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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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: myosin ATPase
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
905 ng/mL
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:
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
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:
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:
healthy
n = 16
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 16
Sources:
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:
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:
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
Disc. AE: ST segment depression...
AEs leading to
discontinuation/dose reduction:
ST segment depression (50%)
Sources:
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:
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
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:
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
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:
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
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:
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
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:
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
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:
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
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:
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
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:
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
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:
healthy
n = 16
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 16
Sources:
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:
healthy
n = 16
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 16
Sources:
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:
healthy
n = 16
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 16
Sources:
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:
healthy
n = 16
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 16
Sources:
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:
healthy
n = 16
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 16
Sources:
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:
healthy
n = 16
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 16
Sources:
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:
healthy
n = 16
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 16
Sources:
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:
healthy
n = 2
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 2
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Discovery of omecamtiv mecarbil the first, selective, small molecule activator of cardiac Myosin.
2010 Dec 9
Patents

Patents

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 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
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY