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

General Information of Drug (ID: DR1365)
Drug Name
Propofol
Synonyms
Propofolum; Propofolum [Latin]; Propovan; Rapinovet; Recofol; propofol; 2,6-Bis(1-methylethyl)phenol; 2,6-DIISOPROPYLPHENOL; 2,6-Diisopropyl phenol; 2,6-bis(propan-2-yl)phenol; 2,6-di(propan-2-yl)phenol; 2078-54-8; C12H18O; CCRIS 9000; Ampofol; Diisopropylphenol; Diprifusor; Diprivan; Diprivan 10; Diprivan Injectable emulsion; Diprofol; Disoprivan; Disoprofol; Fresofol; Ivofol; Phenol, 2,6-bis(1-methylethyl)-; Phenol, 2,6-diisopropyl-; Propofol-Lipuro; EINECS 218-206-6; HSDB 7123; ICI 35868; ICI-35868; NSC 5105; Pofol; UNII-YI7VU623SF
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 178.27 Topological Polar Surface Area 20.2
Heavy Atom Count 13 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
4943
PubChem SID
9726 ; 71265 ; 219945 ; 838001 ; 3132933 ; 5371511 ; 7847615 ; 7889810 ; 7980416 ; 7984535 ; 8001758 ; 8153049 ; 10513227 ; 11111121 ; 11111122 ; 11466959 ; 11468079 ; 11486767 ; 12012653 ; 12055958 ; 14772701 ; 17389856 ; 17405000 ; 24278001 ; 24902022 ; 26612728 ; 26697200 ; 26747380 ; 26753044 ; 26753045 ; 26753046 ; 29224021 ; 29334775 ; 29833842 ; 46504991 ; 47193694 ; 47216867 ; 47216868 ; 47216869 ; 47365303 ; 47662396 ; 47662397 ; 47662398 ; 48416482 ; 48424532 ; 49699215 ; 49855158 ; 50105615 ; 51074363 ; 53777543
ChEBI ID
ChEBI:44915
CAS Number
2078-54-8
TTD Drug ID
D0A3HB
Formula
C12H18O
Canonical SMILES
CC(C)C1=C(C(=CC=C1)C(C)C)O
InChI
1S/C12H18O/c1-8(2)10-6-5-7-11(9(3)4)12(10)13/h5-9,13H,1-4H3
InChIKey
OLBCVFGFOZPWHH-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-hydroxypropofol DM002068
3014064
Oxidation - 4-Hydroxylation 1 [11]
Propofol glucuronide DM003013
71751823
Conjugation - Glucuronidation 1 [11]
1-Quinol glucuronide DM003011
29981923
Oxidation - 4-Hydroxylation 2 [11]
1-Quinol glucuronide DM003011
29981923
Conjugation - Glucuronidation 2 [11]
4-Hydroxypropofol-O-sulphate DM003010
10446031
Other reaction - Sulfonation 2 [11]
4-Quinol glucuronide DM003012
92131911
Conjugation - Glucuronidation 2 [11]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002187 Propofol 4-hydroxypropofol Oxidation - 4-Hydroxylation CYP2B6 ... [11]
MR002188 Propofol Propofol glucuronide Conjugation - Glucuronidation UGT1A8 ... [11]
MR002183 4-hydroxypropofol 4-Quinol sulfate Other reaction - Sulfonation Unclear [11]
MR002184 4-hydroxypropofol 1-Quinol glucuronide Conjugation - Glucuronidation UGT1A8 ... [11]
MR002185 4-hydroxypropofol 4-Quinol glucuronide Conjugation - Glucuronidation UGT1A8 ... [11]
MR002186 Propofol glucuronide 1-Quinol glucuronide Oxidation - 4-Hydroxylation Unclear [11]
⏷ 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
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[5]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[6]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
Oleamide hydrolase 1 (FAAH) DME0208 Homo sapiens
FAAH1_HUMAN
3.5.1.99
[7]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[8]
UDP-glucuronosyltransferase 1A6 (UGT1A6) DME0072 Homo sapiens
UD16_HUMAN
2.4.1.17
[9]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[10]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[11]
⏷ Show the Full List of 15  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Km = 0.0072 microM
UD19_HUMAN
[12]
References
1 Propofol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Inhibition of cytochrome P450 2E1 by propofol in human and porcine liver microsomes. Biochem Pharmacol. 2002 Oct 1;64(7):1151-6.
3 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
4 Involvement of human cytochrome P450 2B6 in the omega- and 4-hydroxylation of the anesthetic agent propofol. Xenobiotica. 2007 Jul;37(7):717-24.
5 Cytochrome P-450 2B6 is responsible for interindividual variability of propofol hydroxylation by human liver microsomes. Anesthesiology. 2001 Jan;94(1):110-9.
6 Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53.
7 Update of TTD: therapeutic target database. Nucleic Acids Res. 2010 Jan;38(Database issue):D787-91.
8 Substrate-dependent modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1) by propofol in recombinant human UGT1A1 and human liver microsomes. Basic Clin Pharmacol Toxicol. 2007 Sep;101(3):211-4.
9 Pharmacokinetics of propofol and extrahepatic UGT1A6 gene expression in anhepatic rats. Pharmacology. 2009;84(4):219-26.
10 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. doi: 10.2174/092986709789057635.
11 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.
12 The "albumin effect" and drug glucuronidation: bovine serum albumin and fatty acid-free human serum albumin enhance the glucuronidation of UDP-glucuronosyltransferase (UGT) 1A9 substrates but not UGT1A1 and UGT1A6 activities. Drug Metab Dispos. 2008 Jun;36(6):1056-62.

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