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

General Information of Drug (ID: DR0903)
Drug Name
Ketamine
Synonyms
Ketaject; Ketalar; Ketalar base; Ketamine Base; Ketamine [INN:BAN]; Ketaminum; Ketaminum [INN-Latin]; Ketanest; Special K; Special K [street name]; CLSTA 20; Cetamina [INN-Spanish]; KETAMINE HCL; dl-Ketamine; ketamina; ketamine; (+-)-Ketamine; (+/-)-Ketamine; 2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone; 2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one; 2-(Methylamino)-2-(2-chlorophenyl)cyclohexanone; 2-(o-Chlorophenyl)-2-(methylamino)-cyclohexanone; 6740-88-1; BRN 2216965; CHEMBL742; CI 581 base; EINECS 229-804-1; NSC 70151
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 237.72 Topological Polar Surface Area 29.1
Heavy Atom Count 16 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
3821
PubChem SID
9728 ; 113688 ; 841263 ; 5316929 ; 7979678 ; 8152419 ; 10502126 ; 11335392 ; 11360631 ; 11461603 ; 15220836 ; 29215438 ; 29215439 ; 29222940 ; 46508295 ; 48034987 ; 48416146 ; 49958360 ; 53789372 ; 56424156 ; 57322007 ; 77699966 ; 96024788 ; 99233266 ; 103199488 ; 103975488 ; 104222089 ; 104304622 ; 105600453 ; 117480213 ; 118232324 ; 124813339 ; 125683401 ; 129832339 ; 134338393 ; 134987353 ; 137010368 ; 142340961 ; 144205256 ; 144205257 ; 160964554 ; 178101050 ; 179148642 ; 216074935 ; 223837115 ; 226406322 ; 250059345
ChEBI ID
CHEBI:6121
CAS Number
6740-88-1
TTD Drug ID
D0UM7O
Formula
C13H16ClNO
Canonical SMILES
CNC1(CCCCC1=O)C2=CC=CC=C2Cl
InChI
1S/C13H16ClNO/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14/h2-3,6-7,15H,4-5,8-9H2,1H3
InChIKey
YQEZLKZALYSWHR-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-hydroxyketamine DM002792
86115985
Oxidation - Hydoxylation 1 [3] , [4]
5-hydroxyketamine DM002791
118753542
Oxidation - Hydoxylation 1 [3] , [4]
6-hydroxyketamine DM002790
133670
Oxidation - Hydoxylation 1 [3] , [4]
Norketamine DM002782
123767
Oxidation - N-Demethylation 1 [2] , [5] , [6] , [7]
4-hydroxynorketamine DM002787
86017433
Oxidation - N-Demethylation 2 [3] , [4]
4-hydroxynorketamine DM002787
86017433
Oxidation - Hydoxylation 2 [3] , [5]
5-hydroxynorketamine DM002785
86115991
Oxidation - N-Demethylation 2 [3] , [4]
5-hydroxynorketamine DM002785
86115991
Oxidation - Hydoxylation 2 [3] , [5]
6-hydroxynorketamine DM002783
133669
Oxidation - N-Demethylation 2 [3] , [4]
6-hydroxynorketamine DM002783
133669
Oxidation - Hydoxylation 2 [3] , [8] , [5]
Dehydronorketamine DM002789
162835
Oxidation - Dehydrogenation 2 [3] , [5]
4-hydroxynorketamine glucuronide DM002788 N. A. Conjugation - Glucuronidation 3 [3] , [4]
4-hydroxynorketamine glucuronide DM002788 N. A. Conjugation - Glucuronidation 3 [3]
5-hydroxynorketamine glucuronide DM002786 N. A. Conjugation - Glucuronidation 3 [3] , [4]
5-hydroxynorketamine glucuronide DM002786 N. A. Conjugation - Glucuronidation 3 [3]
6-hydroxynorketamine glucuronide DM002784 N. A. Conjugation - Glucuronidation 3 [3] , [4]
6-hydroxynorketamine glucuronide DM002784 N. A. Conjugation - Glucuronidation 3 [3]
⏷ Show the Full List of 17  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001321 Ketamine Norketamine Oxidation - N-Demethylation CYP2C9 ... [2], [5], [6], [7]
MR001322 Ketamine 6-hydroxyketamine Oxidation - Hydoxylation Unclear [3], [4]
MR001323 Ketamine 5-hydroxyketamine Oxidation - Hydoxylation Unclear [3], [4]
MR001324 Ketamine 4-hydroxyketamine Oxidation - Hydoxylation Unclear [3], [4]
MR001320 4-hydroxyketamine 4-hydroxynorketamine Oxidation - N-Demethylation Unclear [3], [4]
MR001319 5-hydroxyketamine 5-hydroxynorketamine Oxidation - N-Demethylation Unclear [3], [4]
MR001318 6-hydroxyketamine 6-hydroxynorketamine Oxidation - N-Demethylation Unclear [3], [4]
MR001311 Norketamine 6-hydroxynorketamine Oxidation - Hydoxylation Unclear [3], [8], [5]
MR001312 Norketamine 5-hydroxynorketamine Oxidation - Hydoxylation Unclear [3], [5]
MR001313 Norketamine 4-hydroxynorketamine Oxidation - Hydoxylation Unclear [3], [5]
MR001314 Norketamine Dehydronorketamine Oxidation - Dehydrogenation Unclear [3], [5]
MR001317 4-hydroxynorketamine 4-hydroxynorketamine glucuronide Conjugation - Glucuronidation Unclear [3], [4]
MR001316 5-hydroxynorketamine 5-hydroxynorketamine glucuronide Conjugation - Glucuronidation Unclear [3], [4]
MR001315 6-hydroxynorketamine 6-hydroxynorketamine glucuronide Conjugation - Glucuronidation Unclear [3], [4]
⏷ Show the Full List of 14 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
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
[2]
References
1 Ketamine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Contribution of CYP3A4, CYP2B6, and CYP2C9 isoforms to N-demethylation of ketamine in human liver microsomes. Drug Metab Dispos. 2002 Jul;30(7):853-8.
3 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.
4 Metabolism and metabolomics of ketamine: a toxicological approach. Forensic Sci Res. 2017 Feb 20;2(1):2-10.
5 The clinical toxicology of ketamine. Clin Toxicol (Phila). 2023 Jun;61(6):415-428. doi: 10.1080/15563650.2023.2212125.
6 Pharmacokinetics of Ketamine Transfer Into Human Milk. J Clin Psychopharmacol. 2023 May 23. doi: 10.1097/JCP.0000000000001711.
7 Chronic exposure to (2?R,6?R)-hydroxynorketamine induces developmental neurotoxicity in hESC-derived cerebral organoids. J Hazard Mater. 2023 Jul 5;453:131379. doi: 10.1016/j.jhazmat.2023.131379.
8 Simultaneous quantitation of ketamine, norketamine and dehydronorketamine in human milk using a novel ultra high-performance liquid chromatography-mass spectrometry (UPLC-MS/MS) assay. J Pharm Biomed Anal. 2023 Jun 1;234:115502. doi: 10.1016/j.jpba.2023.115502.

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