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

C[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2CC3=CNC4=C3C(=CC=C4)C2=C1

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 65 Target ID: CHEMBL2095203 Sources: http://www.medsafe.govt.nz/profs/Datasheet/d/DBLErgometrineinj.pdf	Partial Agonist 297
Serotonin (5-HT) receptor 34 Target ID: CHEMBL2096904 Sources: http://www.medsafe.govt.nz/profs/Datasheet/d/DBLErgometrineinj.pdf	Partial Agonist 297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Postpartum haemorrhage 4 Sources: http://www.medsafe.govt.nz/profs/Datasheet/d/DBLErgometrineinj.pdf	Preventing		Approved 8583	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 8583	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
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
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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
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

Doses

Dose	Population	Adverse events
500 ug single, intramuscular 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 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 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 Sources: https://www.medicines.org.uk/emc/product/6265/smpc#CLINICAL_PRECAUTIONS
Acute pulmonary oedema	rare	500 ug single, intramuscular 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 Sources: https://www.medicines.org.uk/emc/product/6265/smpc#CLINICAL_PRECAUTIONS

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 activator 150 inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 CYP1A2 2153 CYP2A6 879 CYP2C19 2057 CYP2E1 1060 OATP1B1 1079 OATP1B3 961 CYP19A1 429

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 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 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExOTQ0MyJ9fQ%3D%3D	no [IC50 >10 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144205575	no
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExOTQ0MyJ9fQ%3D%3D	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExOTQ0MyJ9fQ%3D%3D	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExOTQ0MyJ9fQ%3D%3D	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTE5NDQzIn19	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExOTQ0MyJ9fQ%3D%3D	no
CYP3A4 2633	activator 342 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTE5NDQzIn19	no
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11961113/, http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50390991	weak [Ki 100 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMTMxMzUifX0%3D	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 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 1946	substrate 4014 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 2263	inhibitor 2237 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
Evaluation of health workforce competence in maternal and neonatal issues in public health sector of Pakistan: an Assessment of their training needs.	2010-11-27	21110888
Postpartum hemorrhage in a Jehovah's Witness patient controlled with Tisseel, tranexamic acid, and recombinant factor VIIa.	2010-10	21176309
How HIV/AIDS scale-up has impacted on non- HIV priority services in Zambia.	2010-09-08	20825666
The perspectives of clients and unqualified allopathic practitioners on the management of delivery care in urban slums, Dhaka, Bangladesh - a mixed method study.	2010-09-07	20822521
Can the Non-pneumatic Anti-Shock Garment (NASG) reduce adverse maternal outcomes from postpartum hemorrhage? Evidence from Egypt and Nigeria.	2010-09-01	20809942
Tako-tsubo cardiomyopathy after administration of ergometrine following elective caesarean delivery: a case report.	2010-08-20	20727147
Strengthening the emergency healthcare system for mothers and children in The Gambia.	2010-08-18	20718979
Ergometrinine.	2010-08-11	21588630
Recent trends in the impurity profile of pharmaceuticals.	2010-07	22247862
Argyreia speciosa (Linn. f.) sweet: A comprehensive review.	2010-07	22228958
Policies for care during the third stage of labour: a survey of maternity units in Syria.	2010-06-22	20569439
What measured blood loss tells us about postpartum bleeding: a systematic review.	2010-06	20406227
Challenges of major obstetric haemorrhage.	2010-06	20110196
Care during the third stage of labour: a postal survey of UK midwives and obstetricians.	2010-05-21	20492659
Coronary vasospasm secondary to allergic reaction following food ingestion: a case of type I variant Kounis syndrome.	2010-05	20512455
A novel chemiluminescence method for the determination of ergometrine maleate in serum sample without chemiluminescence reagent.	2010-04-15	20188953
Prinzmetal-variant angina in a patient using zolmitriptan and citalopram.	2010-02	20159412
Care during the third stage of labour: obstetricians views and practice in an Albanian maternity hospital.	2010-01-26	20102601
The roles of dopamine and related compounds in reward-seeking behavior across animal phyla.	2010	21048897
Amniotic fluid embolism.	2009-12-31	20040809
Use of facility assessment data to improve reproductive health service delivery in the Democratic Republic of the Congo.	2009-12-21	20025757
The history of ergot of rye (Claviceps purpurea) II: 1900-1940.	2009-12	20509463
Methyl-ergometrine maleate from synchrotron powder diffraction data.	2009-11-28	21578950
Emergent management of postpartum hemorrhage for the general and acute care surgeon.	2009-11-25	19939251
Associations of drugs routinely given in labour with breastfeeding at 48 hours: analysis of the Cardiff Births Survey.	2009-11	19735379
WITHDRAWN: Active versus expectant management in the third stage of labour.	2009-07-08	19588315
A randomized comparison of rectal misoprostol with syntometrine on blood loss in the third stage of labour.	2009-06	20043525
External aortic compression device: the first aid for postpartum hemorrhage control.	2009-06	19527382
The B-Lynch suture technique for postpartum haemorrhage: a decade of experience and outcome.	2009-05	19835492
Health facility-based Active Management of the Third Stage of Labor: findings from a national survey in Tanzania.	2009-04-16	19371418
Combinatorial assembly of simple and complex D-lysergic acid alkaloid peptide classes in the ergot fungus Claviceps purpurea.	2009-03-13	19139103
Anticonvulsant Activity of Argyreia speciosa in Mice.	2009-03	20336209
Determination of ergot alkaloids: purity and stability assessment of standards and optimization of extraction conditions for cereal samples.	2009-02-11	19202797
Carbetocin versus syntometrine in prevention of post-partum hemorrhage following vaginal delivery.	2009-02	19215547
Active management of the third stage of labour without controlled cord traction: a randomized non-inferiority controlled trial.	2009-01-21	19154621
Postpartum haemorrhage: prevention.	2008-12-15	19445784
Post partum haemorrhage secondary to uterine atony, complicated by platelet storage pool disease and partial placenta diffusa: a case report.	2008-12-13	19077291
Bromocriptine, a dopamine D(2) receptor agonist with the structure of the amino acid ergot alkaloids, induces neurite outgrowth in PC12 cells.	2008-11-19	18835264
A case of permanent retinal disturbance postpartum following administration of ergometrine.	2008-10	18982049
[Anesthetic management of the ex-utero intrapartum treatment (EXIT) procedure for giant epignathus and of the tumor excision].	2008-10	18975539
Intraumbilical veinous injection oxytocin in the active management of third stage of labour.	2008-09	18803892
Misoprostol in addition to routine treatment of postpartum hemorrhage: a hospital-based randomized-controlled trial in Karachi, Pakistan.	2008-08-21	18718007
Association between anaemia during pregnancy and blood loss at and after delivery among women with vaginal births in Pemba Island, Zanzibar, Tanzania.	2008-06	18686556
Strategies to manage major obstetric haemorrhage.	2008-06	18458542
Simultaneous determination of six major ergot alkaloids and their epimers in cereals and foodstuffs by LC-MS-MS.	2008-05	18415090
A randomized comparative study of prophylactic oxytocin versus ergometrine in the third stage of labor.	2008-05	18164304
Oxytocin-ergometrine co-administration does not reduce blood loss at caesarean delivery for labour arrest.	2008-04	18333937
Ergometrine administration for post-partum haemorrhage in an undiagnosed pre-eclamptic.	2008-01	18326144
[Acute myocardial infarction probably induced by the oral administration of bromocriptine: a case report].	1989-06	2636638
The cardiovascular effects of oxytocic drugs.	1972-08	4673361

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 `Mon Mar 31 17:33:12 GMT 2025` Edited by `admin` on `Mon Mar 31 17:33:12 GMT 2025`
Record UNII	WH41D8433D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ERGOMETRINE

Preferred Name

English

ERGONOVINE

Common Name

English

ergometrine [INN]

Common 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