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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H23N3O2
Molecular Weight 325.4048
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERGONOVINE

SMILES

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

InChI

InChIKey=WVVSZNPYNCNODU-XTQGRXLLSA-N
InChI=1S/C19H23N3O2/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/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/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

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
Ergot to ergometrine: an obstetric renaissance?
2001
Prevention of postpartum hemorrhage, safety and efficacy.
2001 Dec
Major postpartum haemorrhage.
2001 Dec
A prospective randomised trial to compare the efficacy and safety of hemabate and syntometrine for the prevention of primary postpartum haemorrhage.
2001 Oct
Chest pain after coronary artery stent implantation.
2002 Mar 1
[Isolation of the ergot (Claviceps purpurea (Fr.) Tul., strain VKM-F-366D), producing the lactamic alkaloid ergocornam].
2002 Nov-Dec
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
Current strategies for the prevention of postpartum haemorrhage in the third stage of labour.
2004 Apr
Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor.
2004 Jan 26
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
Determination and pharmacokinetics of ergometrine maleate in rabbit blood with on line microdialysis sampling and fluorescence detection.
2005 Jun 1
Determination of ergometrine maleate by fluorescence detection.
2005 May-Jun
Managing asthma in expectant mothers.
2006
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
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
Association between anaemia during pregnancy and blood loss at and after delivery among women with vaginal births in Pemba Island, Zanzibar, Tanzania.
2008 Jun
Simultaneous determination of six major ergot alkaloids and their epimers in cereals and foodstuffs by LC-MS-MS.
2008 May
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
Argyreia speciosa (Linn. f.) sweet: A comprehensive review.
2010 Jul
What measured blood loss tells us about postpartum bleeding: a systematic review.
2010 Jun
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 14:58:00 GMT 2023
Edited
by admin
on Fri Dec 15 14:58:00 GMT 2023
Record UNII
WH41D8433D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERGONOVINE
HSDB   MI   VANDF  
Common Name English
ergometrine [INN]
Common Name English
ERGOMETRINE
INN   WHO-DD  
INN  
Official Name English
Ergometrine [WHO-DD]
Common Name English
ERGOSTETRINE
Common Name English
ERGONOVINE [VANDF]
Common Name English
ERGOTOCINE
Common Name English
9,10-DIDEHYDRO-N-((S)-2-HYDROXY-1-METHYLETHYL)-6-METHYLERGOLINE-8.BETA.-CARBOXAMIDE
Systematic Name English
ERGOLINE-8-CARBOXAMIDE, 9,10-DIDEHYDRO-N-(2-HYDROXY-1-METHYLETHYL)-6-METHYL-, (8.BETA.(S))-
Common Name English
ERGONOVINE [HSDB]
Common Name English
ERGOBASINE
Common Name English
ERGONOVINE [MI]
Common Name English
Classification Tree Code System Code
DEA NO. 8675
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
WHO-ATC G02AB03
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
WHO-VATC QG02AC90
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
NCI_THESAURUS C66884
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
NCI_THESAURUS C29709
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 22.1
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
WHO-VATC QG02AB03
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
Code System Code Type Description
INN
390
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID8046323
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
NCI_THESAURUS
C75040
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
ChEMBL
CHEMBL119443
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
SMS_ID
100000084559
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
CHEBI
4822
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
RXCUI
4021
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB01253
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-485-0
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
CAS
60-79-7
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
EVMPD
SUB06597MIG
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
WIKIPEDIA
ERGOMETRINE
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
PUBCHEM
443884
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
HSDB
4075
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
IUPHAR
148
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
MESH
D004874
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
MERCK INDEX
m4982
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY Merck Index
FDA UNII
WH41D8433D
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
LACTMED
Ergonovine
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
DRUG CENTRAL
1042
Created by admin on Fri Dec 15 14:58:00 GMT 2023 , Edited by admin on Fri Dec 15 14:58:00 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT->PRECURSOR
Related Record Type Details
ACTIVE MOIETY