U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11N3O4.ClH
Molecular Weight 261.662
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANCITABINE HYDROCHLORIDE

SMILES

Cl.OC[C@H]1O[C@@H]2[C@@H](OC3=NC(=N)C=CN23)[C@@H]1O

InChI

InChIKey=KZOWNALBTMILAP-JBMRGDGGSA-N
InChI=1S/C9H11N3O4.ClH/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;1H/t4-,6-,7+,8-;/m1./s1

HIDE SMILES / InChI
Molecular Formula C9H11N3O4
Molecular Weight 225.2013
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Cyclocytidine (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

Unknown
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Not Provided
511
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
240 mg/m2 1 times / day multiple, subcutaneous
Studied dose
Dose: 240 mg/m2, 1 times / day
Route: subcutaneous
Route: multiple
Dose: 240 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/77191/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/77191/
Other AEs: Thrombocytopenia, Orthostatic hypotension...
Other AEs:
Thrombocytopenia
Orthostatic hypotension
Jaw pain
Sources:
https://pubmed.ncbi.nlm.nih.gov/77191/
20 mg/kg 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
unhealthy, CHILD|ADULT
Health Status: unhealthy
Age Group: CHILD|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
Other AEs: Leukopenia, Thrombocytopenia...
Other AEs:
Leukopenia (27%)
Thrombocytopenia (37%)
Marrow hypoplasia (44%)
Parotid pain (37%)
Dizziness (16%)
SGOT increased (14.3%)
SGPT increased (33.3%)
Alkaline phosphatase increased (19%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
AEs

AEs

AESignificanceDosePopulation
Jaw pain
240 mg/m2 1 times / day multiple, subcutaneous
Studied dose
Dose: 240 mg/m2, 1 times / day
Route: subcutaneous
Route: multiple
Dose: 240 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/77191/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/77191/
Orthostatic hypotension
240 mg/m2 1 times / day multiple, subcutaneous
Studied dose
Dose: 240 mg/m2, 1 times / day
Route: subcutaneous
Route: multiple
Dose: 240 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/77191/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/77191/
Thrombocytopenia
240 mg/m2 1 times / day multiple, subcutaneous
Studied dose
Dose: 240 mg/m2, 1 times / day
Route: subcutaneous
Route: multiple
Dose: 240 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/77191/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/77191/
SGOT increased 14.3%
20 mg/kg 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
unhealthy, CHILD|ADULT
Health Status: unhealthy
Age Group: CHILD|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
Dizziness 16%
20 mg/kg 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
unhealthy, CHILD|ADULT
Health Status: unhealthy
Age Group: CHILD|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
Alkaline phosphatase increased 19%
20 mg/kg 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
unhealthy, CHILD|ADULT
Health Status: unhealthy
Age Group: CHILD|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
Leukopenia 27%
20 mg/kg 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
unhealthy, CHILD|ADULT
Health Status: unhealthy
Age Group: CHILD|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
SGPT increased 33.3%
20 mg/kg 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
unhealthy, CHILD|ADULT
Health Status: unhealthy
Age Group: CHILD|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
Parotid pain 37%
20 mg/kg 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
unhealthy, CHILD|ADULT
Health Status: unhealthy
Age Group: CHILD|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
Thrombocytopenia 37%
20 mg/kg 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
unhealthy, CHILD|ADULT
Health Status: unhealthy
Age Group: CHILD|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
Marrow hypoplasia 44%
20 mg/kg 1 times / day multiple, intravenous
Studied dose
Dose: 20 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
unhealthy, CHILD|ADULT
Health Status: unhealthy
Age Group: CHILD|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/1057949/
PubMed

PubMed

TitleDatePubMed
DNA methylation and sensitivity to antimetabolites in cancer cell lines.
2008-02
Synthesis and anti-viral activity of a series of d- and l-2'-deoxy-2'-fluororibonucleosides in the subgenomic HCV replicon system.
2005-03-01
Antiviral activities of acyl derivatives of 2,2'-anhydro-1-beta-D-arabinofuranosylcytosine and 1-beta-D-arabinofuranosylcytosine in cell culture.
1977-02
Letter: Myelotoxicity and orthostatic hypotension of cyclocytidine (NSC-145668).
1976-03
Phase I. evaluation of cyclocytidine (NSC-145668).
1975-03-01

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
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:04:50 GMT 2025
Edited
by admin
on Mon Mar 31 18:04:50 GMT 2025
Record UNII
3T6920M469
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANCITABINE HYDROCHLORIDE
JAN   MART.   MI   WHO-DD  
Common Name English
NSC-145668
Preferred Name English
ANCITABINE HYDROCHLORIDE [JAN]
Common Name English
Ancitabine hydrochloride [WHO-DD]
Common Name English
CYCLOCYTIDINE HCL
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, HYDROCHLORIDE
Systematic Name English
ANCITABINE HYDROCHLORIDE [MI]
Common Name English
ANCITABINE HCL
Common Name English
CYCLOCYTIDINE HYDROCHLORIDE
Common Name English
ANCITABINE HYDROCHLORIDE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1557
Created by admin on Mon Mar 31 18:04:50 GMT 2025 , Edited by admin on Mon Mar 31 18:04:50 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL1412614
Created by admin on Mon Mar 31 18:04:50 GMT 2025 , Edited by admin on Mon Mar 31 18:04:50 GMT 2025
PRIMARY
EPA CompTox
DTXSID40907105
Created by admin on Mon Mar 31 18:04:50 GMT 2025 , Edited by admin on Mon Mar 31 18:04:50 GMT 2025
PRIMARY
CAS
10212-25-6
Created by admin on Mon Mar 31 18:04:50 GMT 2025 , Edited by admin on Mon Mar 31 18:04:50 GMT 2025
PRIMARY
FDA UNII
3T6920M469
Created by admin on Mon Mar 31 18:04:50 GMT 2025 , Edited by admin on Mon Mar 31 18:04:50 GMT 2025
PRIMARY
PUBCHEM
25050
Created by admin on Mon Mar 31 18:04:50 GMT 2025 , Edited by admin on Mon Mar 31 18:04:50 GMT 2025
PRIMARY
NSC
145668
Created by admin on Mon Mar 31 18:04:50 GMT 2025 , Edited by admin on Mon Mar 31 18:04:50 GMT 2025
PRIMARY
CHEBI
74843
Created by admin on Mon Mar 31 18:04:50 GMT 2025 , Edited by admin on Mon Mar 31 18:04:50 GMT 2025
PRIMARY
MERCK INDEX
m1893
Created by admin on Mon Mar 31 18:04:50 GMT 2025 , Edited by admin on Mon Mar 31 18:04:50 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
233-515-6
Created by admin on Mon Mar 31 18:04:50 GMT 2025 , Edited by admin on Mon Mar 31 18:04:50 GMT 2025
PRIMARY
NCI_THESAURUS
C403
Created by admin on Mon Mar 31 18:04:50 GMT 2025 , Edited by admin on Mon Mar 31 18:04:50 GMT 2025
PRIMARY
Related Record Type Details
Structure of ANCITABINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of ANCITABINE
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