Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00238)
Name
Ergotamine
Synonyms    Click to Show/Hide the Synonyms of This API
ERGOTAMINE; Ergotamin; Gynergen; Ergostat; 113-15-5; ergotamine tartrate; ergotaminum; Ergotamina; Rigetamin; Ergomar; Ergotamine bitartrate; 12'-Hydroxy-2'-methyl-5'alpha-(phenylmethyl)ergotaman-3',6',18-trione; UNII-PR834Q503T; Ergonsvine; CHEBI:64318; PR834Q503T; 379-79-3; Ergotamine [INN:BAN]; Ergotaminum [INN-Latin]; Ergotamina [INN-Spanish]; (5'alpha)-12'-Hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione; (4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-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; Ergotamine (INN); HSDB 4076; Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha)-, (2R,3R)-2,3-dihydroxybutanedioate (2:1) (salt); EINECS 204-023-9; NSC 95090; BRN 0078890; NSC-95090; Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha)-; CHEMBL442; SCHEMBL1483; GTPL149; DTXSID9043774; Ergotamine tartrate, Avetol, Cornutamin, Ergam, Ergotartrate; HMS2089H22; BDBM50027065; ZINC52955754; (5'alpha)-5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxoergotaman; AKOS015896505; DB00696; Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'-alpha)-; NCGC00356592-02; D07906; AB01275473-01; Q419186; (5''alpha)-12''-hydroxy-2''-methyl-5''-(phenylmethyl)ergotoman-3'',6'',18-trione; (5''alpha)-5''-benzyl-12''-hydroxy-2''-methyl-3'',6'',18-trioxoergotaman; (5alpha,5'beta)-5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxoergotaman; 12''-hydroxy-2''-methyl-5''alpha-(phenylmethyl)ergotaman-3'',6'',18-trione; (6aR,9R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide; 1080650-16-3; N-[(2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxo-8,9,10,10a-tetrahydro-5H-oxazolo[[?]]pyrrolo[[?]]pyrazin-2-yl]-methyl-[?]carboxamide
Clinical Status
Approved
Disease Indication Migraine ICD-11: 8A80 [1]
PubChem CID
8223
Formula
C33H35N5O5
Canonical SMILES
C[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)CC4=CC=CC=C4)NC(=O)[C@H]5CN([C@@H]6CC7=CNC8=CC=CC(=C78)C6=C5)C
InChI
1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1
InChIKey
XCGSFFUVFURLIX-VFGNJEKYSA-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=8223"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 581.7 Topological Polar Surface Area 118
XlogP 2 Complexity 1220
Heavy Atom Count 43 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Full List of Drug Formulations (DFMs) Containing This API
          Ergotamine 2 mg tablet Click to Show/Hide the Full List of Formulation(s):          2 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
D&c yellow no. 10; Saccharin sodium dihydrate; Fd&c blue no. 1; Magnesium stearate; Crospovidone; Aluminum oxide; Cellulose, microcrystalline; Peppermint
                   Dosage Form Sublingual Tablet
                   Company Rosedale Therapeutics
                   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]
Saccharin sodium dihydrate DIG Info Carbonic anhydrase XII (Ki = 633 nM) [3]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             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
D&c yellow no. 10; Fd&c blue no. 1; Magnesium stearate; Aluminum oxide; Crospovidone, unspecified; Microcrystalline cellulose; Saccharin sodium
                   Dosage Form Sublingual Tablet
                   Company TerSera Therapeutics
                   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]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
References
1 FDA label for approved ergotamine 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 Carbonic anhydrase inhibitors: copper(II) complexes of polyamino-polycarboxylamido aromatic/heterocyclic sulfonamides are very potent inhibitors of the tumor-associated isoforms IX and XII. Bioorg Med Chem Lett. 2008 Jan 15; 18(2):836-41.
4 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
5 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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