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Details

Stereochemistry ACHIRAL
Molecular Formula C20H24FN5O3.2ClH.H2O
Molecular Weight 492.372
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OMECAMTIV MECARBIL DIHYDROCHLORIDE MONOHYDRATE

SMILES

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

InChI

InChIKey=FISUSGPPMSVPJR-UHFFFAOYSA-N
InChI=1S/C20H24FN5O3.2ClH.H2O/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);2*1H;1H2

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
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

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 Sat Dec 16 19:10:25 GMT 2023
Edited
by admin
on Sat Dec 16 19:10:25 GMT 2023
Record UNII
352W4DWZ3L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OMECAMTIV MECARBIL DIHYDROCHLORIDE MONOHYDRATE
Common Name English
1-PIPERAZINECARBOXYLIC ACID, 4-((2-FLUORO-3-((((6-METHYL-3-PYRIDINYL)AMINO)CARBONYL)AMINO)PHENYL)METHYL)-, METHYL ESTER, HYDROCHLORIDE, HYDRATE (1:2:1)
Systematic Name English
OMECAMTIV MECARBIL HYDROCHLORIDE HYDRATE [JAN]
Common Name English
OMECAMTIV MECARBIL HYDROCHLORIDE HYDRATE
Common Name English
Code System Code Type Description
FDA UNII
352W4DWZ3L
Created by admin on Sat Dec 16 19:10:25 GMT 2023 , Edited by admin on Sat Dec 16 19:10:25 GMT 2023
PRIMARY
PUBCHEM
78425816
Created by admin on Sat Dec 16 19:10:25 GMT 2023 , Edited by admin on Sat Dec 16 19:10:25 GMT 2023
PRIMARY
CAS
1628699-20-6
Created by admin on Sat Dec 16 19:10:25 GMT 2023 , Edited by admin on Sat Dec 16 19:10:25 GMT 2023
PRIMARY
KEGG
D11809
Created by admin on Sat Dec 16 19:10:25 GMT 2023 , Edited by admin on Sat Dec 16 19:10:25 GMT 2023
PRIMARY
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