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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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
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:
unhealthy, ADULT
n = 7938
Health Status: unhealthy
Condition: acute coronary syndrome
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 7938
Sources:
Disc. AE: Diarrhea...
Other AEs: Hypertension...
AEs leading to
discontinuation/dose reduction:
Diarrhea (1.4%)
Other AEs:
Hypertension (serious, 0.6%)
Sources:
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:
healthy
n = 8
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 8
Sources:
Other AEs: Flatulence, upper abdominal pai...
Other AEs:
Flatulence (25%)
upper abdominal pai (38%)
Nausea (13%)
diarrhoea (75%)
Sources:
4500 mg single, oral (unknown)
Highest studied dose
Dose: 4500 mg
Route: oral
Route: single
Dose: 4500 mg
Sources:
healthy
n = 11
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 11
Sources:
Other AEs: diarrhoea, nausea...
Other AEs:
diarrhoea (45%)
nausea (18%)
Sources:
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:
unhealthy, ADULT
n = 7938
Health Status: unhealthy
Condition: acute coronary syndrome
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 7938
Sources:
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:
unhealthy, ADULT
n = 7938
Health Status: unhealthy
Condition: acute coronary syndrome
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 7938
Sources:
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:
healthy
n = 8
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 8
Sources:
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:
healthy
n = 8
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 8
Sources:
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:
healthy
n = 8
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 8
Sources:
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:
healthy
n = 8
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 8
Sources:
nausea 18%
4500 mg single, oral (unknown)
Highest studied dose
Dose: 4500 mg
Route: oral
Route: single
Dose: 4500 mg
Sources:
healthy
n = 11
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 11
Sources:
diarrhoea 45%
4500 mg single, oral (unknown)
Highest studied dose
Dose: 4500 mg
Route: oral
Route: single
Dose: 4500 mg
Sources:
healthy
n = 11
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 11
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[CETP inhibitor].
2001 Mar
Cholesteryl ester transfer protein inhibitor (JTT-705) and the development of atherosclerosis in rabbits with severe hypercholesterolaemia.
2002 Dec
Cholesteryl ester transfer protein: a novel target for raising HDL and inhibiting atherosclerosis.
2003 Feb 1
Role of CETP inhibitors in the treatment of dyslipidemia.
2004 Dec
JTT-705. Japan Tobacco.
2004 Mar
Effectiveness of inhibition of cholesteryl ester transfer protein by JTT-705 in combination with pravastatin in type II dyslipidemia.
2005 May 1
Consequences of cholesteryl ester transfer protein inhibition in patients with familial hypoalphalipoproteinemia.
2005 Sep
Are human CETP mutations and CETP-inhibiting drugs a good or a bad deal?
2006 Aug
Cholesteryl ester transfer protein promotes the formation of cholesterol-rich remnant like lipoprotein particles in human plasma.
2007 Jan
Gateways to clinical trials. July-August 2008.
2008 Jul-Aug
Cholesterylestertransfer protein inhibition and endothelial function in type II hyperlipidemia.
2009
In vitro and in vivo assessment of the effect of dalcetrapib on a panel of CYP substrates.
2009 Apr
A single-center, open-label, one-sequence study of dalcetrapib coadministered with ketoconazole, and an in vitro study of the S-methyl metabolite of dalcetrapib.
2009 Mar
Mechanism of inhibition defines CETP activity: a mathematical model for CETP in vitro.
2009 Nov
The pharmacology and off-target effects of some cholesterol ester transfer protein inhibitors.
2009 Nov 16
Is a blood pressure rise the only deleterious off-target effect of cholesterol ester transfer protein inhibitors?
2010 Aug
Safety and tolerability of dalcetrapib (RO4607381/JTT-705): results from a 48-week trial.
2010 Feb
Functional assessment of HDL: Moving beyond static measures for risk assessment.
2010 Feb
Coadministration of dalcetrapib with pravastatin, rosuvastatin, or simvastatin: no clinically relevant drug-drug interactions.
2010 Oct
Update on CETP inhibition.
2010 Sep-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

Sample Use Guides

Oral doses of 600 mg once daily for 20 weeks
Route of Administration: Oral
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.
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 Fri Jul 07 00:53:09 UTC 2023 , Edited by admin on Fri Jul 07 00:53:09 UTC 2023
PRIMARY
PUBCHEM
6918816
Created by admin on Fri Jul 07 00:53:09 UTC 2023 , Edited by admin on Fri Jul 07 00:53:09 UTC 2023
PRIMARY
FDA UNII
PEW5P6H57S
Created by admin on Fri Jul 07 00:53:09 UTC 2023 , Edited by admin on Fri Jul 07 00:53:09 UTC 2023
PRIMARY
EPA CompTox
DTXSID10426090
Created by admin on Fri Jul 07 00:53:09 UTC 2023 , Edited by admin on Fri Jul 07 00:53:09 UTC 2023
PRIMARY