U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Evaluation of health workforce competence in maternal and neonatal issues in public health sector of Pakistan: an Assessment of their training needs.
2010-11-27
Postpartum hemorrhage in a Jehovah's Witness patient controlled with Tisseel, tranexamic acid, and recombinant factor VIIa.
2010-10
How HIV/AIDS scale-up has impacted on non- HIV priority services in Zambia.
2010-09-08
The perspectives of clients and unqualified allopathic practitioners on the management of delivery care in urban slums, Dhaka, Bangladesh - a mixed method study.
2010-09-07
Can the Non-pneumatic Anti-Shock Garment (NASG) reduce adverse maternal outcomes from postpartum hemorrhage? Evidence from Egypt and Nigeria.
2010-09-01
Tako-tsubo cardiomyopathy after administration of ergometrine following elective caesarean delivery: a case report.
2010-08-20
Strengthening the emergency healthcare system for mothers and children in The Gambia.
2010-08-18
Ergometrinine.
2010-08-11
Recent trends in the impurity profile of pharmaceuticals.
2010-07
Argyreia speciosa (Linn. f.) sweet: A comprehensive review.
2010-07
Policies for care during the third stage of labour: a survey of maternity units in Syria.
2010-06-22
What measured blood loss tells us about postpartum bleeding: a systematic review.
2010-06
Challenges of major obstetric haemorrhage.
2010-06
Care during the third stage of labour: a postal survey of UK midwives and obstetricians.
2010-05-21
Coronary vasospasm secondary to allergic reaction following food ingestion: a case of type I variant Kounis syndrome.
2010-05
A novel chemiluminescence method for the determination of ergometrine maleate in serum sample without chemiluminescence reagent.
2010-04-15
Prinzmetal-variant angina in a patient using zolmitriptan and citalopram.
2010-02
Care during the third stage of labour: obstetricians views and practice in an Albanian maternity hospital.
2010-01-26
The roles of dopamine and related compounds in reward-seeking behavior across animal phyla.
2010
Amniotic fluid embolism.
2009-12-31
Use of facility assessment data to improve reproductive health service delivery in the Democratic Republic of the Congo.
2009-12-21
The history of ergot of rye (Claviceps purpurea) II: 1900-1940.
2009-12
Methyl-ergometrine maleate from synchrotron powder diffraction data.
2009-11-28
Emergent management of postpartum hemorrhage for the general and acute care surgeon.
2009-11-25
Associations of drugs routinely given in labour with breastfeeding at 48 hours: analysis of the Cardiff Births Survey.
2009-11
WITHDRAWN: Active versus expectant management in the third stage of labour.
2009-07-08
A randomized comparison of rectal misoprostol with syntometrine on blood loss in the third stage of labour.
2009-06
External aortic compression device: the first aid for postpartum hemorrhage control.
2009-06
The B-Lynch suture technique for postpartum haemorrhage: a decade of experience and outcome.
2009-05
Health facility-based Active Management of the Third Stage of Labor: findings from a national survey in Tanzania.
2009-04-16
Combinatorial assembly of simple and complex D-lysergic acid alkaloid peptide classes in the ergot fungus Claviceps purpurea.
2009-03-13
Anticonvulsant Activity of Argyreia speciosa in Mice.
2009-03
Determination of ergot alkaloids: purity and stability assessment of standards and optimization of extraction conditions for cereal samples.
2009-02-11
Carbetocin versus syntometrine in prevention of post-partum hemorrhage following vaginal delivery.
2009-02
Active management of the third stage of labour without controlled cord traction: a randomized non-inferiority controlled trial.
2009-01-21
Postpartum haemorrhage: prevention.
2008-12-15
Post partum haemorrhage secondary to uterine atony, complicated by platelet storage pool disease and partial placenta diffusa: a case report.
2008-12-13
Bromocriptine, a dopamine D(2) receptor agonist with the structure of the amino acid ergot alkaloids, induces neurite outgrowth in PC12 cells.
2008-11-19
A case of permanent retinal disturbance postpartum following administration of ergometrine.
2008-10
[Anesthetic management of the ex-utero intrapartum treatment (EXIT) procedure for giant epignathus and of the tumor excision].
2008-10
Intraumbilical veinous injection oxytocin in the active management of third stage of labour.
2008-09
Misoprostol in addition to routine treatment of postpartum hemorrhage: a hospital-based randomized-controlled trial in Karachi, Pakistan.
2008-08-21
Association between anaemia during pregnancy and blood loss at and after delivery among women with vaginal births in Pemba Island, Zanzibar, Tanzania.
2008-06
Strategies to manage major obstetric haemorrhage.
2008-06
Simultaneous determination of six major ergot alkaloids and their epimers in cereals and foodstuffs by LC-MS-MS.
2008-05
A randomized comparative study of prophylactic oxytocin versus ergometrine in the third stage of labor.
2008-05
Oxytocin-ergometrine co-administration does not reduce blood loss at caesarean delivery for labour arrest.
2008-04
Ergometrine administration for post-partum haemorrhage in an undiagnosed pre-eclamptic.
2008-01
[Acute myocardial infarction probably induced by the oral administration of bromocriptine: a case report].
1989-06
The cardiovascular effects of oxytocic drugs.
1972-08
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
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