Compound: 5-azacytidine
SMILES: O=c1nc(ncn1[C@@H]2O[C@H](CO)[C@H]([C@H]2O)O)N
InChIKey: NMUSYJAQQFHJEW-KVTDHHQDSA-N
Synonyms: 5-azacytidine, Azacitidine, 320-67-2, Azacytidine, Ladakamycin, Mylosar, 5-azacitidine, Azacitidina, Azacitidinum, Antibiotic U 18496, Onureg, U-18496, NSC 102816, 4-Amino-1-beta-d-ribofuranosyl-1,3,5-triazin-2(1H)-one, 4-Amino-1-beta-D-ribofuranosyl-s-triazin-2(1H)-one, DTXSID9020116, NSC102816, 5-AZCR, 5 AZC, CHEBI:2038, M801H13NRU, U 18496, U-18,496, DTXCID10116, 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one, NCI-C01569, 1,3,5-Triazin-2(1H)-one, 4-amino-1-beta-D-ribofuranosyl-, s-Triazin-2(1H)-one, 4-amino-1-beta-D-ribofuranosyl-, 5 Azacytidine, 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one, azacitidine for, 4-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-1,2-dihydro-1,3,5-triazin-2-one, 4-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-1,3,5-triazin-2-one, RefChem:57658, AZACITIDINE AZACITIDINE, L01BC07, 4-Amino-1-beta-D-ribofuranosyl-D-triazin-2(1H)-one, 5'-AZACYTIDINE, Vidaza, Azacitidinum [INN-Latin], Azacitidina [INN-Spanish], NSC-102816, C8H12N4O5, 5-AZAC, MFCD00006539, 4-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1H)-one, WR-183027, NCGC00090851-04, 1,3,5-Triazin-2(1H)-one, 4-amino-1-.beta.-D-ribofuranosyl-, 5-Aza-xylo-cytidine, CCRIS 60, 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2-one, SMR000857239, 4-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Vidaza (TN), HSDB 6879, 5-aza-CR, SR-01000075662, EINECS 206-280-2, Azacitidine;5-AzaC;Ladakamycin, BRN 0620461, UNII-M801H13NRU, cc-486, Azacitidine (JAN/USAN/INN), Azacitidine [USAN:INN:BAN], 4-Amino-1-beta-D-ribofuranosyl-1,3,5-traizin-2(1H)-one, 5-Azacytidine?, NS-17, 1-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-amino-1,3,5-tri azin-2-one, CAS-320-67-2, 5-AzadCyD, Azacitidine (Vidaza), 2-(beta-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-one, Azacitidine, 5-AzaC, Spectrum_001262, 4-Amino-1-beta-D-ribofuranosyl-1,3,5-triazine-2(1H)-one, AZACITIDINE [MI], Spectrum2_000786, Spectrum3_001509, Spectrum4_000922, Spectrum5_001166, AZACITIDINE [INN], AZACITIDINE [JAN], 5-Azacytidine (Standard), AZACITIDINE [HSDB], AZACITIDINE [IARC], AZACITIDINE [USAN], Epitope ID:613415, MolMap_000062, 4-Amino-1-.beta.-D-ribofuranosyl-s-triazin-2(1H)-one, A 2385, AZACITIDINE [VANDF], SCHEMBL3741, AZACITIDINE [MART.], CHEMBL1489, Azacitidine (5-Azacytidine), Lopac0_000035, AZACITIDINE [USP-RS], AZACITIDINE [WHO-DD], BSPBio_003157, KBioGR_001444, KBioGR_002556, KBioSS_001742, KBioSS_002565, MLS001333121, MLS001333122, MLS002153249, MLS002548894, DivK1c_000125, SCHEMBL433074, SPECTRUM1502111, SPBio_000892, AZACITIDINE [EMA EPAR], GTPL6796, orb1308921, BCBcMAP01_000083, HMS500G07, KBio1_000125, KBio2_001742, KBio2_002556, KBio2_004310, KBio2_005124, KBio2_006878, KBio2_007692, KBio3_002657, KBio3_003034, NMUSYJAQQFHJEW-KVTDHHQDSA-, AZACITIDINE [ORANGE BOOK], pyrimidine antimetabolite: inhibits nucleic acid replication, cMAP_000082, NINDS_000125, GLXC-07091, HMS1921J22, HMS2092D08, HMS2231F15, HMS3259D19, HMS3260G11, Pharmakon1600-01502111, 5-Azacytidine, >=98% (HPLC), Tox21_111032, Tox21_302985, Tox21_500035, BDBM50424715, CCG-39046, EBC-11024, HB1374, HY-10586R, NSC758186, s1782, SBB066305, Onureg (CC-486; oral azacitidine), AKOS015896938, Tox21_111032_1, CS-1287, DB00928, LP00035, NA02947, NC00672, NSC-758186, 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triaz, IDI1_000125, NCGC00090851-01, NCGC00090851-02, NCGC00090851-03, NCGC00090851-05, NCGC00090851-06, NCGC00090851-07, NCGC00090851-08, NCGC00090851-10, NCGC00090851-14, NCGC00090851-18, NCGC00090851-22, NCGC00178234-01, NCGC00256541-01, NCGC00260720-01, AS-13697, HY-10586, SRI-10756_10, SRI-10756_12, ST056940, SY023613, DB-006955, SL-000003, EU-0100035, NS00008631, D03021, EN300-118700, F10504, F492447, Q416451, SR-01000075662-1, SR-01000075662-3, SR-01000075662-7, BRD-K03406345-001-02-1, BRD-K03406345-001-21-1, BRD-K03406345-001-27-8, Z1515383340, Azacitidine, United States Pharmacopeia (USP) Reference Standard, 4-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; Ladakamycin, Azacitidine, Pharmaceutical Secondary Standard; Certified Reference Material, 1401238-97-8, 5-Azacytidine, Hybri-Max(TM), gamma-irradiated, lyophilized powder, BioXtra, suitable for hybridoma, 5AE, InChI=1/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
Theoretical properties:
molecular_formula: C8H12N4O5
molecular_weight: 244.20 g/mol
exact_mass: 244.08076950 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 17
topological_polar_surface_area: 141 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from methanol
color: Crystals from methanol
melting_point: 442 to 446 °F (decomposes) (NTP, 1992)
solubility: 5 to 10 mg/mL at 70 °F (NTP, 1992)
Descriptions:
pubchem: Azacitidine can cause cancer according to The World Health Organization's International Agency for Research on Cancer (IARC).
chebi: An <em>N</em>-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1<em>H</em>)-one substituted by a β-<small>D</small>-ribofuranosyl residue via an <em>N</em>-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia.
chembl: AZACITIDINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Azacitidine, sold under the brand name Vidaza among others, is a medication used for the treatment of myelodysplastic syndrome, myeloid leukemia, and juvenile myelomonocytic leukemia. It is a chemical analog of cytidine, a nucleoside in DNA and RNA. Azacitidine and its deoxy derivative, decitabine (also known as 5-aza-2′-deoxycytidine) were first synthesized in Czechoslovakia as potential chemotherapeutic agents for cancer.
The most common adverse reactions in children with juvenile myelomonocytic leukemia include pyrexia, rash, upper respiratory tract infection, and anemia.