ANCITABINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H11N3O4
Molecular Weight	225.2013
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12OC3=NC(=N)C=CN3[C@]1([H])O[C@H](CO)[C@H]2O

InChI

InChIKey=BBDAGFIXKZCXAH-CCXZUQQUSA-N

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

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/76345 | https://www.ncbi.nlm.nih.gov/pubmed/1707336

Cyclocytidine HCl (also known as Ancitabine) is the prodrug of cytarabine, which is structurally similar to human deoxycytidine to be incorporated into human DNA and then kills the cell. Cyclocytidine was introduced as an antineoplastic agent for the treatment of lymphatic leukemia, sinus acceleration and an increase in systemic blood pressure. Cyclocytidine in combination with amsacrine were effective retrieval therapy for pediatric patients with acute nonlymphoblastic leukemia who were in relapse or unresponsive to frontline therapy.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Refractory childhood leukemia 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6189604	Primary		Phase II 1132	Unknown Approved Use Unknown
Acute nonlymphoblastic leukemia 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1707336	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Phase I. evaluation of cyclocytidine (NSC-145668).	1975 Mar-Apr	1097096
Letter: Myelotoxicity and orthostatic hypotension of cyclocytidine (NSC-145668).	1976 Mar	1260775
Antiviral activities of acyl derivatives of 2,2'-anhydro-1-beta-D-arabinofuranosylcytosine and 1-beta-D-arabinofuranosylcytosine in cell culture.	1977 Feb	66909
Synthesis and anti-viral activity of a series of d- and l-2'-deoxy-2'-fluororibonucleosides in the subgenomic HCV replicon system.	2005 Mar 1	15698782
DNA methylation and sensitivity to antimetabolites in cancer cell lines.	2008 Feb	18202788

Sample Use Guides

In Vivo Use Guide

acute nonlymphoblastic leukemia: Induction therapy consisted of intravenous (IV) Amsacrine (75 mg/m2) from days 1 to 5 and subcutaneous cyclocytidine (600 mg/m2) from days 1 to 7.

Route of Administration: Other

In Vitro Use Guide

Unknown

Name

Type

Language

ANCITABINE

Official Name

English

ANCITABINE [MI]

Common Name

English

Ancitabine [WHO-DD]

Common Name

English

(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

Common Name

English

ancitabine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1557