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

General Information of Drug (ID: DR0188)
Drug Name
Bendamustine
Synonyms
Bendamustina; Bendamustina [Spanish]; Bendamustine; Bendamustine (INN); Bendamustine [INN]; Bendamustinum; Bendamustinum [Latin]; bendamustin; 16506-27-7; 1H-Benzimidazole-2-butanoic acid, 5-(bis(2-chloroethyl)amino)-1-methyl-; 4-(5-(Bis(2-chloroethyl)amino)-1-methyl-1H-benzo[d]imidazol-2-yl)butanoic acid; 4-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]butanoic acid; 9266D9P3PQ; DSSTox_CID_26888; DSSTox_GSID_46888; DSSTox_RID_81991; NCGC00181170-01; UNII-9266D9P3PQ
Indication Chronic lymphocytic leukaemia [ICD11: 2A82] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 358.3 Topological Polar Surface Area 58.4
Heavy Atom Count 23 Rotatable Bond Count 9
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
65628
PubChem SID
590536 ; 6267839 ; 8189814 ; 14901248 ; 43122399 ; 49882625 ; 50064534 ; 50125886 ; 51091826 ; 53790479 ; 57315623 ; 77194776 ; 103590063 ; 104334244 ; 125093188 ; 126616720 ; 126646730 ; 126669991 ; 135021598 ; 135200933 ; 136946484 ; 137006822 ; 143108248 ; 144115692 ; 144206324 ; 163305696 ; 170465340 ; 174007431 ; 175267866 ; 176225504 ; 176484647 ; 176484951 ; 179322551 ; 187051781 ; 196111115 ; 198993387 ; 215780746 ; 224321241 ; 226414200 ; 242059805 ; 244970987 ; 249862320 ; 250201937 ; 251899454 ; 251916785 ; 251918024 ; 252076446 ; 252345440 ; 252416248
ChEBI ID
CHEBI:135515
CAS Number
16506-27-7
TTD Drug ID
D01CYA
Formula
C16H21Cl2N3O2
Canonical SMILES
CN1C2=C(C=C(C=C2)N(CCCl)CCCl)N=C1CCCC(=O)O
InChI
1S/C16H21Cl2N3O2/c1-20-14-6-5-12(21(9-7-17)10-8-18)11-13(14)19-15(20)3-2-4-16(22)23/h5-6,11H,2-4,7-10H2,1H3,(H,22,23)
InChIKey
YTKUWDBFDASYHO-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
#NAME? DM005661
50943747
Oxidation - Hydrolyzationn 1 [2]
Beta-hydroxybendamustine DM005663 N. A. Unclear 1 [3]
Monohydroxy-bendamustine (bendamustine metabolite HP1) DM005659
23238076
Hydrolysis - Hydrolysis 1 [2]
N-desmethyl-bendamustine (Bendamustine metabolite M4) DM005662
24882536
Oxidation - Dealkylation 1 [2]
Dihydroxy-bendamustine (bendamustine metabolite HP2) DM005660
13755672
Hydrolysis - Hydrolysis 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006036 Bendamustine Monohydroxy-bendamustine (bendamustine metabolite HP1) Hydrolysis - Hydrolysis Unclear [2]
MR006038 Bendamustine -hydroxybendamustine (Bendamustine metabolite M3) Oxidation - Hydrolyzationn CYP1A2 [2]
MR006039 Bendamustine N-desmethyl-bendamustine (Bendamustine metabolite M4) Oxidation - Dealkylation CYP1A2 [2]
MR006040 Bendamustine Beta-hydroxybendamustine Unclear Unclear [3]
MR006037 Monohydroxy-bendamustine (bendamustine metabolite HP1) Dihydroxy-bendamustine (bendamustine metabolite HP2) Hydrolysis - Hydrolysis Unclear [2]
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]
References
1 Bendamustine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacokinetic and pharmacodynamic profile of bendamustine and its metabolites. Cancer Chemother Pharmacol. 2015 Jun;75(6):1143-54.
3 Metabolite profiling of bendamustine in urine of cancer patients after administration of [14C]bendamustine

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