A prodrug form of zofenoprilat
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Active Metabolite(s)
38124Zofenoprilat
Labeled Version(s)
43425Zofenopril-d5
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Zofenopril (calcium salt)

Item No. 29525

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4S)-1-[(2S)-3-(benzoylthio)-2-methyl-1-oxopropyl]-4-(phenylthio)-L-proline, hemicalcium salt
CAS Number
81938-43-4
Synonyms
  • SQ 26,911
Molecular Formula
C22H22NO4S2 • 1/2Ca
Formula Weight
448.6
Purity
≥98%
Formulation
A solid
λmax
238 nm
SMILES
O=C(SC[C@@H](C)C(N1C[C@@H](SC2=CC=CC=C2)C[C@H]1C([O-])=O)=O)C3=CC=CC=C3.O=C(SC[C@@H](C)C(N4C[C@@H](SC5=CC=CC=C5)C[C@H]4C([O-])=O)=O)C6=CC=CC=C6.[Ca+2]
InChi Code
InChI=1S/2C22H23NO4S2.Ca/c2*1-15(14-28-22(27)16-8-4-2-5-9-16)20(24)23-13-18(12-19(23)21(25)26)29-17-10-6-3-7-11-17;/h2*2-11,15,18-19H,12-14H2,1H3,(H,25,26);/q;;+2/p-2/t2*15-,18+,19+;/m11./s1
InChi Key
NSYUKKYYVFVMST-LETVYOFWSA-L
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Zofenopril is a prodrug form of the angiotensin-converting enzyme (ACE) inhibitor zofenoprilat.1 Zofenopril is hydrolyzed by cardiac esterases in vivo to form zofenoprilat. It inhibits ACE with an IC50 value of 0.9 nM in heart tissue homogenates and inhibits cardiac ACE activity in isolated perfused rat hearts. It reduces mean arterial blood pressure in two kidney-one clip renal hypertensive (2K-1C) rats and spontaneously hypertensive rats (SHRs) when administered at doses of 2.2, 6.6, and 22 mg/kg.2 Unlike the ACE inhibitor ramipril (Item No. 15558), zofenopril does not affect bronchoalveolar lavage fluid (BALF) levels of bradykinin or prostaglandin E2 (PGE2; Item No. 14010) or increase coughing induced by citric acid in guinea pigs.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Grover, G.J., Sleph, P.G., Dzwonczyk, S., et al. Effects of different angiotensin-converting enzyme (ACE) inhibitors on ischemic isolated rat hearts: Relationship between cardiac ACE inhibition and cardioprotection. J. Pharmacol. Exp. Ther. 257(3), 919-929 (1991).

    2. DeForrest, J.M., Waldron, T.L., Krapcho, J., et al. Preclinical pharmacology of zofenopril, an inhibitor of angiotensin I converting enzyme. J. Cardiovasc. Pharmacol. 13(6), 887-894 (1989).

    3. Cialdai, C., Giuliani, S., Valenti, C., et al. Differences between zofenopril and ramipril, two ACE inhibitors, on cough induced by citric acid in guinea pigs: Role of bradykinin and PGE2. Naunyn Schmiedebergs Arch. Pharmacol. 382(5-6), 455-461 (2010).