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
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
| 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 |
| 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 |
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2095203 |
|||
Target ID: CHEMBL2096904 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | ERGOMETRINE Approved UseErgometrine 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. |
|||
| Preventing | ERGOMETRINE Approved UseErgometrine 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. |
Cmax
| 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 |
T1/2
| 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: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Vasoconstriction, Acute pulmonary oedema... Other AEs: Vasoconstriction Sources: Acute pulmonary oedema (rare) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Vasoconstriction | 500 ug single, intramuscular Recommended Dose: 500 ug Route: intramuscular Route: single Dose: 500 ug Sources: |
unhealthy Health Status: unhealthy Sources: |
|
| Acute pulmonary oedema | rare | 500 ug single, intramuscular Recommended Dose: 500 ug Route: intramuscular Route: single Dose: 500 ug Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| inconclusive [IC50 19.9526 uM] | ||||
| no [IC50 >10 uM] | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| weak [Ki 100 uM] | ||||
| yes [Inhibition 10 uM] | ||||
| yes [Inhibition 10 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
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 |
|
| Postpartum hemorrhage in a Jehovah's Witness patient controlled with Tisseel, tranexamic acid, and recombinant factor VIIa. | 2010-10 |
|
| How HIV/AIDS scale-up has impacted on non- HIV priority services in Zambia. | 2010-09-08 |
|
| 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 |
|
| Can the Non-pneumatic Anti-Shock Garment (NASG) reduce adverse maternal outcomes from postpartum hemorrhage? Evidence from Egypt and Nigeria. | 2010-09-01 |
|
| Tako-tsubo cardiomyopathy after administration of ergometrine following elective caesarean delivery: a case report. | 2010-08-20 |
|
| Strengthening the emergency healthcare system for mothers and children in The Gambia. | 2010-08-18 |
|
| Ergometrinine. | 2010-08-11 |
|
| Recent trends in the impurity profile of pharmaceuticals. | 2010-07 |
|
| Argyreia speciosa (Linn. f.) sweet: A comprehensive review. | 2010-07 |
|
| Policies for care during the third stage of labour: a survey of maternity units in Syria. | 2010-06-22 |
|
| What measured blood loss tells us about postpartum bleeding: a systematic review. | 2010-06 |
|
| Challenges of major obstetric haemorrhage. | 2010-06 |
|
| Care during the third stage of labour: a postal survey of UK midwives and obstetricians. | 2010-05-21 |
|
| Coronary vasospasm secondary to allergic reaction following food ingestion: a case of type I variant Kounis syndrome. | 2010-05 |
|
| A novel chemiluminescence method for the determination of ergometrine maleate in serum sample without chemiluminescence reagent. | 2010-04-15 |
|
| Prinzmetal-variant angina in a patient using zolmitriptan and citalopram. | 2010-02 |
|
| Care during the third stage of labour: obstetricians views and practice in an Albanian maternity hospital. | 2010-01-26 |
|
| The roles of dopamine and related compounds in reward-seeking behavior across animal phyla. | 2010 |
|
| Amniotic fluid embolism. | 2009-12-31 |
|
| Use of facility assessment data to improve reproductive health service delivery in the Democratic Republic of the Congo. | 2009-12-21 |
|
| The history of ergot of rye (Claviceps purpurea) II: 1900-1940. | 2009-12 |
|
| Methyl-ergometrine maleate from synchrotron powder diffraction data. | 2009-11-28 |
|
| Emergent management of postpartum hemorrhage for the general and acute care surgeon. | 2009-11-25 |
|
| Associations of drugs routinely given in labour with breastfeeding at 48 hours: analysis of the Cardiff Births Survey. | 2009-11 |
|
| WITHDRAWN: Active versus expectant management in the third stage of labour. | 2009-07-08 |
|
| A randomized comparison of rectal misoprostol with syntometrine on blood loss in the third stage of labour. | 2009-06 |
|
| External aortic compression device: the first aid for postpartum hemorrhage control. | 2009-06 |
|
| The B-Lynch suture technique for postpartum haemorrhage: a decade of experience and outcome. | 2009-05 |
|
| Health facility-based Active Management of the Third Stage of Labor: findings from a national survey in Tanzania. | 2009-04-16 |
|
| Combinatorial assembly of simple and complex D-lysergic acid alkaloid peptide classes in the ergot fungus Claviceps purpurea. | 2009-03-13 |
|
| Anticonvulsant Activity of Argyreia speciosa in Mice. | 2009-03 |
|
| Determination of ergot alkaloids: purity and stability assessment of standards and optimization of extraction conditions for cereal samples. | 2009-02-11 |
|
| Carbetocin versus syntometrine in prevention of post-partum hemorrhage following vaginal delivery. | 2009-02 |
|
| Active management of the third stage of labour without controlled cord traction: a randomized non-inferiority controlled trial. | 2009-01-21 |
|
| Postpartum haemorrhage: prevention. | 2008-12-15 |
|
| Post partum haemorrhage secondary to uterine atony, complicated by platelet storage pool disease and partial placenta diffusa: a case report. | 2008-12-13 |
|
| 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 |
|
| A case of permanent retinal disturbance postpartum following administration of ergometrine. | 2008-10 |
|
| [Anesthetic management of the ex-utero intrapartum treatment (EXIT) procedure for giant epignathus and of the tumor excision]. | 2008-10 |
|
| Intraumbilical veinous injection oxytocin in the active management of third stage of labour. | 2008-09 |
|
| Misoprostol in addition to routine treatment of postpartum hemorrhage: a hospital-based randomized-controlled trial in Karachi, Pakistan. | 2008-08-21 |
|
| Association between anaemia during pregnancy and blood loss at and after delivery among women with vaginal births in Pemba Island, Zanzibar, Tanzania. | 2008-06 |
|
| Strategies to manage major obstetric haemorrhage. | 2008-06 |
|
| Simultaneous determination of six major ergot alkaloids and their epimers in cereals and foodstuffs by LC-MS-MS. | 2008-05 |
|
| A randomized comparative study of prophylactic oxytocin versus ergometrine in the third stage of labor. | 2008-05 |
|
| Oxytocin-ergometrine co-administration does not reduce blood loss at caesarean delivery for labour arrest. | 2008-04 |
|
| Ergometrine administration for post-partum haemorrhage in an undiagnosed pre-eclamptic. | 2008-01 |
|
| [Acute myocardial infarction probably induced by the oral administration of bromocriptine: a case report]. | 1989-06 |
|
| The cardiovascular effects of oxytocic drugs. | 1972-08 |
Patents
Sample Use Guides
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:57:47 GMT 2025
by
admin
on
Mon Mar 31 17:57:47 GMT 2025
|
| Record UNII |
CFD408L3CG
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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Preferred Name | English | ||
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Common Name | English |
| Code System | Code | Type | Description | ||
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76962251
Created by
admin on Mon Mar 31 17:57:47 GMT 2025 , Edited by admin on Mon Mar 31 17:57:47 GMT 2025
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PRIMARY | |||
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5004-95-5
Created by
admin on Mon Mar 31 17:57:47 GMT 2025 , Edited by admin on Mon Mar 31 17:57:47 GMT 2025
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PRIMARY | |||
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CFD408L3CG
Created by
admin on Mon Mar 31 17:57:47 GMT 2025 , Edited by admin on Mon Mar 31 17:57:47 GMT 2025
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PRIMARY |
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
