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

General Information of Drug (ID: DR0400)
Drug Name
Dabigatran etexilate
Synonyms
Dabigatran etexilate (USAN/INN); EBD35035; NCGC00262929-01; Pradaxa (TN); SCHEMBL505829; STL450990; STL483396; Tox21_113924; cc-72; ethyl N-[(2-{[(4-{N'-[(hexyloxy)carbonyl]carbamimidoyl}phenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl]-N-pyridin-2-yl-beta-alaninate; s2154; Dabigatran; I0VM4M70GC; N-[(2-{[(4-Carbamimidoylphenyl)amino]methyl}-1-Methyl-1h-Benzimidazol-5-Yl)carbonyl]-N-Pyridin-2-Yl-Beta-Alanine; Q-102529; UNII-I0VM4M70GC; 211914-51-1; 3-[[2-[(4-carbamimidoylanilino)methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoic acid; 3-[[2-[[(4-CARBAMIMIDOYLPHENYL)AMINO]METHYL]-1-METHYL-BENZOIMIDAZOLE-5-CARBONYL]-PYRIDIN-2-YL-AMINO]PROPANOIC ACID; BIBR 953; BIBR 953 (Dabigatran, Pradaxa); BIBR-953; BIBR953; C25H25N7O3; CHEBI:70752; CHEMBL48361; 211915-06-9; A815191; AB01274780-01; AB01274780_02; BDBM50432209; BIBR-1048; BIBR1048; CAS-211915-06-9; D07144; DSSTox_CID_31470; DSSTox_GSID_57681; DSSTox_RID_97355
Indication Venous thromboembolism [ICD11: BD72] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 627.7 Topological Polar Surface Area 154
Heavy Atom Count 46 Rotatable Bond Count 17
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
9578572
ChEBI ID
CHEBI:70746
CAS Number
211915-06-9
TTD Drug ID
D0KI5R
Formula
C34H41N7O5
Canonical SMILES
CCCCCCOC(=O)N=C(C1=CC=C(C=C1)NCC2=NC3=C(N2C)C=CC(=C3)C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)N
InChI
1S/C34H41N7O5/c1-4-6-7-10-21-46-34(44)39-32(35)24-12-15-26(16-13-24)37-23-30-38-27-22-25(14-17-28(27)40(30)3)33(43)41(20-18-31(42)45-5-2)29-11-8-9-19-36-29/h8-9,11-17,19,22,37H,4-7,10,18,20-21,23H2,1-3H3,(H2,35,39,44)
InChIKey
KSGXQBZTULBEEQ-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
BIBR0951/M2 DM006129
446804
Hydrolysis - Hydrolysis 1 [4] , [5]
BIBR1087/M1 DM006147
10290289
Hydrolysis - Hydrolysis 1 [4] , [5] , [6]
Dabigatran DM006130
216210
Hydrolysis - Hydrolysis 2 [7]
Dabigatran DM006130
216210
Hydrolysis - Hydrolysis 2 [5]
Dabigatran M630 DM006148 N. A. Oxidation - Oxidationn 2 [7]
Dabigatran 1-O-acylglucuronide metabolite DM006140 N. A. Conjugation - Glucuronidation 3 [7]
Dabigatran M400 DM003777
141348660
Hydrolysis - Hydrolysis 3 [7]
Dabigatran M486 DM006136 N. A. Oxidation - Oxidationn 3 [7]
Dabigatran M602 DM006149 N. A. Unclear 3 [7]
Dabigatran metabolite M324 DM003779
69624070
Hydrolysis - Hydrolysis 3 [7]
Dabigatran metabolite M355 DM003773
146675101
Hydrolysis - Hydrolysis 3 [7]
Dabigatran 2-O-acylglucuronide metabolite DM006146 N. A. Unclear 4 [7]
Dabigatran 3-O-acylglucuronide metabolite DM006145 N. A. Unclear 4 [7]
Dabigatran 4-O-acylglucuronide metabolite DM006144 N. A. Unclear 4 [7]
Dabigatran M354 DM006132
144920619
Unclear 4 [7]
Dabigatran M369 DM006134
156028097
Hydrolysis - Hydrolysis 4 [7]
Dabigatran M369 DM006134
156028097
Oxidation - Oxidationn 4 [7]
Dabigatran M486-2 DM006142
18412517
Unclear 4 [7]
Dabigatran M500 DM006138 N. A. Conjugation - Glucuronidation 4 [7]
Dabigatran M574 DM006150 N. A. Unclear 4 [7]
Dabigatran M636 DM006141 N. A. Unclear 4 [7]
Dabigatran M690 DM006143 N. A. Unclear 4 [7]
Dabigatran M325 DM006135
156596423
Oxidation - Decarboxylation 5 [7]
Dabigatran M396 DM006133
146675109
Conjugation - Acetylation 5 [7]
⏷ Show the Full List of 24  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013409 Dabigatran etexilate BIBR0951/M2 Hydrolysis - Hydrolysis CES2 [4], [5]
MR013428 Dabigatran etexilate BIBR1087/M1 Hydrolysis - Hydrolysis CES1 ... [4], [5], [6]
MR013432 Dabigatran etexilate Dabigatran Hydrolysis - Hydrolysis CES1 [7]
MR013410 BIBR0951/M2 Dabigatran Hydrolysis - Hydrolysis CES1 ... [5]
MR013429 BIBR1087/M1 Dabigatran M630 Oxidation - Oxidationn Unclear [7]
MR013411 Dabigatran Dabigatran M355 Hydrolysis - Hydrolysis Unclear [7]
MR013416 Dabigatran Dabigatran M486 Oxidation - Oxidationn Unclear [7]
MR013418 Dabigatran BIBR1151/M324 Hydrolysis - Hydrolysis Unclear [7]
MR013420 Dabigatran Dabigatran M400 Hydrolysis - Hydrolysis Unclear [7]
MR013421 Dabigatran Dabigatran 1-O-acylglucuronide metabolite Conjugation - Glucuronidation Unclear [7]
MR013423 Dabigatran Dabigatran M486-2 Unclear Unclear [7]
MR013424 Dabigatran Dabigatran M690 Unclear Unclear [7]
MR013425 Dabigatran Dabigatran 4-O-acylglucuronide metabolite Unclear Unclear [7]
MR013426 Dabigatran Dabigatran 3-O-acylglucuronide metabolite Unclear Unclear [7]
MR013427 Dabigatran Dabigatran 2-O-acylglucuronide metabolite Unclear Unclear [7]
MR013430 Dabigatran M630 Dabigatran M602 Unclear Unclear [7]
MR013419 BIBR1151/M324 Dabigatran M500 Conjugation - Glucuronidation Unclear [7]
MR013422 Dabigatran 1-O-acylglucuronide metabolite Dabigatran M636 Unclear Unclear [7]
MR013412 Dabigatran M355 Dabigatran M354 Unclear Unclear [7]
MR013414 Dabigatran M355 Dabigatran M369 Oxidation - Oxidationn Unclear [7]
MR013417 Dabigatran M486 Dabigatran M369 Hydrolysis - Hydrolysis Unclear [7]
MR013431 Dabigatran M602 Dabigatran M574 Unclear Unclear [7]
MR013413 Dabigatran M354 Dabigatran M396 Conjugation - Acetylation Unclear [7]
MR013415 Dabigatran M369 Dabigatran M325 Oxidation - Decarboxylation Unclear [7]
⏷ Show the Full List of 24 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]
Carboxylesterase 2 (CES2) DME0057 Homo sapiens
EST2_HUMAN
3.1.1.1
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[3]
References
1 Dabigatran Etexilate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacogenomics of novel direct oral anticoagulants: newly identified genes and genetic variants. J Pers Med. 2019 Jan 17;9(1). pii: E7.
3 Dabigatran acylglucuronide, the major human metabolite of dabigatran: in vitro formation, stability, and pharmacological activity. Drug Metab Dispos. 2010 Sep;38(9):1567-75.
4 The metabolism and disposition of the oral direct thrombin inhibitor, dabigatran, in humans
5 Conventional liquid chromatography/triple quadrupole mass spectrometry based metabolite identification and semi-quantitative estimation approach in the investigation of in vitro dabigatran etexilate metabolism. Anal Bioanal Chem. 2013 Feb;405(5):1695-704.
6 Identification of carboxylesterase-dependent dabigatran etexilate hydrolysis
7 DrugBank(Pharmacology-Metabolism): Dabigatran etexilate

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