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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H16N3O14P3
Molecular Weight 483.1563
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYTARABINE TRIPHOSPHATE

SMILES

NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@@H]2O

InChI

InChIKey=PCDQPRRSZKQHHS-CCXZUQQUSA-N
InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7+,8-/m1/s1

HIDE SMILES / InChI

Molecular Formula C9H16N3O14P3
Molecular Weight 483.1563
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Elacytarabine (CP-4055 or araC-5'elaidic acid ester) is a lipid-conjugated derivative of the nucleoside analog cytarabine. Elacytarabine blocks cell division and may kill cancer cells. It is a type of antimetabolite. It was studied in clinical trials for the treatment of solid tumors. In preclinical and clinical studies, elacytarabine has demonstrated both safety and efficacy in acute myeloid leukemia (AML), with noteworthy activity among the cytarabine-refractory AML population. Elacytarabine was granted orphan drug designation status from the European Commission in 2007 and from the US FDA in 2008, with a fast-track approval designation from the FDA in 2010. Elacytarabine development has been discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
Assessment of the effect of phosphorylated metabolites of anti-human immunodeficiency virus and anti-hepatitis B virus pyrimidine analogs on the behavior of human deoxycytidylate deaminase.
2003 Jan
Anti proliferative activity of ELACY (CP-4055) in combination with cloretazine (VNP40101M), idarubicin, gemcitabine, irinotecan and topotecan in human leukemia and lymphoma cells.
2008 Apr
2'-deoxy-4'-azido nucleoside analogs are highly potent inhibitors of hepatitis C virus replication despite the lack of 2'-alpha-hydroxyl groups.
2008 Jan 25
Intravenous administration of CP-4055 (ELACYT) in patients with solid tumours. A Phase I study.
2009
Patents

Patents

Sample Use Guides

Thirty-four patients (19 malignant melanoma, 8 ovarian cancers and 7 NSCLC) received CP-4055 as a 30 min, or 2 hr intravenous (IV) infusion daily for 5 consecutive days every 3 or 4 weeks (D1-5 q3w or D1-5 q4w) in a dose escalation designed study with doses ranging from 30 to 240 mg/m(2)/day.
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:55:45 GMT 2023
Edited
by admin
on Sat Dec 16 09:55:45 GMT 2023
Record UNII
S78SFW950O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYTARABINE TRIPHOSPHATE
Common Name English
ARABINOFURANOSYLCYTOSINE TRIPHOSPHATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C709
Created by admin on Sat Dec 16 09:55:45 GMT 2023 , Edited by admin on Sat Dec 16 09:55:45 GMT 2023
Code System Code Type Description
FDA UNII
S78SFW950O
Created by admin on Sat Dec 16 09:55:45 GMT 2023 , Edited by admin on Sat Dec 16 09:55:45 GMT 2023
PRIMARY
NCI_THESAURUS
C105950
Created by admin on Sat Dec 16 09:55:45 GMT 2023 , Edited by admin on Sat Dec 16 09:55:45 GMT 2023
PRIMARY
CAS
13191-15-6
Created by admin on Sat Dec 16 09:55:45 GMT 2023 , Edited by admin on Sat Dec 16 09:55:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID40927388
Created by admin on Sat Dec 16 09:55:45 GMT 2023 , Edited by admin on Sat Dec 16 09:55:45 GMT 2023
PRIMARY
PUBCHEM
25774
Created by admin on Sat Dec 16 09:55:45 GMT 2023 , Edited by admin on Sat Dec 16 09:55:45 GMT 2023
PRIMARY
WIKIPEDIA
Arabinofuranosylcytosine triphosphate
Created by admin on Sat Dec 16 09:55:45 GMT 2023 , Edited by admin on Sat Dec 16 09:55:45 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE ACTIVE