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Details

Stereochemistry ACHIRAL
Molecular Formula C20H24FN5O3
Molecular Weight 401.4347
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OMECAMTIV MECARBIL

SMILES

COC(=O)N1CCN(CC2=CC=CC(NC(=O)NC3=CC=C(C)N=C3)=C2F)CC1

InChI

InChIKey=RFUBTTPMWSKEIW-UHFFFAOYSA-N
InChI=1S/C20H24FN5O3/c1-14-6-7-16(12-22-14)23-19(27)24-17-5-3-4-15(18(17)21)13-25-8-10-26(11-9-25)20(28)29-2/h3-7,12H,8-11,13H2,1-2H3,(H2,23,24,27)

HIDE SMILES / InChI

Description

Omecamtiv mecarbil (CK-1827452) is a specific cardiac myosin activator and a clinical drug for left ventricular systolic heart failure (in Phase 2 of development). Omecamtiv mecarbil is an inotropic agent that prolongs systolic ejection time and increases ejection fraction through myosin ATPase activation.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
905 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21856480
0.5 mg/kg/h 1 times / week multiple, intravenous
dose: 0.5 mg/kg/h
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
OMECAMTIV MECARBIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 mg/kg 1 times / week multiple, intravenous (unknown)
Highest studied dose
Dose: 1 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 1 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
Disc. AE: Chest discomfort, ST segment depression...
Other AEs: Feeling ho, Chest discomfort...
AEs leading to
discontinuation/dose reduction:
Chest discomfort (100%)
ST segment depression (50%)
increased troponin concentrations (50%)
Other AEs:
Feeling ho (100%)
Chest discomfort (100%)
Catheter-site pain (50%)
Postural dizziness (50%)
Dizziness (50%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
0.5 mg/kg 1 times / week multiple, intravenous (unknown)
MTD
Dose: 0.5 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 0.5 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 16
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
Other AEs: Catheter-site pain, Headache...
Other AEs:
Catheter-site pain (31%)
Headache (19%)
Dizziness (12%)
Catheter site haematoma (6%)
Catheter-site pain (6%)
Pharyngolaryngeal pai (6%)
Postural dizziness (31%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
0.75 mg/kg 1 times / week multiple, intravenous (unknown)
Studied dose
Dose: 0.75 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 0.75 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
Disc. AE: ST segment depression...
AEs leading to
discontinuation/dose reduction:
ST segment depression (50%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
AEs

AEs

AESignificanceDosePopulation
Chest discomfort 100%
1 mg/kg 1 times / week multiple, intravenous (unknown)
Highest studied dose
Dose: 1 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 1 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
Feeling ho 100%
1 mg/kg 1 times / week multiple, intravenous (unknown)
Highest studied dose
Dose: 1 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 1 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
Chest discomfort 100%
Disc. AE
1 mg/kg 1 times / week multiple, intravenous (unknown)
Highest studied dose
Dose: 1 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 1 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
Catheter-site pain 50%
1 mg/kg 1 times / week multiple, intravenous (unknown)
Highest studied dose
Dose: 1 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 1 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
Dizziness 50%
1 mg/kg 1 times / week multiple, intravenous (unknown)
Highest studied dose
Dose: 1 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 1 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
Postural dizziness 50%
1 mg/kg 1 times / week multiple, intravenous (unknown)
Highest studied dose
Dose: 1 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 1 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
ST segment depression 50%
Disc. AE
1 mg/kg 1 times / week multiple, intravenous (unknown)
Highest studied dose
Dose: 1 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 1 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
increased troponin concentrations 50%
Disc. AE
1 mg/kg 1 times / week multiple, intravenous (unknown)
Highest studied dose
Dose: 1 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 1 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
Dizziness 12%
0.5 mg/kg 1 times / week multiple, intravenous (unknown)
MTD
Dose: 0.5 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 0.5 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 16
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
Headache 19%
0.5 mg/kg 1 times / week multiple, intravenous (unknown)
MTD
Dose: 0.5 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 0.5 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 16
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
Catheter-site pain 31%
0.5 mg/kg 1 times / week multiple, intravenous (unknown)
MTD
Dose: 0.5 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 0.5 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 16
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
Postural dizziness 31%
0.5 mg/kg 1 times / week multiple, intravenous (unknown)
MTD
Dose: 0.5 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 0.5 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 16
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
Catheter site haematoma 6%
0.5 mg/kg 1 times / week multiple, intravenous (unknown)
MTD
Dose: 0.5 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 0.5 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 16
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
Catheter-site pain 6%
0.5 mg/kg 1 times / week multiple, intravenous (unknown)
MTD
Dose: 0.5 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 0.5 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 16
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
Pharyngolaryngeal pai 6%
0.5 mg/kg 1 times / week multiple, intravenous (unknown)
MTD
Dose: 0.5 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 0.5 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 16
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
ST segment depression 50%
Disc. AE
0.75 mg/kg 1 times / week multiple, intravenous (unknown)
Studied dose
Dose: 0.75 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 0.75 mg/kg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/21856480
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY443033
https://www.001chemical.com/chem/search?q=DY443033
1PlusChem LLC
1P00GULR
https://www.1pchem.com/search?query=1P00GULR
AChemBlock
O33827
http://www.achemblock.com/catalogsearch/result/?q=O33827
AK Scientific
X7581
https://aksci.com/item_detail.php?cat=X7581
Aceschem
ACF019897
https://www.aceschem.com/catalog/search.do?q=ACF019897
Angene
AGN-PC-0VCVES
http://www.angenechemical.com/productshow/AGN-PC-0VCVES.html
ApexBio Technology
A8349
https://www.apexbt.com/catalogsearch/result/?q=A8349
AstaTech
F15273
http://astatechinc.com/CPSResult.php?CRNO=F15273
Axon MedChem
1835
https://www.axonmedchem.com/product/1835
BOC Sciences
873697-71-3
http://www.bocsci.com/description.asp?cas=873697-71-3
Capot Chemical
34016
https://www.capotchem.com/search.do?q=34016
Cayman Chemical
21074
http://www.caymanchem.com/app/template/Product.vm/catalog/21074
Chem Scene
CS-0460
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0460
ChemShuttle
111865
https://www.chemshuttle.com/catalogsearch/result/?q=111865
Excenen
EX-A714
http://www.excenen.com/searchresultlist.php?id=EX-A714
Hairui
HR33048
http://www.hairuichem.com/en/product/search.do?q=HR33048
KeyOrganics
AS-60560
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-60560
Lab Seeker
SC-96609
http://www.labseeker.com/search.php?keywords=SC-96609&category=0
LabSeeker
SC-96609
http://www.labseeker.com/search.php?keywords=SC-96609&category=0
Matrix Scientific
147210
http://www.matrixscientific.com/147210.html
MedChem Express
HY-14233
https://www.medchemexpress.com/search.html?q=HY-14233&ft=&fa=&fp=
MolPort
MolPort-021-804-982
https://www.molport.com/shop/molecule-link/MolPort-021-804-982
Molcore
MC443033
http://www.molcore.com/CatMC443033.html
Molnova
M16353
https://www.molnova.com/en/serch-list.html?keywords=M16353
MuseChem
I005262
https://www.musechem.com/product/I005262.html
Ryan Scientific
AEE788
https://ryansci.com/products?q=AEE788&list_q=&search_type=exact
Selleck Chemicals
S2623
http://www.selleckchem.com/search.html?searchDTO.searchParam=S2623
ShangHai Biochempartner
BCP000486
http://www.biochempartner.com/search_BCP000486
ShangHai Biochempartner
BCP03048
http://www.biochempartner.com/search_BCP03048
TargetMol
T2006
https://www.targetmol.com/search?keyword=T2006
Toronto Research Chemicals
C544000
https://www.trc-canada.com/product-detail/?CatNum=C544000
Toronto Research Chemicals
M327092
https://www.trc-canada.com/product-detail/?CatNum=M327092
eMolecules
36516867
https://orderbb.emolecules.com/search/#?query=36516867
eNovation Chemicals
D372393
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D372393&searchbtn.x=0&searchbtn.y=0
mcule
MCULE-9121272903
https://mcule.com/MCULE-9121272903/
PubMed

PubMed

TitleDatePubMed
Discovery of omecamtiv mecarbil the first, selective, small molecule activator of cardiac Myosin.
2010 Dec 9
The effects of the cardiac myosin activator, omecamtiv mecarbil, on cardiac function in systolic heart failure: a double-blind, placebo-controlled, crossover, dose-ranging phase 2 trial.
2011 Aug 20
Dose-dependent augmentation of cardiac systolic function with the selective cardiac myosin activator, omecamtiv mecarbil: a first-in-man study.
2011 Aug 20
Patents

Patents

20060014761
2

Sample Use Guides

In Vivo Use Guide
Curator's Comment: https://clinicaltrials.gov/ct2/show/NCT00941681?term=OMECAMTIV+MECARBIL&rank=5
50 mg dose (oral) of CK-1827452 (OMECAMTIV MECARBIL) twice a day (BID) for 10 days. Omecamtiv mecarbil infusion (ranging from 0·005 to 1·0 mg/kg per h)
Route of Administration: Other
In Vitro Use Guide
In vitro Ventricular myosin (βMys) step-size, motility velocity, and actin-activated myosin ATPase were measured to determine duty cycle in the absence and presence of 1.5 μM OMECAMTIV MECARBIL (OM). A new parameter, the relative step-frequency, was introduced and measured to characterize βMys motility due to the involvement of its three unitary step-sizes. OM decreases motility velocity 10-fold without affecting step-size, indicating a large increase in duty cycle converting βMys to a near processive myosin. The OM conversion dramatically increases force and modestly increases power over the native βMys.
Name Type Language
OMECAMTIV MECARBIL
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
omecamtiv mecarbil [INN]
Common Name English
Omecamtiv mecarbil [WHO-DD]
Common Name English
CK-1827452
Code English
Methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate
Systematic Name English
OMECAMTIV MECARBIL [USAN]
Common Name English
1-PIPERAZINECARBOXYLIC ACID, 4-((2-FLUORO-3-((((6-METHYL-3-PYRIDINYL)AMINO)CARBONYL)AMINO)PHENYL)METHYL)-, METHYL ESTER
Common Name English
Code System Code Type Description
DRUG BANK
DB11816
Created by admin on Sat Dec 16 17:09:00 GMT 2023 , Edited by admin on Sat Dec 16 17:09:00 GMT 2023
PRIMARY
NCI_THESAURUS
C166579
Created by admin on Sat Dec 16 17:09:00 GMT 2023 , Edited by admin on Sat Dec 16 17:09:00 GMT 2023
PRIMARY
FDA UNII
2M19539ERK
Created by admin on Sat Dec 16 17:09:00 GMT 2023 , Edited by admin on Sat Dec 16 17:09:00 GMT 2023
PRIMARY
SMS_ID
100000138839
Created by admin on Sat Dec 16 17:09:00 GMT 2023 , Edited by admin on Sat Dec 16 17:09:00 GMT 2023
PRIMARY
WIKIPEDIA
Omecamtiv mecarbil
Created by admin on Sat Dec 16 17:09:00 GMT 2023 , Edited by admin on Sat Dec 16 17:09:00 GMT 2023
PRIMARY
ChEMBL
CHEMBL1800955
Created by admin on Sat Dec 16 17:09:00 GMT 2023 , Edited by admin on Sat Dec 16 17:09:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID901025949
Created by admin on Sat Dec 16 17:09:00 GMT 2023 , Edited by admin on Sat Dec 16 17:09:00 GMT 2023
PRIMARY
EVMPD
SUB79172
Created by admin on Sat Dec 16 17:09:00 GMT 2023 , Edited by admin on Sat Dec 16 17:09:00 GMT 2023
PRIMARY
CAS
873697-71-3
Created by admin on Sat Dec 16 17:09:00 GMT 2023 , Edited by admin on Sat Dec 16 17:09:00 GMT 2023
PRIMARY
USAN
TT-119
Created by admin on Sat Dec 16 17:09:00 GMT 2023 , Edited by admin on Sat Dec 16 17:09:00 GMT 2023
PRIMARY
PUBCHEM
11689883
Created by admin on Sat Dec 16 17:09:00 GMT 2023 , Edited by admin on Sat Dec 16 17:09:00 GMT 2023
PRIMARY
INN
9088
Created by admin on Sat Dec 16 17:09:00 GMT 2023 , Edited by admin on Sat Dec 16 17:09:00 GMT 2023
PRIMARY
NIH
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