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Details

Stereochemistry ACHIRAL
Molecular Formula C23H35NO2S
Molecular Weight 389.595
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DALCETRAPIB

SMILES

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

InChI

InChIKey=YZQLWPMZQVHJED-UHFFFAOYSA-N
InChI=1S/C23H35NO2S/c1-5-18(6-2)16-23(14-10-7-11-15-23)22(26)24-19-12-8-9-13-20(19)27-21(25)17(3)4/h8-9,12-13,17-18H,5-7,10-11,14-16H2,1-4H3,(H,24,26)

HIDE SMILES / InChI
Molecular Formula C23H35NO2S
Molecular Weight 389.595
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
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
846
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
665
Unknown

Approved Use

Unknown
Primary
Phase III
665
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
8.26 μg/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/21366361
4500 mg single, oral
dose: 4500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DALCETRAPIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
88.4 μg × h/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/21366361
4500 mg single, oral
dose: 4500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DALCETRAPIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
19.2 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/21366361
4500 mg single, oral
dose: 4500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DALCETRAPIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
600 mg 1 times / day multiple, oral
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
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
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
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
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
Other AEs: diarrhoea, Nausea...
Other AEs:
diarrhoea (75%)
Nausea (13%)
upper abdominal pai (38%)
Flatulence (25%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
4500 mg single, oral
Highest studied dose
Dose: 4500 mg
Route: oral
Route: single
Dose: 4500 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
healthy
Health Status: healthy
Sex: M
Food Status: UNKNOWN
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
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
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/23126252
Hypertension serious, 0.6%
600 mg 1 times / day multiple, oral
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
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/23126252
Nausea 13%
3900 mg 1 times / day multiple, oral
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
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
Flatulence 25%
3900 mg 1 times / day multiple, oral
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
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
upper abdominal pai 38%
3900 mg 1 times / day multiple, oral
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
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
diarrhoea 75%
3900 mg 1 times / day multiple, oral
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
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
nausea 18%
4500 mg single, oral
Highest studied dose
Dose: 4500 mg
Route: oral
Route: single
Dose: 4500 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
healthy
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
diarrhoea 45%
4500 mg single, oral
Highest studied dose
Dose: 4500 mg
Route: oral
Route: single
Dose: 4500 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21366361
healthy
Health Status: healthy
Sex: M
Food Status: UNKNOWN
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
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
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
mcule
MCULE-1065383104
https://mcule.com/MCULE-1065383104/
MedChem Express
HY-14950
https://www.medchemexpress.com/search.html?q=HY-14950&ft=&fa=&fp=
Molcore
MC105508
http://www.molcore.com/CatMC105508.html
Molnova
M17429
https://www.molnova.com/en/serch-list.html?keywords=M17429
MolPort
MolPort-020-008-066
https://www.molport.com/shop/molecule-link/MolPort-020-008-066
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
PubMed

PubMed

TitleDatePubMed
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.
2012-03-15
Cholesteryl ester transfer protein inhibition in cardiovascular risk management: ongoing trials will end the confusion.
2011-12
Lack of clinically relevant drug-drug interactions when dalcetrapib is co-administered with ezetimibe.
2010-12
Modulating cholesteryl ester transfer protein activity maintains efficient pre-β-HDL formation and increases reverse cholesterol transport.
2010-12
Good news for 'good' cholesterol.
2010-11-18
Low high-density lipoprotein cholesterol: current status and future strategies for management.
2010-10-29
No clinically relevant drug-drug interactions when dalcetrapib is co-administered with atorvastatin.
2010-10
Coadministration of dalcetrapib with pravastatin, rosuvastatin, or simvastatin: no clinically relevant drug-drug interactions.
2010-10
Biochemical characterization of cholesteryl ester transfer protein inhibitors.
2010-09
Emerging drugs for hyperlipidemia.
2010-09
Update on CETP inhibition.
2010-08-02
Is a blood pressure rise the only deleterious off-target effect of cholesterol ester transfer protein inhibitors?
2010-08
Lack of effect of dalcetrapib on QT interval in healthy subjects following multiple dosing.
2010-08
Mechanisms underlying off-target effects of the cholesteryl ester transfer protein inhibitor torcetrapib involve L-type calcium channels.
2010-08
Dissociating HDL cholesterol from cardiovascular risk.
2010-07-31
Insights from recent meta-analysis: role of high-density lipoprotein cholesterol in reducing cardiovascular events and rates of atherosclerotic disease progression.
2010-07-26
High density lipoproteins-based therapies for cardiovascular disease.
2010-07
Dalcetrapib: a review of Phase II data.
2010-06
High-density lipoprotein-mediated anti-atherosclerotic and endothelial-protective effects: a potential novel therapeutic target in cardiovascular disease.
2010-05
MARCO, a macrophage scavenger receptor highly expressed in rodents, mediates dalcetrapib-induced uptake of lipids by rat and mouse macrophages.
2010-04
Mulling over the odds of CETP inhibition.
2010-02
Safety and tolerability of dalcetrapib (RO4607381/JTT-705): results from a 48-week trial.
2010-02
Functional assessment of HDL: Moving beyond static measures for risk assessment.
2010-02
[HDL and CETP in atherogenesis].
2010-02
Cholesteryl ester transfer protein: at the heart of the action of lipid-modulating therapy with statins, fibrates, niacin, and cholesteryl ester transfer protein inhibitors.
2010-01
Dalcetrapib: JTT 705; JTT-705; R 1658; R1658; RG1658; RO 4607381; RO4607381.
2010
Rationale and design of the dal-OUTCOMES trial: efficacy and safety of dalcetrapib in patients with recent acute coronary syndrome.
2009-12
Dalcetrapib: no off-target toxicity on blood pressure or on genes related to the renin-angiotensin-aldosterone system in rats.
2009-12
The pharmacology and off-target effects of some cholesterol ester transfer protein inhibitors.
2009-11-16
Mechanism of inhibition defines CETP activity: a mathematical model for CETP in vitro.
2009-11
Gateways to clinical trials.
2009-09
Anacetrapib, a cholesterol ester transfer protein (CETP) inhibitor for the treatment of atherosclerosis.
2009-09
Cholesteryl ester transfer protein inhibitors as high-density lipoprotein raising agents.
2009-09
Free thiol group of MD-2 as the target for inhibition of the lipopolysaccharide-induced cell activation.
2009-07-17
Safety and tolerability of dalcetrapib.
2009-07-01
The end of the road for CETP inhibitors after torcetrapib?
2009-07
In vitro and in vivo assessment of the effect of dalcetrapib on a panel of CYP substrates.
2009-04
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.
2009-03
Cholesterylestertransfer protein inhibition and endothelial function in type II hyperlipidemia.
2009
Gateways to clinical trials. July-August 2008.
2008-10-14
JTT-705: is there still future for a CETP inhibitor after torcetrapib?
2008-10
Gateways to clinical trials.
2008-05
HDL metabolism and CETP inhibition.
2008-04-17
Cholesteryl ester transfer protein inhibition and HDL increase: has the dream ended?
2008-04
Is raising HDL a futile strategy for atheroprotection?
2008-02
The role of CETP inhibition in dyslipidemia.
2007-08
Inhibition of CETP as a novel therapeutic strategy for reducing the risk of atherosclerotic disease.
2007-01
Cholesteryl ester transfer protein promotes the formation of cholesterol-rich remnant like lipoprotein particles in human plasma.
2007-01
Are human CETP mutations and CETP-inhibiting drugs a good or a bad deal?
2006-08
Cholesteryl ester transfer protein inhibition, high-density lipoprotein metabolism and heart disease risk reduction.
2006-08
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 Wed Apr 02 08:41:25 GMT 2025
Edited
by admin
on Wed Apr 02 08:41:25 GMT 2025
Record UNII
3D050LIQ3H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DALCETRAPIB
INN   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
JTT-705
Preferred Name English
Dalcetrapib [WHO-DD]
Common Name English
PROPANETHIOIC ACID, 2-METHYL-, S-(2-(((1-(2-ETHYLBUTYL)CYCLOHEXYL)CARBONYL)AMINO)PHENYL) ESTER
Common Name English
RO4607381
Code English
dalcetrapib [INN]
Common Name English
RO-4607381
Code English
S-[2-({[1-(2-Ethylbutyl)cyclohexyl]carbonyl}amino)phenyl] 2-methylpropanethioate
Systematic Name English
DALCETRAPIB [MI]
Common Name English
S-(2-(1-(2-ETHYLBUTYL)CYCLOHEXANECARBOXAMIDO)PHENYL) 2-METHYLPROPANETHIOATE
Systematic Name English
DALCETRAPIB [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29703
Created by admin on Wed Apr 02 08:41:25 GMT 2025 , Edited by admin on Wed Apr 02 08:41:25 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL313006
Created by admin on Wed Apr 02 08:41:25 GMT 2025 , Edited by admin on Wed Apr 02 08:41:25 GMT 2025
PRIMARY
EPA CompTox
DTXSID70943475
Created by admin on Wed Apr 02 08:41:25 GMT 2025 , Edited by admin on Wed Apr 02 08:41:25 GMT 2025
PRIMARY
MERCK INDEX
m4071
Created by admin on Wed Apr 02 08:41:25 GMT 2025 , Edited by admin on Wed Apr 02 08:41:25 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB12181
Created by admin on Wed Apr 02 08:41:25 GMT 2025 , Edited by admin on Wed Apr 02 08:41:25 GMT 2025
PRIMARY
NCI_THESAURUS
C81529
Created by admin on Wed Apr 02 08:41:25 GMT 2025 , Edited by admin on Wed Apr 02 08:41:25 GMT 2025
PRIMARY
INN
8782
Created by admin on Wed Apr 02 08:41:25 GMT 2025 , Edited by admin on Wed Apr 02 08:41:25 GMT 2025
PRIMARY
WIKIPEDIA
DALCETRAPIB
Created by admin on Wed Apr 02 08:41:25 GMT 2025 , Edited by admin on Wed Apr 02 08:41:25 GMT 2025
PRIMARY
USAN
TT-92
Created by admin on Wed Apr 02 08:41:25 GMT 2025 , Edited by admin on Wed Apr 02 08:41:25 GMT 2025
PRIMARY
CAS
211513-37-0
Created by admin on Wed Apr 02 08:41:25 GMT 2025 , Edited by admin on Wed Apr 02 08:41:25 GMT 2025
PRIMARY
MESH
C411602
Created by admin on Wed Apr 02 08:41:25 GMT 2025 , Edited by admin on Wed Apr 02 08:41:25 GMT 2025
PRIMARY
SMS_ID
100000124381
Created by admin on Wed Apr 02 08:41:25 GMT 2025 , Edited by admin on Wed Apr 02 08:41:25 GMT 2025
PRIMARY
PUBCHEM
6918540
Created by admin on Wed Apr 02 08:41:25 GMT 2025 , Edited by admin on Wed Apr 02 08:41:25 GMT 2025
PRIMARY
EVMPD
SUB32549
Created by admin on Wed Apr 02 08:41:25 GMT 2025 , Edited by admin on Wed Apr 02 08:41:25 GMT 2025
PRIMARY
FDA UNII
3D050LIQ3H
Created by admin on Wed Apr 02 08:41:25 GMT 2025 , Edited by admin on Wed Apr 02 08:41:25 GMT 2025
PRIMARY
Related Record Type Details
Structure of 1-(2-Ethylbutyl)-N-(2-mercaptophenyl)cyclohexanecarboxamide
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
Structure of 1-(2-Ethylbutyl)-N-(2-mercaptophenyl)cyclohexanecarboxamide
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