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.[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
| 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 |
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 |
|---|---|---|---|---|
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 |
T1/2
| 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: |
unhealthy Health Status: unhealthy Condition: Postpartum Haemorrhage 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 (max) Recommended Dose: 500 ug Route: intramuscular Route: single Dose: 500 ug Sources: |
unhealthy Health Status: unhealthy Condition: Postpartum Haemorrhage Sources: |
|
| Acute pulmonary oedema | rare | 500 ug single, intramuscular (max) Recommended Dose: 500 ug Route: intramuscular Route: single Dose: 500 ug Sources: |
unhealthy Health Status: unhealthy Condition: Postpartum Haemorrhage 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 |
|---|---|---|
| The cardiovascular effects of oxytocic drugs. | 1972 Aug |
|
| [Acute myocardial infarction probably induced by the oral administration of bromocriptine: a case report]. | 1989 Jun |
|
| 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 |
|
| Ergometrine given during caesarean section and incidence of delayed postpartum haemorrhage due to uterine atony. | 2007 Nov |
|
| Effect of oxytocics on the blood pressure of normotensive Nigerian parturients. | 2007 Sep |
|
| Oxytocin-ergometrine co-administration does not reduce blood loss at caesarean delivery for labour arrest. | 2008 Apr |
|
| Misoprostol in addition to routine treatment of postpartum hemorrhage: a hospital-based randomized-controlled trial in Karachi, Pakistan. | 2008 Aug 21 |
|
| Post partum haemorrhage secondary to uterine atony, complicated by platelet storage pool disease and partial placenta diffusa: a case report. | 2008 Dec 13 |
|
| 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 |
|
| A case of permanent retinal disturbance postpartum following administration of ergometrine. | 2008 Oct |
|
| [Anesthetic management of the ex-utero intrapartum treatment (EXIT) procedure for giant epignathus and of the tumor excision]. | 2008 Oct |
|
| Intraumbilical veinous injection oxytocin in the active management of third stage of labour. | 2008 Sep |
|
| The history of ergot of rye (Claviceps purpurea) II: 1900-1940. | 2009 Dec |
|
| Use of facility assessment data to improve reproductive health service delivery in the Democratic Republic of the Congo. | 2009 Dec 21 |
|
| Carbetocin versus syntometrine in prevention of post-partum hemorrhage following vaginal delivery. | 2009 Feb |
|
| Active management of the third stage of labour without controlled cord traction: a randomized non-inferiority controlled trial. | 2009 Jan 21 |
|
| Amniotic fluid embolism. | 2009 Jul-Sep |
|
| 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 |
|
| The B-Lynch suture technique for postpartum haemorrhage: a decade of experience and outcome. | 2009 May |
|
| Associations of drugs routinely given in labour with breastfeeding at 48 hours: analysis of the Cardiff Births Survey. | 2009 Nov |
|
| 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
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
Fri Dec 15 15:26:24 GMT 2023
by
admin
on
Fri Dec 15 15:26:24 GMT 2023
|
| Record UNII |
CFD408L3CG
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| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
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| Code System | Code | Type | Description | ||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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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 |
