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CAPTOPRIL DISULFIDE

Product Name
CAPTOPRIL DISULFIDE
CAS No.
64806-05-9
Chemical Name
CAPTOPRIL DISULFIDE
Synonyms
SQ 14551;CAPTOPRDS;CAPTOPRIL DISULFIDE;Captopril-Disuphide;Captopril Impurity J;Captopril Impurity G;Captopril Impurity A;Captopril IMp. A (BP);CAPTOPRIL DISULFIDE USP;Captopril EP IMpurity A
CBNumber
CB9129834
Molecular Formula
C18H28N2O6S2
Formula Weight
432.55
MOL File
64806-05-9.mol
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CAPTOPRIL DISULFIDE Property

Melting point:
224-226°C
Boiling point:
714.8±60.0 °C(Predicted)
Density 
1.383±0.06 g/cm3(Predicted)
storage temp. 
-20°C Freezer
solubility 
DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly, Sonicated)
form 
Solid
pka
3.29±0.20(Predicted)
color 
White to Off-White
Major Application
pharmaceutical
pharmaceutical small molecule
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
InChIKey
ZWKRXBCJAUKDCI-KRCVMZOZSA-N
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Safety

WGK Germany 
3
HS Code 
2933999552
Storage Class
11 - Combustible Solids
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
1091221
Product name
Captopril disulfide
Packaging
100mg
Price
$1290
Updated
2026/03/19
Sigma-Aldrich
Product number
BP500
Product name
Captopril disulfide
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
25MG
Price
$266
Updated
2024/03/01
Cayman Chemical
Product number
28018
Product name
Captopril Disulfide
Packaging
5mg
Price
$121
Updated
2024/03/01
Cayman Chemical
Product number
28018
Product name
Captopril Disulfide
Packaging
25mg
Price
$513
Updated
2024/03/01
Cayman Chemical
Product number
28018
Product name
Captopril Disulfide
Packaging
10mg
Price
$230
Updated
2024/03/01
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CAPTOPRIL DISULFIDE Chemical Properties,Usage,Production

Description

Captopril disulfide is a metabolite and symmetrical disulfide form of the angiotensin converting enzyme (ACE) inhibitor captopril . Captopril disulfide is the main degradation product of captopril and is formed by oxidation. 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.).

Chemical Properties

White Solid

Uses

Captopril Disulfide (Captopril EP Impurity A) is a metabolite of Captopril. A new antihypertensive agent.

Definition

ChEBI: An organic disulfide in which the disulfide bond links two units of captopril. It is a secondary metabolite of captopril.

Synthesis

50 g of free acid, 200 g of water and 66 g of ammonia were added to a 1000 ml three-necked flask. The reaction was held at a controlled temperature of 35C for 2 hours. At the end of the reaction, control at this temperature dropwise addition of hydrochloric acid 102g until the pH to 0.5, stirring for 30 minutes to re-test the pH. add 3g of zinc powder, heating to 38 , holding reaction for 2h. After the completion of the reaction was lowered to room temperature was extracted with 300g of dichloromethane in three times. The organic phases were combined and the dichloromethane was distilled under normal reduced pressure. After evaporation and drying with 80g ethyl acetate recrystallization, warming to 70 dissolved clear, slow cooling to 5 crystallization. Filtering, drying under reduced pressure. Got Captopril 33g. . It was tested to meet the standards of the 2015 edition of the Chinese Pharmacopoeia. Among them, the melting point of the product was 105-108C (Pharmacopoeia standard 104-110C), the specific rotation was -126-130 (Pharmacopoeia standard -126-132), and the disulfide was 0.2% (Pharmacopoeia standard less than 1%). The purity is above 99.6%.

References

[1] T KOMAI. In vitro studies on the metabolic pathway of SQ 14225 (Captopril) and mechanism of mixed disulfide formation.[J]. Journal of pharmacobio-dynamics, 1981, 4 9: 677-684. DOI: 10.1248/bpb1978.4.677
[2] BENEDETTA PASQUINI . Cyclodextrin- and solvent-modified micellar electrokinetic chromatography for the determination of captopril, hydrochlorothiazide and their impurities: A Quality by Design approach[J]. Talanta, 2016, 160: Pages 332-339. DOI: 10.1016/j.talanta.2016.07.038
[3] N O’HARA  K H  H Ono. Potentiation of bradykinin-induced decrease of blood pressure in dogs by SO 14,551, the disulfide metabolite of captopril.[J]. Japanese journal of pharmacology, 1982, 32 5: 934-937. DOI: 10.1254/jjp.32.934

CAPTOPRIL DISULFIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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CAPTOPRIL DISULFIDE Suppliers

Tianjin Aiyuxuan Pharmaceutical Technology?Co.,Ltd
Tel
13312134804
Email
mark_zhang@yuxuanpharm.com
Country
China
ProdList
327
Advantage
58
J & K SCIENTIFIC LTD.
Tel
18210857532; 18210857532
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9815
Advantage
79
Spectrum Chemical Manufacturing Corp.
Tel
021-021-021-67601398-809-809-809 15221380277
Fax
021-57711696
Email
marketing_china@spectrumchemical.com
Country
China
ProdList
9658
Advantage
60
S.Z. PhyStandard Bio-Tech. Co., Ltd.
Tel
0755-4000505016 13380397412
Fax
0755 28094224
Email
3001272453@qq.com
Country
China
ProdList
5157
Advantage
50
S.Z. PhyStandard Bio-Tech. Co., Ltd.
Tel
0755-83725681-603
Fax
+86 755 28094224
Country
China
ProdList
4496
Advantage
50
Clearsynth Labs Limited
Tel
+91-22-26355700
Fax
+91-22-26355701
Email
info@clearsynth.com
Country
India
ProdList
9679
Advantage
58
AdooQ BioScience, LLC
Tel
+1 (866) 930-6790
Fax
+1 (866) 333-9607
Email
info@adooq.com
Country
United States
ProdList
2782
Advantage
58
Cato Research Chemicals Inc.
Tel
020-81960175
Fax
+1-541-2553641
Email
min.he@cato-chem.com
Country
China
ProdList
1955
Advantage
55

64806-05-9, CAPTOPRIL DISULFIDERelated Search:


  • CAPTOPRIL DISULFIDE
  • CAPTOPRIL DISULFIDE USP
  • CAPTOPRIL DISULFIDE USP(CRM STANDARD)
  • CAPTOPRIL DISULFIDE WHO(CRM STANDARD)
  • CAPTOPRIL DISULPHIDE BP STANDARD
  • Captopril ImpurityⅠ:Captopril Disulfide{ 1,1'-[Dithiobis[(2S)-2-methyl-1-oxo-3,1-propanediyl]]bis-L-proline CAPTOPRDS}
  • Imp. A (EP):1,1'-[Disulfanediylbis-[(2S)-2-methyl-1-oxopropane-3,1-diyl]]-bis[(2S)-pyrrolidine-2-carboxylic] Acid(Captopril Disulfide)
  • Captopril Impurity A
  • Captopril Impurity G
  • Captopril Impurity J
  • (2S,2'S)-1,1'-[Disulphanediylbis[(2S)-2-methyl-1-oxopropane-3,1-diyl]-bis[pyrrolidine-2-carboxylic] acid
  • Captopril Impurity 1(Captopril EP Impurity A)
  • CAPTOPRIL DISULPHIDE BP STANDARD(CRM STANDARD)
  • CAPTOPRIL DISULPHIDE BP(CRM STANDARD)
  • 1,1'-[Dithiobis[(2S)-2-methyl-1-oxo-3,1-propanediyl]]bis-L-proline
  • CAPTOPRDS
  • SQ 14551
  • (1,1-[Dithiobis[(2S)-2-methyl-1-oxo-3,1-propanediyl]]bis-L-proline CAPTOPRDS
  • 1,1'-[Dithiobis[(S)-2-methyl-1-oxo-3,1-propanediyl]]bis-L-proline
  • Captopril Disulfide (100 mg)
  • Captopril Disulde (100 mg)
  • Captopril IMp. A (BP)
  • Captopril EP IMpurity A
  • Captopril-Disuphide
  • 1,1'-[Disulfanediylbis-[(2S)-2-meth
  • L-Proline, 1,1'-[dithiobis[(2S)-2-methyl-1-oxo-3,1-propanediyl]]bis-
  • CaptoprilDisuphide(CaptoprilImpurityI)
  • Captopril EP Impurity A-d6
  • Captopril EP Impurity A (Captopril disulphide)
  • Captopril ImpurityⅠ:Captopril Disulfide{ 1,1’-[Dithiobis[(2S)-2-methyl-1-oxo-3,1-propanediyl]]bis-L-proline CAPTOPRDS}
  • Captopril Disulfide (1091221)
  • (2S,2'S)-1,1'-((2S,2'S)-3,3'-disulfanediylbis(2-methylpropanoyl))bis(pyrrolidine-2-carboxylic acid)
  • 1,1′-[disulfanediylbis[(2S)-2-methyl-1-oxopropane-3,1- diyl]]bis[(2S)-pyrrolidine-2-carboxylic] acid
  • 1,1'-[Disulfanediylbis-[(2S)-2-methyl-1-oxopropane-3,1-diyl]]-bis[(2S)-pyrrolidine-2-carboxylic] Aci
  • 1,1'-[Disulfanediylbis-[(2S)-2-methyl-1-oxopropane-3,1-diyl]]-bis[(2S)-pyrrolidine-2-carboxylic] Acid (Captopril Disulfide)
  • (2S,2'S)-1,1'-((2S,2'S)-3,3'-Disulfanediyldi(2-methylpropanoyl))bis(pyrrolidine-2-carboxylic acid)
  • 64806-05-9
  • 64806-05-09
  • C18H28N2O6S2
  • 43255
  • Intermediates & Fine Chemicals
  • Metabolites & Impurities
  • Pharmaceuticals