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Details

Stereochemistry ACHIRAL
Molecular Formula C13H24N2O
Molecular Weight 224.3425
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1,3-DICYCLOHEXYLUREA

SMILES

O=C(NC1CCCCC1)NC2CCCCC2

InChI

InChIKey=ADFXKUOMJKEIND-UHFFFAOYSA-N
InChI=1S/C13H24N2O/c16-13(14-11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h11-12H,1-10H2,(H2,14,15,16)

HIDE SMILES / InChI

Molecular Formula C13H24N2O
Molecular Weight 224.3425
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24685540 | https://www.ncbi.nlm.nih.gov/pubmed/22489687

1,3-Dicyclohexylurea (DCU) is a potent endogenous inhibitor of soluble epoxide hydrolase (sEH), that has been found in human serum. Soluble epoxide hydrolase has been implicated in cardiovascular disease and inflammation in mammals. Endogenously produced 1,3-dicyclohexylurea may have physiological significance via regulation of soluble epoxide hydrolase activity in vivo.

Originator

Sources: Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1920), 53B, 1242-55.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Pathways of epoxyeicosatrienoic acid metabolism in endothelial cells. Implications for the vascular effects of soluble epoxide hydrolase inhibition.
2001 May 4
Impurity profile study of repaglinide.
2003 Jul 14
Structure-activity relationships of dinucleotides: Potent and selective agonists of P2Y receptors.
2005 Jun
Novel dexamethasone-HPMA copolymer conjugate and its potential application in treatment of rheumatoid arthritis.
2007
4-Methyl-3-(2-phenoxy-acet-yl)-5-phenyl-1,3,4-oxadiazinan-2-one.
2009 Jun 6
2-(2-Chloro-3-quinol-yl)-3-phenyl-thia-zolidin-4-one.
2009 Oct 17
Targeting the OB-Folds of Replication Protein A with Small Molecules.
2010 Dec 6
Hypericins as potential leads for new therapeutics.
2010 Feb 4
Spacer/Linker based synthesis and biological evaluation of mutual prodrugs as antiinflammatory agents.
2010 Sep
Patents

Sample Use Guides

From day 10 to day 14, rats were dosed orally with vehicle or 1,3-Dicyclohexylu at 30 mg/kg twice daily
Route of Administration: Oral
Cyano(6-methoxy-naphthalen-2-yl)methyl trans-[(3-phenyloxyran-2-yl)methyl] carbonate (CMNPC) is the substrate used for the fluorescent assay. The assay was carried out using a 96 well-plate format. There was a lane for background with PB buffer (100 mM sodium phosphate, pH = 7.4, 200 µL) and two lanes for positive control. Each inhibitor IC50¬ was determined based on triplicate experiments. Each inhibitor (the highest desired concentration, 2 µL, DMSO) was added to the PB buffer (100 mM sodium phosphate, pH = 7.4, 150 µL) at the first set of wells. A series of 2-fold dilution was applied from the first set till to the last set of wells. hSEH solution (25 nM, 100 mM sodium phosphate, pH = 7.4, 20 µL) was added and mixed for 30s. The inhibitor-enzyme mixtures were mixed and incubated at 30 ˚C for 5 min. CMNPC solution (33 µM, 100 mM sodium phosphate, pH = 7.4, 30 µL) was added and mixed. The enzyme activity was measured based on the fluorescence increase.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:41:44 UTC 2023
Edited
by admin
on Fri Dec 15 17:41:44 UTC 2023
Record UNII
ZV7823VVIM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1,3-DICYCLOHEXYLUREA
Systematic Name English
DCU
Common Name English
NSC-30023
Code English
DICYCLOHEXYLCARBODIAMIDE
Common Name English
N,N'-DICYCLOHEXYLUREA
Systematic Name English
UREA, N,N'-DICYCLOHEXYL-
Systematic Name English
LOMUSTINE RELATED COMPOUND C [USP IMPURITY]
USP-RS  
Common Name English
LOMUSTINE IMPURITY C [EP IMPURITY]
Common Name English
LOMUSTINE RELATED COMPOUND C [USP-RS]
Common Name English
NSC-17013
Code English
DICYCLOHEXYLUREA, N,N'-
Systematic Name English
Code System Code Type Description
PUBCHEM
4277
Created by admin on Fri Dec 15 17:41:44 UTC 2023 , Edited by admin on Fri Dec 15 17:41:44 UTC 2023
PRIMARY
CAS
2387-23-7
Created by admin on Fri Dec 15 17:41:44 UTC 2023 , Edited by admin on Fri Dec 15 17:41:44 UTC 2023
PRIMARY
RS_ITEM_NUM
1369442
Created by admin on Fri Dec 15 17:41:44 UTC 2023 , Edited by admin on Fri Dec 15 17:41:44 UTC 2023
PRIMARY
EPA CompTox
DTXSID3062366
Created by admin on Fri Dec 15 17:41:44 UTC 2023 , Edited by admin on Fri Dec 15 17:41:44 UTC 2023
PRIMARY
WIKIPEDIA
Dicyclohexylurea
Created by admin on Fri Dec 15 17:41:44 UTC 2023 , Edited by admin on Fri Dec 15 17:41:44 UTC 2023
PRIMARY
ECHA (EC/EINECS)
219-213-7
Created by admin on Fri Dec 15 17:41:44 UTC 2023 , Edited by admin on Fri Dec 15 17:41:44 UTC 2023
PRIMARY
NSC
30023
Created by admin on Fri Dec 15 17:41:44 UTC 2023 , Edited by admin on Fri Dec 15 17:41:44 UTC 2023
PRIMARY
NSC
17013
Created by admin on Fri Dec 15 17:41:44 UTC 2023 , Edited by admin on Fri Dec 15 17:41:44 UTC 2023
PRIMARY
FDA UNII
ZV7823VVIM
Created by admin on Fri Dec 15 17:41:44 UTC 2023 , Edited by admin on Fri Dec 15 17:41:44 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
No more than one such impurity (carmustine related compound A, lomustine related compound B, or lomustine related compound C) is greater than 0.2%.
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP