Description

Azacitidine (CAS 320-67-2) is a nucleoside analog and cytidine derivative with the molecular formula C₈H₁₂N₄O₅. It is a potent DNA methyltransferase inhibitor, widely used in epigenetic research and oncology. Azacitidine is a pyrimidine antimetabolite that incorporates into DNA and RNA, leading to hypomethylation of DNA and subsequent reactivation of tumor suppressor genes. This mechanism makes it a critical therapeutic agent for myelodysplastic syndromes (MDS) and acute myeloid leukemia (AML), marketed under the brand names Vidaza and Onureg. It is supplied as a lyophilized powder or solution for injection/subcutaneous use, with ≥98% purity (HPLC).

Key applications include epigenetic modulation, cancer research, and drug development. Store at controlled room temperature (20-25°C) and protect from light. Available as USP/Pharmaceutical Secondary Standards for quality control. Synonyms include 5-azacytidine, Ladakamycin, and Mylosar.

Properties

• CAS Number: 320-67-2
• Complexity: 384
• IUPAC Name: 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2-one
• InChI: 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
• InChI Key: NMUSYJAQQFHJEW-KVTDHHQDSA-N
• Exact Mass: 244.08076950
• Molecular Formula: C8H12N4O5
• Molecular Weight: 244.20
• SMILES: C1=NC(=NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N
• Topological: 141
• Monoisotopic Mass: 244.08076950
• Physical Description: 5-azacytidine is a white crystalline powder.
• Color/Form: Crystals from methanol
• Melting Point: 442 to 446 °F
• Solubility: >36.6 [ug/mL]
• Stability/Shelf Life: Intact vials should be stored under refrigeration & are stable for a least 4 yr. Although the drug is stable for 3 yr at room temp, refrigeration is recommended because degradation may result at elevated temperatures. The constituted soln hydrolyzes at room temp & should be used within 30 min. The pH providing optimum soln stability has been reported to be about 6.5-7. Azacitidine 0.5 & 2 mg/ml in Ringer’s injection, lactated, was stable for up to one month when frozen at -20 °C in polypropylene syringes.
• Synonyms: 5-azacytidine, Azacitidine, Ladakamycin, Mylosar, 5-azacitidine, Azacitidina, Azacitidinum, Azacitidinum [INN-Latin], Azacitidina [INN-Spanish], Antibiotic U 18496, 5-AZAC, Onureg, U-18496, CCRIS 60, 4-Amino-1-beta-D-ribofuranosyl-s-triazin-2(1H)-one, HSDB 6879, 4-Amino-1-beta-d-ribofuranosyl-1,3,5-triazin-2(1H)-one, WR-183027, EINECS 206-280-2, UNII-M801H13NRU, 5-AZCR, 5 AZC, BRN 0620461, CHEBI:2038, M801H13NRU, U 18496, DTXSID9020116, 5-AC, 4-Amino-1-beta-D-ribofuranosyl-1,3,5-traizin-2(1H)-one, U-18,496, DTXCID10116, NCI-C01569, Onureg (CC-486; oral azacitidine), s-Triazin-2(1H)-one, 4-amino-1-beta-D-ribofuranosyl-, 5 Azacytidine, AZACITIDINE (IARC), AZACITIDINE [IARC], Azacitidinum (INN-Latin), Azacitidina (INN-Spanish), AZACITIDINE (MART.), AZACITIDINE [MART.], AZACITIDINE (USP-RS), AZACITIDINE [USP-RS], 1,3,5-Triazin-2(1H)-one, 4-amino-1-beta-D-ribofuranosyl-, wr 183027, azacitidine for, AZACITIDINEAZACITIDINE, 5-ACZ, L01BC07, NSC 103-627, 4-Amino-1-beta-D-ribofuranosyl-D-triazin-2(1H)-one, 206-280-2, 320-67-2, Azacytidine, Vidaza, NSC-102816, 5AzaC, MFCD00006539, NSC102816, 4-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, NSC 102816, 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one, 4-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1H)-one, 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one, NCGC00090851-04, C8H12N4O5, 1,3,5-Triazin-2(1H)-one, 4-amino-1-.beta.-D-ribofuranosyl-, 5-Aza-xylo-cytidine, SMR000857239, Vidaza (TN), 5-aza-CR, SR-01000075662, Azacitidine;5-AzaC;Ladakamycin, Azacitidine (JAN/USAN/INN), Azacitidine [USAN:INN:BAN], 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, 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2-one, CAS-320-67-2, 5-AzadCyD, Azacitidine (Vidaza), 2-(beta-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-one, 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 [USAN], MolMap_000062, 4-Amino-1-.beta.-D-ribofuranosyl-s-triazin-2(1H)-one, A 2385, AZACITIDINE [VANDF], SCHEMBL3741, CHEMBL1489, Azacitidine (5-Azacytidine), Lopac0_000035, 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, 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, HB1374, HY-10586R, NSC758186, s1782, SBB066305, AKOS015896938, Azacitidine, 5-AzaC;Vidaza;CC-486, 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, DB-006955, SL-000003, EU-0100035, NS00008631, D03021, EN300-118700, F10504, 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

Azacitidine is primarily used in the treatment of myelodysplastic syndromes (MDS) and acute myeloid leukemia (AML) due to its DNA hypomethylating activity. It is also employed in epigenetic research to study gene silencing mechanisms. The compound is suitable for in vitro and in vivo studies targeting aberrant DNA methylation patterns. Clinical formulations include injectable and oral preparations (e.g., CC-486).

Safety and Hazards

GHS Hazard Statements

• H302: Harmful if swallowed [Warning Acute toxicity, oral]
• H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]
• H350: May cause cancer [Danger Carcinogenicity]
• H360: May damage fertility or the unborn child [Danger Reproductive toxicity]
• H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]

Precautionary Statements

• P203, P260, P264, P270, P280, P301+P317, P318, P319, P330, P405, and P501

Hazard Classes and Categories

• Acute toxicity – Category 4
• Germ cell mutagenicity – Category 2
• Carcinogenicity – Category 1B
• Reproductive toxicity – Category 1B
• Specific target organ toxicity – Repeated exposure – Category 1

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