Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0504)
Drug Name
Dihydroergotamine
Synonyms
Dehydroergotamine; Dihidroergotamina; Dihidroergotamina [INN-Spanish]; Dihydergot; Dihydroergotamine mesylate; Dihydroergotamine methanesulfonate; Dihydroergotaminum; Dihydroergotaminum [INN-Latin]; Diidroergotamina; Diidroergotamina [DCIT]; Angionorm; DHE-45; Ergomimet; Ergotamine, 9,10-dihydro-; Levadex; Migranal; Orstanorm; Verladyn; dihydroergotamine; 436O5HM03C; 511-12-6; 9,10-Dihydroergotamine; 9,10-dihydro-ergotamine; BRN 5720196; C33H37N5O5; CHEBI:4562; CHEMBL1732; D.H.E. 45; EINECS 208-123-3; NCGC00017400-05; UNII-436O5HM03C
Indication Migraine [ICD11: 8A80] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 583.7 Topological Polar Surface Area 118
Heavy Atom Count 43 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
10531
PubChem SID
10000 ; 7979087 ; 8157604 ; 11335767 ; 11361006 ; 11363951 ; 11366513 ; 11369075 ; 11371529 ; 11374714 ; 11377237 ; 11461978 ; 11484971 ; 11489004 ; 11490211 ; 11492773 ; 11494871 ; 14788984 ; 14935810 ; 29229015 ; 46507711 ; 47291112 ; 47885391 ; 48110437 ; 48334472 ; 49963030 ; 49965612 ; 50153282 ; 57326281 ; 85789540 ; 90341683 ; 93166278 ; 96024534 ; 99313633 ; 103684622 ; 103905875 ; 104137088 ; 104171355 ; 104323551 ; 119501400 ; 124749650 ; 124883197 ; 124883198 ; 126688923 ; 127323995 ; 127323996 ; 127323997 ; 127323998 ; 127323999 ; 127324000
ChEBI ID
CHEBI:4562
CAS Number
6190-39-2
TTD Drug ID
D0V3ZA
Formula
C33H37N5O5
Canonical SMILES
CC1(C(=O)N2C(C(=O)N3CCCC3C2(O1)O)CC4=CC=CC=C4)NC(=O)C5CC6C(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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
11-OH-hydroxydihydroergotamine DM000094 N. A. Oxidation - Hydroxylation 1 [3]
5-OH-hydroxydihydroergotamine DM000093 N. A. Oxidation - Hydroxylation 1 [3]
8'-beta-hydroxydihydroergotamine DM000092
146217
Oxidation - Hydroxylation 1 [3]
Dihydrolysergic acid DM000095
12940526
Unclear 1 [3]
Dihydrolysergic amide DM000096
21122984
Unclear 1 [3]
Unclear DM009999 N. A. Unclear 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000857 Dihydroergotamine 8'-beta-hydroxydihydroergotamine Oxidation - Hydroxylation CYP [3]
MR000858 Dihydroergotamine 5-OH-hydroxydihydroergotamine Oxidation - Hydroxylation CYP [3]
MR000859 Dihydroergotamine 11-OH-hydroxydihydroergotamine Oxidation - Hydroxylation CYP [3]
MR000860 Dihydroergotamine Dihydrolysergic acid Unclear Unclear [3]
MR000861 Dihydroergotamine Dihydrolysergic amide Unclear Unclear [3]
MR000862 Dihydroergotamine . Unclear Unclear [3]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Dihydroergotamine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 CYP2D6 and CYP3A4 involvement in the primary oxidative metabolism of hydrocodone by human liver microsomes. Br J Clin Pharmacol. 2004 Mar;57(3):287-97.
3 LABEL:IHYDROERGOTAMINE MESYLATE- dihydroergotamine spray

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