Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00199)
Name
Dihydroergotamine
Synonyms    Click to Show/Hide the Synonyms of This API
dihydroergotamine; 511-12-6; 9,10-Dihydroergotamine; Dihidroergotamina; Dihydroergotaminum; Migranal; Dihydroergotaminum [INN-Latin]; Dihidroergotamina [INN-Spanish]; Dehydroergotamine; UNII-436O5HM03C; MAP0004; CHEMBL1732; CHEBI:4562; D.H.E. 45; 436O5HM03C; Ergotamine, 9,10-dihydro-; NCGC00017400-05; Levadex; Diidroergotamina; 5'-Benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman; Diidroergotamina [DCIT]; 9,10-Dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione; DSSTox_CID_25614; DSSTox_RID_81003; DSSTox_GSID_45614; 9,10-dihydro-ergotamine; Neomigran (TN); (2R,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),9,12,14-tetraene-4-carboxamide; (6aR,9R,10aR)-N-((2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-8H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide; CAS-511-12-6; Dihydroergotamine (INN); EINECS 208-123-3; BRN 5720196; Dihydroergotamine [INN:BAN]; NCGC00017400-10; MAP 0004; MAP-0004; Spectrum_001057; Spectrum2_001188; Spectrum3_000395; Spectrum4_000958; Spectrum5_000905; Lopac0_000357; SCHEMBL44931; BSPBio_002209; GTPL121; KBioGR_001576; KBioSS_001537; Ergotaman-3',6',18-trione, 9,10-dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha,10alpha)-; BIDD:GT0120; DivK1c_000592; SPBio_001235; DTXSID6045614; KBio1_000592; KBio2_001537; KBio2_004105; KBio2_006673; KBio3_001429; NINDS_000592; 7-Methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid ((2R,5S,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxo-octahydro-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-amide; ZINC3978005; Tox21_110821; BDBM50295557; Tox21_110821_1; CCG-204452; DB00320; SDCCGSBI-0050345.P005; (10alphaH)-5'alpha-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman; IDI1_000592; NCGC00017400-06; NCGC00017400-07; NCGC00017400-08; SBI-0050345.P004; C07798; D07837; 42124-EP2275420A1; 42124-EP2280008A2; 42124-EP2298764A1; 42124-EP2298765A1; 42124-EP2311808A1; 42124-EP2311829A1; AB00053458_03; 511D126; Q421336; BRD-K72166146-066-02-1; BRD-K72166146-066-03-9; (2R,4R,7R)-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]-6-methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),9,12,14-tetraene-4-carboxamide; (5alpha,5'beta,10alpha)-5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman; (6aR,9R,10aR)-N-((2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-2H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide; 7-Methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (5-benzyl-10b-hydroxy-2-methyl-3,6-dioxo-octahydro-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-amide
Clinical Status
Approved
Disease Indication Migraine ICD-11: 8A80 [1]
PubChem CID
10531
Formula
C33H37N5O5
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]5C[C@H]6[C@@H](CC7=CNC8=CC=CC6=C78)N(C5)C
InChI
1S/C33H37N5O5/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/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39)/t21-,23-,25-,26+,27+,32-,33+/m1/s1
InChIKey
LUZRJRNZXALNLM-JGRZULCMSA-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=10531"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 583.7 Topological Polar Surface Area 118
XlogP 2.4 Complexity 1160
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
          Dihydroergotamine 1 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 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
Stearic acid; Lactose; Mannitol; Butylated hydroxyanisole; Talc; Hydrogenated cottonseed oil; Povidone k90; Starch, corn
                   Dosage Form Oral Tablet
                   Company AvKARE; Carilion Materials Management; Mutual Pharmaceutical
                   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) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Butylhydroxyanisole DIG Info Prostaglandin G/H synthase 2 (IC50 = 2.6 uM) [2]
References
1 FDA label for approved dihydroergotamine from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.

If you find any error in data or bug in web service, please kindly report it to Dr. Zhang and Dr. Mou.