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

General Information of Drug (ID: DR1328)
Drug Name
Prazepam
Synonyms
Prazeene; Prazene; Prazepamum; Prazepamum [INN-Latin]; Q30VCC064M; Sedapran; Settima; Trepidan; Verstran; W 4020; W-4020; Centrax; Demetrin; Lysanxia; MWQCHHACWWAQLJ-UHFFFAOYSA-N; prazepam; 2955-38-6; 2H-1,4-Benzodiazepin-2-one, 7-chloro-1-(cyclopropylmethyl)-1,3-dihydro-5-phenyl-; 7-Chloro-1-(cyclopropylmethyl)-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one; 7-Chloro-1-cyclopropylmethyl-5-phenyl-1H-1,4-benzodiazepin-2(3H)-one; BRN 0895797; C19H17ClN2O; CHEBI:8362; DEA No. 2764; EINECS 220-975-8; K-373; NSC 277179; UNII-Q30VCC064M
Indication Anxiety disorder [ICD11: 6B00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 324.8 Topological Polar Surface Area 32.7
Heavy Atom Count 23 Rotatable Bond Count 3
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
4890
PubChem SID
9570 ; 142196 ; 4500851 ; 7847536 ; 8153008 ; 10517477 ; 14874926 ; 24898436 ; 29223968 ; 46505417 ; 48414363 ; 48416458 ; 49857642 ; 50113069 ; 57322504 ; 58107012 ; 75711993 ; 103252286 ; 104307721 ; 124893449 ; 125823415 ; 128658510 ; 134224569 ; 134337978 ; 134982453 ; 136949643 ; 137005591 ; 137440705 ; 137783726 ; 144206168 ; 144207274 ; 160964826 ; 162946637 ; 164788802 ; 178103849 ; 179116857 ; 198988005 ; 198991803 ; 223440729 ; 224927321 ; 226457573 ; 250107476 ; 252356174
ChEBI ID
CHEBI:8362
CAS Number
2955-38-6
TTD Drug ID
D0G3AQ
Formula
C19H17ClN2O
Canonical SMILES
C1CC1CN2C(=O)CN=C(C3=C2C=CC(=C3)Cl)C4=CC=CC=C4
InChI
1S/C19H17ClN2O/c20-15-8-9-17-16(10-15)19(14-4-2-1-3-5-14)21-11-18(23)22(17)12-13-6-7-13/h1-5,8-10,13H,6-7,11-12H2
InChIKey
MWQCHHACWWAQLJ-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
3-hydroxyprazepam DM002910
205841
Oxidation - Hydroxylation 1 [4] , [5]
Desmethyldiazepam DM000834
2997
Oxidation - N-Dealkylation 1 [2] , [4] , [5]
Oxazepam DM003073
4616
Oxidation - Hydroxylation 2 [2] , [4] , [5]
Oxazepam DM003073
4616
Oxidation - N-Dealkylation 2 [4] , [5]
p-Hydroxynordiazepam DM002912
87025
Oxidation - Hydroxylation 2 [4] , [5]
4'-hydroxyoxazepam DM002911
135428089
Oxidation - Hydroxylation 3 [4] , [5]
Oxazepam glucuronide DM001106
160870
Conjugation - Glucuronidation 3 [4] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002106 Prazepam 3-hydroxyprazepam Oxidation - Hydroxylation Unclear [4], [5]
MR002107 Prazepam Nordazepam Oxidation - N-Dealkylation CYP3A4 [2], [4], [5]
MR002104 3-hydroxyprazepam Oxazepam Oxidation - N-Dealkylation Unclear [4], [5]
MR002110 Nordazepam 4'-hydroxdesalkylprazepam Oxidation - Hydroxylation Unclear [4], [5]
MR002111 Nordazepam Oxazepam Oxidation - Hydroxylation CYP3A4 ... [2], [4], [5]
MR002105 4'-hydroxdesalkylprazepam 4'-hydroxyoxazepam Oxidation - Hydroxylation Unclear [4], [5]
MR002108 Oxazepam Oxazepam glucuronide Conjugation - Glucuronidation Unclear [4], [5]
MR002109 Oxazepam 4'-hydroxyoxazepam Oxidation - Hydroxylation Unclear [4], [5]
⏷ Show the Full List of 8 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]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
References
1 Prazepam was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Metabolic profile of oxazepam and related benzodiazepines: clinical and forensic aspects. Drug Metab Rev. 2017 Nov;49(4):451-463.
3 Metabolic profile of oxazepam and related benzodiazepines: clinical and forensic aspects Drug Metab Rev. 2017 Nov;49(4):451-463. doi: 10.1080/03602532.2017.1377223.
4 Prazepam metabolism by man Clin Pharmacol Ther. 1970 Nov-Dec;11(6):890-7. doi: 10.1002/cpt1970116890.
5 Prazepam metabolites in dog urine J Pharm Sci. 1970 Mar;59(3):322-5. doi: 10.1002/jps.2600590309.

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