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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 of ANCITABINE

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

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

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Letter: Myelotoxicity and orthostatic hypotension of cyclocytidine (NSC-145668).
1976 Mar
DNA methylation and sensitivity to antimetabolites in cancer cell lines.
2008 Feb

Sample Use Guides

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 Thu Jul 06 00:54:40 UTC 2023
Edited
by admin
on Thu Jul 06 00:54:40 UTC 2023
Record UNII
DO2D32W0VC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANCITABINE
INN   MI   WHO-DD  
INN  
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
Created by admin on Thu Jul 06 00:54:40 UTC 2023 , Edited by admin on Thu Jul 06 00:54:40 UTC 2023
Code System Code Type Description
MESH
D003504
Created by admin on Thu Jul 06 00:54:40 UTC 2023 , Edited by admin on Thu Jul 06 00:54:40 UTC 2023
PRIMARY
MERCK INDEX
M1893
Created by admin on Thu Jul 06 00:54:40 UTC 2023 , Edited by admin on Thu Jul 06 00:54:40 UTC 2023
PRIMARY Merck Index
CHEBI
74838
Created by admin on Thu Jul 06 00:54:40 UTC 2023 , Edited by admin on Thu Jul 06 00:54:40 UTC 2023
PRIMARY
PUBCHEM
25051
Created by admin on Thu Jul 06 00:54:40 UTC 2023 , Edited by admin on Thu Jul 06 00:54:40 UTC 2023
PRIMARY
EPA CompTox
DTXSID6020357
Created by admin on Thu Jul 06 00:54:40 UTC 2023 , Edited by admin on Thu Jul 06 00:54:40 UTC 2023
PRIMARY
CAS
31698-14-3
Created by admin on Thu Jul 06 00:54:40 UTC 2023 , Edited by admin on Thu Jul 06 00:54:40 UTC 2023
PRIMARY
SMS_ID
100000086922
Created by admin on Thu Jul 06 00:54:40 UTC 2023 , Edited by admin on Thu Jul 06 00:54:40 UTC 2023
PRIMARY
CHEBI
74843
Created by admin on Thu Jul 06 00:54:40 UTC 2023 , Edited by admin on Thu Jul 06 00:54:40 UTC 2023
PRIMARY
INN
3992
Created by admin on Thu Jul 06 00:54:40 UTC 2023 , Edited by admin on Thu Jul 06 00:54:40 UTC 2023
PRIMARY
EVMPD
SUB05507MIG
Created by admin on Thu Jul 06 00:54:40 UTC 2023 , Edited by admin on Thu Jul 06 00:54:40 UTC 2023
PRIMARY
FDA UNII
DO2D32W0VC
Created by admin on Thu Jul 06 00:54:40 UTC 2023 , Edited by admin on Thu Jul 06 00:54:40 UTC 2023
PRIMARY
DRUG CENTRAL
212
Created by admin on Thu Jul 06 00:54:40 UTC 2023 , Edited by admin on Thu Jul 06 00:54:40 UTC 2023
PRIMARY
ChEMBL
CHEMBL1412614
Created by admin on Thu Jul 06 00:54:40 UTC 2023 , Edited by admin on Thu Jul 06 00:54:40 UTC 2023
PRIMARY
NCI_THESAURUS
C80636
Created by admin on Thu Jul 06 00:54:40 UTC 2023 , Edited by admin on Thu Jul 06 00:54:40 UTC 2023
PRIMARY
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SALT/SOLVATE -> PARENT
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CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY