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
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 |
|---|---|---|
| Prophylactic use of oxytocin in the third stage of labour. | 2001 |
|
| Ergot to ergometrine: an obstetric renaissance? | 2001 |
|
| Discrimination between the functional and biochemical effects of two herbal oxytocics on the rat myometrium. | 2001 Aug |
|
| Evidence for postjunctional serotonin (5-HT1) receptors in the trigeminocervical complex. | 2001 Dec |
|
| Oxytocics reverse the tocolytic effect of glyceryl trinitrate on the human uterus. | 2001 Feb |
|
| Effects of serotonin, dopamine and ergometrine on locomotion in the pulmonate mollusc Helix lucorum. | 2001 May |
|
| A prospective randomised trial to compare the efficacy and safety of hemabate and syntometrine for the prevention of primary postpartum haemorrhage. | 2001 Oct |
|
| Chest pain after coronary artery stent implantation. | 2002 Mar 1 |
|
| [Hawaiian baby woodrose: (Psycho-) Pharmacological effects of the seeds of Argyreia nervosa. A case-orientated demonstration]. | 2002 Sep |
|
| John Chassar Moir (1900-1977) and the discovery of ergometrine. | 2002 Sep |
|
| Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor. | 2004 Jan 26 |
|
| Fungal secondary metabolism - from biochemistry to genomics. | 2005 Dec |
|
| Ergometrine. | 2005 Jan |
|
| Determination of ergometrine maleate by fluorescence detection. | 2005 May-Jun |
|
| Activity of aqueous extract of the bark of Vitex doniana on uterine muscle response to drugs. | 2005 Sep |
|
| Misoprostol in the management of the third stage of labour in the home delivery setting in rural Gambia: a randomised controlled trial. | 2005 Sep |
|
| The role of serendipity in drug discovery. | 2006 |
|
| Misoprostol and active management of the third stage of labor. | 2006 Aug |
|
| Oral misoprostol in the third stage of labor. | 2006 Jan |
|
| Comparison of flow characteristics and vascular reactivity of radial artery and long saphenous vein grafts [NCT00139399]. | 2006 Mar 3 |
|
| Successful management of uterine incision hemorrhage in caesarean section with topical oxidized regenerated cellulose (Surgicel Nu Knit): a case report. | 2006 May |
|
| Oxytocin-ergometrine co-administration does not reduce blood loss at caesarean delivery for labour arrest. | 2008 Apr |
|
| Post partum haemorrhage secondary to uterine atony, complicated by platelet storage pool disease and partial placenta diffusa: a case report. | 2008 Dec 13 |
|
| Postpartum haemorrhage: prevention. | 2008 Dec 15 |
|
| Simultaneous determination of six major ergot alkaloids and their epimers in cereals and foodstuffs by LC-MS-MS. | 2008 May |
|
| 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 |
|
| A case of permanent retinal disturbance postpartum following administration of ergometrine. | 2008 Oct |
|
| Health facility-based Active Management of the Third Stage of Labor: findings from a national survey in Tanzania. | 2009 Apr 16 |
|
| Active management of the third stage of labour without controlled cord traction: a randomized non-inferiority controlled trial. | 2009 Jan 21 |
|
| WITHDRAWN: Active versus expectant management in the third stage of labour. | 2009 Jul 8 |
|
| External aortic compression device: the first aid for postpartum hemorrhage control. | 2009 Jun |
|
| Combinatorial assembly of simple and complex D-lysergic acid alkaloid peptide classes in the ergot fungus Claviceps purpurea. | 2009 Mar 13 |
|
| The roles of dopamine and related compounds in reward-seeking behavior across animal phyla. | 2010 |
|
| 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 |
|
| Care during the third stage of labour: obstetricians views and practice in an Albanian maternity hospital. | 2010 Jan 26 |
|
| Policies for care during the third stage of labour: a survey of maternity units in Syria. | 2010 Jun 22 |
|
| 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
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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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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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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 |
ACTIVE MOIETY
PARENT (SALT/SOLVATE)
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
