ERGONOVINE

US Previously Marketed

First approved in 1959

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 Search

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

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
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
Safety of ergot stress echocardiography for non-invasive detection of coronary vasospasm.	2001 Dec	11811330
Major postpartum hemorrhage: survey of maternity units in the United Kingdom.	2002 Aug	12174156
Uterine compression sutures: surgical management of postpartum hemorrhage.	2002 Mar	11864681
[Isolation of the ergot (Claviceps purpurea (Fr.) Tul., strain VKM-F-366D), producing the lactamic alkaloid ergocornam].	2002 Nov-Dec	12449796
Amphetamine-related acute myocardial infarction due to coronary artery spasm.	2003 Jan-Feb	12587947
The effect of varying concentrations of ergometrine maleate on the pituitary prolactin of the lizard, Uromastix hardwickii.	2003 Jul	16414579
Effects of methylergometrine and oxytocin on thoracic epidural pressure during cesarean section.	2003 Jun	12841703
Prostaglandins in the prevention and management of postpartum haemorrhage.	2003 Oct	12972016
Prophylactic ergometrine-oxytocin versus oxytocin for the third stage of labour.	2004	14973949
Current strategies for the prevention of postpartum haemorrhage in the third stage of labour.	2004 Apr	15017343
Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor.	2004 Jan 26	14744596
Comparative studies on the effect of ergot contaminated feed on performance and health of piglets and chickens.	2005 Apr	16080303
Determination and pharmacokinetics of ergometrine maleate in rabbit blood with on line microdialysis sampling and fluorescence detection.	2005 Jun 1	15907615
The quality of antimalarials available in Yemen.	2005 Jun 29	15987508
Determination of ergometrine maleate by fluorescence detection.	2005 May-Jun	15924314
Misoprostol in the management of the third stage of labour in the home delivery setting in rural Gambia: a randomised controlled trial.	2005 Sep	16101608
The role of serendipity in drug discovery.	2006	17117615
Managing asthma in expectant mothers.	2006	16409012
Using clinical audit to improve the quality of obstetric care at the Tibetan Delek Hospital in North India: a longitudinal study.	2006 Jun 7	16759384
Comparison of flow characteristics and vascular reactivity of radial artery and long saphenous vein grafts [NCT00139399].	2006 Mar 3	16722590
Successful management of uterine incision hemorrhage in caesarean section with topical oxidized regenerated cellulose (Surgicel Nu Knit): a case report.	2006 May	16408181
Prospective study of intramuscular ergometrine compared with intramuscular oxytocin for prevention of postpartum hemorrhage.	2007 Jun	17578351
Post partum haemorrhage secondary to uterine atony, complicated by platelet storage pool disease and partial placenta diffusa: a case report.	2008 Dec 13	19077291
A randomized comparative study of prophylactic oxytocin versus ergometrine in the third stage of labor.	2008 May	18164304
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
A case of permanent retinal disturbance postpartum following administration of ergometrine.	2008 Oct	18982049
[Anesthetic management of the ex-utero intrapartum treatment (EXIT) procedure for giant epignathus and of the tumor excision].	2008 Oct	18975539
Intraumbilical veinous injection oxytocin in the active management of third stage of labour.	2008 Sep	18803892
Health facility-based Active Management of the Third Stage of Labor: findings from a national survey in Tanzania.	2009 Apr 16	19371418
The history of ergot of rye (Claviceps purpurea) II: 1900-1940.	2009 Dec	20509463
Active management of the third stage of labour without controlled cord traction: a randomized non-inferiority controlled trial.	2009 Jan 21	19154621
Amniotic fluid embolism.	2009 Jul-Sep	20040809
A randomized comparison of rectal misoprostol with syntometrine on blood loss in the third stage of labour.	2009 Jun	20043525
Combinatorial assembly of simple and complex D-lysergic acid alkaloid peptide classes in the ergot fungus Claviceps purpurea.	2009 Mar 13	19139103
The roles of dopamine and related compounds in reward-seeking behavior across animal phyla.	2010	21048897
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
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
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: 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

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Name

Type

Language

ERGONOVINE

Common Name

English

ergometrine [INN]

Common Name

English

ERGOMETRINE

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