorrhage in caesarean section with topical oxidized regenerated cellulose (Surgicel Nu Knit): a case report. | 2006 May |
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Treatment for primary postpartum haemorrhage. | 2007 Jan 24 |
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Variations in policies for management of the third stage of labour and the immediate management of postpartum haemorrhage in Europe. | 2007 Jul |
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Carbetocin versus a combination of oxytocin and ergometrine in control of postpartum blood loss. | 2007 May |
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Ergometrine given during caesarean section and incidence of delayed postpartum haemorrhage due to uterine atony. | 2007 Nov |
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Oxytocin-ergometrine co-administration does not reduce blood loss at caesarean delivery for labour arrest. | 2008 Apr |
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Misoprostol in addition to routine treatment of postpartum hemorrhage: a hospital-based randomized-controlled trial in Karachi, Pakistan. | 2008 Aug 21 |
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Post partum haemorrhage secondary to uterine atony, complicated by platelet storage pool disease and partial placenta diffusa: a case report. | 2008 Dec 13 |
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Postpartum haemorrhage: prevention. | 2008 Dec 15 |
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Ergometrine administration for post-partum haemorrhage in an undiagnosed pre-eclamptic. | 2008 Jan |
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Association between anaemia during pregnancy and blood loss at and after delivery among women with vaginal births in Pemba Island, Zanzibar, Tanzania. | 2008 Jun |
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Strategies to manage major obstetric haemorrhage. | 2008 Jun |
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Simultaneous determination of six major ergot alkaloids and their epimers in cereals and foodstuffs by LC-MS-MS. | 2008 May |
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A randomized comparative study of prophylactic oxytocin versus ergometrine in the third stage of labor. | 2008 May |
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Determination of ergot alkaloids: purity and stability assessment of standards and optimization of extraction conditions for cereal samples. | 2008 Nov-Dec |
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A case of permanent retinal disturbance postpartum following administration of ergometrine. | 2008 Oct |
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[Anesthetic management of the ex-utero intrapartum treatment (EXIT) procedure for giant epignathus and of the tumor excision]. | 2008 Oct |
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Intraumbilical veinous injection oxytocin in the active management of third stage of labour. | 2008 Sep |
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Health facility-based Active Management of the Third Stage of Labor: findings from a national survey in Tanzania. | 2009 Apr 16 |
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The history of ergot of rye (Claviceps purpurea) II: 1900-1940. | 2009 Dec |
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Use of facility assessment data to improve reproductive health service delivery in the Democratic Republic of the Congo. | 2009 Dec 21 |
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Carbetocin versus syntometrine in prevention of post-partum hemorrhage following vaginal delivery. | 2009 Feb |
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Active management of the third stage of labour without controlled cord traction: a randomized non-inferiority controlled trial. | 2009 Jan 21 |
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WITHDRAWN: Active versus expectant management in the third stage of labour. | 2009 Jul 8 |
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Amniotic fluid embolism. | 2009 Jul-Sep |
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A randomized comparison of rectal misoprostol with syntometrine on blood loss in the third stage of labour. | 2009 Jun |
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External aortic compression device: the first aid for postpartum hemorrhage control. | 2009 Jun |
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The B-Lynch suture technique for postpartum haemorrhage: a decade of experience and outcome. | 2009 May |
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Methyl-ergometrine maleate from synchrotron powder diffraction data. | 2009 Nov 28 |
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The roles of dopamine and related compounds in reward-seeking behavior across animal phyla. | 2010 |
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A novel chemiluminescence method for the determination of ergometrine maleate in serum sample without chemiluminescence reagent. | 2010 Apr 15 |
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Ergometrinine. | 2010 Aug 11 |
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Strengthening the emergency healthcare system for mothers and children in The Gambia. | 2010 Aug 18 |
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Tako-tsubo cardiomyopathy after administration of ergometrine following elective caesarean delivery: a case report. | 2010 Aug 20 |
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Care during the third stage of labour: obstetricians views and practice in an Albanian maternity hospital. | 2010 Jan 26 |
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Recent trends in the impurity profile of pharmaceuticals. | 2010 Jul |
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Argyreia speciosa (Linn. f.) sweet: A comprehensive review. | 2010 Jul |
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Coronary vasospasm secondary to allergic reaction following food ingestion: a case of type I variant Kounis syndrome. | 2010 May |
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Care during the third stage of labour: a postal survey of UK midwives and obstetricians. | 2010 May 21 |
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Evaluation of health workforce competence in maternal and neonatal issues in public health sector of Pakistan: an Assessment of their training needs. | 2010 Nov 27 |
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Postpartum hemorrhage in a Jehovah's Witness patient controlled with Tisseel, tranexamic acid, and recombinant factor VIIa. | 2010 Oct |
|
How HIV/AIDS scale-up has impacted on non- HIV priority services in Zambia. | 2010 Sep 8 |
Patents
Sample Use Guides
Prophylaxis of postpartum haemorrhage and postabortion haemorrhage: the immediate postpartum dose of ergonovine (ergometrine maleate) is 200 ug administered intramuscularly. The injection should not be given until completion of the delivery is assured, and until the possibility of a second twin has been excluded. In an emergency situation, 200 ug may be injected intravenously. IV doses should be given slowly, over a period of at least 1 min. Treatment of postpartum haemorrhage and postabortion haemorrhage: 200 ug may be injected intramuscularly.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3220119
Isolated rat uterus was treated with ergometrine at concentrations 0.01, 0.03, 0.1, 0.3, 1, 10 uM and the drug was shown to act as a partial agonist for serotonin receptors.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:45:14 GMT 2025
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on
Mon Mar 31 18:45:14 GMT 2025
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Record UNII |
YMH3D0ZJWV
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C66884
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NCI_THESAURUS |
C66885
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100000091892
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24313
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6437065
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204-953-5
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93752
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m4982
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DBSALT001151
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C76962
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31554
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ERGONOVINE MALEATE
Created by
admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
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PRIMARY | Description: A white or faintly yellow, crystalline powder; odourless.Solubility. Sparingly soluble in water and ethanol (~750 g/l) TS; practically insoluble in ether R.Category: Oxytocic.Storage: Ergometrine hydrogen maleate should be kept in a hermetically closed container, preferably in an inert atmosphere, such as nitrogen, protected from light and stored at a temperature between 2? and 8?C.Additional information: Ergometrine hydrogen maleate darkens in colour on exposure to light. Even in the absence of light, Ergometrine hydrogen maleate is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures.Definition: Ergometrine hydrogen maleate contains not less than 98.0% and not more than 101.0% of C19H23N3O2,C4H4O4 calculated with reference to the dried substance. | ||
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1240004
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CHEMBL119443
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