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Details

Stereochemistry ACHIRAL
Molecular Formula C19H29NOS
Molecular Weight 319.505
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1-(2-Ethylbutyl)-N-(2-mercaptophenyl)cyclohexanecarboxamide

SMILES

CCC(CC)CC1(CCCCC1)C(=O)NC2=C(S)C=CC=C2

InChI

InChIKey=OVRLABAFXJPIMU-UHFFFAOYSA-N
InChI=1S/C19H29NOS/c1-3-15(4-2)14-19(12-8-5-9-13-19)18(21)20-16-10-6-7-11-17(16)22/h6-7,10-11,15,22H,3-5,8-9,12-14H2,1-2H3,(H,20,21)

HIDE SMILES / InChI
Molecular Formula C19H29NOS
Molecular Weight 319.505
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 based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20861162

Dalcetrapib (JTT-705) is a modulator than an inhibitor of cholesteryl ester transfer protein (CETP) activity and it may interact with and decrease CETP activity by a unique mechanism without an off-target effect. Dalcetrapib increased high-density lipoprotein (HDL) cholesterol levels but did not reduce the risk of cardiovascular events. It is in phase III of clinical trials for the treatment of acute coronary syndrome.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
828
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
600 mg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/23126252
unhealthy, ADULT
n = 7938
Health Status: unhealthy
Condition: acute coronary syndrome
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 7938
Sources:
https://pubmed.ncbi.nlm.nih.gov/23126252
Disc. AE: Diarrhea...
Other AEs: Hypertension...
AEs leading to
discontinuation/dose reduction:
Diarrhea (1.4%)
Other AEs:
Hypertension (serious, 0.6%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/23126252
3900 mg 1 times / day multiple, oral (unknown)
Highest studied dose
Dose: 3900 mg, 1 times / day
Route: oral
Route: multiple
Dose: 3900 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
healthy
n = 8
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
Other AEs: Flatulence, upper abdominal pai...
Other AEs:
Flatulence (25%)
upper abdominal pai (38%)
Nausea (13%)
diarrhoea (75%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
4500 mg single, oral (unknown)
Highest studied dose
Dose: 4500 mg
Route: oral
Route: single
Dose: 4500 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
healthy
n = 11
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
Other AEs: diarrhoea, nausea...
Other AEs:
diarrhoea (45%)
nausea (18%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
AEs

AEs

AESignificanceDosePopulation
Diarrhea 1.4%
Disc. AE
600 mg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/23126252
unhealthy, ADULT
n = 7938
Health Status: unhealthy
Condition: acute coronary syndrome
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 7938
Sources:
https://pubmed.ncbi.nlm.nih.gov/23126252
Hypertension serious, 0.6%
600 mg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/23126252
unhealthy, ADULT
n = 7938
Health Status: unhealthy
Condition: acute coronary syndrome
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 7938
Sources:
https://pubmed.ncbi.nlm.nih.gov/23126252
Nausea 13%
3900 mg 1 times / day multiple, oral (unknown)
Highest studied dose
Dose: 3900 mg, 1 times / day
Route: oral
Route: multiple
Dose: 3900 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
healthy
n = 8
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
Flatulence 25%
3900 mg 1 times / day multiple, oral (unknown)
Highest studied dose
Dose: 3900 mg, 1 times / day
Route: oral
Route: multiple
Dose: 3900 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
healthy
n = 8
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
upper abdominal pai 38%
3900 mg 1 times / day multiple, oral (unknown)
Highest studied dose
Dose: 3900 mg, 1 times / day
Route: oral
Route: multiple
Dose: 3900 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
healthy
n = 8
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
diarrhoea 75%
3900 mg 1 times / day multiple, oral (unknown)
Highest studied dose
Dose: 3900 mg, 1 times / day
Route: oral
Route: multiple
Dose: 3900 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
healthy
n = 8
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
nausea 18%
4500 mg single, oral (unknown)
Highest studied dose
Dose: 4500 mg
Route: oral
Route: single
Dose: 4500 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
healthy
n = 11
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
diarrhoea 45%
4500 mg single, oral (unknown)
Highest studied dose
Dose: 4500 mg
Route: oral
Route: single
Dose: 4500 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
healthy
n = 11
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 11
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY105508
https://www.001chemical.com/chem/search?q=DY105508
1PlusChem LLC
1P00BFJP
https://www.1pchem.com/search?query=1P00BFJP
AK Scientific
Y0342
https://aksci.com/item_detail.php?cat=Y0342
Ambeed
A162985
http://www.ambeed.com/search/Search.html?keyword=A162985
Angene
AGN-PC-0LVEYH
http://www.angenechemical.com/productshow/AGN-PC-0LVEYH.html
ApexBio Technology
A4376
https://www.apexbt.com/catalogsearch/result/?q=A4376
AstaTech
33578
http://astatechinc.com/CPSResult.php?CRNO=33578
Axon MedChem
1962
https://www.axonmedchem.com/product/1962
BLD Pharm
BD315456
http://www.bldpharm.com/search/Search.html?keyword=BD315456
BOC Sciences
211513-37-0
http://www.bocsci.com/description.asp?cas=211513-37-0
Capot Chemical
22426
https://www.capotchem.com/search.do?q=22426
Cayman Chemical
89450
http://www.caymanchem.com/app/template/Product.vm/catalog/89450
Chem Scene
CS-0916
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0916
ChemShuttle
104810
https://www.chemshuttle.com/catalogsearch/result/?q=104810
Excenen
EX-A092
http://www.excenen.com/searchresultlist.php?id=EX-A092
Fluorochem
467031
http://www.fluorochem.co.uk/Products/Product?code=467031
Hairui
DAJL014
http://www.hairuichem.com/en/product/search.do?q=DAJL014
KeyOrganics
AS-55940
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-55940
Lab Network
LN01270473
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01270473
Lab Seeker
SC-94115
http://www.labseeker.com/search.php?keywords=SC-94115&category=0
LabSeeker
SC-94115
http://www.labseeker.com/search.php?keywords=SC-94115&category=0
Matrix Scientific
125207
http://www.matrixscientific.com/125207.html
MedChem Express
HY-14950
https://www.medchemexpress.com/search.html?q=HY-14950&ft=&fa=&fp=
MolPort
MolPort-020-008-066
https://www.molport.com/shop/molecule-link/MolPort-020-008-066
Molcore
MC105508
http://www.molcore.com/CatMC105508.html
Molnova
M17429
https://www.molnova.com/en/serch-list.html?keywords=M17429
MuseChem
I002624
https://www.musechem.com/product/I002624.html
ShangHai Biochempartner
BCP000194
http://www.biochempartner.com/search_BCP000194
ShangHai Biochempartner
BCP01932
http://www.biochempartner.com/search_BCP01932
Sigma Aldrich
SML2091
http://www.sigmaaldrich.com/catalog/search?term=SML2091&interface=All&N=0&mode=match%20partialmax&lang=en®ion=US&focus=product
Synthonix
14551
https://synthonix.com/catalogsearch/result/?q=14551
TargetMol
T6048
https://www.targetmol.com/search?keyword=T6048
Tetrahedron
TS86097
http://www.thsci.com/search.do?q=TS86097
Toronto Research Chemicals
A163862
https://www.trc-canada.com/product-detail/?CatNum=A163862
Toronto Research Chemicals
D113200
https://www.trc-canada.com/product-detail/?CatNum=D113200
eMolecules
35999377
https://orderbb.emolecules.com/search/#?query=35999377
eNovation Chemicals
D210837
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D210837&searchbtn.x=0&searchbtn.y=0
mcule
MCULE-1065383104
https://mcule.com/MCULE-1065383104/
PubMed

PubMed

TitleDatePubMed
Cholesteryl ester transfer protein: a novel target for raising HDL and inhibiting atherosclerosis.
2003 Feb 1
Dual effects on HDL metabolism by cholesteryl ester transfer protein inhibition in HepG2 cells.
2003 Jun
Inhibition of cholesteryl ester transfer protein increases serum apolipoprotein (apo) A-I levels by increasing the synthesis of apo A-I in rabbits.
2004 Feb
Increasing high-density lipoprotein cholesterol through cholesteryl Ester transfer protein inhibition: a next step in the fight against cardiovascular disease?
2005 Dec
Cholesteryl ester transfer protein inhibition, high-density lipoprotein metabolism and heart disease risk reduction.
2006 Aug
In vitro and in vivo assessment of the effect of dalcetrapib on a panel of CYP substrates.
2009 Apr
Rationale and design of the dal-OUTCOMES trial: efficacy and safety of dalcetrapib in patients with recent acute coronary syndrome.
2009 Dec
Free thiol group of MD-2 as the target for inhibition of the lipopolysaccharide-induced cell activation.
2009 Jul 17
Mechanism of inhibition defines CETP activity: a mathematical model for CETP in vitro.
2009 Nov
Gateways to clinical trials.
2009 Sep
Cholesteryl ester transfer protein inhibitors as high-density lipoprotein raising agents.
2009 Sep
Lack of effect of dalcetrapib on QT interval in healthy subjects following multiple dosing.
2010 Aug
Lack of clinically relevant drug-drug interactions when dalcetrapib is co-administered with ezetimibe.
2010 Dec
Safety and tolerability of dalcetrapib (RO4607381/JTT-705): results from a 48-week trial.
2010 Feb
[HDL and CETP in atherogenesis].
2010 Feb
Cholesteryl ester transfer protein: at the heart of the action of lipid-modulating therapy with statins, fibrates, niacin, and cholesteryl ester transfer protein inhibitors.
2010 Jan
High density lipoproteins-based therapies for cardiovascular disease.
2010 Jul
Dalcetrapib: a review of Phase II data.
2010 Jun
Good news for 'good' cholesterol.
2010 Nov 18
Coadministration of dalcetrapib with pravastatin, rosuvastatin, or simvastatin: no clinically relevant drug-drug interactions.
2010 Oct
Monitoring Cyp2b10 mRNA expression at cessation of 2-year carcinogenesis bioassay in mouse liver provides evidence for a carcinogenic mechanism devoid of human relevance: the dalcetrapib experience.
2012 Mar 15
Patents

Patents

20020103225
2
JP2011052006A
2
JP2013544861A
2

Sample Use Guides

In Vivo Use Guide
Oral doses of 600 mg once daily for 20 weeks
Route of Administration: Oral
In Vitro Use Guide
Human liver microsomes and a panel of substrates for CYP enzymes were used to determine IC(50) for inhibition of CYP1A2, CYP2C8, CYP2C9, CYP2C19, CYP2D6, and CYP3A4 by dalcetrapib. Drug was inhibitory to all CYP enzymes tested. IC(50) values ranged from 1.5 +/- 0.1 uM for CYP2C8 to 82 +/- 4 uM for CYP2D6.
Substance Class Chemical
Created
by admin
on Sat Dec 16 19:47:16 UTC 2023
Edited
by admin
on Sat Dec 16 19:47:16 UTC 2023
Record UNII
PEW5P6H57S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1-(2-Ethylbutyl)-N-(2-mercaptophenyl)cyclohexanecarboxamide
Systematic Name English
N-(2-Mercaptophenyl)-1-(2-ethylbutyl)cyclohexanecarboxamide
Systematic Name English
Cyclohexanecarboxamide, 1-(2-ethylbutyl)-N-(2-mercaptophenyl)-
Systematic Name English
Code System Code Type Description
CAS
211513-21-2
Created by admin on Sat Dec 16 19:47:16 UTC 2023 , Edited by admin on Sat Dec 16 19:47:16 UTC 2023
PRIMARY
PUBCHEM
6918816
Created by admin on Sat Dec 16 19:47:16 UTC 2023 , Edited by admin on Sat Dec 16 19:47:16 UTC 2023
PRIMARY
FDA UNII
PEW5P6H57S
Created by admin on Sat Dec 16 19:47:16 UTC 2023 , Edited by admin on Sat Dec 16 19:47:16 UTC 2023
PRIMARY
EPA CompTox
DTXSID10426090
Created by admin on Sat Dec 16 19:47:16 UTC 2023 , Edited by admin on Sat Dec 16 19:47:16 UTC 2023
PRIMARY
Related Record Type Details
CHOLESTERYL ESTER TRANSFER PROTEIN
TARGET -> INHIBITOR
Related Record Type Details
Structure of DALCETRAPIB
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
Structure of 1-(2-Ethylbutyl)-N-(2-mercaptophenyl)cyclohexanecarboxamide
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