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Details

Stereochemistry ACHIRAL
Molecular Formula C16H16O2
Molecular Weight 240.297
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FELBINAC ETHYL ESTER

SMILES

CCOC(=O)CC1=CC=C(C=C1)C2=CC=CC=C2

InChI

InChIKey=NPPJLSILDPVHCM-UHFFFAOYSA-N
InChI=1S/C16H16O2/c1-2-18-16(17)12-13-8-10-15(11-9-13)14-6-4-3-5-7-14/h3-11H,2,12H2,1H3

HIDE SMILES / InChI

Molecular Formula C16H16O2
Molecular Weight 240.297
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created using several sources including: http://adisinsight.springer.com/drugs/800008296; https://www.ncbi.nlm.nih.gov/pubmed/2399865; https://www.ncbi.nlm.nih.gov/pubmed/16256708; https://www.ncbi.nlm.nih.gov/pubmed/1447717; https://www.ncbi.nlm.nih.gov/pubmed/2870154; http://www.kegg.jp/entry/D01675

Felbinac ethyl ester or ethyl 4-biphenylyl acetate (EBA) is a small molecule drug class of analgesics, antipyretics, nonsteroidal anti-inflammatories, phenylacetates. It is a prodrug of non-steroidal anti-inflammatory drug 4-biphenylylacetic acid (BPAA)- an active metabolite of EBA. The use of EBA instead of free BPAA in the form of lipid microspheres or solubilized in cyclodextrins enhances the anti-inflammatory effects of biphenylylacetic acid. Solubilization of EBA in hydroxypropyl-beta-cyclodextrin (HP-beta-CyD) increases absorption and localized activation of the prodrug metabolic process in the epidermis when applied topically to the skin of rats and mice. Felbinac ethyl ester is a prostaglandin inhibitor. When intravenously administered felbinac ethyl ester incorporated in lipid microsphere at the onset of stone pain or vesical urgency in 54 patients with pain from urinary tract stones and 32 with vesical urgency after an operation on bladder or prostate be was found to be a useful drug for controlling stone pain and vesical urgency since an immediate effect, long durability and high response rates were obtained without severe side affects.

Originator

Curator's Comment: Developed by Pfizer as a drug for treatment of inflammation and pain

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: 1.00725208E8
Gene Symbol: Ptges2
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Enhancement of anti-inflammatory effects of biphenylylacetic acid by its incorporation into lipid microspheres.
1986 Feb
[Clinical effect of LM-001, prostaglandin synthetic inhibitor, on pain from urinary tract stone and vesical urgency after operation of the bladder or prostate].
1990 May
Enhancement of the antiinflammatory effect of ethyl 4-biphenylyl acetate in ointment by beta-cyclodextrin derivatives: increased absorption and localized activation of the prodrug in rats.
1990 Nov
Enhanced rectal absorption and reduced local irritation of the anti-inflammatory drug ethyl 4-biphenylylacetate in rats by complexation with water-soluble beta-cyclodextrin derivatives and formulation as oleaginous suppository.
1992 Nov
6A-O-[(4-biphenylyl)acetyl]-alpha-, -beta-, and -gamma-cyclodextrins and 6A-deoxy-6A-[[(4-biphenylyl)acetyl]amino]-alpha-, -beta-, and -gamma-cyclodextrins: potential prodrugs for colon-specific delivery.
1997 Aug 15
Route dependent pulmonary first-pass metabolism of a series of biphenylacetic acid esters in rats.
1998 Jan
Patents

Patents

Sample Use Guides

Unknown
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:37:23 GMT 2023
Edited
by admin
on Sat Dec 16 01:37:23 GMT 2023
Record UNII
978ZPS989U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FELBINAC ETHYL ESTER
MI   WHO-DD  
Common Name English
ACETIC ACID, (4-BIPHENYLYL)-, ETHYL ESTER
Common Name English
DIATEC
Brand Name English
FELBINAC ETHYL
JAN  
Common Name English
ETHYL 4-BIPHENYLYLACETATE
Systematic Name English
LM-001
Code English
Felbinac ethyl ester [WHO-DD]
Common Name English
(1,1'-BIPHENYL)-4-ACETIC ACID, ETHYL ESTER
Common Name English
FELBINAC ETHYL ESTER [MI]
Common Name English
4-BIPHENYLACETIC ACID, ETHYL ESTER
Common Name English
ETHYL P-BIPHENYLYLACETATE
Common Name English
FELBINAC ETHYL [JAN]
Common Name English
Code System Code Type Description
PUBCHEM
26436
Created by admin on Sat Dec 16 01:37:23 GMT 2023 , Edited by admin on Sat Dec 16 01:37:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID3046160
Created by admin on Sat Dec 16 01:37:23 GMT 2023 , Edited by admin on Sat Dec 16 01:37:23 GMT 2023
PRIMARY
CAS
14062-23-8
Created by admin on Sat Dec 16 01:37:23 GMT 2023 , Edited by admin on Sat Dec 16 01:37:23 GMT 2023
PRIMARY
MERCK INDEX
m5255
Created by admin on Sat Dec 16 01:37:23 GMT 2023 , Edited by admin on Sat Dec 16 01:37:23 GMT 2023
PRIMARY Merck Index
SMS_ID
100000172882
Created by admin on Sat Dec 16 01:37:23 GMT 2023 , Edited by admin on Sat Dec 16 01:37:23 GMT 2023
PRIMARY
FDA UNII
978ZPS989U
Created by admin on Sat Dec 16 01:37:23 GMT 2023 , Edited by admin on Sat Dec 16 01:37:23 GMT 2023
PRIMARY
ChEMBL
CHEMBL413965
Created by admin on Sat Dec 16 01:37:23 GMT 2023 , Edited by admin on Sat Dec 16 01:37:23 GMT 2023
PRIMARY