An ACE and NEP inhibitor
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Omapatrilat

Item No. 31738

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4S,7S,10aS)-octahydro-4-[[(2S)-2-mercapto-1-oxo-3-phenylpropyl]amino]-5-oxo-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid
CAS Number
167305-00-2
Synonyms
  • BMS-186716
Molecular Formula
C19H24N2O4S2
Formula Weight
408.5
Purity
≥90%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 30 mg/ml
SMILES
OC([C@H]1N2[C@](SCC[C@@H](C2=O)NC([C@@H](S)CC3=CC=CC=C3)=O)([H])CCC1)=OOC([C@H]1N2[C@](SCC[C@@H](C2=O)NC([C@@H](S)CC3=CC=CC=C3)=O)([H])CCC1)=O
InChi Code
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
InChi Key
LVRLSYPNFFBYCZ-VGWMRTNUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $49

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    1 mg

    $93

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    5 mg

    $259

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    10 mg

    $469

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    Product Description

    Omapatrilat is an orally bioavailable angiotensin-converting enzyme (ACE) and neprilysin (NEP) inhibitior (IC50s = 1.7 and 5.3 nM, respectively, for the human enzymes).1 It inhibits the pressor response induced by angiotensin I (Item No. 24737) in normotensive rats (ED50 = 0.07 µmol/kg) and lowers mean arterial pressure (MAP) in sodium-depleted spontaneously hypertensive rats when administered at a dose of 30 µmol/kg.2 Omapatrilat lowers MAP in rats when co-administered with bradykinin (Item No. 37408).3 It also increases tracheal plasma extravasation in a rat model of upper airway angioedema in a dose-dependent manner.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sulpizio, A.C., Pullen, M.A., Edwards, R.M., et al. Mechanism of vasopeptidase inhibitor-induced plasma extravasation: Comparison of omapatrilat and the novel neutral endopeptidase 24.11/angiotensin-converting enzyme inhibitor GW796406. J. Pharmacol. Exp. Ther. 315(3), 1306-1313 (2005).

    2. Robl, J.A., Sun, C.-Q., Stevenson, J., et al. Dual metalloprotease inhibitors: Mercaptoacetyl-based fused heterocyclic dipeptide mimetics as inhibitors of angiotensin-converting enzyme and neutral endopeptidase. J. Med. Chem. 40(11), 1570-1577 (1997).

    3. Fryer, R.M., Segreti, J., Banfor, P.N., et al. Effect of bradykinin metabolism inhibitors on evoked hypotension in rats: Rank efficacy of enzymes associated with bradykinin-mediated angioedema. Br. J. Pharmacol. 153(5), 947-955 (2008).

    4. Murray McKinnell, R., Fatheree, P., Choi, S.-K., et al. Discovery of TD-0212, an orally active dual pharmacology AT1 antagonist and neprilysin inhibitor (ARNI). ACS Med. Chem. Lett. 10(1), 86-91 (2018).