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

General Information of Drug (ID: DR0075)
Drug Name
Alprazolam
Synonyms
Alcelam; Alplax; Alpram; Alprax; Alprazolam intensol; Alprazolamum; Alpronax; Alprox; Alzolam; Anpress; Apo-Alpraz; Bestrol; Cassadan; Constan; Esparon; Frontal; Intensol; Ksalol; Mialin; Neurol; Niravam; Novo-Alprazol; Nu-Alpraz; Pharnax; Prazam; Prazolan; Prinox; Ralozam; Relaxol; Restyl; Solanax; Tensivan; Trankimazin; Tranquinal; Tricalma; Unilan; Valeans; Xanagis; Xanax XR; Xanolam; Zacetin; Zanapam; Zolarem; Zoldac; Zoldax; Zotran; alprazolam; 28981-97-7; Algad; Alpaz; Alzam; Alzon; Helex; Panix; TUS-1; Tafil; Xanax; Xanor; Zaxan; Zenax; Zolam; Zopax; Zopic
Indication Anxiety disorder [ICD11: 6B00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 308.8 Topological Polar Surface Area 43.1
Heavy Atom Count 22 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
2118
PubChem SID
9035 ; 866237 ; 7403853 ; 7847292 ; 7849651 ; 7978675 ; 8151436 ; 10517236 ; 12013413 ; 14742608 ; 14800856 ; 22396017 ; 24882050 ; 24891103 ; 24891366 ; 26719699 ; 29215419 ; 29215420 ; 29221298 ; 46386679 ; 46507078 ; 48415537 ; 50057265 ; 50823025 ; 53790970 ; 56313723 ; 57321151 ; 57651813 ; 57653873 ; 81093308 ; 92308240 ; 92716916 ; 93166633 ; 93167168 ; 93620403 ; 103189284 ; 103916140 ; 104299658 ; 109613253 ; 117786302 ; 124658860 ; 125347118 ; 126622623 ; 126651409 ; 126723170 ; 129515347 ; 131309066 ; 134221861 ; 134337553 ; 134997022
ChEBI ID
ChEBI:2611
CAS Number
28981-97-7
TTD Drug ID
D0L9GG
Formula
C17H13ClN4
Canonical SMILES
CC1=NN=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4
InChI
1S/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3
InChIKey
VREFGVBLTWBCJP-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
4-hydroxyalprazolam DM015240
182017
Unclear - Unclear 1 [7] , [4]
5-N-O?alprazolam DM015267
327554
Unclear - Unclear 1 [8]
Alpha-hydroxyalprazolam DM001711
162244
Unclear - Unclear 1 [4]
6-Keto?alprazolam DM015923
15567865
Unclear - Unclear 2 [8]
Benzophenone DM003161
3102
Unclear - Unclear 2 [9]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009844 Alprazolam 5-N-O?alprazolam Unclear - Unclear Unclear [8]
MR009846 Alprazolam 4-hydroxyalprazolam Unclear - Unclear CYP3A4 ... [7], [4]
MR009848 Alprazolam Alpha-hydroxyalprazolam Unclear - Unclear CYP3A43 [4]
MR009847 4-hydroxyalprazolam Benzophenone Unclear - Unclear Unclear [9]
MR009845 5-N-O?alprazolam 6-Keto?alprazolam Unclear - Unclear Unclear [8]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A43 (CYP3A43) DME0022 Homo sapiens
CP343_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[6]
References
1 Alprazolam was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
3 No relevant interaction with alprazolam, caffeine, tolbutamide, and digoxin by treatment with a low-hyperforin St John's wort extract. Planta Med. 2005 Apr;71(4):331-7.
4 Drug metabolism in human brain: high levels of cytochrome P4503A43 in brain and metabolism of anti-anxiety drug alprazolam to its active metabolite
5 Identification and phenotype characterization of two CYP3A haplotypes causing different enzymatic capacity in fetal livers. Clin Pharmacol Ther. 2005 Apr;77(4):259-70.
6 Drug Interactions Flockhart Table
7 Alprazolam metabolism in vitro: studies of human, monkey, mouse, and rat liver microsomes
8 Changes in Alprazolam Metabolism by CYP3A43 Mutants
9 In vitro/in vivo scaling of alprazolam metabolism by CYP3A4 and CYP3A5 in humans

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