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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H24N2O4S2
Molecular Weight 408.535
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OMAPATRILAT

SMILES

[H][C@]12CCC[C@H](N1C(=O)[C@H](CCS2)NC(=O)[C@@H](S)CC3=CC=CC=C3)C(O)=O

InChI

InChIKey=LVRLSYPNFFBYCZ-VGWMRTNUSA-N
InChI=1S/C19H24N2O4S2/c22-17(15(26)11-12-5-2-1-3-6-12)20-13-9-10-27-16-8-4-7-14(19(24)25)21(16)18(13)23/h1-3,5-6,13-16,26H,4,7-11H2,(H,20,22)(H,24,25)/t13-,14-,15-,16-/m0/s1

HIDE SMILES / InChI
Molecular Formula C19H24N2O4S2
Molecular Weight 408.535
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.drugbank.ca/drugs/DB00886

Omapatrilat is an antihypertensive agent that inhibits both neprilysin (neutral endopeptidase, NEP) and angiotensin-converting enzyme (ACE). The drug was developed for possible use in heart failure and hypertension, but was not approved by the FDA due to angioedema safety concerns.

CNS Activity

CNS Non-penetrant
1014
Curator's Comment: Known to be CNS non-penetrant in rats. Human data not available.

Originator

Bristol-Myers Squibb
145
Curator's Comment: # Bristol-Myers Squibb

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Angiotensin-converting enzyme
97
Target ID: P12821
Gene ID: 1636.0
Gene Symbol: ACE
Target Organism: Homo sapiens (Human)
Inhibitor
8297
 0.06 nM [Ki]
Inhibitor
8297
 9.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Not Provided
504
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effect of bradykinin metabolism inhibitors on evoked hypotension in rats: rank efficacy of enzymes associated with bradykinin-mediated angioedema.
2008 Mar
Patents

Patents

20020111512
2

Sample Use Guides

In Vivo Use Guide
In phase III trial, omapatrilat was administered at dose 40 mg every day.
Route of Administration: Oral
In Vitro Use Guide
Inhibition studies of recombinant angiotensin-converting enzyme (ACE) and were performed with the use of Ang I, HHL, and the new synthetic peptide AcSDAcKP as substrates. The inhibitory potency of omapatrilat and toward recombinant wild-type ACE was determined by establishing dose dependent inhibition curves at equilibrium. Inhibition of Ang I, HHL, and AcSDAcKP hydrolysis was determined with the use of 0.1 nmol/L, 0.1 nmol/L, and 0.4 nmol/L of wild-type ACE respectively. After preincubation with 0.05 to 2.5 nmol/L of inhibitor at 37°C for 1 hour, reactions were initiated by substrate addition at 2 different concentrations (0.53Km and 33Km) and performed for 5, 10, 30, and 60 minutes. The rate of hydrolysis of all the substrates used was quantified by high-performance liquid chromatography.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:54:11 UTC 2023
Edited
by admin
on Fri Dec 15 15:54:11 UTC 2023
Record UNII
36NLI90E7T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OMAPATRILAT
INN   JAN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
omapatrilat [INN]
Common Name English
OMAPATRILATE
Common Name English
OMAPATRILAT [USAN]
Common Name English
OMAPATRILAT [MART.]
Common Name English
BMS-186716-01
Code English
BMS-186716
Code English
(4S-(4.ALPHA.(R*),7.ALPHA.,10A.BETA.))-OCTAHYDRO-4-((2-MERCAPTO-1-OXO-3-PHENYLPROPYL)AMINO)-5-OXO-7H-PYRIDO(2,1-B)(1,3)THIAZEPINE-7-CARBOXYLIC ACID
Common Name English
OMAPATRILAT [VANDF]
Common Name English
Omapatrilat [WHO-DD]
Common Name English
OMAPATRILAT [MI]
Common Name English
(4S,7S,10aS)-Octahydro-4-[(S)-α-mercaptohydrocinnamamido]-5-oxo-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid
Common Name English
OMAPATRILAT [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C247
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
NCI_THESAURUS C783
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
Code System Code Type Description
CAS
167305-00-2
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
PRIMARY
ChEMBL
CHEMBL289556
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
PRIMARY
EPA CompTox
DTXSID80168273
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
PRIMARY
WIKIPEDIA
Omapatrilat
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
PRIMARY
MERCK INDEX
m8207
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
PRIMARY Merck Index
FDA UNII
36NLI90E7T
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
PRIMARY
DRUG BANK
DB00886
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
PRIMARY
INN
7714
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
PRIMARY
NCI_THESAURUS
C1782
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
PRIMARY
USAN
JJ-01
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
PRIMARY
EVMPD
SUB12450MIG
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
PRIMARY
PUBCHEM
656629
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
PRIMARY
MESH
C106266
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
PRIMARY
SMS_ID
100000078754
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
PRIMARY
DRUG CENTRAL
1989
Created by admin on Fri Dec 15 15:54:11 UTC 2023 , Edited by admin on Fri Dec 15 15:54:11 UTC 2023
PRIMARY
Related Record Type Details
ANGIOTENSIN-CONVERTING ENZYME
TARGET -> INHIBITOR
NEPRILYSIN
TARGET -> INHIBITOR
Related Record Type Details
Structure of 7H-PYRIDO(2,1-B)(1,3)THIAZEPINE-7-CARBOXYLIC ACID, OCTAHYDRO-4-(((2S)-2-(METHYLTHIO)-1-OXO-3-PHENYLPROPYL)AMINO)-5-OXO-, 1-OXIDE, (4S,7S,10AS)-
METABOLITE -> PARENT
PLASMA; URINE
Structure of 1-((.ALPHA.S)-.ALPHA.-(METHYLTHIO)BENZENEPROPANOATE)-.BETA.-D-GLUCOPYRANURONIC ACID
METABOLITE -> PARENT
URINE
Structure of (4S,7S,10AS)-4-AMINOOCTAHYDRO-5-OXO-7H-PYRIDO(2,1-B)(1,3)THIAZEPINE-7-CARBOXYLIC ACID
METABOLITE -> PARENT
PLASMA; URINE
Structure of .BETA.-D-GLUCOPYRANURONIC ACID, 1-((4S,7S,10AS)-OCTAHYDRO-4-(((2S)-2-(METHYLTHIO)-1-OXO-3-PHENYLPROPYL)AMINO)-5-OXO-7H-PYRIDO(2,1-B)(1,3)THIAZEPINE-7-CARBOXYLATE)
METABOLITE -> PARENT
PLASMA; URINE
Structure of (4S,7S,10AS)-OCTAHYDRO-4-(((2S)-2-(METHYLTHIO)-1-OXO-3-PHENYLPROPYL)AMINO)-5-OXO-7H-PYRIDO(2,1-B)(1,3)THIAZEPINE-7-CARBOXYLIC ACID
METABOLITE -> PARENT
PLASMA; URINE
Structure of (4S,7S,10AS)-4-(((2S)-2-(((2R)-2-AMINO-2-CARBOXYETHYL)DITHIO)-1-OXO-3-PHENYLPROPYL)AMINO)OCTAHYDRO-5-OXO-7H-PYRIDO(2,1-B)(1,3)THIAZEPINE-7-CARBOXYLIC ACID
METABOLITE -> PARENT
PLASMA; URINE
Structure of (2S)-3-PHENYL-2-SULFANYLPROPANOIC ACID
METABOLITE -> PARENT
PLASMA
Structure of BENZENEPROPANOIC ACID, .ALPHA.-(METHYLTHIO)-, (.ALPHA.S)-
METABOLITE -> PARENT
PLASMA
Related Record Type Details
Structure of OMAPATRILAT
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