methylergometrine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
ergot alkaloid derivatives 1764 113-42-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • methylergometrine maleate
  • methylergonovine
  • methergine
  • methergen
  • methylergobasin
  • methylergobasine
  • methylergobrevin
  • partergin
  • methylergonovine maleate
  • methylergometrine
  • methylergometrin
A homolog of ERGONOVINE containing one more CH2 group. (Merck Index, 11th ed)
  • Molecular weight: 339.44
  • Formula: C20H25N3O2
  • CLOGP: 1.76
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 3
  • TPSA: 68.36
  • ALOGS: -3.22
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.20 mg O
0.20 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability) 60 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.96 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 7.18 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.85 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Nov. 19, 1946 FDA EDISON THERAPS LLC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Arteriospasm coronary 83.07 58.25 13 194 672 2357206
Wrong product administered 80.72 58.25 14 193 1368 2356510
Disseminated intravascular coagulation 62.47 58.25 13 194 3337 2354541
Cerebral vasoconstriction 60.96 58.25 9 198 311 2357567

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Wrong product administered 221.60 118.61 29 32 1130 1745590

Pharmacologic Action:

SourceCodeDescription
ATC G02AB01 GENITO URINARY SYSTEM AND SEX HORMONES
OTHER GYNECOLOGICALS
UTEROTONICS
Ergot alkaloids
ATC G02AC01 GENITO URINARY SYSTEM AND SEX HORMONES
OTHER GYNECOLOGICALS
UTEROTONICS
Ergot alkaloids and oxytocin incl. analogues, in combination
FDA CS M0007652 Ergolines
FDA EPC N0000175827 Ergot Derivative
MeSH PA D010120 Oxytocics
MeSH PA D012102 Reproductive Control Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Postpartum hemorrhage indication 47821001
Postabortal Hemorrhage indication
Incomplete miscarriage off-label use 156072005
Hypertensive disorder contraindication 38341003 DOID:10763
Pregnancy-induced hypertension contraindication 48194001
Kidney disease contraindication 90708001 DOID:557
Seizure disorder contraindication 128613002
Cerebrovascular accident contraindication 230690007
Disease of liver contraindication 235856003 DOID:409
Sepsis syndrome contraindication 238150007
Pregnancy, function contraindication 289908002
Arteriosclerosis obliterans contraindication 361133006 DOID:5160

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 12.56 acidic
pKa2 13.6 acidic
pKa3 7.01 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
D(1A) dopamine receptor GPCR ANTAGONIST Ki 6.27 DRUG MATRIX CHEMBL
5-hydroxytryptamine receptor 2A GPCR AGONIST Ki 9.40 IUPHAR
5-hydroxytryptamine receptor 2C GPCR AGONIST Ki 8.30 IUPHAR
5-hydroxytryptamine receptor 1F GPCR ANTAGONIST Ki 7.50 IUPHAR
D(2) dopamine receptor GPCR Ki 6.56 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 6.22 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR Ki 8.63 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 8.93 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 6.68 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 7.24 DRUG MATRIX
Cytochrome P450 2D6 Enzyme IC50 6.70 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR PARTIAL AGONIST Ki 9.10 CHEMBL
5-hydroxytryptamine receptor 1E GPCR ANTAGONIST Ki 7.20 IUPHAR
5-hydroxytryptamine receptor 1B GPCR Ki 8.03 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR IC50 8.39 CHEMBL
5-hydroxytryptamine receptor 2C GPCR AGONIST Ki 7.90 IUPHAR
5-hydroxytryptamine receptor 2A GPCR AGONIST Ki 7.90 IUPHAR

External reference:

IDSource
4018757 VUID
N0000179466 NUI
C0289432 UMLSCUI
D00680 KEGG_DRUG
40562000 SNOMEDCT_US
6883 RXNORM
126074008 SNOMEDCT_US
d00587 MMSL
4019831 VANDF
004941 NDDF
DB00353 DRUGBANK_ID
CHEMBL1200843 ChEMBL_ID
IR84JPZ1RK UNII
57432-61-8 SECONDARY_CAS_RN
2900 INN_ID
H8D PDB_CHEM_ID
CHEBI:6874 CHEBI
CHEMBL1201356 ChEMBL_ID
D008755 MESH_DESCRIPTOR_UI
8226 PUBCHEM_CID
150 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Methylergonovine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 0054-0639 TABLET 0.20 mg ORAL ANDA 12 sections
Methylergonovine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 0093-3655 TABLET 0.20 mg ORAL ANDA 12 sections
Methylergonovine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 0517-0740 INJECTION, SOLUTION 0.20 mg INTRAMUSCULAR ANDA 12 sections
METHERGINE HUMAN PRESCRIPTION DRUG LABEL 1 12634-179 TABLET, COATED 0.20 mg ORAL NDA 13 sections
Methylergonovine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 17478-501 INJECTION 0.20 mg INTRAVENOUS ANDA 13 sections
Methylergonovine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 17856-3655 TABLET 0.20 mg ORAL ANDA 12 sections
Methergine HUMAN PRESCRIPTION DRUG LABEL 1 27437-050 TABLET 0.20 mg ORAL ANDA 12 sections
Methylergonovine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 40032-140 TABLET 0.20 mg ORAL ANDA 14 sections
Methylergonovine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 43386-140 TABLET 0.20 mg ORAL ANDA 12 sections
METHYLERGONOVINE MALEATE HUMAN PRESCRIPTION DRUG LABEL 1 50090-4536 INJECTION 0.20 mg INTRAVENOUS ANDA 14 sections
METHYLERGONOVINE MALEATE HUMAN PRESCRIPTION DRUG LABEL 1 51991-144 INJECTION 0.20 mg INTRAVENOUS ANDA 13 sections
Methylergonovine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 60687-410 TABLET 0.20 mg ORAL ANDA 13 sections
Methergine HUMAN PRESCRIPTION DRUG LABEL 1 63629-3791 TABLET, COATED 0.20 mg ORAL NDA 12 sections
METHYLERGONOVINE MALEATE HUMAN PRESCRIPTION DRUG LABEL 1 63704-004 INJECTION, SOLUTION 0.20 mg INTRAVENOUS ANDA 13 sections
methylergonovine maleate HUMAN PRESCRIPTION DRUG LABEL 1 63704-006 TABLET 0.20 mg ORAL ANDA 14 sections
Methergine HUMAN PRESCRIPTION DRUG LABEL 1 66336-402 TABLET, COATED 0.20 mg ORAL NDA 14 sections
Methylergonovine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 69238-1605 TABLET 0.20 mg ORAL ANDA 12 sections