Description

Ancitabine (CAS No. 10212-25-6), also known as Cyclocytidine, is a synthetic nucleoside analog with the molecular formula C₉H₁₁N₃O₄. This compound is a derivative of cytidine, featuring a unique 2,2′-anhydro bridge that enhances its stability and biological activity. Ancitabine is widely recognized for its role as an antimetabolite and antiviral agent, particularly in research applications involving nucleic acid metabolism and cancer therapeutics. Its mechanism of action involves interference with DNA synthesis, making it a valuable tool in biochemical and pharmacological studies.

This high-purity compound is supplied as a white to off-white crystalline powder, rigorously tested for quality and consistency. It is soluble in water and dimethyl sulfoxide (DMSO), ensuring compatibility with a variety of experimental protocols. Ancitabine is ideal for researchers investigating nucleoside analogs, antiviral therapies, and chemotherapy mechanisms. Store at 2-8°C in a tightly sealed container to maintain stability.

Properties

• CAS Number: 10212-25-6
• Complexity: 394
• IUPAC Name: (2R,4R,5R,6S)-4-(hydroxymethyl)-10-imino-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-5-ol
• InChI: InChI=1S/C9H11N3O4/c10-5-1-2-12-8-7(16-9(12)11-5)6(14)4(3-13)15-8/h1-2,4,6-8,10,13-14H,3H2/t4-,6-,7+,8-/m1/s1
• InChI Key: BBDAGFIXKZCXAH-CCXZUQQUSA-N
• Exact Mass: 225.07495584
• Molecular Formula: C9H11N3O4
• Molecular Weight: 225.20
• SMILES: C1=CN2[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)OC2=NC1=N
• Topological: 98.4
• Monoisotopic Mass: 225.07495584
• Solubility: H2O 200
• Stability/Shelf Life: Bulk: A sample stored at 60°C for 30 days showed no decomposition as indicated by optical rotation. Solution: A 1% solution in water after 24 hours at room temperature showed no decomposition as indicated by optical rotation.
• Synonyms: ANCITABINE, Cyclocytidine, Ancytabine, Ancitabina, Anhydrocytidine, Anhydroara C, Ancitabine [INN], Ancitabinum, Ancitabinum [INN-Latin], Ancitabina [INN-Spanish], 2,2′-O-Cyclocytidine, O(sup 2),2′-Cyclocytidine, CCRIS 2757, UNII-DO2D32W0VC, DO2D32W0VC, DTXSID6020357, CHEBI:74838, 2,2′-anhydro-AraC, 10212-25-6, ANCITABINE [MI], O(2,2′)-cyclocytidine, NSC145668, (2R,3R,3aS,9aR)-2,3,3a,9a-Tetrahydro-3-hydroxy-6-imino-6H-furo(2′,3′;4,5)oxazolo(3,2-a)pyrimidine-2-methanol, ANCITABINE [WHO-DD], DTXCID40357, NSC 145668, NSC-145668, (2R,3R,3aS,9aR)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydro-6H-furo[2′,3′:4,5][1,3]oxazolo[3,2-a]pyrimidin-3-ol, 6H-Furo(2′,3′:4,5)oxazolo(3,2-a)pyrimidine-2-methanol, 2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-, (2R-(2alpha,3beta,3abeta,9abeta))-, Ancitabinum (INN-Latin), Ancitabina (INN-Spanish), Anhydro-Ara-C, 2,2′-anhydro-1-(beta-D-arabinofuranosyl)cytosine, 6H-Furo(2′,3′:4,5)oxazolo(3,2-alpha)pyrimidine-2-methanol, 2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-, stereoisomer, O2,2′-Cyclocytidine, (2R,3R,3aS,9aR)-6-imino-2-methylol-2,3,3a,9a-tetrahydrofuro[1,2]oxazolo[3,4-a]pyrimidin-3-ol, [2R-(2alpha,3beta,3abeta,9abeta)]-2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-6H-furo[2′,3′:4,5]pxazolo[3,2-a]pyrimidine-2-methanol, OCTD hydrochloride (Salt/Mix), NSC-145,668, Ancitabine hydrochloride (Salt/Mix), U-33,624A, Cyclocytidine hydrochloride (Salt/Mix), (2R,3R,3aS,9aR)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydro-6H-furo(2′,3′:4,5)(1,3)oxazolo(3,2-a)pyrimidin-3-ol, (2R,3R,3aS,9aR)-6-imino-2-methylol-2,3,3a,9a-tetrahydrofuro(1,2)oxazolo(3,4-a)pyrimidin-3-ol, (2R-(2alpha,3beta,3abeta,9abeta))-2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-6H-furo(2′,3′:4,5)pxazolo(3,2-a)pyrimidine-2-methanol, (2R,3R,3aS,9aR)-2,3,3a,9a-Tetrahydro-3-hydroxy-6-imino-6H-furo(2′,3′:4,5)oxazolo(3,2-a)pyrimidine-2-methanol, 6H-Furo(2′,3′:4,5)oxazolo(3,2-a)pyrimidine-2-methanol, 2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-, (2R-(2.alpha.,3.beta.,3a.beta.,9a.beta.))-, 6H-Furo(2′,3′:4,5)oxazolo(3,2-a)pyrimidine-2-methanol, 2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-, stereoisomer, bbdagfixkzcxah-ccxzuqqusa-n, bbdagfixkzcxah-uhfffaoysa-n, 31698-14-3, 2,2′-Cyclocytidine, 2,2′-Anhydrocytidine, 2,2′-Anhydroarabinosylcytosine, Cyclo-C, NCGC00159322-02, MLS001173324, (2R,4R,5R,6S)-4-(hydroxymethyl)-10-imino-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-5-ol, CAS-31698-14-3, SMR000538927, OCTD, NSC129220, SCHEMBL8708, Cyclocytidine hydrochloride;Cyclo-CMP hydrochloride;Cyclo-C, cid_25050, CHEMBL1412614, BDBM58407, HY-N0093A, HMS2090A16, TNP00125, Tox21_111571, Tox21_301815, AKOS025312528, NA02790, SMP1_000022, NCGC00017239-01, NCGC00159322-04, NCGC00159322-05, NCGC00159322-06, NCGC00159322-14, NCGC00159322-18, NCGC00255140-01, BP-43568, DA-50457, 4,5)oxazolo(3,2-a)pyrimidine-2-methanol, CS-0013321, AB00430480-02, 2,2′-Anhydro-1-.beta.-D-arabinofuranosylcytosine, EN300-19740102, BRD-K67536197-003-11-4, Q27144950, (2R,3R,3aS,9aR)-2,3,3a,9a-Tetrahydro-3-hydroxy-6-imino-6H-furo(2′,3′, 2,2’Anhydro-b-D-arabinofuranosyl cytosine;Ancitabine;2,2′-Anhydro-D-cytidine, (2R,3R,3aS,9aR)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydro-6H-furo[2′,3′:4,5]oxazolo[3,2-a]pyrimidin-3-ol, (2R,3R,3aS,9aR)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydrofuro[[?]:[?]]oxazolo[[?]]pyrimidin-3-ol, (2R,3R,3aS,9aR)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydrofuro[1,2][1,3]oxazolo[3,4-a]pyrimidin-3-ol;hydrochloride, (2R,3R,3aS,9aR)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydrofuro[1,2]oxazolo[3,4-a]pyrimidin-3-ol;hydrochloride, (2R,3R,3aS,9aR)-6-azanylidene-2-(hydroxymethyl)-2,3,3a,9a-tetrahydrofuro[1,2][1,3]oxazolo[3,4-a]pyrimidin-3-ol;hydrochloride, (2R,3R,3aS,9aR)-6-imino-2-methylol-2,3,3a,9a-tetrahydrofuro[1,2]oxazolo[3,4-a]pyrimidin-3-ol;hydrochloride, (2R,4R,5R,6S)-4-(hydroxymethyl)-10-imino-3,7-dioxa-1,9-diazatricyclo[6.4.0.0,2,6]dodeca-8,11-dien-5-ol

Ancitabine is primarily used in biochemical research as a nucleoside analog to study DNA synthesis inhibition and antiviral mechanisms. It serves as a precursor in the synthesis of cytarabine (Ara-C), a critical chemotherapeutic agent. Researchers also utilize Ancitabine to explore its potential in treating viral infections and hematologic malignancies. Its unique structural properties make it a valuable reference standard in analytical chemistry and pharmaceutical development.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.