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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 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

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
The effect of varying concentrations of ergometrine maleate on the pituitary prolactin of the lizard, Uromastix hardwickii.
2003 Jul
Fungal secondary metabolism - from biochemistry to genomics.
2005 Dec
Activity of aqueous extract of the bark of Vitex doniana on uterine muscle response to drugs.
2005 Sep
The role of serendipity in drug discovery.
2006
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
Misoprostol and active management of the third stage of labor.
2006 Aug
A randomised trial of carbetocin versus syntometrine in the management of the third stage of labour.
2006 Dec
Successful management of uterine incision hemorrhage in caesarean section with topical oxidized regenerated cellulose (Surgicel Nu Knit): a case report.
2006 May
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
Oxytocin-ergometrine co-administration does not reduce blood loss at caesarean delivery for labour arrest.
2008 Apr
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
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
Carbetocin versus syntometrine in prevention of post-partum hemorrhage following vaginal delivery.
2009 Feb
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
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 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
  • Download
Name Type Language
ERGOSTINE MALEATE
Common Name English
ERGOTAMAN-3',6',18-TRIONE, 2'-ETHYL-12'-HYDROXY-5'-(PHENYLMETHYL)-, (5'.ALPHA.)-, (Z)-2-BUTENEDIOATE (1:2)(SALT)
Common Name English
Code System Code Type Description
PUBCHEM
76962251
Created by admin on Tue Oct 22 19:49:16 UTC 2019 , Edited by admin on Tue Oct 22 19:49:16 UTC 2019
PRIMARY
CAS
5004-95-5
Created by admin on Tue Oct 22 19:49:16 UTC 2019 , Edited by admin on Tue Oct 22 19:49:16 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY