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

General Information of Drug (ID: DR1118)
Drug Name
Mycophenolate mofetil
Synonyms
Mycophenolate mofetil (CellCept); Mycophenolatemofetil; Mycophenylate mofetil; Myfenax; RS 61443; RS-61443; TM-MMF; mycophenolate mofetil; CellCept; Cellcept (TN); Munoloc; 115007-34-6; 128794-94-5; 2-(morpholin-4-yl)ethyl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate; 2-Morpholinoethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoate; 9242ECW6R0; C23H31NO7; CHEBI:8764; HSDB 7436; MFCD00867568; Mycophenolic acid morpholinoethyl ester; UNII-9242ECW6R0
Indication Crohn disease [ICD11: DD70] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 433.5 Topological Polar Surface Area 94.5
Heavy Atom Count 31 Rotatable Bond Count 10
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
5281078
PubChem SID
10110 ; 537396 ; 623972 ; 7847817 ; 8616507 ; 12014254 ; 14758955 ; 29215410 ; 39289999 ; 46505626 ; 48416299 ; 49830660 ; 49976609 ; 50064190 ; 56310881 ; 56312885 ; 57358003 ; 62129612 ; 77319688 ; 80954261 ; 92308999 ; 92718908 ; 93619754 ; 96099842 ; 103524891 ; 103831140 ; 104253178 ; 113854519 ; 117622077 ; 118053002 ; 124757298 ; 125164102 ; 125275456 ; 126592936 ; 126621236 ; 126622394 ; 126651543 ; 126669998 ; 126682700 ; 131295332 ; 131297141 ; 132003527 ; 134338068 ; 134339833 ; 135016986 ; 135039794 ; 136949095 ; 137004579 ; 142385187 ; 144075766
ChEBI ID
CHEBI:8764
CAS Number
128794-94-5
TTD Drug ID
D04FBR
Formula
C23H31NO7
Canonical SMILES
CC1=C2COC(=O)C2=C(C(=C1OC)CC=C(C)CCC(=O)OCCN3CCOCC3)O
InChI
1S/C23H31NO7/c1-15(5-7-19(25)30-13-10-24-8-11-29-12-9-24)4-6-17-21(26)20-18(14-31-23(20)27)16(2)22(17)28-3/h4,26H,5-14H2,1-3H3/b15-4+
InChIKey
RTGDFNSFWBGLEC-SYZQJQIISA-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
7-O-glucoside DM004492 N. A. Unclear 1 [9]
Acyl glucuronide DM004493 N. A. Unclear 1 [9]
Mycophenolic acid DM004483
446541
Unclear 1 [2] , [3] , [4]
Mycophenolic acid glucuronide DM004487
6442661
Conjugation - Glucuronidation 1 [4]
Mycophenolic acyl-glucuronide (AcMPAG) DM004488
5281078
Conjugation - Glucuronidation 1 [4]
N-(2-carboxymethyl)-morpholine DM004489
438968
Hydrolysis - Hydrolyzation 1 [4]
N-(2-hydroxyethyl)-morpholine DM004490
61163
Unclear 1 [4]
N-(2-hydroxyethyl)-morpholine N-oxide DM004491
130392110
Unclear 1 [4]
6-O-desmethyl-MPA (DM-MPA) DM004484 N. A. Unclear 2 [7]
7-O-MPA glucoside DM004486 N. A. Unclear 2 [7]
Desmethyl-MPA glucuronides DM004485 N. A. Unclear 3 [9]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004811 Mycophenolate mofetil Mycophenolic acid Unclear CES1 ... [2], [3], [4]
MR004815 Mycophenolate mofetil Mycophenolic acid glucuronide Conjugation - Glucuronidation UGT1A9 ... [4]
MR004816 Mycophenolate mofetil Mycophenolic acyl-glucuronide (AcMPAG) Conjugation - Glucuronidation UGT1A9 ... [4]
MR004817 Mycophenolate mofetil N-(2-carboxymethyl)-morpholine Hydrolysis - Hydrolyzation CEH [4]
MR004818 Mycophenolate mofetil N-(2-hydroxyethyl)-morpholine Unclear CEH [4]
MR004819 Mycophenolate mofetil N-(2-hydroxyethyl)-morpholine N-oxide Unclear CEH [4]
MR004820 Mycophenolate mofetil 7-O-glucoside Unclear Unclear [9]
MR004821 Mycophenolate mofetil Acyl glucuronide Unclear Unclear [9]
MR004812 Mycophenolic acid 6-O-desmethyl-MPA (DM-MPA) Unclear CYP3A4 ... [7]
MR004814 Mycophenolic acid 7-O-MPA glucoside Unclear UGT1A9 [7]
MR004813 6-O-desmethyl-MPA (DM-MPA) Desmethyl-MPA glucuronides Unclear Unclear [9]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Carboxylesterase 1 (CES1) DME0054 Homo sapiens
EST1_HUMAN
3.1.1.1
[2] , [3] , [4]
Carboxylic ester hydrolase (CEH) DME1112 Butyrivibrio fibrisolvens
A0A317G4I6_BUTFI
3.1.1.1
[2] , [3] , [4]
Carboxylic ester hydrolase (CEH) DME1112 Butyrivibrio fibrisolvens
A0A317G4I6_BUTFI
3.1.1.1
[4]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 1A10 (UGT1A10) DME0075 Homo sapiens
UD110_HUMAN
2.4.1.17
[6]
UDP-glucuronosyltransferase 1A6 (UGT1A6) DME0072 Homo sapiens
UD16_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 1A7 (UGT1A7) DME0065 Homo sapiens
UD17_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[7]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[4]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1257 Bifidobacterium longum Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1267 Anaerobutyricum hallii Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1355 Akkermansia muciniphila Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1357 Alistipes indistinctus Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1358 Anaerococcus hydrogenalis Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1360 Anaerostipes hadrus Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1375 Bacteroides intestinalis Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1377 Bacteroides pectinophilus Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1378 Bacteroides uniformis Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1386 Bifidobacterium adolescentis Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1388 Bifidobacterium breve Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1394 Blautia luti Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1398 Clostridioides difficile Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1399 Enterocloster asparagiformis Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1400 Enterocloster bolteae Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1401 Clostridium scindens Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1403 Clostridium spiroforme Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1407 Collinsella intestinalis Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1408 Coprococcus comes Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1412 Dorea formicigenerans Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1413 Edwardsiella tarda Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1415 Eggerthella lenta Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1416 Enterobacter cancerogenus Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1418 Enterococcus faecalis Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1420 Erysipelatoclostridium ramosum Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1425 Eubacterium rectale Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1432 Hungatella hathewayi Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1435 Lactobacillus reuteri Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1439 Marvinbryantia formatexigens Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1451 Proteus penneri Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1452 Providencia alcalifaciens Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1453 Providencia rettgeri Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1454 Providencia stuartii Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1456 Roseburia intestinalis Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1460 Ruminococcus torques Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1462 Salmonella enterica Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1467 Subdoligranulum variabile Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1470 Victivallis vadensis Not Available Not Available [8]
⏷ Show the Full List of 72  DME(s)
References
1 Mycophenolate Mofetil was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The emergence of mycophenolate mofetilin dermatology: from its roots in the world of organ transplantation to its versatile role in the dermatology treatment room
3 The evolution of population pharmacokinetic models to describe the enterohepatic recycling of mycophenolic acid in solid organ transplantation and autoimmune disease. Clin Pharmacokinet. 2011 Jan;50(1):1-24.
4 PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9.
5 Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9.
6 [Pharmacology of mycophenolate mofetil: recent data and clinical consequences]. Nephrologie. 2001;22(7):331-7.
7 DrugBank(Pharmacology-Metabolism):Mycophenolate mofetil
8 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
9 Mycophenolate mofetil in organ transplantation: focus on metabolism, safety and tolerability

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