U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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
Structure of ERGONOVINE MALEATE

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

HIDE SMILES / InChI

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
ERGOMETRINE

Approved Use

Ergometrine 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.
Preventing
ERGOMETRINE

Approved Use

Ergometrine 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

Cmax

ValueDoseCo-administeredAnalytePopulation
1.07 μg/L
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

AUC

ValueDoseCo-administeredAnalytePopulation
3.11 μg × h/L
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.9 h
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
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

Doses

DosePopulationAdverse events​
500 ug single, intramuscular
Recommended
Dose: 500 ug
Route: intramuscular
Route: single
Dose: 500 ug
Sources:
unhealthy
Other AEs: Vasoconstriction, Acute pulmonary oedema...
Other AEs:
Vasoconstriction
Acute pulmonary oedema (rare)
Sources:
AEs

AEs

AESignificanceDosePopulation
Vasoconstriction
500 ug single, intramuscular
Recommended
Dose: 500 ug
Route: intramuscular
Route: single
Dose: 500 ug
Sources:
unhealthy
Acute pulmonary oedema rare
500 ug single, intramuscular
Recommended
Dose: 500 ug
Route: intramuscular
Route: single
Dose: 500 ug
Sources:
unhealthy
Overview

OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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 victimTox targets
PubMed

PubMed

TitleDatePubMed
The cardiovascular effects of oxytocic drugs.
1972 Aug
[Acute myocardial infarction probably induced by the oral administration of bromocriptine: a case report].
1989 Jun
The effect of varying concentrations of ergometrine maleate on the pituitary prolactin of the lizard, Uromastix hardwickii.
2003 Jul
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
Ergometrine.
2005 Jan
A randomised trial of carbetocin versus syntometrine in the management of the third stage of labour.
2006 Dec
Oral misoprostol in the third stage of labor.
2006 Jan
Comparison of flow characteristics and vascular reactivity of radial artery and long saphenous vein grafts [NCT00139399].
2006 Mar 3
Successful management of uterine incision hemorrhage in caesarean section with topical oxidized regenerated cellulose (Surgicel Nu Knit): a case report.
2006 May
Treatment for primary postpartum haemorrhage.
2007 Jan 24
Variations in policies for management of the third stage of labour and the immediate management of postpartum haemorrhage in Europe.
2007 Jul
Carbetocin versus a combination of oxytocin and ergometrine in control of postpartum blood loss.
2007 May
Ergometrine given during caesarean section and incidence of delayed postpartum haemorrhage due to uterine atony.
2007 Nov
Oxytocin-ergometrine co-administration does not reduce blood loss at caesarean delivery for labour arrest.
2008 Apr
Misoprostol in addition to routine treatment of postpartum hemorrhage: a hospital-based randomized-controlled trial in Karachi, Pakistan.
2008 Aug 21
Post partum haemorrhage secondary to uterine atony, complicated by platelet storage pool disease and partial placenta diffusa: a case report.
2008 Dec 13
Postpartum haemorrhage: prevention.
2008 Dec 15
Ergometrine administration for post-partum haemorrhage in an undiagnosed pre-eclamptic.
2008 Jan
Association between anaemia during pregnancy and blood loss at and after delivery among women with vaginal births in Pemba Island, Zanzibar, Tanzania.
2008 Jun
Strategies to manage major obstetric haemorrhage.
2008 Jun
Simultaneous determination of six major ergot alkaloids and their epimers in cereals and foodstuffs by LC-MS-MS.
2008 May
A randomized comparative study of prophylactic oxytocin versus ergometrine in the third stage of labor.
2008 May
Determination of ergot alkaloids: purity and stability assessment of standards and optimization of extraction conditions for cereal samples.
2008 Nov-Dec
A case of permanent retinal disturbance postpartum following administration of ergometrine.
2008 Oct
[Anesthetic management of the ex-utero intrapartum treatment (EXIT) procedure for giant epignathus and of the tumor excision].
2008 Oct
Intraumbilical veinous injection oxytocin in the active management of third stage of labour.
2008 Sep
Health facility-based Active Management of the Third Stage of Labor: findings from a national survey in Tanzania.
2009 Apr 16
The history of ergot of rye (Claviceps purpurea) II: 1900-1940.
2009 Dec
Use of facility assessment data to improve reproductive health service delivery in the Democratic Republic of the Congo.
2009 Dec 21
Carbetocin versus syntometrine in prevention of post-partum hemorrhage following vaginal delivery.
2009 Feb
Active management of the third stage of labour without controlled cord traction: a randomized non-inferiority controlled trial.
2009 Jan 21
WITHDRAWN: Active versus expectant management in the third stage of labour.
2009 Jul 8
Amniotic fluid embolism.
2009 Jul-Sep
A randomized comparison of rectal misoprostol with syntometrine on blood loss in the third stage of labour.
2009 Jun
External aortic compression device: the first aid for postpartum hemorrhage control.
2009 Jun
The B-Lynch suture technique for postpartum haemorrhage: a decade of experience and outcome.
2009 May
Methyl-ergometrine maleate from synchrotron powder diffraction data.
2009 Nov 28
The roles of dopamine and related compounds in reward-seeking behavior across animal phyla.
2010
A novel chemiluminescence method for the determination of ergometrine maleate in serum sample without chemiluminescence reagent.
2010 Apr 15
Ergometrinine.
2010 Aug 11
Strengthening the emergency healthcare system for mothers and children in The Gambia.
2010 Aug 18
Tako-tsubo cardiomyopathy after administration of ergometrine following elective caesarean delivery: a case report.
2010 Aug 20
Care during the third stage of labour: obstetricians views and practice in an Albanian maternity hospital.
2010 Jan 26
Recent trends in the impurity profile of pharmaceuticals.
2010 Jul
Argyreia speciosa (Linn. f.) sweet: A comprehensive review.
2010 Jul
Coronary vasospasm secondary to allergic reaction following food ingestion: a case of type I variant Kounis syndrome.
2010 May
Care during the third stage of labour: a postal survey of UK midwives and obstetricians.
2010 May 21
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
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
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 Mon Mar 31 18:45:14 GMT 2025
Edited
by admin
on Mon Mar 31 18:45:14 GMT 2025
Record UNII
YMH3D0ZJWV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERGOMETRINE MALEATE
EP   MART.   WHO-DD  
Preferred Name English
ERGONOVINE MALEATE
MI   USP   USP-RS   VANDF  
Common Name English
ERGONOVINE MALEATE [USP MONOGRAPH]
Common Name English
ERGOMETRINE MALEATE [MART.]
Common Name English
NSC-93752
Code English
ERGONOVINE MALEATE [MI]
Common Name English
ERGONOVINE MALEATE [USP-RS]
Common Name English
ERGOMETRINE MALEATE [EP MONOGRAPH]
Common Name English
ERGOMETRINE MALEATE [JAN]
Common Name English
Ergometrine maleate [WHO-DD]
Common Name English
ERMETRINE
Brand Name English
ERGOMETRINI HYDROGENOMALEAS [WHO-IP LATIN]
Common Name English
ERGOTRATE MALEATE
Brand Name English
ERGOMETRINE HYDROGEN MALEATE [WHO-IP]
Common Name English
9,10-Didehydro-N-[(S)-2-hydroxy-1-methylethyl]-6-methylergoline-8?-carboxamide maleate (1:1) (salt)
Common Name English
ERGONOVINE MALEATE [VANDF]
Common Name English
CORNOCENTIN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C66884
Created by admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
NCI_THESAURUS C66885
Created by admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
Code System Code Type Description
SMS_ID
100000091892
Created by admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
PRIMARY
RXCUI
24313
Created by admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
PRIMARY RxNorm
PUBCHEM
6437065
Created by admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
PRIMARY
ECHA (EC/EINECS)
204-953-5
Created by admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
PRIMARY
CAS
129-51-1
Created by admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
PRIMARY
FDA UNII
YMH3D0ZJWV
Created by admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
PRIMARY
EVMPD
SUB01931MIG
Created by admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
PRIMARY
NSC
93752
Created by admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
PRIMARY
MERCK INDEX
m4982
Created by admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
PRIMARY Merck Index
DRUG BANK
DBSALT001151
Created by admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
PRIMARY
NCI_THESAURUS
C76962
Created by admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
PRIMARY
CHEBI
31554
Created by admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
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
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.
RS_ITEM_NUM
1240004
Created by admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
PRIMARY
ChEMBL
CHEMBL119443
Created by admin on Mon Mar 31 18:45:14 GMT 2025 , Edited by admin on Mon Mar 31 18:45:14 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY