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

General Information of Drug (ID: DR0163)
Drug Name
Azacitidine
Synonyms
Azacitidina; Azacitidina [INN-Spanish]; Azacitidine; Azacitidinum; Azacitidinum [INN-Latin]; Azacytidine; Antibiotic U 18496; Ladakamycin; M801H13NRU; Mylosar; U-18496; Vidaza; WR-183027; 320-67-2; 4-Amino-1-beta-D-ribofuranosyl-1,3,5-traizin-2(1H)-one; 4-Amino-1-beta-D-ribofuranosyl-s-triazin-2(1H)-one; 4-Amino-1-beta-d-ribofuranosyl-1,3,5-triazin-2(1H)-one; 5 AZC; 5-AC; 5-AZAC; 5-AZCR; 5-azacitidine; 5-azacytidine; 5AzaC; BRN 0620461; CCRIS 60; CHEBI:2038; EINECS 206-280-2; HSDB 6879; NSC-102816; NSC102816; UNII-M801H13NRU
Indication Myelodysplastic syndrome [ICD11: 2A36] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 244.2 Topological Polar Surface Area 141
Heavy Atom Count 17 Rotatable Bond Count 2
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
9444
PubChem SID
13439 ; 596456 ; 3139592 ; 8140000 ; 8148227 ; 8149830 ; 8156757 ; 11335300 ; 11360539 ; 11364156 ; 11364964 ; 11366718 ; 11367526 ; 11369280 ; 11370088 ; 11372756 ; 11373127 ; 11374582 ; 11375688 ; 11377442 ; 11378259 ; 11461511 ; 11484628 ; 11488602 ; 11491324 ; 11492737 ; 11495076 ; 12013374 ; 14749656 ; 15019893 ; 17390033 ; 17397176 ; 17404599 ; 24278211 ; 24890525 ; 26612306 ; 26679741 ; 26752817 ; 29228037 ; 46509032 ; 47216641 ; 47662119 ; 47810606 ; 47885263 ; 48034961 ; 48259073 ; 48334340 ; 48413245 ; 48415593 ; 48422584
ChEBI ID
ChEBI:2038
CAS Number
320-67-2
TTD Drug ID
D09FAZ
Formula
C8H12N4O5
Canonical SMILES
C1=NC(=NC(=O)N1C2C(C(C(O2)CO)O)O)N
InChI
1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1
InChIKey
NMUSYJAQQFHJEW-KVTDHHQDSA-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
5-Azacytidine monophosphate DM018059 N. A. Unclear - Unclear 1 [4]
5-Azacytidine diphosphate DM018060 N. A. Unclear - Unclear 2 [4]
5-Aza2' deoxycytidine diphosphate DM018061 N. A. Unclear - Unclear 3 [4]
5-Azacytidine triphosphate DM018063 N. A. Unclear - Unclear 3 [4]
5-Aza2' -dexycytidine triphosphate DM018062 N. A. Unclear - Unclear 4 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009892 Azacitidine 5-Azacytidine monophosphate Unclear - Unclear UDK [4]
MR009893 5-Azacytidine monophosphate 5-Azacytidine diphosphate Unclear - Unclear PMPK [4]
MR009894 5-Azacytidine diphosphate 5-Aza2' deoxycytidine diphosphate Unclear - Unclear RCR [4]
MR009896 5-Azacytidine diphosphate 5-Azacytidine triphosphate Unclear - Unclear PDPK [4]
MR009895 5-Aza2' deoxycytidine diphosphate 5-Aza2' -dexycytidine triphosphate Unclear - Unclear NME4 [4]
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 deaminase (cdd) DME1196 Mycoplasma hyorhinis
E0TLJ6_MYCHH
3.5.4.5
[3]
References
1 Azacitidine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 A pilot pharmacokinetic study of oral azacitidine. Leukemia. 2008 Sep;22(9):1680-4.
3 Mycoplasma hyorhinis-encoded cytidine deaminase efficiently inactivates cytosine-based anticancer drugs. FEBS Open Bio. 2015 Aug 3;5:634-9.
4 5-Azacytidine/Azacitidine

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