Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00418)
Name
Methylergonovine
Synonyms    Click to Show/Hide the Synonyms of This API
methylergonovine; Methylergometrine; Methylergobasin; Methylergometrin; Methergine; Methylergobasine; Methylergobrevin; Methylergonovin; Methergen; Partergin; Basofortina; Methylergometrine maleate; 113-42-8; UNII-W53L6FE61V; Ergometrine, methyl-; W53L6FE61V; CHEMBL1201356; ME 277; D-Lysergic acid-(+)-butanolamide-(2); (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide; NCGC00017258-04; Metilergometrina; Metilergometrinio; DSSTox_CID_3283; Methylergometrinum; Metilergometrina [DCIT]; (8beta)-N-[(2S)-1-hydroxybutan-2-yl]-6-methyl-9,10-didehydroergoline-8-carboxamide; DSSTox_RID_76957; Lysergic acid butanolamide; DSSTox_GSID_23283; Methylergometrine [INN:BAN]; Ergotyl; Lysergamide, N-((S)-1-(hydroxymethyl)propyl)-; Methylergometrinum [INN-Latin]; Metilergometrinio [INN-Spanish]; Ergotyl (TN); D-Lysergic acid-dl-hydroxybutylamide-2; HSDB 3364; Methylergometrine (INN); N-(alpha-(Hydroxymethyl)propyl)-D-lysergamide; EINECS 204-027-0; CAS-113-42-8; 9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-6-methylergoline-8-carboxamide; 9,10-Didehydro-N-(alpha-(hydroxymethyl)propyl)-6-methyl-ergoline-8-beta-carboxamide; Ergoline-8-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-6-methyl-, (8beta(S))-; Spectrum_000263; Prestwick3_000374; Spectrum2_000613; Spectrum3_000502; Spectrum5_001879; Biomol-NT_000154; Lopac0_000794; SCHEMBL78176; BSPBio_000527; BSPBio_002023; GTPL150; KBioSS_000743; DivK1c_000357; SPBio_000546; D-lysergic acid 1-butanolamide; BPBio1_000442; BPBio1_000581; DTXSID1023283; CHEBI:92607; KBio1_000357; KBio2_000743; KBio2_003311; KBio2_005879; KBio3_001523; NINDS_000357; Tox21_110809; BDBM50330860; ZINC95619105; Tox21_110809_1; CCG-204878; DB00353; SDCCGSBI-0050771.P005; (8beta)-N-[(1S)-1-(hydroxymethyl)propyl]-6-methyl-9,10-didehydroergoline-8-carboxamide; Ergoline-8-beta-carboxamide, 9,10-didehydro-N-((S)-1-(hydroxymethyl)propyl)-6-methyl-; IDI1_000357; NCGC00017258-03; NCGC00017258-05; NCGC00017258-06; NCGC00017258-08; NCGC00017258-12; NCGC00024646-02; NCGC00024646-03; SBI-0050771.P004; AB00514664; D08207; AB00053497_03; 191038-EP2275420A1; 191038-EP2280008A2; Q424477; BRD-K34685430-001-01-1; BRD-K34685430-050-04-2; BRD-K34685430-050-06-7; (4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
Clinical Status
Approved
Disease Indication Migraine ICD-11: 8A80 [1]
PubChem CID
8226
Formula
C20H25N3O2
Canonical SMILES
CC[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
InChI
1S/C20H25N3O2/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25)/t13-,14+,18-/m1/s1
InChIKey
UNBRKDKAWYKMIV-QWQRMKEZSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=8226"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 339.4 Topological Polar Surface Area 68.4
XlogP 2.3 Complexity 549
Heavy Atom Count 25 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Full List of Drug Formulations (DFMs) Containing This API
          Methylergonovine 0.2 mg tablet Click to Show/Hide the Full List of Formulation(s):          7 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Methylparaben; Stearic acid; Lactose; Sodium benzoate; Maleic acid; D&c red no. 7; Fd&c blue no. 1; Propylparaben; Sodium hydroxide; Sucrose; Talc; Titanium dioxide; Povidone; Acacia; Carnauba wax; Gelatin; Starch, corn
                   Dosage Form Oral Tablet
                   Company Dispensing Solution; PD-Rx Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [4]
Sodium benzoate DIG Info Carbonic anhydrase II (Ki = 30000 nM) [5]
Propyl 4-hydroxybenzoate DIG Info Estrogen receptor alpha (IC50 = 11 uM) [4]
Maleic acid DIG Info D-amino acid oxidase (IC50 = 357000 nM) [6]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [7]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Methylparaben; Stearic acid; Lactose; Sodium benzoate; Maleic acid; D&c red no. 7; Fd&c blue no. 1; Propylparaben; Sodium hydroxide; Sucrose; Talc; Titanium dioxide; Acacia; Carnauba wax; Gelatin; Povidones; Starch, corn
                   Dosage Form Oral Tablet
                   Company Bryant Ranch Prepack; Novartis Pharmaceuticals Corporation
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [4]
Sodium benzoate DIG Info Carbonic anhydrase II (Ki = 30000 nM) [5]
Propyl 4-hydroxybenzoate DIG Info Estrogen receptor alpha (IC50 = 11 uM) [4]
Maleic acid DIG Info D-amino acid oxidase (IC50 = 357000 nM) [6]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Lactose monohydrate; Methylparaben sodium; Propylparaben sodium; Tartaric acid, d-; Gelatin hydrolysate (porcine skin, mw 3000); Povidone k30; Acacia angustissima bark; Cellulose, microcrystalline; Starch, corn
                   Dosage Form Oral Tablet
                   Company RemedyRepack
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
D-tartaric acid DIG Info Olfactory receptor 51E2 (EC50 = 1.9 nM) [8]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [4]
Sodium methylparaben DIG Info Estrogen receptor beta (EC50 = 1860 nM) [9]
Propylparaben sodium DIG Info Estrogen receptor alpha (EC50 = 38200 nM) [9]
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [7]
             Drug Formulation 4 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Lactose; Sodium benzoate; Maleic acid; Sodium hydroxide; Sucrose; Talc; Titanium dioxide; Povidone; Acacia; Carnauba wax; Gelatin
                   Dosage Form Oral Tablet
                   Company Apotheca
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [4]
Sodium benzoate DIG Info Carbonic anhydrase II (Ki = 30000 nM) [5]
Maleic acid DIG Info D-amino acid oxidase (IC50 = 357000 nM) [6]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [7]
             Drug Formulation 5 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Methylparaben; Stearic acid; Lactose monohydrate; Propylparaben; Tartaric acid; Povidone; Acacia; Cellulose, microcrystalline; Gelatin; Starch, corn
                   Dosage Form Oral Tablet
                   Company PD-Rx Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [4]
Propyl 4-hydroxybenzoate DIG Info Estrogen receptor alpha (IC50 = 11 uM) [4]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [7]
             Drug Formulation 6 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Methylparaben; Stearic acid; Lactose monohydrate; Propylparaben; Tartaric acid; Povidone k30; Acacia; Cellulose, microcrystalline; Gelatin; Starch, corn
                   Dosage Form Oral Tablet
                   Company Avera McKennan Hospital; Lupin Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [4]
Propyl 4-hydroxybenzoate DIG Info Estrogen receptor alpha (IC50 = 11 uM) [4]
             Drug Formulation 7 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Methylparaben; Stearic acid; Lactose monohydrate; Propylparaben; Tartaric acid; Povidone k30; Acacia; Cellulose, microcrystalline; Gelatin; Starch, corn
                   Dosage Form Oral Tablet
                   Company American Health Packaging; GAVIS Pharmaceuticals; Kaiser Foundation Hospitals; Novel Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [3]
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [4]
Propyl 4-hydroxybenzoate DIG Info Estrogen receptor alpha (IC50 = 11 uM) [4]
References
1 FDA label for approved methylergonovine from the official website of the U.S. Food and Drug Administration.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15; 21(6):1564-9.
4 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
5 Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1; 15(3):573-8.
6 Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro. J Med Chem. 2013 Mar 14; 56(5):1894-907.
7 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
8 US patent application no. 20180116992A1, Modulators of Prostate-Specific G-Protein Receptor (PSGR/OR51E2) and Methods of Using Same.
9 Discovery of natural estrogen receptor modulators with structure-based virtual screening. Bioorg Med Chem Lett. 2013 Jun 1; 23(11):3329-33.

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