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Identification
NameOmapatrilat
Accession NumberDB00886  (APRD00443)
TypeSmall Molecule
GroupsInvestigational
DescriptionOmapatrilat is an investigational drug that inhibits both neutral endopeptidase (NEP) and angiotensin converting enzyme (ACE). NEP inhibition results in elevated natriuretic peptide levels, promoting natriuresis, diuresis, vasodilation, and reductions in preload and ventricular remodeling. This drug from BMS was not approved by the FDA due to angioedema safety concerns.
Structure
Thumb
Synonyms
Omapatrilate
External Identifiers
  • BMS 186716
  • BMS-186716
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
VanlevNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII36NLI90E7T
CAS number167305-00-2
WeightAverage: 408.53
Monoisotopic: 408.117749609
Chemical FormulaC19H24N2O4S2
InChI KeyLVRLSYPNFFBYCZ-VGWMRTNUSA-N
InChI
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
IUPAC Name
(4S,7S,10aS)-5-oxo-4-[(2S)-3-phenyl-2-sulfanylpropanamido]-octahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid
SMILES
[H][C@]12CCC[[email protected]](N1C(=O)[[email protected]](CCS2)NC(=O)[C@@H](S)CC1=CC=CC=C1)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Piperidinecarboxylic acid
  • Monocyclic benzene moiety
  • Fatty amide
  • Piperidine
  • Benzenoid
  • Fatty acyl
  • Tertiary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Lactam
  • Alkylthiol
  • Hemithioaminal
  • Thioether
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxide
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of hypertension.
PharmacodynamicsOmapatrilat is used to treat hypertension. Vasopeptidase inhibitor that simultaneously inhibits angiotensin-converting enzyme (ACE) and neutral endopeptidase (NEP). Omapatrilat lowers blood pressure by inhibiting the action of the angiotensin converting enzyme (ACE), which causes blood vessels to constrict. But unlike other drugs, omapatrilat also inhibits another enzyme known as neutral endopeptidase (NEP), which helps blood vessels relax. Omapatrilat demonstrated greater reduction in blood pressure than the ACE inhibitor lisinopril in individuals with salt-sensitive hypertension who typically do not respond well to ACE inhibitors.
Mechanism of actionOmapatrilat binds to both angiotensin converting enzyme and neutral endopeptidase. This results in a decrease renin-angiotensin-aldosterone production and increase natriuretic peptidase circulation.
Related Articles
AbsorptionThe absolute oral bioavailability of omapatrilat is 20% to 30% and the absorption is not affected by food intake.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySide effects include hyperkalemia, cough, hypotension, increased SrCr, and dizziness. Dizziness, diarrhea, vision disturbance, hypotension and angioedema
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9567
Blood Brain Barrier-0.9219
Caco-2 permeable-0.7793
P-glycoprotein substrateSubstrate0.7377
P-glycoprotein inhibitor INon-inhibitor0.7782
P-glycoprotein inhibitor IINon-inhibitor0.9778
Renal organic cation transporterNon-inhibitor0.8896
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateNon-substrate0.5745
CYP450 1A2 substrateNon-inhibitor0.8791
CYP450 2C9 inhibitorNon-inhibitor0.8218
CYP450 2D6 inhibitorNon-inhibitor0.8781
CYP450 2C19 inhibitorNon-inhibitor0.7666
CYP450 3A4 inhibitorInhibitor0.5854
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.93
Ames testNon AMES toxic0.8423
CarcinogenicityNon-carcinogens0.9497
BiodegradationNot ready biodegradable0.9922
Rat acute toxicity2.0641 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9918
hERG inhibition (predictor II)Non-inhibitor0.624
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP2.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0769 mg/mLALOGPS
logP2.15ALOGPS
logP2.06ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.71 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity106.68 m3·mol-1ChemAxon
Polarizability41.8 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General References
  1. Rabkin SW, Klassen SS: Omapatrilat enhances adrenomedullin's reduction of cardiomyocyte cell death. Eur J Pharmacol. 2007 May 21;562(3):174-82. Epub 2007 Feb 8. [PubMed:17343842 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypotensive activities of Omapatrilat.
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with Omapatrilat.
AcebutololOmapatrilat may increase the hypotensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Aceclofenac.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Acetylsalicylic acid.
Acetylsalicylic acidAcetylsalicylic acid may decrease the antihypertensive activities of Omapatrilat.
AdapaleneThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Adapalene.
AlfuzosinAlfuzosin may increase the hypotensive activities of Omapatrilat.
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Omapatrilat.
AliskirenOmapatrilat may increase the hypotensive activities of Aliskiren.
AllopurinolThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Omapatrilat.
AlogliptinThe risk or severity of adverse effects can be increased when Alogliptin is combined with Omapatrilat.
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Omapatrilat.
AlprenololAlprenolol may increase the hypotensive activities of Omapatrilat.
AmbrisentanOmapatrilat may increase the hypotensive activities of Ambrisentan.
AmifostineOmapatrilat may increase the hypotensive activities of Amifostine.
AmilorideAmiloride may increase the hyperkalemic activities of Omapatrilat.
AmineptineThe serum concentration of Amineptine can be increased when it is combined with Omapatrilat.
AminophyllineThe serum concentration of Aminophylline can be decreased when it is combined with Omapatrilat.
Aminosalicylic AcidAminosalicylic Acid may decrease the antihypertensive activities of Omapatrilat.
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Omapatrilat.
AmlodipineAmlodipine may increase the hypotensive activities of Omapatrilat.
AntipyrineThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Antipyrine.
ApremilastThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Apremilast.
AprotininAprotinin may decrease the antihypertensive activities of Omapatrilat.
ArdeparinArdeparin may increase the hyperkalemic activities of Omapatrilat.
AtenololAtenolol may increase the hypotensive activities of Omapatrilat.
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Omapatrilat.
AtorvastatinThe risk or severity of adverse effects can be increased when Atorvastatin is combined with Omapatrilat.
AzapropazoneThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Azapropazone.
AzathioprineOmapatrilat may increase the myelosuppressive activities of Azathioprine.
AzelastineThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Azelastine.
Azilsartan medoxomilThe risk or severity of adverse effects can be increased when Azilsartan medoxomil is combined with Omapatrilat.
BalsalazideThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Balsalazide.
BemiparinBemiparin may increase the hyperkalemic activities of Omapatrilat.
BenazeprilBenazepril may increase the hypotensive activities of Omapatrilat.
BendroflumethiazideBendroflumethiazide may increase the hypotensive activities of Omapatrilat.
BenmoxinBenmoxin may increase the hypotensive activities of Omapatrilat.
BenoxaprofenThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Benoxaprofen.
BepridilOmapatrilat may increase the hypotensive activities of Bepridil.
BetaxololBetaxolol may increase the hypotensive activities of Omapatrilat.
BethanidineBethanidine may increase the hypotensive activities of Omapatrilat.
BimatoprostOmapatrilat may increase the hypotensive activities of Bimatoprost.
BisoprololBisoprolol may increase the hypotensive activities of Omapatrilat.
BoceprevirThe serum concentration of Omapatrilat can be decreased when it is combined with Boceprevir.
BosentanBosentan may increase the hypotensive activities of Omapatrilat.
BretyliumOmapatrilat may increase the hypotensive activities of Bretylium.
BrimonidineOmapatrilat may increase the hypotensive activities of Brimonidine.
BrimonidineBrimonidine may increase the antihypertensive activities of Omapatrilat.
BromfenacThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Bromfenac.
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Omapatrilat.
BumetanideBumetanide may increase the hypotensive activities of Omapatrilat.
BupranololOmapatrilat may increase the hypotensive activities of Bupranolol.
CabergolineThe serum concentration of Cabergoline can be increased when it is combined with Omapatrilat.
CanagliflozinCanagliflozin may increase the hyperkalemic activities of Omapatrilat.
CandesartanCandesartan may increase the hypotensive activities of Omapatrilat.
CandoxatrilCandoxatril may increase the hypotensive activities of Omapatrilat.
CaptoprilOmapatrilat may increase the hypotensive activities of Captopril.
CarbamazepineThe metabolism of Omapatrilat can be increased when combined with Carbamazepine.
CaroxazoneCaroxazone may increase the hypotensive activities of Omapatrilat.
CarprofenThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Carprofen.
CarteololCarteolol may increase the hypotensive activities of Omapatrilat.
CarvedilolOmapatrilat may increase the hypotensive activities of Carvedilol.
CastanospermineThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Castanospermine.
CelecoxibThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Celecoxib.
CeliprololOmapatrilat may increase the hypotensive activities of Celiprolol.
CertoparinCertoparin may increase the hyperkalemic activities of Omapatrilat.
ChloroquineThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Chloroquine.
ChlorothiazideChlorothiazide may increase the hypotensive activities of Omapatrilat.
ChlorthalidoneChlorthalidone may increase the hypotensive activities of Omapatrilat.
CilazaprilOmapatrilat may increase the hypotensive activities of Cilazapril.
CiprofloxacinOmapatrilat may increase the arrhythmogenic activities of Ciprofloxacin.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Omapatrilat.
ClarithromycinThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Omapatrilat.
ClomipramineThe serum concentration of Clomipramine can be increased when it is combined with Omapatrilat.
ClonidineClonidine may increase the hypotensive activities of Omapatrilat.
ClonixinThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Clonixin.
CryptenamineCryptenamine may increase the hypotensive activities of Omapatrilat.
CyclobenzaprineThe serum concentration of Cyclobenzaprine can be increased when it is combined with Omapatrilat.
CyclophosphamideThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Cyclophosphamide.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Omapatrilat.
CyclothiazideCyclothiazide may increase the hypotensive activities of Omapatrilat.
D-LimoneneThe risk or severity of adverse effects can be increased when Omapatrilat is combined with D-Limonene.
DalteparinDalteparin may increase the hyperkalemic activities of Omapatrilat.
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Omapatrilat.
DebrisoquinOmapatrilat may increase the hypotensive activities of Debrisoquin.
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Omapatrilat.
DeserpidineOmapatrilat may increase the hypotensive activities of Deserpidine.
DesipramineThe serum concentration of Desipramine can be increased when it is combined with Omapatrilat.
DiazoxideDiazoxide may increase the hypotensive activities of Omapatrilat.
DiclofenacThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Diclofenac.
DiflunisalThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Diflunisal.
DiflunisalDiflunisal may decrease the antihypertensive activities of Omapatrilat.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Omapatrilat.
DihydroergotamineThe serum concentration of Dihydroergotamine can be increased when it is combined with Omapatrilat.
DiltiazemDiltiazem may increase the hypotensive activities of Omapatrilat.
DorzolamideDorzolamide may increase the hypotensive activities of Omapatrilat.
DosulepinThe serum concentration of Dosulepin can be increased when it is combined with Omapatrilat.
DoxazosinDoxazosin may increase the hypotensive activities of Omapatrilat.
DoxepinThe serum concentration of Doxepin can be increased when it is combined with Omapatrilat.
DrospirenoneOmapatrilat may increase the hyperkalemic activities of Drospirenone.
DroxicamThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Droxicam.
DyphyllineThe serum concentration of Dyphylline can be decreased when it is combined with Omapatrilat.
EfonidipineOmapatrilat may increase the hypotensive activities of Efonidipine.
EnalaprilEnalapril may increase the hypotensive activities of Omapatrilat.
EnalaprilatOmapatrilat may increase the hypotensive activities of Enalaprilat.
EnfuvirtideThe serum concentration of Enfuvirtide can be increased when it is combined with Omapatrilat.
EnoxaparinEnoxaparin may increase the hyperkalemic activities of Omapatrilat.
EpirizoleThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Epirizole.
EplerenoneEplerenone may increase the hyperkalemic activities of Omapatrilat.
EpoprostenolOmapatrilat may increase the hypotensive activities of Epoprostenol.
EprosartanEprosartan may increase the hypotensive activities of Omapatrilat.
Ergoloid mesylateThe serum concentration of Ergoloid mesylate can be increased when it is combined with Omapatrilat.
ErgonovineThe serum concentration of Ergonovine can be increased when it is combined with Omapatrilat.
ErgotamineThe serum concentration of Ergotamine can be increased when it is combined with Omapatrilat.
EsmirtazapineThe serum concentration of Esmirtazapine can be increased when it is combined with Omapatrilat.
Etacrynic acidEtacrynic acid may increase the hypotensive activities of Omapatrilat.
EtanerceptThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Etanercept.
EtodolacThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Etodolac.
EtofenamateThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Etofenamate.
EtoricoxibThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Etoricoxib.
EtravirineThe serum concentration of Etravirine can be decreased when it is combined with Omapatrilat.
Evening primrose oilThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Evening primrose oil.
EverolimusThe risk or severity of adverse effects can be increased when Everolimus is combined with Omapatrilat.
exisulindThe risk or severity of adverse effects can be increased when Omapatrilat is combined with exisulind.
FelodipineOmapatrilat may increase the hypotensive activities of Felodipine.
FenbufenThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Fenbufen.
FenoldopamFenoldopam may increase the hypotensive activities of Omapatrilat.
FenoprofenThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Fenoprofen.
FloctafenineThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Floctafenine.
FlunixinThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Flunixin.
FlurbiprofenThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Flurbiprofen.
ForasartanThe risk or severity of adverse effects can be increased when Forasartan is combined with Omapatrilat.
FosinoprilFosinopril may increase the hypotensive activities of Omapatrilat.
FurazolidoneFurazolidone may increase the hypotensive activities of Omapatrilat.
FurosemideFurosemide may increase the hypotensive activities of Omapatrilat.
GarlicThe serum concentration of Omapatrilat can be decreased when it is combined with Garlic.
GuanabenzGuanabenz may increase the hypotensive activities of Omapatrilat.
GuanadrelGuanadrel may increase the hypotensive activities of Omapatrilat.
GuanethidineOmapatrilat may increase the hypotensive activities of Guanethidine.
GuanfacineOmapatrilat may increase the hypotensive activities of Guanfacine.
HeparinHeparin may increase the hyperkalemic activities of Omapatrilat.
HexamethoniumOmapatrilat may increase the hypotensive activities of Hexamethonium.
HMPL-004The risk or severity of adverse effects can be increased when Omapatrilat is combined with HMPL-004.
HydracarbazineHydracarbazine may increase the hypotensive activities of Omapatrilat.
HydralazineOmapatrilat may increase the hypotensive activities of Hydralazine.
HydrochlorothiazideOmapatrilat may increase the hypotensive activities of Hydrochlorothiazide.
HydroflumethiazideHydroflumethiazide may increase the hypotensive activities of Omapatrilat.
IbuprofenThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Ibuprofen.
IbuproxamThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Ibuproxam.
IcatibantIcatibant may decrease the antihypertensive activities of Omapatrilat.
IcatibantThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Icatibant.
IloprostIloprost may increase the hypotensive activities of Omapatrilat.
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Omapatrilat.
IndapamideIndapamide may increase the hypotensive activities of Omapatrilat.
IndenololOmapatrilat may increase the hypotensive activities of Indenolol.
IndomethacinThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Indomethacin.
IndoprofenThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Indoprofen.
IndoraminOmapatrilat may increase the hypotensive activities of Indoramin.
IproclozideIproclozide may increase the hypotensive activities of Omapatrilat.
IproniazidIproniazid may increase the hypotensive activities of Omapatrilat.
IrbesartanOmapatrilat may increase the hypotensive activities of Irbesartan.
IronThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Iron.
Iron DextranThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Iron Dextran.
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Omapatrilat.
IsoxicamThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Isoxicam.
IsradipineIsradipine may increase the hypotensive activities of Omapatrilat.
KebuzoneThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Kebuzone.
KetoprofenThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Ketoprofen.
KetorolacThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Ketorolac.
LabetalolLabetalol may increase the hypotensive activities of Omapatrilat.
LacidipineOmapatrilat may increase the hypotensive activities of Lacidipine.
Lanthanum carbonateThe serum concentration of Omapatrilat can be decreased when it is combined with Lanthanum carbonate.
LatanoprostLatanoprost may increase the hypotensive activities of Omapatrilat.
LeflunomideThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Leflunomide.
LercanidipineLercanidipine may increase the hypotensive activities of Omapatrilat.
LinagliptinThe risk or severity of adverse effects can be increased when Linagliptin is combined with Omapatrilat.
LisinoprilLisinopril may increase the hypotensive activities of Omapatrilat.
LithiumThe serum concentration of Lithium can be increased when it is combined with Omapatrilat.
LofexidineOmapatrilat may increase the hypotensive activities of Lofexidine.
LornoxicamThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Lornoxicam.
LosartanLosartan may increase the hypotensive activities of Omapatrilat.
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Omapatrilat.
LoxoprofenThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Loxoprofen.
LumiracoxibThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Lumiracoxib.
MacitentanOmapatrilat may increase the hypotensive activities of Macitentan.
Magnesium salicylateThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Magnesium salicylate.
ManidipineOmapatrilat may increase the hypotensive activities of Manidipine.
MasoprocolThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Masoprocol.
MebanazineMebanazine may increase the hypotensive activities of Omapatrilat.
MecamylamineMecamylamine may increase the hypotensive activities of Omapatrilat.
Meclofenamic acidThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Meclofenamic acid.
Mefenamic acidThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Mefenamic acid.
MeloxicamThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Meloxicam.
MesalazineThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Mesalazine.
MesalazineMesalazine may decrease the antihypertensive activities of Omapatrilat.
MetamizoleThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Metamizole.
MethyclothiazideMethyclothiazide may increase the hypotensive activities of Omapatrilat.
MethyldopaOmapatrilat may increase the hypotensive activities of Methyldopa.
Methylene blueMethylene blue may increase the hypotensive activities of Omapatrilat.
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Omapatrilat.
MetipranololOmapatrilat may increase the hypotensive activities of Metipranolol.
MetolazoneMetolazone may increase the hypotensive activities of Omapatrilat.
MetoprololMetoprolol may increase the hypotensive activities of Omapatrilat.
MibefradilOmapatrilat may increase the hypotensive activities of Mibefradil.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Omapatrilat.
MinaprineMinaprine may increase the hypotensive activities of Omapatrilat.
MinoxidilMinoxidil may increase the hypotensive activities of Omapatrilat.
MirtazapineThe serum concentration of Mirtazapine can be increased when it is combined with Omapatrilat.
MoclobemideMoclobemide may increase the hypotensive activities of Omapatrilat.
MoexiprilMoexipril may increase the hypotensive activities of Omapatrilat.
MolsidomineMolsidomine may increase the hypotensive activities of Omapatrilat.
MoxonidineOmapatrilat may increase the hypotensive activities of Moxonidine.
Mycophenolate mofetilThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Mycophenolate mofetil.
Mycophenolic acidThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Mycophenolic acid.
NabumetoneThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Nabumetone.
NadololOmapatrilat may increase the hypotensive activities of Nadolol.
NadroparinNadroparin may increase the hyperkalemic activities of Omapatrilat.
NaftifineThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Naftifine.
NaproxenThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Naproxen.
NCX 4016The risk or severity of adverse effects can be increased when Omapatrilat is combined with NCX 4016.
NebivololOmapatrilat may increase the hypotensive activities of Nebivolol.
NefazodoneThe serum concentration of Nefazodone can be increased when it is combined with Omapatrilat.
NepafenacThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Nepafenac.
NialamideNialamide may increase the hypotensive activities of Omapatrilat.
NicardipineNicardipine may increase the hypotensive activities of Omapatrilat.
NicorandilNicorandil may increase the hyperkalemic activities of Omapatrilat.
NicorandilOmapatrilat may increase the hypotensive activities of Nicorandil.
Niflumic AcidThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Niflumic Acid.
NiguldipineOmapatrilat may increase the hypotensive activities of Niguldipine.
NilvadipineOmapatrilat may increase the hypotensive activities of Nilvadipine.
NimesulideThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Nimesulide.
NimodipineNimodipine may increase the hypotensive activities of Omapatrilat.
NisoldipineNisoldipine may increase the hypotensive activities of Omapatrilat.
NitrendipineOmapatrilat may increase the hypotensive activities of Nitrendipine.
NitroprussideNitroprusside may increase the hypotensive activities of Omapatrilat.
NortriptylineThe serum concentration of Nortriptyline can be increased when it is combined with Omapatrilat.
ObinutuzumabOmapatrilat may increase the hypotensive activities of Obinutuzumab.
OctamoxinOctamoxin may increase the hypotensive activities of Omapatrilat.
OlmesartanOlmesartan may increase the hypotensive activities of Omapatrilat.
OlopatadineThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Olopatadine.
OlsalazineThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Olsalazine.
OrgoteinThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Orgotein.
OxaprozinThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Oxaprozin.
OxprenololOmapatrilat may increase the hypotensive activities of Oxprenolol.
OxyphenbutazoneThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Oxyphenbutazone.
ParecoxibThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Parecoxib.
PargylineOmapatrilat may increase the hypotensive activities of Pargyline.
ParnaparinParnaparin may increase the hyperkalemic activities of Omapatrilat.
PenbutololOmapatrilat may increase the hypotensive activities of Penbutolol.
PentoliniumOmapatrilat may increase the hypotensive activities of Pentolinium.
PentoxifyllinePentoxifylline may increase the hypotensive activities of Omapatrilat.
PerindoprilPerindopril may increase the hypotensive activities of Omapatrilat.
PethidineThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Pethidine.
PhenelzinePhenelzine may increase the hypotensive activities of Omapatrilat.
PheniprazinePheniprazine may increase the hypotensive activities of Omapatrilat.
PhenoxybenzamineOmapatrilat may increase the hypotensive activities of Phenoxybenzamine.
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Omapatrilat.
PhentolaminePhentolamine may increase the hypotensive activities of Omapatrilat.
PhenylbutazoneThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Phenylbutazone.
PimecrolimusThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Pimecrolimus.
PimozideThe serum concentration of Pimozide can be increased when it is combined with Omapatrilat.
PinacidilOmapatrilat may increase the hypotensive activities of Pinacidil.
PindololOmapatrilat may increase the hypotensive activities of Pindolol.
PiretanidePiretanide may increase the hypotensive activities of Omapatrilat.
PirfenidoneThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Pirfenidone.
PirlindolePirlindole may increase the hypotensive activities of Omapatrilat.
PiroxicamThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Piroxicam.
PivhydrazinePivhydrazine may increase the hypotensive activities of Omapatrilat.
PolythiazideOmapatrilat may increase the hypotensive activities of Polythiazide.
PrazosinPrazosin may increase the hypotensive activities of Omapatrilat.
PregabalinThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Pregabalin.
PropacetamolThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Propacetamol.
PropranololPropranolol may increase the hypotensive activities of Omapatrilat.
ProtriptylineThe serum concentration of Protriptyline can be increased when it is combined with Omapatrilat.
PTC299The risk or severity of adverse effects can be increased when Omapatrilat is combined with PTC299.
QuinaprilQuinapril may increase the hypotensive activities of Omapatrilat.
QuinethazoneQuinethazone may increase the hypotensive activities of Omapatrilat.
QuinineQuinine may increase the hypotensive activities of Omapatrilat.
RamiprilRamipril may increase the hypotensive activities of Omapatrilat.
RasagilineRasagiline may increase the hypotensive activities of Omapatrilat.
RemikirenRemikiren may increase the hypotensive activities of Omapatrilat.
RescinnamineOmapatrilat may increase the hypotensive activities of Rescinnamine.
ReserpineReserpine may increase the hypotensive activities of Omapatrilat.
ResveratrolThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Resveratrol.
ReviparinReviparin may increase the hyperkalemic activities of Omapatrilat.
RiociguatOmapatrilat may increase the hypotensive activities of Riociguat.
RituximabOmapatrilat may increase the hypotensive activities of Rituximab.
RofecoxibThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Rofecoxib.
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Omapatrilat.
SacubitrilThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Sacubitril.
SafrazineSafrazine may increase the hypotensive activities of Omapatrilat.
SalicylamideThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Salicylamide.
Salicylic acidThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Salicylic acid.
Salicylic acidSalicylic acid may decrease the antihypertensive activities of Omapatrilat.
SalsalateThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Salsalate.
SaprisartanOmapatrilat may increase the hypotensive activities of Saprisartan.
SaralasinThe risk or severity of adverse effects can be increased when Saralasin is combined with Omapatrilat.
SaxagliptinThe risk or severity of adverse effects can be increased when Saxagliptin is combined with Omapatrilat.
SelegilineSelegiline may increase the hypotensive activities of Omapatrilat.
SelexipagOmapatrilat may increase the hypotensive activities of Selexipag.
SeratrodastThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Seratrodast.
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Omapatrilat.
SildenafilSildenafil may increase the antihypertensive activities of Omapatrilat.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Omapatrilat.
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Omapatrilat.
SirolimusThe risk or severity of adverse effects can be increased when Sirolimus is combined with Omapatrilat.
SitagliptinThe risk or severity of adverse effects can be increased when Sitagliptin is combined with Omapatrilat.
SitaxentanOmapatrilat may increase the hypotensive activities of Sitaxentan.
Sodium aurothiomalateThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Sodium aurothiomalate.
SpiraprilOmapatrilat may increase the hypotensive activities of Spirapril.
SpironolactoneSpironolactone may increase the hyperkalemic activities of Omapatrilat.
SRT501The risk or severity of adverse effects can be increased when Omapatrilat is combined with SRT501.
St. John's WortThe metabolism of Omapatrilat can be increased when combined with St. John's Wort.
SulfasalazineThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Sulfasalazine.
SulindacThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Sulindac.
SuprofenThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Suprofen.
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Omapatrilat.
TadalafilTadalafil may increase the antihypertensive activities of Omapatrilat.
TasosartanThe risk or severity of adverse effects can be increased when Tasosartan is combined with Omapatrilat.
TelmisartanOmapatrilat may increase the hypotensive activities of Telmisartan.
TemocaprilOmapatrilat may increase the hypotensive activities of Temocapril.
TemsirolimusThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Omapatrilat.
TenoxicamThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Tenoxicam.
TepoxalinThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Tepoxalin.
TeriflunomideThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Teriflunomide.
TerlipressinOmapatrilat may increase the hypotensive activities of Terlipressin.
TheophyllineThe serum concentration of Theophylline can be decreased when it is combined with Omapatrilat.
TianeptineThe serum concentration of Tianeptine can be increased when it is combined with Omapatrilat.
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Tiaprofenic acid.
TiboloneOmapatrilat may increase the hypotensive activities of Tibolone.
TicrynafenOmapatrilat may increase the hypotensive activities of Ticrynafen.
TimololTimolol may increase the hypotensive activities of Omapatrilat.
TinzaparinTinzaparin may increase the hyperkalemic activities of Omapatrilat.
TipranavirThe serum concentration of Omapatrilat can be decreased when it is combined with Tipranavir.
TizanidineTizanidine may increase the hypotensive activities of Omapatrilat.
TolazolineTolazoline may increase the hypotensive activities of Omapatrilat.
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Tolfenamic Acid.
TolmetinThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Tolmetin.
ToloxatoneToloxatone may increase the hypotensive activities of Omapatrilat.
TolvaptanTolvaptan may increase the hyperkalemic activities of Omapatrilat.
TorasemideTorasemide may increase the hypotensive activities of Omapatrilat.
TrandolaprilTrandolapril may increase the hypotensive activities of Omapatrilat.
TranilastThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Tranilast.
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypotensive activities of Omapatrilat.
TranylcypromineTranylcypromine may increase the hypotensive activities of Omapatrilat.
TravoprostTravoprost may increase the hypotensive activities of Omapatrilat.
TreprostinilTreprostinil may increase the hypotensive activities of Omapatrilat.
TriamtereneTriamterene may increase the hyperkalemic activities of Omapatrilat.
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Omapatrilat.
TrichlormethiazideOmapatrilat may increase the hypotensive activities of Trichlormethiazide.
TrimazosinOmapatrilat may increase the hypotensive activities of Trimazosin.
TrimethaphanOmapatrilat may increase the hypotensive activities of Trimethaphan.
TrimethoprimTrimethoprim may increase the hyperkalemic activities of Omapatrilat.
TrimipramineThe serum concentration of Trimipramine can be increased when it is combined with Omapatrilat.
Trisalicylate-cholineThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Trisalicylate-choline.
UdenafilUdenafil may increase the antihypertensive activities of Omapatrilat.
UnoprostoneOmapatrilat may increase the hypotensive activities of Unoprostone.
ValdecoxibThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Valdecoxib.
ValsartanValsartan may increase the hypotensive activities of Omapatrilat.
VardenafilVardenafil may increase the antihypertensive activities of Omapatrilat.
VildagliptinThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Omapatrilat.
XylometazolineOmapatrilat may increase the hypotensive activities of Xylometazoline.
YohimbineYohimbine may decrease the antihypertensive activities of Omapatrilat.
ZaltoprofenThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Zaltoprofen.
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Omapatrilat.
ZileutonThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Zileuton.
ZomepiracThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Zomepirac.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent vasodilator. Has also a glycosidase activity which releases GPI-anchored proteins from the membrane by cleaving the mannose linkage in the GPI moiety.
Gene Name:
ACE
Uniprot ID:
P12821
Molecular Weight:
149713.675 Da
References
  1. Azizi M, Massien C, Michaud A, Corvol P: In vitro and in vivo inhibition of the 2 active sites of ACE by omapatrilat, a vasopeptidase inhibitor. Hypertension. 2000 Jun;35(6):1226-31. [PubMed:10856268 ]
  2. Ferdinand KC: Advances in antihypertensive combination therapy: benefits of low-dose thiazide diuretics in conjunction with omapatrilat, a vasopeptidase inhibitor. J Clin Hypertens (Greenwich). 2001 Sep-Oct;3(5):307-12. [PubMed:11588409 ]
  3. Heudi O, Ramirez-Molina C, Marshall P, Amour A, Peace S, McKeown S, Abou-Shakra F: Investigation of bradykinin metabolism in human and rat plasma in the presence of the dual ACE/NEP inhibitors GW660511X and omapatrilat. J Pept Sci. 2002 Nov;8(11):591-600. [PubMed:12487427 ]
  4. Neal B, MacMahon S, Ohkubo T, Brnabic A, Tonkin A: Effects of the vasopeptidase inhibitor, omapatrilat, in 723 patients with coronary heart disease. J Renin Angiotensin Aldosterone Syst. 2002 Dec;3(4):270-6. [PubMed:12584671 ]
  5. Trippodo NC, Fox M, Monticello TM, Panchal BC, Asaad MM: Vasopeptidase inhibition with omapatrilat improves cardiac geometry and survival in cardiomyopathic hamsters more than does ACE inhibition with captopril. J Cardiovasc Pharmacol. 1999 Dec;34(6):782-90. [PubMed:10598120 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
General Function:
Zinc ion binding
Specific Function:
Thermolysin-like specificity, but is almost confined on acting on polypeptides of up to 30 amino acids (PubMed:15283675, PubMed:8168535). Biologically important in the destruction of opioid peptides such as Met- and Leu-enkephalins by cleavage of a Gly-Phe bond (PubMed:17101991). Able to cleave angiotensin-1, angiotensin-2 and angiotensin 1-9 (PubMed:15283675). Involved in the degradation of at...
Gene Name:
MME
Uniprot ID:
P08473
Molecular Weight:
85513.225 Da
References
  1. Intengan HD, Schiffrin EL: Vasopeptidase inhibition has potent effects on blood pressure and resistance arteries in stroke-prone spontaneously hypertensive rats. Hypertension. 2000 Jun;35(6):1221-5. [PubMed:10856267 ]
  2. Azizi M, Massien C, Michaud A, Corvol P: In vitro and in vivo inhibition of the 2 active sites of ACE by omapatrilat, a vasopeptidase inhibitor. Hypertension. 2000 Jun;35(6):1226-31. [PubMed:10856268 ]
  3. McClean DR, Ikram H, Garlick AH, Richards AM, Nicholls MG, Crozier IG: The clinical, cardiac, renal, arterial and neurohormonal effects of omapatrilat, a vasopeptidase inhibitor, in patients with chronic heart failure. J Am Coll Cardiol. 2000 Aug;36(2):479-86. [PubMed:10933361 ]
  4. Troughton RW, Rademaker MT, Powell JD, Yandle TG, Espiner EA, Frampton CM, Nicholls MG, Richards AM: Beneficial renal and hemodynamic effects of omapatrilat in mild and severe heart failure. Hypertension. 2000 Oct;36(4):523-30. [PubMed:11040230 ]
  5. Burrell LM, Droogh J, Man in't Veld O, Rockell MD, Farina NK, Johnston CI: Antihypertensive and antihypertrophic effects of omapatrilat in SHR. Am J Hypertens. 2000 Oct;13(10):1110-6. [PubMed:11041166 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23