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Merck
CN

1091221

USP

Captopril disulfide

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

1,1′-[Dithiobis[(2S)-2-methyl-1-oxo-3,1-propanediyl]]bis-L-proline

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About This Item

Empirical Formula (Hill Notation):
C18H28N2O6S2
CAS Number:
64806-05-9
Molecular Weight:
432.55
MDL number:
MFCD08063643
UNSPSC Code:
41116107
NACRES:
NA.24

Key Documents

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Product Name

Captopril disulfide, United States Pharmacopeia (USP) Reference Standard

SMILES string

S(SCC(C)C(=O)N2[C@@H](CCC2)C(=O)O)C[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)O

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-KRCVMZOZSA-N

grade

pharmaceutical primary standard

API family

captopril

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

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Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Application

Captopril disulfide USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:
  • Captopril Tablets
  • Captopril
  • Captopril and Hydrochlorothiazide Tablets

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Other Notes

Sales restrictions may apply.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Potentiation of bradykinin-induced decrease of blood pressure in dogs by SO 14,551, the disulfide metabolite of captopril.
N O'Hara et al.
Japanese journal of pharmacology, 32(5), 934-937 (1982-10-01)
O H Drummer et al.
Biochemical pharmacology, 33(22), 3567-3571 (1984-11-15)
The absorption and metabolism of the disulfide dimer conjugate of captopril has been studied in the rat following both oral and intravenous dosing and compared with that of the active monomer, captopril. Metabolism of the dimer to captopril has been
K J Kripalani et al.
Xenobiotica; the fate of foreign compounds in biological systems, 13(12), 701-705 (1983-12-01)
The metabolism of [14C]captopril-L-cysteine was studied in spontaneously hypertensive rats and pure-bred beagles after a single i.v. dose (4 mg/kg). During the first 24 h, concn. of total radioactivity in blood were similar in both species. Captopril was found in
O H Drummer et al.
European journal of clinical pharmacology, 32(3), 267-271 (1987-01-01)
We have measured the plasma concentrations of captopril and total disulfide conjugates of captopril after a 50 mg oral dose in 6 uraemic patients on maintenance dialysis and in 8 hypertensive subjects with normal renal function. The mean peak plasma
D Zhong et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 33(8), 605-609 (2002-05-23)
A new and sensitive HPLC method has been developed for the determination of captopril plus its disulfide metabolites (total captopril) in human plasma. Captopril disulfides and the drug covalently bound to protein were reduced with sodium borohydride to captopril. After
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