ELACYTARABINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H45N3O6
Molecular Weight	507.6627
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCC\C=C\CCCCCCCC(=O)OC[C@H]1O[C@H]([C@@H](O)[C@@H]1O)N2C=CC(N)=NC2=O

InChI

InChIKey=FLFGNMFWNBOBGE-FNNZEKJRSA-N

InChI=1S/C27H45N3O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(31)35-20-21-24(32)25(33)26(36-21)30-19-18-22(28)29-27(30)34/h9-10,18-19,21,24-26,32-33H,2-8,11-17,20H2,1H3,(H2,28,29,34)/b10-9+/t21-,24-,25+,26-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C27H45N3O6
Molecular Weight	507.6627
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800019100 | https://www.ncbi.nlm.nih.gov/pubmed/23902239 | https://www.cancer.gov/publications/dictionaries/cancer-terms/def/elacytarabine | https://www.ncbi.nlm.nih.gov/pubmed/18607882

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.

Originator

Approval Year

PubMed

Title	Date	PubMed
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	12488542
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	18398748
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	18003608
Intravenous administration of CP-4055 (ELACYT) in patients with solid tumours. A Phase I study.	2009	18607882

Patents

Sample Use Guides

In Vivo Use Guide

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 `Fri Dec 15 16:30:35 UTC 2023` Edited by `admin` on `Fri Dec 15 16:30:35 UTC 2023`
Record UNII	TA7WJG93AR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ELACYTARABINE

Official Name

English

elacytarabine [INN]

Common Name

English

ELACYTARABINE [USAN]

Common Name

English

5'-O-(TRANS-9''-OCTADECENOYL)-1-SS-D-ARABINOFURANOSYL CYTOSINE

Common Name

English

CP-4055

Code

English

P-4055

Code

English

Elacytarabine [WHO-DD]

Common Name

English

2(1H)-PYRIMIDINONE, 4-AMINO-1-(5-O-((9E)-1-OXO-9-OCTADECENYL)-.BETA.-D-ARABINOFURANOSYL)-

Common Name

English

2(1H)-PYRIMIDINONE, 4-AMINO-1-(5-O-((9E)-1-OXO-9-OCTADECEN-1-YL)-.BETA.-D-ARABINOFURANOSYL)-

Common Name

English

4-AMINO-1-(5-O-((9E)-OCTADEC-9-ENOYL)-.BETA.-D-ARABINOFURANOSYL)PYRIMIDIN-2(1H)-ONE

Common Name

English

CP4055

Code

English

CYTARABINE ELIADATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1557