ERGOSTINE MALEATE

US Previously Marketed

First approved in 1959

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 Search

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	C34H37N5O5
Molecular Weight	595.6881
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

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

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

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin (5-HT) receptor 30	Partial Agonist 249	Postpartum Hemorrhage
Adrenergic receptor alpha 60	Partial Agonist 249	Postpartum Hemorrhage

Conditions

Condition	Modality	Targets	Highest Phase	Product
Postoperative Hemorrhage 4	Preventing	Adrenergic receptor alpha Serotonin (5-HT) receptor	Approved 7777	ERGOMETRINE
Postpartum Hemorrhage 7	Preventing	Adrenergic receptor alpha Serotonin (5-HT) receptor	Approved 7777	ERGOMETRINE

PubMed

Title	Date	PubMed
The cardiovascular effects of oxytocic drugs.	1972 Aug	4673361
[Acute myocardial infarction probably induced by the oral administration of bromocriptine: a case report].	1989 Jun	2636638
The effect of varying concentrations of ergometrine maleate on the pituitary prolactin of the lizard, Uromastix hardwickii.	2003 Jul	16414579
Fungal secondary metabolism - from biochemistry to genomics.	2005 Dec	16322742
Activity of aqueous extract of the bark of Vitex doniana on uterine muscle response to drugs.	2005 Sep	16220576
The role of serendipity in drug discovery.	2006	17117615
Effect of enhancement of uterine involution and earlier initiation of post-partum cyclicity on the reproductive performance of buffalo.	2006	16836961
Managing asthma in expectant mothers.	2006	16409012
Misoprostol and active management of the third stage of labor.	2006 Aug	16828767
A randomised trial of carbetocin versus syntometrine in the management of the third stage of labour.	2006 Dec	17176279
Successful management of uterine incision hemorrhage in caesarean section with topical oxidized regenerated cellulose (Surgicel Nu Knit): a case report.	2006 May	16408181
Variations in policies for management of the third stage of labour and the immediate management of postpartum haemorrhage in Europe.	2007 Jul	17567419
Prospective study of intramuscular ergometrine compared with intramuscular oxytocin for prevention of postpartum hemorrhage.	2007 Jun	17578351
Carbetocin versus a combination of oxytocin and ergometrine in control of postpartum blood loss.	2007 May	17379220
Ergometrine given during caesarean section and incidence of delayed postpartum haemorrhage due to uterine atony.	2007 Nov	18097896
Oxytocin-ergometrine co-administration does not reduce blood loss at caesarean delivery for labour arrest.	2008 Apr	18333937
Postpartum haemorrhage: prevention.	2008 Dec 15	19445784
Ergometrine administration for post-partum haemorrhage in an undiagnosed pre-eclamptic.	2008 Jan	18326144
Association between anaemia during pregnancy and blood loss at and after delivery among women with vaginal births in Pemba Island, Zanzibar, Tanzania.	2008 Jun	18686556
Strategies to manage major obstetric haemorrhage.	2008 Jun	18458542
Simultaneous determination of six major ergot alkaloids and their epimers in cereals and foodstuffs by LC-MS-MS.	2008 May	18415090
A randomized comparative study of prophylactic oxytocin versus ergometrine in the third stage of labor.	2008 May	18164304
Determination of ergot alkaloids: purity and stability assessment of standards and optimization of extraction conditions for cereal samples.	2008 Nov-Dec	19202797
The history of ergot of rye (Claviceps purpurea) II: 1900-1940.	2009 Dec	20509463
Carbetocin versus syntometrine in prevention of post-partum hemorrhage following vaginal delivery.	2009 Feb	19215547
A randomized comparison of rectal misoprostol with syntometrine on blood loss in the third stage of labour.	2009 Jun	20043525
External aortic compression device: the first aid for postpartum hemorrhage control.	2009 Jun	19527382
Anticonvulsant Activity of Argyreia speciosa in Mice.	2009 Mar	20336209
Combinatorial assembly of simple and complex D-lysergic acid alkaloid peptide classes in the ergot fungus Claviceps purpurea.	2009 Mar 13	19139103
Emergent management of postpartum hemorrhage for the general and acute care surgeon.	2009 Nov 25	19939251
Methyl-ergometrine maleate from synchrotron powder diffraction data.	2009 Nov 28	21578950
The roles of dopamine and related compounds in reward-seeking behavior across animal phyla.	2010	21048897
A novel chemiluminescence method for the determination of ergometrine maleate in serum sample without chemiluminescence reagent.	2010 Apr 15	20188953
Ergometrinine.	2010 Aug 11	21588630
Strengthening the emergency healthcare system for mothers and children in The Gambia.	2010 Aug 18	20718979
Tako-tsubo cardiomyopathy after administration of ergometrine following elective caesarean delivery: a case report.	2010 Aug 20	20727147
Prinzmetal-variant angina in a patient using zolmitriptan and citalopram.	2010 Feb	20159412
Care during the third stage of labour: obstetricians views and practice in an Albanian maternity hospital.	2010 Jan 26	20102601
Recent trends in the impurity profile of pharmaceuticals.	2010 Jul	22247862
Argyreia speciosa (Linn. f.) sweet: A comprehensive review.	2010 Jul	22228958
What measured blood loss tells us about postpartum bleeding: a systematic review.	2010 Jun	20406227
Challenges of major obstetric haemorrhage.	2010 Jun	20110196
Policies for care during the third stage of labour: a survey of maternity units in Syria.	2010 Jun 22	20569439
Coronary vasospasm secondary to allergic reaction following food ingestion: a case of type I variant Kounis syndrome.	2010 May	20512455
Care during the third stage of labour: a postal survey of UK midwives and obstetricians.	2010 May 21	20492659
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	21110888
Postpartum hemorrhage in a Jehovah's Witness patient controlled with Tisseel, tranexamic acid, and recombinant factor VIIa.	2010 Oct	21176309
Can the Non-pneumatic Anti-Shock Garment (NASG) reduce adverse maternal outcomes from postpartum hemorrhage? Evidence from Egypt and Nigeria.	2010 Sep 1	20809942
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	20822521
How HIV/AIDS scale-up has impacted on non- HIV priority services in Zambia.	2010 Sep 8	20825666

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 19:49:16 UTC 2019` Edited by `admin` on `Tue Oct 22 19:49:16 UTC 2019`
Record UNII	CFD408L3CG
Record Status	`Validated (UNII)`
Record Version