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.[H][C@@]12CCCN1C(=O)[C@H](CC3=CC=CC=C3)N4C(=O)[C@](CC)(NC(=O)[C@H]5CN(C)[C@]6([H])CC7=CNC8=CC=CC(=C78)C6=C5)O[C@@]24O.[H][C@@]9%10CCCN9C(=O)[C@H](CC%11=CC=CC=C%11)N%12C(=O)[C@](CC)(NC(=O)[C@H]%13CN(C)[C@]%14([H])CC%15=CNC%16=CC=CC(=C%15%16)C%14=C%13)O[C@@]%10%12O

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	No
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	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12193527 | http://www.medsafe.govt.nz/profs/Datasheet/d/DBLErgometrineinj.pdf

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
Adrenergic receptor alpha 64 Target ID: CHEMBL2095203 Sources: http://www.medsafe.govt.nz/profs/Datasheet/d/DBLErgometrineinj.pdf	Partial Agonist 290
Serotonin (5-HT) receptor 34 Target ID: CHEMBL2096904 Sources: http://www.medsafe.govt.nz/profs/Datasheet/d/DBLErgometrineinj.pdf	Partial Agonist 290

Conditions

Condition	Modality	Targets	Highest Phase	Product
Postpartum haemorrhage 4 Sources: http://www.medsafe.govt.nz/profs/Datasheet/d/DBLErgometrineinj.pdf	Preventing		Approved 8429	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.
Postabortion haemorrhage 4 Sources: http://www.medsafe.govt.nz/profs/Datasheet/d/DBLErgometrineinj.pdf	Preventing		Approved 8429	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.

C_max

Value	Dose	Co-administered	Analyte	Population
1.07 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8161717/	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

Value	Dose	Co-administered	Analyte	Population
1.69 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8161717/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8161717/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.06 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8161717/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8161717/	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

Dose	Population	Adverse events
500 ug single, intramuscular (max) Recommended Dose: 500 ug Route: intramuscular Route: single Dose: 500 ug Sources: https://www.medicines.org.uk/emc/product/6265/smpc#CLINICAL_PRECAUTIONS	unhealthy Health Status: unhealthy Condition: Postpartum Haemorrhage Sources: https://www.medicines.org.uk/emc/product/6265/smpc#CLINICAL_PRECAUTIONS	Other AEs: Vasoconstriction, Acute pulmonary oedema... Other AEs: Vasoconstriction Acute pulmonary oedema (rare) Sources: https://www.medicines.org.uk/emc/product/6265/smpc#CLINICAL_PRECAUTIONS

AEs

AE	Significance	Dose	Population
Vasoconstriction		500 ug single, intramuscular (max) Recommended Dose: 500 ug Route: intramuscular Route: single Dose: 500 ug Sources: https://www.medicines.org.uk/emc/product/6265/smpc#CLINICAL_PRECAUTIONS	unhealthy Health Status: unhealthy Condition: Postpartum Haemorrhage Sources: https://www.medicines.org.uk/emc/product/6265/smpc#CLINICAL_PRECAUTIONS
Acute pulmonary oedema	rare	500 ug single, intramuscular (max) Recommended Dose: 500 ug Route: intramuscular Route: single Dose: 500 ug Sources: https://www.medicines.org.uk/emc/product/6265/smpc#CLINICAL_PRECAUTIONS	unhealthy Health Status: unhealthy Condition: Postpartum Haemorrhage Sources: https://www.medicines.org.uk/emc/product/6265/smpc#CLINICAL_PRECAUTIONS

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 activator 80 inhibitor 1587	inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461 CYP1A2 1524 CYP2A6 707 CYP2C19 1478 CYP2E1 882 OATP1B1 788 OATP1B3 706 CYP19A1 60

Drug as perpetrator

Target	Modality	Activity
CYP3A4 1925	inhibitor 3277 Sources: https://www.scirp.org/html/1-3000180_16854.htm \| https://academic.oup.com/jas/article-abstract/94/suppl_1/32/4700243 \| https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTE5NDQzIn19	inconclusive [IC50 19.9526 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExOTQ0MyJ9fQ%3D%3D	no [IC50 >10 uM]
CYP19A1 60	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144205575	no
CYP2A6 739	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExOTQ0MyJ9fQ%3D%3D	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExOTQ0MyJ9fQ%3D%3D	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExOTQ0MyJ9fQ%3D%3D	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTE5NDQzIn19	no
CYP2E1 970	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExOTQ0MyJ9fQ%3D%3D	no
CYP3A4 1925	activator 214 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTE5NDQzIn19	no
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11961113/, http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50390991	weak [Ki 100 uM]
OATP1B1 803	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMTMxMzUifX0%3D	yes [Inhibition 10 uM]
OATP1B3 715	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMTMxMzUifX0%3D	yes [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1737	substrate 3367 Sources: https://go.drugbank.com/drugs/DB01253, https://pubmed.ncbi.nlm.nih.gov/17948937/, https://www.genome.jp/kegg/drug/br08309.html	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTE5NDQzIn19

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1440	http://www.3bsc.com/index/pro_info.php?id=55156
AHH Chemical co.,ltd	MT-50822	http://www.ahhchemical.com/product/MT-50822.html
ChemFish Tokyo co.,ltd	443884	http://www.chemfish.co.jp/index.php?id=3965&project=product
ChemMol	99117812	http://www.chemmol.com/chemmol/99117812.html
Finetech	FT-0625687	http://www.finetechnology-ind.com/product/All%20product%20List/60-79-7.html
LGC Standards	DRE-C13201290	https://www.lgcstandards.com/US/en/p/DRE-C13201290
Parchem	26859	http://www.parchem.com/chemical-supplier-distributor/Ergonovine-016859.aspx
Smolecule	S527371	http://www.smolecule.com/products/s527371
Smolecule	S775998	https://www.smolecule.com/products/s775998
THE BioTek	bt-267628	https://www.thebiotek.com/product/inhibitors/bt-267628
TimTec	ST057158	http://www.echemstore.com/st057158-ergonovine-maleate-salt-ergometrine-maleate-salt.html

PubMed

Title	Date	PubMed
Life threatening coronary artery spasm in childhood Kimura's disease.	2000 Aug	10908272
Discrimination between the functional and biochemical effects of two herbal oxytocics on the rat myometrium.	2001 Aug	11518025
Safety of ergot stress echocardiography for non-invasive detection of coronary vasospasm.	2001 Dec	11811330
Prevention of postpartum hemorrhage, safety and efficacy.	2001 Dec	11802188
Oxytocics reverse the tocolytic effect of glyceryl trinitrate on the human uterus.	2001 Feb	11236116
Effects of serotonin, dopamine and ergometrine on locomotion in the pulmonate mollusc Helix lucorum.	2001 May	11398751
Major postpartum hemorrhage: survey of maternity units in the United Kingdom.	2002 Aug	12174156
Chest pain after coronary artery stent implantation.	2002 Mar 1	11867031
St Anthony's fire and living ligatures: a short history of ergometrine.	2002 May 18	12049883
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
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
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	18835264
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
Combinatorial assembly of simple and complex D-lysergic acid alkaloid peptide classes in the ergot fungus Claviceps purpurea.	2009 Mar 13	19139103
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
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

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: 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 15:26:24 GMT 2023` Edited by `admin` on `Fri Dec 15 15:26:24 GMT 2023`
Record UNII	CFD408L3CG
Record Status	`Validated (UNII)`
Record Version

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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 Fri Dec 15 15:26:24 GMT 2023 , Edited by admin on Fri Dec 15 15:26:24 GMT 2023

PRIMARY

CAS

5004-95-5

Created by admin on Fri Dec 15 15:26:24 GMT 2023 , Edited by admin on Fri Dec 15 15:26:24 GMT 2023

PRIMARY

FDA UNII

CFD408L3CG

Created by admin on Fri Dec 15 15:26:24 GMT 2023 , Edited by admin on Fri Dec 15 15:26:24 GMT 2023

PRIMARY

Related Record Type Details


					91XW058U2C

MALEIC ACID

PARENT -> SALT/SOLVATE


					8RM45QOC5P

ERGOSTINE

PARENT -> SALT/SOLVATE

Related Record Type Details


					WH41D8433D

ERGONOVINE

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/12193527 | http://www.medsafe.govt.nz/profs/Datasheet/d/DBLErgometrineinj.pdf

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12193527 | http://www.medsafe.govt.nz/profs/Datasheet/d/DBLErgometrineinj.pdf

C_max

T_1/2

Drug as perpetrator