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.[H][C@@]12CC3=CNC4=C3C(=CC=C4)C1=C[C@H](CN2C)C(=O)N[C@@H](C)CO

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 C19H23N3O2
Molecular Weight 325.4048
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
Doses

Doses

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

AEs

AESignificanceDosePopulation
Vasoconstriction
500 ug single, intramuscular (max)
Recommended
Dose: 500 ug
Route: intramuscular
Route: single
Dose: 500 ug
Sources:
unhealthy
Health Status: unhealthy
Condition: Postpartum Haemorrhage
Sources:
Acute pulmonary oedema rare
500 ug single, intramuscular (max)
Recommended
Dose: 500 ug
Route: intramuscular
Route: single
Dose: 500 ug
Sources:
unhealthy
Health Status: unhealthy
Condition: Postpartum Haemorrhage
Sources:
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
Major postpartum hemorrhage: survey of maternity units in the United Kingdom.
2002 Aug
[Isolation of the ergot (Claviceps purpurea (Fr.) Tul., strain VKM-F-366D), producing the lactamic alkaloid ergocornam].
2002 Nov-Dec
[Hawaiian baby woodrose: (Psycho-) Pharmacological effects of the seeds of Argyreia nervosa. A case-orientated demonstration].
2002 Sep
John Chassar Moir (1900-1977) and the discovery of ergometrine.
2002 Sep
Effects of methylergometrine and oxytocin on thoracic epidural pressure during cesarean section.
2003 Jun
Prostaglandins in the prevention and management of postpartum haemorrhage.
2003 Oct
Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor.
2004 Jan 26
Comparative studies on the effect of ergot contaminated feed on performance and health of piglets and chickens.
2005 Apr
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
Fungal secondary metabolism - from biochemistry to genomics.
2005 Dec
Ergometrine.
2005 Jan
Determination and pharmacokinetics of ergometrine maleate in rabbit blood with on line microdialysis sampling and fluorescence detection.
2005 Jun 1
The quality of antimalarials available in Yemen.
2005 Jun 29
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
Effect of enhancement of uterine involution and earlier initiation of post-partum cyclicity on the reproductive performance of buffalo.
2006
Managing asthma in expectant mothers.
2006
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
Prophylactic use of ergot alkaloids in the third stage of labour.
2007 Apr 18
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
Prospective study of intramuscular ergometrine compared with intramuscular oxytocin for prevention of postpartum hemorrhage.
2007 Jun
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
Effect of oxytocics on the blood pressure of normotensive Nigerian parturients.
2007 Sep
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
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
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
Active management of the third stage of labour without controlled cord traction: a randomized non-inferiority controlled trial.
2009 Jan 21
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
Combinatorial assembly of simple and complex D-lysergic acid alkaloid peptide classes in the ergot fungus Claviceps purpurea.
2009 Mar 13
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
Challenges of major obstetric haemorrhage.
2010 Jun
Policies for care during the third stage of labour: a survey of maternity units in Syria.
2010 Jun 22
The perspectives of clients and unqualified allopathic practitioners on the management of delivery care in urban slums, Dhaka, Bangladesh - a mixed method study.
2010 Sep 7
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 Fri Dec 15 17:20:59 GMT 2023
Edited
by admin
on Fri Dec 15 17:20:59 GMT 2023
Record UNII
YMH3D0ZJWV
Record Status Validated (UNII)
Record Version
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Name Type Language
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
ERGOMETRINE MALEATE
EP   MART.   WHO-DD  
Common 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-8β-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 Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
NCI_THESAURUS C66885
Created by admin on Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
Code System Code Type Description
SMS_ID
100000091892
Created by admin on Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
PRIMARY
RXCUI
24313
Created by admin on Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
PRIMARY RxNorm
PUBCHEM
6437065
Created by admin on Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-953-5
Created by admin on Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
PRIMARY
CAS
129-51-1
Created by admin on Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
PRIMARY
FDA UNII
YMH3D0ZJWV
Created by admin on Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
PRIMARY
EVMPD
SUB01931MIG
Created by admin on Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
PRIMARY
NSC
93752
Created by admin on Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
PRIMARY
MERCK INDEX
m4982
Created by admin on Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
PRIMARY Merck Index
DRUG BANK
DBSALT001151
Created by admin on Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
PRIMARY
NCI_THESAURUS
C76962
Created by admin on Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
PRIMARY
CHEBI
31554
Created by admin on Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
ERGONOVINE MALEATE
Created by admin on Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
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 Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
PRIMARY
ChEMBL
CHEMBL119443
Created by admin on Fri Dec 15 17:20:59 GMT 2023 , Edited by admin on Fri Dec 15 17:20:59 GMT 2023
PRIMARY
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