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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 of GEMCITABINE ELAIDATE

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
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.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Metabolism and accumulation of the lipophilic deoxynucleoside analogs elacytarabine and CP-4126.
2012 Oct
Patents

Sample Use Guides

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
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.
Name Type Language
GEMCITABINE ELAIDATE
INN   USAN   WHO-DD  
INN   USAN  
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
Created by admin on Sat Dec 16 01:40:42 GMT 2023 , Edited by admin on Sat Dec 16 01:40:42 GMT 2023
NCI_THESAURUS C2150
Created by admin on Sat Dec 16 01:40:42 GMT 2023 , Edited by admin on Sat Dec 16 01:40:42 GMT 2023
NCI_THESAURUS C1557
Created by admin on Sat Dec 16 01:40:42 GMT 2023 , Edited by admin on Sat Dec 16 01:40:42 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C79803
Created by admin on Sat Dec 16 01:40:42 GMT 2023 , Edited by admin on Sat Dec 16 01:40:42 GMT 2023
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ChEMBL
CHEMBL3039516
Created by admin on Sat Dec 16 01:40:42 GMT 2023 , Edited by admin on Sat Dec 16 01:40:42 GMT 2023
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FDA UNII
231C73W7LG
Created by admin on Sat Dec 16 01:40:42 GMT 2023 , Edited by admin on Sat Dec 16 01:40:42 GMT 2023
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USAN
ZZ-13
Created by admin on Sat Dec 16 01:40:42 GMT 2023 , Edited by admin on Sat Dec 16 01:40:42 GMT 2023
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DRUG BANK
DB12564
Created by admin on Sat Dec 16 01:40:42 GMT 2023 , Edited by admin on Sat Dec 16 01:40:42 GMT 2023
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EPA CompTox
DTXSID00175308
Created by admin on Sat Dec 16 01:40:42 GMT 2023 , Edited by admin on Sat Dec 16 01:40:42 GMT 2023
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PUBCHEM
9828310
Created by admin on Sat Dec 16 01:40:42 GMT 2023 , Edited by admin on Sat Dec 16 01:40:42 GMT 2023
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SMS_ID
100000175012
Created by admin on Sat Dec 16 01:40:42 GMT 2023 , Edited by admin on Sat Dec 16 01:40:42 GMT 2023
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CAS
210829-30-4
Created by admin on Sat Dec 16 01:40:42 GMT 2023 , Edited by admin on Sat Dec 16 01:40:42 GMT 2023
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INN
9409
Created by admin on Sat Dec 16 01:40:42 GMT 2023 , Edited by admin on Sat Dec 16 01:40:42 GMT 2023
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