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 2C34H37N5O5.C4H4O4
Molecular Weight 1307.4483
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ERGOSTINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CC[C@@]5(NC(=O)[C@H]1CN(C)[C@@H]2CC3=CNC4=C3C(=CC=C4)C2=C1)O[C@@]6(O)[C@@H]7CCCN7C(=O)[C@H](CC8=CC=CC=C8)N6C5=O.CC[C@@]%13(NC(=O)[C@H]9CN(C)[C@@H]%10CC%11=CNC%12=C%11C(=CC=C%12)C%10=C9)O[C@@]%14(O)[C@@H]%15CCCN%15C(=O)[C@H](CC%16=CC=CC=C%16)N%14C%13=O

InChI

InChIKey=MFJIQZWRWKDUSA-YXBKWZMVSA-N
InChI=1S/2C34H37N5O5.C4H4O4/c2*1-3-33(36-30(40)22-16-24-23-11-7-12-25-29(23)21(18-35-25)17-26(24)37(2)19-22)32(42)39-27(15-20-9-5-4-6-10-20)31(41)38-14-8-13-28(38)34(39,43)44-33;5-3(6)1-2-4(7)8/h2*4-7,9-12,16,18,22,26-28,35,43H,3,8,13-15,17,19H2,1-2H3,(H,36,40);1-2H,(H,5,6)(H,7,8)/b;;2-1-/t2*22-,26-,27+,28+,33-,34+;/m11./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 C34H37N5O5
Molecular Weight 595.6881
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
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
Prevention of postpartum hemorrhage, safety and efficacy.
2001 Dec
The effect of varying concentrations of ergometrine maleate on the pituitary prolactin of the lizard, Uromastix hardwickii.
2003 Jul
Comparative studies on the effect of ergot contaminated feed on performance and health of piglets and chickens.
2005 Apr
Ergometrine.
2005 Jan
Activity of aqueous extract of the bark of Vitex doniana on uterine muscle response to drugs.
2005 Sep
Misoprostol in the management of the third stage of labour in the home delivery setting in rural Gambia: a randomised controlled trial.
2005 Sep
Misoprostol and active management of the third stage of labor.
2006 Aug
Oral misoprostol in the third stage of labor.
2006 Jan
Prospective study of intramuscular ergometrine compared with intramuscular oxytocin for prevention of postpartum hemorrhage.
2007 Jun
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
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
The history of ergot of rye (Claviceps purpurea) II: 1900-1940.
2009 Dec
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
Anticonvulsant Activity of Argyreia speciosa in Mice.
2009 Mar
Combinatorial assembly of simple and complex D-lysergic acid alkaloid peptide classes in the ergot fungus Claviceps purpurea.
2009 Mar 13
The B-Lynch suture technique for postpartum haemorrhage: a decade of experience and outcome.
2009 May
Associations of drugs routinely given in labour with breastfeeding at 48 hours: analysis of the Cardiff Births Survey.
2009 Nov
Emergent management of postpartum hemorrhage for the general and acute care surgeon.
2009 Nov 25
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
Prinzmetal-variant angina in a patient using zolmitriptan and citalopram.
2010 Feb
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
What measured blood loss tells us about postpartum bleeding: a systematic review.
2010 Jun
Challenges of major obstetric haemorrhage.
2010 Jun
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
Can the Non-pneumatic Anti-Shock Garment (NASG) reduce adverse maternal outcomes from postpartum hemorrhage? Evidence from Egypt and Nigeria.
2010 Sep 1
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 17:57:47 GMT 2025
Edited
by admin
on Mon Mar 31 17:57:47 GMT 2025
Record UNII
CFD408L3CG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERGOTAMAN-3',6',18-TRIONE, 2'-ETHYL-12'-HYDROXY-5'-(PHENYLMETHYL)-, (5'.ALPHA.)-, (Z)-2-BUTENEDIOATE (1:2)(SALT)
Preferred Name English
ERGOSTINE MALEATE
Common Name English
Code System Code Type Description
PUBCHEM
76962251
Created by admin on Mon Mar 31 17:57:47 GMT 2025 , Edited by admin on Mon Mar 31 17:57:47 GMT 2025
PRIMARY
CAS
5004-95-5
Created by admin on Mon Mar 31 17:57:47 GMT 2025 , Edited by admin on Mon Mar 31 17:57:47 GMT 2025
PRIMARY
FDA UNII
CFD408L3CG
Created by admin on Mon Mar 31 17:57:47 GMT 2025 , Edited by admin on Mon Mar 31 17:57:47 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY