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

General Information of Drug (ID: DR1136)
Drug Name
Nelarabine
Synonyms
Nelarabine; Nelarabine (Arranon); Nelzarabine; Nelzarabine (USAN); Arranon; ArranonG; Atriance; (2R,3S,4S,5R)-2-(2-Amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol; (2R,3S,4S,5R)-2-(2-amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol; 121032-29-9; 2-Amino-9-beta-D-arabinofuranosyl-6-methoxy-9H-purine; 506U; 506U78; 60158CV180; CHEBI:63612; DSSTox_CID_26842; DSSTox_GSID_46842; DSSTox_RID_81952; GW 506U78; GW-506U78; MAY; NCGC00181098-01; NSC-686673; S1213; UNII-60158CV180
Indication Acute lymphoblastic leukemia [ICD11: 2B33] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 297.27 Topological Polar Surface Area 149
Heavy Atom Count 21 Rotatable Bond Count 3
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
3011155
PubChem SID
3723610 ; 10039476 ; 12015013 ; 14775959 ; 14922755 ; 36059494 ; 46506325 ; 47206859 ; 50125808 ; 57410212 ; 71821532 ; 80796537 ; 99437030 ; 103771095 ; 111631431 ; 124757087 ; 125163891 ; 126592934 ; 128235087 ; 131296361 ; 134223564 ; 134338255 ; 135108408 ; 135611106 ; 136368093 ; 136375852 ; 136949086 ; 137006687 ; 140519970 ; 144074932 ; 144115623 ; 144206267 ; 151991744 ; 152059610 ; 152213835 ; 152344115 ; 160964602 ; 162011505 ; 164175279 ; 170464759 ; 172914301 ; 174477095 ; 175266277 ; 176484949 ; 178103668 ; 179116965 ; 185998139 ; 196376328 ; 210274937 ; 210280574
ChEBI ID
CHEBI:63612
CAS Number
121032-29-9
TTD Drug ID
D0B8UJ
Formula
C11H15N5O5
Canonical SMILES
COC1=NC(=NC2=C1N=CN2C3C(C(C(O3)CO)O)O)N
InChI
1S/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/m1/s1
InChIKey
IXOXBSCIXZEQEQ-UHTZMRCNSA-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
Ara-G DM002147
135499520
Other reaction - Phosphorylation 1 [4] , [5]
Arabinofuranosylguanine DM002149
136125470
Oxidation - Demethylation 1 [6] , [3]
Ara-GTP DM002148
135544356
Unclear 2 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002950 Nelarabine Ara-G Other reaction - Phosphorylation DCK ... [4], [5]
MR002951 Nelarabine Arabinofuranosylguanine Oxidation - Demethylation ADA [6], [3]
MR002949 Ara-G Ara-GTP Unclear Unclear [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Adenosine aminohydrolase (ADA) DME0060 Homo sapiens
ADA_HUMAN
3.5.4.4
[2] , [3]
Deoxyguanosine kinase (dgk) DMEN053 Bacillus subtilis
DGK_BACSU
2.5.1.22
[4]
References
1 Nelarabine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Profile of nelarabine: use in the treatment of T-cell acute lymphoblastic leukemia. Onco Targets Ther. 2009 Feb 18;2:219-28.
3 FDA Approved Drug Products: ARRANON? (nelarabine) Injection FOR INTRAVENOUS USE
4 A new high-performance liquid chromatography method determines low production of 9-beta-D-arabinofuranosylguanine triphosphate, an active metabolite of nelarabine, in adult T-cell leukemia cells Oncol Rep. 2010 Feb;23(2):499-504.
5 Nelarabine Drugs. 2008;68(4):439-47. doi: 10.2165/00003495-200868040-00004.
6 DrugBank(Pharmacology-Metabolism)Nelarabine
7 U. S. FDA Label -Nelarabine

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