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

General Information of Drug (ID: DR0398)
Drug Name
Cytarabine
Synonyms
Citarabina; Cytarabin; Cytarabina; Cytarabinoside; Cytarabinum; Cytarabinum [INN-Latin]; Cytonal; Cytosar; Cytosar-U; Cytosine arabinofuranoside; Cytosine arabinoside; Cytosine beta-D-arabinofuranoside; Cytosine-beta-D-arabinofuranoside; Cytosinearabinoside; DepoCyte; Depocyt; Depocyt (liposomal); Erpalfa; Tarabine; Udicil; beta-D-Arabinosylcytosine; cytarabine; Alexan; Arabinocytidine; Arabinofuranosylcytosine; Arabinosylcytosine; Arabitin; Aracytidine; Aracytin; Aracytine; Arafcyt; 1-beta-D-Arabinofuranosylcytosine; 147-94-4; Ara-C
Indication Acute lymphoblastic leukemia [ICD11: 2B33] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 243.22 Topological Polar Surface Area 129
Heavy Atom Count 17 Rotatable Bond Count 2
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
6253
PubChem SID
5877 ; 598052 ; 829245 ; 3260118 ; 7847236 ; 7885952 ; 7979015 ; 8153933 ; 11528303 ; 11533128 ; 12146044 ; 14774115 ; 15196510 ; 24858315 ; 24892435 ; 26527898 ; 26719755 ; 29215144 ; 29225249 ; 46386862 ; 46505879 ; 47193873 ; 47573376 ; 48415837 ; 49831046 ; 50105698 ; 53787662 ; 56310997 ; 56311029 ; 56312269 ; 56312943 ; 56313129 ; 56313612 ; 76890970 ; 83110442 ; 87558791 ; 90341066 ; 92308449 ; 92309014 ; 93166529 ; 93167157 ; 103210760 ; 103986361 ; 104253284 ; 104311532 ; 117529237 ; 118048876 ; 124648720 ; 124757405 ; 124799562
ChEBI ID
ChEBI:28680
CAS Number
147-94-4
TTD Drug ID
D07XSN
Formula
C9H13N3O5
Canonical SMILES
C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)O
InChI
1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m1/s1
InChIKey
UHDGCWIWMRVCDJ-CCXZUQQUSA-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
Cytarabine triphosphate DM003767
25774
Unclear 1 [3]
Uracil arabinoside DM003769
18323
Unclear 1 [3]
Uracil derivative DM003768 N. A. Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004139 Cytarabine Cytarabine triphosphate Unclear DCK [3]
MR004141 Cytarabine Uracil arabinoside Unclear CDA [3]
MR004140 Cytarabine triphosphate Uracil derivative Unclear RYND [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytidine aminohydrolase (CDA) DME0080 Homo sapiens
CDD_HUMAN
3.5.4.5
[2]
Cytidine aminohydrolase (CDA) DME0080 Homo sapiens
CDD_HUMAN
3.5.4.5
[3]
Cytidine deaminase (cdd) DME1196 Mycoplasma hyorhinis
E0TLJ6_MYCHH
3.5.4.5
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Deoxycytidine kinase (DCK) DME0443 Homo sapiens
DCK_HUMAN
2.7.1.74
[3]
Deoxycytidylate deaminase (DCTD) DME0112 Homo sapiens
DCTD_HUMAN
3.5.4.12
[2]
Ecto-5'-nucleotidase (NT5E) DME0111 Homo sapiens
5NTD_HUMAN
3.1.3.5
[2]
pyrimidine nucleoside deaminase (RYND) DMEN148 Homo sapiens Not Available Not Available [3]
⏷ Show the Full List of 8  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Cytidine deaminase (cdd) DME1196 Km = 6172 microM
E0TLJ6_MYCHH
[4]
References
1 Cytarabine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Genetic factors influencing cytarabine therapy. Pharmacogenomics. 2009 Oct;10(10):1657-74.
3 PubChem:Cytarabine
4 Mycoplasma hyorhinis-encoded cytidine deaminase efficiently inactivates cytosine-based anticancer drugs. FEBS Open Bio. 2015 Aug 3;5:634-9.
5 Synthesis and characterization of a novel liver-targeted prodrug of cytosine-1-beta-D-arabinofuranoside monophosphate for the treatment of hepatocellular carcinoma. J Med Chem. 2006 Dec 28;49(26):7711-20.

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