GEMCITABINE ELAIDATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H43F2N3O5
Molecular Weight	527.6442
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=HESSNRGIEVBPRB-QDDPNBLJSA-N

InChI=1S/C27H43F2N3O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(33)36-20-21-24(34)27(28,29)25(37-21)32-19-18-22(30)31-26(32)35/h9-10,18-19,21,24-25,34H,2-8,11-17,20H2,1H3,(H2,30,31,35)/b10-9+/t21-,24-,25-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C27H43F2N3O5
Molecular Weight	527.6442
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: http://adisinsight.springer.com/drugs/800025123 | https://www.ncbi.nlm.nih.gov/pubmed/20066470 | https://www.ncbi.nlm.nih.gov/pubmed/22002019

Gemcitabine elaidate is an ester of anticancer drug gemcitabine and elaidic fatty acid. The motivation to make an ester was to facilitate gemcitabine uptake and prolong retention in the cell. The drug is converted to parent compound gemcitabine both inside and outside the cell. Gemcitabine elaidate was developed by Clavis Pharma for treatment of solid tumors, including non-small cell lung cancer and pancreatic cancer, but its development was discontinued after product missed the primary endpoint in the Phase II LEAP trial to treat metastatic pancreatic cancer.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA replication 10 Target ID: map03030 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7481842 \| https://www.ncbi.nlm.nih.gov/pubmed/22002019	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pancreatic cancer 97 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25278310	Primary		Phase II 1132	Unknown Approved Use Unknown
Non-small cell lung cancer 206 Sources: https://clinicaltrials.gov/ct2/show/NCT01641575	Primary		Phase I 428	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antiproliferative activity, mechanism of action and oral antitumor activity of CP-4126, a fatty acid derivative of gemcitabine, in in vitro and in vivo tumor models.	2011 Jun	20066470
Metabolism and accumulation of the lipophilic deoxynucleoside analogs elacytarabine and CP-4126.	2012 Oct	22002019

Patents

Sample Use Guides

In Vivo Use Guide

In phase 2 study against pancreatic cancer, the drug was administered intravenously at 1250 mg/m2/d on day 1, 8 and 15 of each 4-week cycle.

Route of Administration: Intravenous

In Vitro Use Guide

The in vitro experiments were performed in cell lines of leukemia and solid tumor origin, both sensitive and resistant to gemcitabine. All populations were cultured at 37°C in a humidified atmosphere of 95% air and 5% CO2. Sensitivity to drugs was defined by the concentration of the drug causing a growth inhibition of 50% (IC50) after 72 h drug exposure of the cells. The cells were plated in 24-well plates in different densities, depending on their doubling times, to enable log-linear growth for 72 h. Drugs were added directly after plating the cells. Final concentrations of the drugs in the wells ranged from 2.10−10 to 10−3 M.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:40:42 UTC 2023` Edited by `admin` on `Sat Dec 16 01:40:42 UTC 2023`
Record UNII	231C73W7LG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GEMCITABINE ELAIDATE

Official Name

English

2'-DEOXY-2',2'-DIFLUOROCYTIDINE 5'-(9E)-OCTADEC-9-ENOATE

Common Name

English

GEMCITABINE ELAIDATE [USAN]

Common Name

English

CO-1.01

Code

English

gemcitabine elaidate [INN]

Common Name

English

5'-O-(TRANS-9''-OCTADECENOYL)-1-.BETA.-D-2'DEOXY-2',2'-DIFLUOROCYTIDINE

Common Name

English

CP-4126

Code

English

Gemcitabine elaidate [WHO-DD]

Common Name

English

CO-101

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

295909