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

General Information of Drug (ID: DR5967)
Drug Name
Tetramethylpyrazine
Synonyms Ligustizine; Ligustrazine; 2,3,5,6-Tetramethylpyrazine
Indication Neurological disorder [ICD11: 6B60] Discontinued in Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 136.19 Topological Polar Surface Area 25.8
Heavy Atom Count 10 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
14296
ChEBI ID
CHEBI:133246
CAS Number
1124-11-4
TTD Drug ID
D09WFI
Formula
C8H12N2
Canonical SMILES
CC1=C(N=C(C(=N1)C)C)C
InChI
InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3
InChIKey
FINHMKGKINIASC-UHFFFAOYSA-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
2-hydroxymethyl-3,5,6-trimethylpyrazine DM017205 N. A. Unclear 1 [4]
BDNA DM016402
90658509
Unclear 1 [2]
Tetramethylpyrazine metabolite M1 DM016048
25218318
Oxidation - Oxidation 1 [5]
OBNA DM015112
97923
Unclear 2 [2]
N-(3-hydroxybutan-2-yl)acetamide DM015964
19845146
Unclear 3 [2]
5-3-amino-2-butanol DM015258
226831
Unclear 4 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013710 Tetramethylpyrazine BDNA Unclear TpdAB [2]
MR013714 Tetramethylpyrazine 2-hydroxymethyl-3,5,6-trimethylpyrazine Unclear Unclear [4]
MR013715 Tetramethylpyrazine Tetramethylpyrazine metabolite M1 Oxidation - Oxidation Unclear [5]
MR013711 BDNA OBNA Unclear TpdC [2]
MR013712 OBNA N-(3-hydroxybutan-2-yl)acetamide Unclear tpdE [2]
MR013713 N-(3-hydroxybutan-2-yl)acetamide 5-3-amino-2-butanol Unclear Unclear [2]
⏷ 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
(Z)-N,N'-(but-2-ene-2,3-diyl)diacetamide hydrolase (TpdC) DMEN752 . Not Available Not Available [2]
aminoalcohol dehydrogenase (tpdE) DMEN753 . Not Available Not Available [2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
tetramethylpyrazine oxygenase (TpdAB) DMEN751 . Not Available Not Available [2]
⏷ Show the Full List of 6  DME(s)
References
1 Determination of tetramethylpyrazine in animal serum and cerebrospinal fluid by high performance liquid chromatography. Se Pu. 2000 Jan;18(1):46-8.
2 Identification and characterization of a tetramethylpyrazine catabolic pathway in Rhodococcus jostii TMP1
3 [Investigation of metabolic kinetics and reaction phenotyping of ligustrazin by using liver microsomes and recombinant human enzymes]
4 Interactions of heterocyclic Maillard products with the hepatic microsomal monooxygenase system
5 [Studies on the metabolites of tetramethylpyrazine in human urine]

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