A metabolite and degradation product of captopril
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Parent Compound(s)
15313Captopril
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Captopril Disulfide

Item No. 28018

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,1'-[dithiobis[(2S)-2-methyl-1-oxo-3,1-propanediyl]]bis-L-proline
CAS Number
64806-05-9
Synonyms
  • SQ 14,551
Molecular Formula
C18H28N2O6S2
Formula Weight
432.6
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: slightly solubleEthanol: slightly, sonicated
SMILES
O=C(O)[C@H]1N(C([C@H](C)CSSC[C@@H](C)C(N2CCC[C@H]2C(O)=O)=O)=O)CCC1
InChi Code
InChI=1S/C18H28N2O6S2/c1-11(15(21)19-7-3-5-13(19)17(23)24)9-27-28-10-12(2)16(22)20-8-4-6-14(20)18(25)26/h11-14H,3-10H2,1-2H3,(H,23,24)(H,25,26)/t11-,12-,13+,14+/m1/s1
InChi Key
ZWKRXBCJAUKDCI-MQYQWHSLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $134

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    10 mg

    $253

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    25 mg

    $565

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    Cayman Chemical
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    Product Description

    Captopril disulfide is a metabolite and symmetrical disulfide form of the angiotensin converting enzyme (ACE) inhibitor captopril (Item No. 15313).1 Captopril disulfide is the main degradation product of captopril and is formed by oxidation.2 It is a potential impurity in commercial preparations of captopril. Captopril disulfide inhibits angiotensin I-induced increases in mean arterial pressure in anesthetized dogs (ID50 = 0.231 mg/kg, i.v.).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Komai, T., Ikeda, T., Kawai, K., et al. In vitro studies on the metabolic pathway of SQ 14225 (Captopril) and mechanism of mixed disulfide formation. J. Pharmacobiodyn. 4(9), 677-684 (1981).

    2. Pasquini, B., Orlandini, S., Caprini, C., et al. Cyclodextrin- and solvent-modified micellar electrokinetic chromatography for the determination of captopril, hydrochlorothiazide and their impurities: A quality by design approach. Talanta 160, 332-339 (2016).

    3. O'Hara, N., Ono, H., and Hashimoto, K. Potentiation of bradykinin-induced decrease of blood pressure in dogs by SO 14,551, the disulfide metabolite of captopril. Jpn. J. Pharmacol. 32(5), 934-937 (1982).