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

General Information of Drug (ID: DR2673)
Drug Name
Linagliptin
Synonyms
Linagliptin [INN]; Linagliptin [USAN]; BI 1356; BI-1356; BI-1356-BS; Ondero; Ondero (TN); (R)-8-(3-Amino-piperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione
Indication Diabetes mellitus [ICD11: 5A10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 472.5 Topological Polar Surface Area 114
Heavy Atom Count 35 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
10096344
PubChem SID
15083733 ; 22505980 ; 29196126 ; 39156222 ; 56310616 ; 80795936 ; 103537922 ; 104097872 ; 124490306 ; 124772145 ; 126626882 ; 126665800 ; 134345106 ; 135257632 ; 135693249 ; 136367897 ; 137171672 ; 141692239 ; 144116143 ; 152090598 ; 152134670 ; 152159563 ; 152258162 ; 160644541 ; 160645740 ; 160646999 ; 162011748 ; 162198501 ; 164020949 ; 164193945 ; 164228213 ; 164761585 ; 172653134 ; 174006340 ; 174530256 ; 175267212 ; 175427132 ; 178102936 ; 184817874 ; 198992878 ; 223377286 ; 223554902 ; 223678280 ; 223704799 ; 226523537 ; 241125887 ; 242588098 ; 249072929 ; 249737177 ; 251971307
ChEBI ID
CHEBI:68610
CAS Number
668270-12-0
TTD Drug ID
D02EYG
Formula
C25H28N8O2
Canonical SMILES
CC#CCN1C2=C(N=C1N3CCCC(C3)N)N(C(=O)N(C2=O)CC4=NC5=CC=CC=C5C(=N4)C)C
InChI
1S/C25H28N8O2/c1-4-5-13-32-21-22(29-24(32)31-12-8-9-17(26)14-31)30(3)25(35)33(23(21)34)15-20-27-16(2)18-10-6-7-11-19(18)28-20/h6-7,10-11,17H,8-9,12-15,26H2,1-3H3/t17-/m1/s1
InChIKey
LTXREWYXXSTFRX-QGZVFWFLSA-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
Linagliptin CD10604 DM000347
90891485
Oxidation - Oxidation 1 [2] , [3]
Linagliptin M487(1) DM000360
138320018
Reduction - Reduction 1 [3]
Linagliptin M489(1) DM000356
146014909
Oxidation - Hydroxylation 1 [3]
Linagliptin M503(1) DM000359
138319987
Unclear 1 [3]
Linagliptin M515 DM000353
122189866
Unclear 1 [3]
M665(3) DM000361 N. A. Conjugation - Glucuronidation 1 [3]
M665(8) DM000362 N. A. Conjugation - Glucuronidation 1 [3]
N-acetylcyteine M636 DM000357 N. A. Conjugation - N-Acetylation 1 [3]
Linagliptin CD1790 DM000348
91971625
Reduction - Reduction 2 [3]
Linagliptin M531(1) DM000355 N. A. Conjugation - Acetylation 2 [3]
Linagliptin M531(1) DM000355 N. A. Oxidation - Hydroxylation 2 [3]
Linagliptin M531(2) DM000354 N. A. Oxidation - Hydroxylation 2 [3]
Linagliptin M716 DM000358 N. A. Unclear 2 [3]
Linagliptin M490 DM000352
138319972
Oxidation - Hydroxylation 3 [3]
Linagliptin M506 DM000349
138756717
Oxidation - Hydroxylation 3 [3]
Linagliptin M504 DM000350
138319974
Oxidation - Oxidation 4 [3]
Linagliptin M476 DM000351
138320004
Unclear 5 [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
MR001565 Linagliptin Linagliptin CD10604 Oxidation - Oxidation CYP3A4 [2], [3]
MR001566 Linagliptin Linagliptin M515 Unclear Unclear [3]
MR001567 Linagliptin Linagliptin M489(1) Oxidation - Hydroxylation Unclear [3]
MR001568 Linagliptin N-acetylcyteine M636 Conjugation - N-Acetylation Unclear [3]
MR001569 Linagliptin Linagliptin M503(1) Unclear Unclear [3]
MR001570 Linagliptin Linagliptin M487(1) Reduction - Reduction Unclear [3]
MR001571 Linagliptin M665(3) Conjugation - Glucuronidation Unclear [3]
MR001572 Linagliptin M665(8) Conjugation - Glucuronidation Unclear [3]
MR001556 Linagliptin CD10604 Linagliptin CD1790 Reduction - Reduction AKR [3]
MR001563 Linagliptin M489(1) Linagliptin M531(1) Conjugation - Acetylation Unclear [3]
MR001561 Linagliptin M515 Linagliptin M531(2) Oxidation - Hydroxylation Unclear [3]
MR001562 Linagliptin M515 Linagliptin M531(1) Oxidation - Hydroxylation Unclear [3]
MR001564 N-acetylcyteine M636 Linagliptin M716 Unclear Unclear [3]
MR001557 Linagliptin CD1790 Linagliptin M506 Oxidation - Hydroxylation Unclear [3]
MR001558 Linagliptin CD1790 Linagliptin M490 Oxidation - Hydroxylation Unclear [3]
MR001559 Linagliptin M506 Linagliptin M504 Oxidation - Oxidation Unclear [3]
MR001560 Linagliptin M504 Linagliptin M476 Unclear Unclear [3]
⏷ Show the Full List of 17 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]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1367 Bacteroides finegoldii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1375 Bacteroides intestinalis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [4]
⏷ Show the Full List of 14  DME(s)
References
1 Linagliptin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Clinical pharmacokinetics and pharmacodynamics of linagliptin Clin Pharmacokinet. 2012 Jul 1;51(7):411-27. doi: 10.2165/11630900-000000000-00000.
3 The metabolism and disposition of the oral dipeptidyl peptidase-4 inhibitor, linagliptin, in humans Drug Metab Dispos. 2010 Apr;38(4):667-78. doi: 10.1124/dmd.109.031476.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

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