OMECAMTIV MECARBIL DIHYDROCHLORIDE MONOHYDRATE

Investigational

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

Structure Search

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	C20H24FN5O3
Molecular Weight	401.4347
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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27322915

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

Targets

Primary Target	Pharmacology	Condition	Potency
myosin ATPase 2 Target ID: myosin ATPase Sources: https://www.ncbi.nlm.nih.gov/pubmed/26025342	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Heart failure 106 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21856481	Primary		Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
211 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/34131942/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	OMECAMTIV MECARBIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
416 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/34131942/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	OMECAMTIV MECARBIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
537 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/34415673/	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OMECAMTIV MECARBIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
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

AUC

Value	Dose	Analyte	Population
935 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/34131942/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	OMECAMTIV MECARBIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4790 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/34131942/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	OMECAMTIV MECARBIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5490 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/34415673/	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OMECAMTIV MECARBIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
20 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/34131942/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		OMECAMTIV MECARBIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
81.5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/34415673/	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:		OMECAMTIV MECARBIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

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

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY443033	https://www.001chemical.com/chem/search?q=DY443033
1PlusChem LLC	1P00GULR	https://www.1pchem.com/search?query=1P00GULR
Aceschem	ACF019897	https://www.aceschem.com/catalog/search.do?q=ACF019897
AChemBlock	O33827	http://www.achemblock.com/catalogsearch/result/?q=O33827
AK Scientific	X7581	https://aksci.com/item_detail.php?cat=X7581
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
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
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
mcule	MCULE-9121272903	https://mcule.com/MCULE-9121272903/
MedChem Express	HY-14233	https://www.medchemexpress.com/search.html?q=HY-14233&ft=&fa=&fp=
Molcore	MC443033	http://www.molcore.com/CatMC443033.html
Molnova	M16353	https://www.molnova.com/en/serch-list.html?keywords=M16353
MolPort	MolPort-021-804-982	https://www.molport.com/shop/molecule-link/MolPort-021-804-982
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

PubMed

Title	Date	PubMed
		252160494
Discovery of omecamtiv mecarbil the first, selective, small molecule activator of cardiac Myosin.	2010 Dec 9	24900233
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	21856481
Dose-dependent augmentation of cardiac systolic function with the selective cardiac myosin activator, omecamtiv mecarbil: a first-in-man study.	2011 Aug 20	21856480

Patents

Sample Use Guides

In Vivo Use Guide

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 `Wed Apr 02 13:51:12 GMT 2025` Edited by `admin` on `Wed Apr 02 13:51:12 GMT 2025`
Record UNII	352W4DWZ3L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OMECAMTIV MECARBIL DIHYDROCHLORIDE MONOHYDRATE

Common Name

English

OMECAMTIV MECARBIL HYDROCHLORIDE HYDRATE

Preferred 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

Code System Code Type Description

SMS_ID

300000043564