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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
Molecular Formula C20H24FN5O3
Molecular Weight 401.4347
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
134361
Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: myosin ATPase
Activator
1410
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1144
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
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.
Substance Class Chemical
Created
by admin
on Thu Jul 06 22:34:23 UTC 2023
Edited
by admin
on Thu Jul 06 22:34:23 UTC 2023
Record UNII
2M19539ERK
Record Status Validated (UNII)
Record Version
  • Download
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 Thu Jul 06 22:34:23 UTC 2023 , Edited by admin on Thu Jul 06 22:34:23 UTC 2023
PRIMARY
NCI_THESAURUS
C166579
Created by admin on Thu Jul 06 22:34:23 UTC 2023 , Edited by admin on Thu Jul 06 22:34:23 UTC 2023
PRIMARY
FDA UNII
2M19539ERK
Created by admin on Thu Jul 06 22:34:23 UTC 2023 , Edited by admin on Thu Jul 06 22:34:23 UTC 2023
PRIMARY
SMS_ID
100000138839
Created by admin on Thu Jul 06 22:34:23 UTC 2023 , Edited by admin on Thu Jul 06 22:34:23 UTC 2023
PRIMARY
WIKIPEDIA
Omecamtiv mecarbil
Created by admin on Thu Jul 06 22:34:23 UTC 2023 , Edited by admin on Thu Jul 06 22:34:23 UTC 2023
PRIMARY
ChEMBL
CHEMBL1800955
Created by admin on Thu Jul 06 22:34:23 UTC 2023 , Edited by admin on Thu Jul 06 22:34:23 UTC 2023
PRIMARY
EPA CompTox
DTXSID901025949
Created by admin on Thu Jul 06 22:34:23 UTC 2023 , Edited by admin on Thu Jul 06 22:34:23 UTC 2023
PRIMARY
EVMPD
SUB79172
Created by admin on Thu Jul 06 22:34:23 UTC 2023 , Edited by admin on Thu Jul 06 22:34:23 UTC 2023
PRIMARY
CAS
873697-71-3
Created by admin on Thu Jul 06 22:34:23 UTC 2023 , Edited by admin on Thu Jul 06 22:34:23 UTC 2023
PRIMARY
USAN
TT-119
Created by admin on Thu Jul 06 22:34:23 UTC 2023 , Edited by admin on Thu Jul 06 22:34:23 UTC 2023
PRIMARY
PUBCHEM
11689883
Created by admin on Thu Jul 06 22:34:23 UTC 2023 , Edited by admin on Thu Jul 06 22:34:23 UTC 2023
PRIMARY
INN
9088
Created by admin on Thu Jul 06 22:34:23 UTC 2023 , Edited by admin on Thu Jul 06 22:34:23 UTC 2023
PRIMARY
Related Record Type Details
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of OMECAMTIV MECARBIL DIHYDROCHLORIDE MONOHYDRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of OMECAMTIV MECARBIL
ACTIVE MOIETY
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