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Details

Stereochemistry RACEMIC
Molecular Formula C19H32N2O5
Molecular Weight 368.4678
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BW-245C

SMILES

O[C@H](CCN1[C@@H](CCCCCCC(O)=O)C(=O)NC1=O)C2CCCCC2

InChI

InChIKey=ZIDQIOZJEJFMOH-JKSUJKDBSA-N
InChI=1S/C19H32N2O5/c22-16(14-8-4-3-5-9-14)12-13-21-15(18(25)20-19(21)26)10-6-1-2-7-11-17(23)24/h14-16,22H,1-13H2,(H,23,24)(H,20,25,26)/t15-,16+/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6727564 | https://www.ncbi.nlm.nih.gov/pubmed/1937072

BW 245C is a DP receptor agonist. Systemic administration of BW 245C to healthy volunteers lead to inhibition of platelet aggregation responses to ADP. BW245C was found to be effective in reducing human intraocular pressure, but its clinical usefulness as anti-glaucoma drugs is limited by the extraocular side effects.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.14 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Behavioural, ECoG spectrum power and body temperature effects of BW 245C, a prostaglandin analogue after intraventricular microinjection in chicks.
1981 May
Pharmacological and cardiovascular properties of a hydantoin derivative, BW 245 C, with high affinity and selectivity for PGD2 receptors.
1983 Jan
Effects of single oral dose administration of a hydantoin prostaglandin analogue BW 245C in man.
1984 Jun 4
Effects of prostaglandin D2 and its analogue, BW245C, on intraocular pressure in humans.
1991
Patents

Sample Use Guides

In a pilot study in man BW 245C was administered orally in an aqueous solution, at doses 50 and 150 micrograms. Platelet aggregation responses to ADP were significantly inhibited only at 120 minutes after 150 micrograms of BW 245C. Topical application of BW245C reduces intraocular pressure in humans.
Route of Administration: Other
In Vitro Use Guide
In a platelet aggregation assays performed using human blood, BW 245C inhibited 0.5 uM ADP-induced aggregation with an IC50 of 8.7 nM.
Name Type Language
BW-245C
Code English
4-IMIDAZOLIDINEHEPTANOIC ACID, 3-((3S)-3-CYCLOHEXYL-3-HYDROXYPROPYL)-2,5-DIOXO-, (4R)-REL-
Systematic Name English
4-IMIDAZOLIDINEHEPTANOIC ACID, 3-(3-CYCLOHEXYL-3-HYDROXYPROPYL)-2,5-DIOXO-, (R*,S*)-(±)-
Systematic Name English
REL-(4R)-3-((3S)-3-CYCLOHEXYL-3-HYDROXYPROPYL)-2,5-DIOXO-4-IMIDAZOLIDINEHEPTANOIC ACID
Systematic Name English
Code System Code Type Description
FDA UNII
5B26TJM1L8
Created by admin on Sat Dec 16 05:31:56 GMT 2023 , Edited by admin on Sat Dec 16 05:31:56 GMT 2023
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PUBCHEM
3080928
Created by admin on Sat Dec 16 05:31:56 GMT 2023 , Edited by admin on Sat Dec 16 05:31:56 GMT 2023
PRIMARY
CAS
72814-32-5
Created by admin on Sat Dec 16 05:31:56 GMT 2023 , Edited by admin on Sat Dec 16 05:31:56 GMT 2023
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