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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
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
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

Originator

Approval Year

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
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
Bromocriptine, a dopamine D(2) receptor agonist with the structure of the amino acid ergot alkaloids, induces neurite outgrowth in PC12 cells.
2008 Nov 19
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
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
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
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
Policies for care during the third stage of labour: a survey of maternity units in Syria.
2010 Jun 22
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
Can the Non-pneumatic Anti-Shock Garment (NASG) reduce adverse maternal outcomes from postpartum hemorrhage? Evidence from Egypt and Nigeria.
2010 Sep 1
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
How HIV/AIDS scale-up has impacted on non- HIV priority services in Zambia.
2010 Sep 8
Patents

Sample Use Guides

In Vivo Use Guide
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: Intramuscular; Intravenous
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 Tue Oct 22 00:45:51 UTC 2019
Edited
by admin
on Tue Oct 22 00:45:51 UTC 2019
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]
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
ERMETRINE
Brand Name English
ERGOMETRINE MALEATE
EP   MART.   WHO-DD  
Common Name English
ERGOMETRINI HYDROGENOMALEAS [WHO-IP LATIN]
Common Name English
ERGOMETRINE MALEATE [WHO-DD]
Common Name English
ERGOTRATE MALEATE
Brand Name English
ERGOMETRINE HYDROGEN MALEATE [WHO-IP]
Common Name English
ERGOMETRINE MALEATE [EP]
Common Name English
9,10-DIDEHYDRO-N-((S)-2-HYDROXY-1-METHYLETHYL)-6-METHYLERGOLINE-8.BETA.-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 Tue Oct 22 00:45:51 UTC 2019 , Edited by admin on Tue Oct 22 00:45:51 UTC 2019
NCI_THESAURUS C66885
Created by admin on Tue Oct 22 00:45:51 UTC 2019 , Edited by admin on Tue Oct 22 00:45:51 UTC 2019
Code System Code Type Description
RXCUI
24313
Created by admin on Tue Oct 22 00:45:51 UTC 2019 , Edited by admin on Tue Oct 22 00:45:51 UTC 2019
PRIMARY RxNorm
PUBCHEM
6437065
Created by admin on Tue Oct 22 00:45:51 UTC 2019 , Edited by admin on Tue Oct 22 00:45:51 UTC 2019
PRIMARY
ECHA (EC/EINECS)
204-953-5
Created by admin on Tue Oct 22 00:45:51 UTC 2019 , Edited by admin on Tue Oct 22 00:45:51 UTC 2019
PRIMARY
CAS
129-51-1
Created by admin on Tue Oct 22 00:45:51 UTC 2019 , Edited by admin on Tue Oct 22 00:45:51 UTC 2019
PRIMARY
EVMPD
SUB01931MIG
Created by admin on Tue Oct 22 00:45:51 UTC 2019 , Edited by admin on Tue Oct 22 00:45:51 UTC 2019
PRIMARY
MERCK INDEX
M4982
Created by admin on Tue Oct 22 00:45:51 UTC 2019 , Edited by admin on Tue Oct 22 00:45:51 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C76962
Created by admin on Tue Oct 22 00:45:51 UTC 2019 , Edited by admin on Tue Oct 22 00:45:51 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
ERGONOVINE MALEATE
Created by admin on Tue Oct 22 00:45:51 UTC 2019 , Edited by admin on Tue Oct 22 00:45:51 UTC 2019
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.
ChEMBL
CHEMBL119443
Created by admin on Tue Oct 22 00:45:51 UTC 2019 , Edited by admin on Tue Oct 22 00:45:51 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY