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

General Information of Drug (ID: DR0813)
Drug Name
Hydralazine hydrochloride
Synonyms
Hydralazin; Hydralazinum; Hydrallazine; Hydrazinophthalazine; Hydrazone 1(2H)-phthalazinone; Hypophthalin; Idralazina; Idralazina [DCIT]; Idralazina [Italian]; hydralazine; phthalazin-1-ylhydrazine; (E)-1-Hydrazono-1,2-dihydrophthalazine; 1(2H)-Phthalazinone, hydrazone; 1-Hydrazinophthalazine; 1-Hydrazinylphthalazine; 1-Phthalazinylhydrazine; 59275-69-3; 6-Hydralazine; 86-54-4; Apresolin; Apressin; Apressin (pharmaceutical); Aprezolin; Ciba 5968; Hidralazin; Hidralazina; Hidralazina [Spanish]; Hipoftalin; Aiselazine; Apresoline hydrochloride; Dralzine; HYDRALAZINE HCL; HYDRALAZINE HYDROCHLORIDE; Hydralazine (hydrochloride); Hydralazine chloride; Hydralazine monohydrochloride; Hydrallazine hydrochloride; Hyperazin; Hyperex; Lopress; Praparat 5968; Slow-Apresolin; 1(2H)-Phthalazinone, hydrazone, hydrochloride; 1(2H)-Phthalazinone, hydrazone, monohydrochloride; 1-Hydrazinophthalazine hydrochloride; 1-Hydrazinophthalazine monohydrochloride; 1-Hydrazinylphthalazine hydrochloride; 304-20-1; CHEBI:31672
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 196.64 Topological Polar Surface Area 63.8
Heavy Atom Count 13 Rotatable Bond Count 1
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
9351
ChEBI ID
CHEBI:31672
CAS Number
304-20-1
TTD Drug ID
D0K1XK
Formula
C8H9ClN4
Canonical SMILES
C1=CC=C2C(=C1)C=NN=C2NN.Cl
InChI
1S/C8H8N4.ClH/c9-11-8-7-4-2-1-3-6(7)5-10-12-8;/h1-5H,9H2,(H,11,12);1H
InChIKey
ZUXNZUWOTSUBMN-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
Alpha-ketoglutarate hydrazone DM004747
23527007
Unclear 1 [4]
Hydralazine acetone hydrazone DM004752
41772
Unclear 1 [5] , [6]
Hydralazine pyruvate hydrazone DM004750
9576792
Unclear 1 [4] , [7]
Hydrazinophthalazinone DM004748
167015
Unclear 1 [4] , [8]
Phthalazine DM004745
9207
Unclear 1 [4] , [8]
Phthalazinone DM004746
8394
Unclear 1 [4]
Unnamed hydralazine metabolite DM004740
31507
Unclear 1 [4] , [8]
3-methyl-s-triazolophthalazine DM004741
97339
Other reaction - Dehydration 2 [8]
Acetylhydrazinophthalazinone DM004749
149284
Unclear 2 [4]
Hydralazine pyruvate hydrazone tricyclic dehydration product DM004751
13812917
Unclear 2 [9]
Phthalazinone DM004746
8394
Unclear 2 [4]
3-hydroxy-methyltriazolophthalazine DM004742
150272
Oxidation - Hydrolyzationn 3 [4]
9-hydroxy-methyltriazolophthalazine DM004744
136271515
Oxidation - Hydrolyzationn 3 [4]
Hydralazine pyruvate hydrazone DM004750
9576792
Unclear 3 [9]
Triazolophthalazine DM004743
97337
Unclear 4 [4]
⏷ Show the Full List of 15  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005093 Hydralazine hydrochloride Unnamed hydralazine metabolite Unclear Unclear [4], [8]
MR005098 Hydralazine hydrochloride Phthalazine Unclear Unclear [4], [8]
MR005100 Hydralazine hydrochloride Alpha-ketoglutarate hydrazone Unclear Unclear [4]
MR005102 Hydralazine hydrochloride Hydrazinophthalazinone Unclear Unclear [4], [8]
MR005104 Hydralazine pyruvate hydrazone Hydralazine pyruvate hydrazone Unclear Unclear [4], [7]
MR005105 Hydralazine pyruvate hydrazone Hydralazine pyruvate hydrazone tricyclic dehydration product Unclear Unclear [9]
MR005107 Hydralazine pyruvate hydrazone Hydralazine acetone hydrazone Unclear Unclear [5], [6]
MR005108 Hydralazine pyruvate hydrazone Phthalazinone Unclear Unclear [4]
MR005101 Alpha-ketoglutarate hydrazone Phthalazinone Unclear Unclear [4]
MR005103 Hydrazinophthalazinone Acetylhydrazinophthalazinone Unclear Unclear [4]
MR005099 Phthalazine Phthalazinone Unclear Unclear [4]
MR005094 Unnamed hydralazine metabolite 3-methyl-s-triazolophthalazine Other reaction - Dehydration Unclear [8]
MR005095 3-methyl-s-triazolophthalazine 3-hydroxy-methyltriazolophthalazine Oxidation - Hydrolyzationn Unclear [4]
MR005097 3-methyl-s-triazolophthalazine 9-hydroxy-methyltriazolophthalazine Oxidation - Hydrolyzationn Unclear [4]
MR005106 Hydralazine pyruvate hydrazone tricyclic dehydration product Hydralazine pyruvate hydrazone Unclear Unclear [9]
MR005096 3-hydroxy-methyltriazolophthalazine Triazolophthalazine Unclear Unclear [4]
⏷ Show the Full List of 16 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
N-acetyltransferase 1 (NAT1) DME0050 Homo sapiens
ARY1_HUMAN
2.3.1.5
[2]
N-acetyltransferase 2 (NAT2) DME0051 Homo sapiens
ARY2_HUMAN
2.3.1.5
[2]
RNA cytidine acetyltransferase (hALP) DME0007 Homo sapiens
NAT10_HUMAN
2.3.1.5
[3]
References
1 Hydralazine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 N-acetyltransferase 2 genotype-dependent N-acetylation of hydralazine in human hepatocytes. Drug Metab Dispos. 2017 Dec;45(12):1276-1281.
3 Prizidilol, an antihypertensive with precapillary vasodilator and beta-adrenoceptor blocking actions, in primary hypertension. Clin Pharmacol Ther. 1981 May;29(5):588-93.
4 Metabolism of hydralazine: relevance to drug-induced lupus
5 Hypotensive effect of the hydralazine--acetone hydrazone in conscious rabbits: evidence for its back-conversion to hydralazine in vivo
6 Pharmacokinetics and biotransformation of hydralazine acetone hydrazone, a metabolite of hydralazine, in the rat
7 Quantitative analysis of hydralazine pyruvic acid hydrazone, the major plasma metabolite of hydralazine
8 Hydralazine elimination in man
9 DrugBank(Pharmacology-Metabolism):Hydralazine

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