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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 of ELACYTARABINE

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

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 Fri Dec 15 16:30:35 GMT 2023
Edited
by admin
on Fri Dec 15 16:30:35 GMT 2023
Record UNII
TA7WJG93AR
Record Status Validated (UNII)
Record Version
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Name Type Language
ELACYTARABINE
INN   USAN   WHO-DD  
USAN   INN  
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
Created by admin on Fri Dec 15 16:30:35 GMT 2023 , Edited by admin on Fri Dec 15 16:30:35 GMT 2023
FDA ORPHAN DRUG 259408
Created by admin on Fri Dec 15 16:30:35 GMT 2023 , Edited by admin on Fri Dec 15 16:30:35 GMT 2023
Code System Code Type Description
EU-Orphan Drug
EU/3/07/476(POSITIVE)
Created by admin on Fri Dec 15 16:30:35 GMT 2023 , Edited by admin on Fri Dec 15 16:30:35 GMT 2023
PRIMARY TREATMENT OF ACUTE MYELOID LEUKAEMIA 14/09/2007 POSITIVE
NCI_THESAURUS
C53401
Created by admin on Fri Dec 15 16:30:35 GMT 2023 , Edited by admin on Fri Dec 15 16:30:35 GMT 2023
PRIMARY
EVMPD
SUB32961
Created by admin on Fri Dec 15 16:30:35 GMT 2023 , Edited by admin on Fri Dec 15 16:30:35 GMT 2023
PRIMARY
SMS_ID
100000125911
Created by admin on Fri Dec 15 16:30:35 GMT 2023 , Edited by admin on Fri Dec 15 16:30:35 GMT 2023
PRIMARY
CAS
188181-42-2
Created by admin on Fri Dec 15 16:30:35 GMT 2023 , Edited by admin on Fri Dec 15 16:30:35 GMT 2023
PRIMARY
PUBCHEM
6438895
Created by admin on Fri Dec 15 16:30:35 GMT 2023 , Edited by admin on Fri Dec 15 16:30:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID601031218
Created by admin on Fri Dec 15 16:30:35 GMT 2023 , Edited by admin on Fri Dec 15 16:30:35 GMT 2023
PRIMARY
DRUG BANK
DB05494
Created by admin on Fri Dec 15 16:30:35 GMT 2023 , Edited by admin on Fri Dec 15 16:30:35 GMT 2023
PRIMARY
INN
8609
Created by admin on Fri Dec 15 16:30:35 GMT 2023 , Edited by admin on Fri Dec 15 16:30:35 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105665
Created by admin on Fri Dec 15 16:30:35 GMT 2023 , Edited by admin on Fri Dec 15 16:30:35 GMT 2023
PRIMARY
FDA UNII
TA7WJG93AR
Created by admin on Fri Dec 15 16:30:35 GMT 2023 , Edited by admin on Fri Dec 15 16:30:35 GMT 2023
PRIMARY
USAN
SS-126
Created by admin on Fri Dec 15 16:30:35 GMT 2023 , Edited by admin on Fri Dec 15 16:30:35 GMT 2023
PRIMARY
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