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MedKoo Cat#: 597846 | Name: Captopril disulfide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Captopril disulfide is a metabolite of Captopril. A new antihypertensive agent.

Chemical Structure

Captopril disulfide
Captopril disulfide
CAS#64806-05-9

Theoretical Analysis

MedKoo Cat#: 597846

Name: Captopril disulfide

CAS#: 64806-05-9

Chemical Formula: C18H28N2O6S2

Exact Mass: 432.1389

Molecular Weight: 432.55

Elemental Analysis: C, 49.98; H, 6.53; N, 6.48; O, 22.19; S, 14.82

Price and Availability

Size Price Availability Quantity
25mg USD 350.00 2 Weeks
50mg USD 550.00 2 Weeks
100mg USD 950.00 2 Weeks
250mg USD 1,850.00 2 Weeks
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Related CAS #
No Data
Synonym
Captopril disulfide; SQ 14,551; SQ-14,551; SQ14,551;
IUPAC/Chemical Name
(2'S)-((2S,2'S)-3,3'-disulfanediylbis(2-methylpropanoyl))di-L-proline
InChi Key
ZWKRXBCJAUKDCI-MQYQWHSLSA-N
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
SMILES Code
O=C(N1[C@@H](CCC1)C(O)=O)[C@H](C)CSSC[C@@H](C)C(N2[C@@H](CCC2)C(O)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 432.55 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Bojarska J, Maniukiewicz W, Fruziński A, Sieroń L, Remko M. Captopril and its dimer captopril disulfide: comparative structural and conformational studies. Acta Crystallogr C Struct Chem. 2015 Mar;71(Pt 3):199-203. doi: 10.1107/S2053229615002582. Epub 2015 Feb 18. PubMed PMID: 25734850. 2: Mahmoud WM, Kümmerer K. Captopril and its dimer captopril disulfide: photodegradation, aerobic biodegradation and identification of transformation products by HPLC-UV and LC-ion trap-MS(n). Chemosphere. 2012 Aug;88(10):1170-7. doi: 10.1016/j.chemosphere.2012.03.064. Epub 2012 Apr 24. PubMed PMID: 22534199. 3: Drummer OH, Jarrott B. Captopril disulfide conjugates may act as prodrugs: disposition of the disulfide dimer of captopril in the rat. Biochem Pharmacol. 1984 Nov 15;33(22):3567-71. PubMed PMID: 6095854. 4: Bathala MS, Weinstein SH, Meeker FS Jr, Singhvi SM, Migdalof BH. Quantitative determination of captopril in blood and captopril and its disulfide metabolites in plasma by gas chromatography. J Pharm Sci. 1984 Mar;73(3):340-4. PubMed PMID: 6371216. 5: Drummer OH, Workman BS, Miach PJ, Jarrott B, Louis WJ. The pharmacokinetics of captopril and captopril disulfide conjugates in uraemic patients on maintenance dialysis: comparison with patients with normal renal function. Eur J Clin Pharmacol. 1987;32(3):267-71. PubMed PMID: 3297733. 6: Zhong D, Li X, Wang A, Chen X. [Determination of captopril plus its disulfide metabolites in human plasma]. Yao Xue Xue Bao. 1998 Aug;33(8):605-9. Chinese. PubMed PMID: 12016901. 7: Nishikawa T, Abe R, Sudo Y, Yamada A, Tahara K. HPLC profile of captopril disulfide that undergoes reversible cis-trans conversion among three isomers. Anal Sci. 2004 Oct;20(10):1395-8. PubMed PMID: 15524189. 8: Drummer OH, Routley L, Christophidis N. Reversibility of disulfide formation. Comparison of chemical and enzyme-mediated reduction of penicillamine and captopril disulfides. Biochem Pharmacol. 1987 Apr 15;36(8):1197-201. PubMed PMID: 3297070. 9: Ivashkiv E. Spectrofluorometric determination of captopril plus captopril disulfide metabolites in plasma. J Pharm Sci. 1984 Oct;73(10):1427-30. PubMed PMID: 6389826. 10: Li MJ, Lin SY. Vibrational spectroscopic studies on the disulfide formation and secondary conformational changes of captopril-HSA mixture after UV-B irradiation. Photochem Photobiol. 2005 Nov-Dec;81(6):1404-10. PubMed PMID: 16354113. 11: O'Hara N, Ono H, Hashimoto K. Potentiation of bradykinin-induced decrease of blood pressure in dogs by SO 14,551, the disulfide metabolite of captopril. Jpn J Pharmacol. 1982 Oct;32(5):934-7. PubMed PMID: 6757503. 12: Huang KP, Huang FL, Shetty PK, Yergey AL. Modification of protein by disulfide S-monoxide and disulfide S-dioxide: distinctive effects on PKC. Biochemistry. 2007 Feb 20;46(7):1961-71. Epub 2007 Jan 24. PubMed PMID: 17249696. 13: Pramar Y, Das Gupta V, Bethea C. Stability of captopril in some aqueous systems. J Clin Pharm Ther. 1992 Jun;17(3):185-9. PubMed PMID: 1639881. 14: França Lde M, Pimentel MF, Simões Sda S, Grangeiro S Jr, Prats-Montalbán JM, Ferrer A. NIR hyperspectral imaging to evaluate degradation in captopril commercial tablets. Eur J Pharm Biopharm. 2016 Jul;104:180-8. doi: 10.1016/j.ejpb.2016.05.005. Epub 2016 May 7. PubMed PMID: 27163244. 15: Kripalani KJ, Dean AV, Migdalof BH. Metabolism of captopril-L-cysteine, a captopril metabolite, in rats and dogs. Xenobiotica. 1983 Dec;13(12):701-5. PubMed PMID: 6372264. 16: Elferink JG, de Koster BM. Modulation of neutrophil migration by captopril. Naunyn Schmiedebergs Arch Pharmacol. 1993 May;347(5):562-7. PubMed PMID: 8391658. 17: Creasey WA, Morrison RA, Singhvi SM, Willard DA. Pharmacokinetics of intravenous captopril in healthy men. Eur J Clin Pharmacol. 1988;35(4):367-70. PubMed PMID: 3058486. 18: Drummer OH, Kourtis S. Bradykinin-potentiating activity of captopril disulphide dimer (SQ 14,551). Eur J Pharmacol. 1988 Aug 9;153(1):11-7. PubMed PMID: 3063549. 19: Chan DS, Sato AK, Claybaugh JR. Degradation of captopril in solutions compounded from tablets and standard powder. Am J Hosp Pharm. 1994 May 1;51(9):1205-7. PubMed PMID: 8042640. 20: Kripalani KJ, McKinstry DN, Singhvi SM, Willard DA, Vukovich RA, Migdalof BH. Disposition of captopril in normal subjects. Clin Pharmacol Ther. 1980 May;27(5):636-41. PubMed PMID: 6989546.

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