CAPTOPRIL DISULFIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H28N2O6S2
Molecular Weight	432.555
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H](CSSC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O)C(=O)N2CCC[C@H]2C(O)=O

InChI

InChIKey=ZWKRXBCJAUKDCI-MQYQWHSLSA-N

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

HIDE SMILES / InChI

Molecular Formula	C18H28N2O6S2
Molecular Weight	432.555
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
angiotensin I converting enzyme 1 Target ID: 610668.0 Gene Symbol: ACE Sources: https://www.ncbi.nlm.nih.gov/pubmed/6757503	Inhibitor 8297

C_max

Value	Dose	Analyte	Population
230 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6989546/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CAPTOPRIL DISULFIDE blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
824 μg/L REVIEW https://pubmed.ncbi.nlm.nih.gov/3292102/	100 mg 3 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CAPTOPRIL blood	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
878 μg/L REVIEW https://pubmed.ncbi.nlm.nih.gov/3292102/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CAPTOPRIL blood	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1.31 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6324834/	1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	CAPTOPRIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
800 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6989546/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CAPTOPRIL blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
260 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6989546/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CAPTOPRIL DISULFIDE blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1197 μg × h/L REVIEW https://pubmed.ncbi.nlm.nih.gov/3292102/	100 mg 3 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CAPTOPRIL blood	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1235 μg × h/L REVIEW https://pubmed.ncbi.nlm.nih.gov/3292102/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CAPTOPRIL blood	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1150 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6989546/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CAPTOPRIL blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
20.1 μg × h/L/(mg dose) REVIEW https://pubmed.ncbi.nlm.nih.gov/3292102/	2.5 mg single, intravenous dose: 2.5 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CAPTOPRIL blood	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
20.5 μg × h/L/(mg dose) REVIEW https://pubmed.ncbi.nlm.nih.gov/3292102/	10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CAPTOPRIL blood	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
21 μg × h/L/(mg dose) REVIEW https://pubmed.ncbi.nlm.nih.gov/3292102/	5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CAPTOPRIL blood	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
0.66 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6324834/	1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	CAPTOPRIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.1 h REVIEW https://pubmed.ncbi.nlm.nih.gov/3292102/	10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CAPTOPRIL blood	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
2.2 h REVIEW https://pubmed.ncbi.nlm.nih.gov/3292102/	5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CAPTOPRIL blood	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
69.4% EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/10.1002/cpt1978231107	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		CAPTOPRIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
750 mg single, oral Overdose Dose: 750 mg Route: oral Route: single Dose: 750 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1758810	healthy, 22 n = 1 Health Status: healthy Age Group: 22 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/1758810	Disc. AE: Hypotension, Loss of consciousness... AEs leading to discontinuation/dose reduction: Hypotension Loss of consciousness Sources: https://pubmed.ncbi.nlm.nih.gov/1758810
500 mg single, oral Overdose Dose: 500 mg Route: oral Route: single Dose: 500 mg Co-administed with:: alprazolam, p.o(10 mg; single) Sources: https://pubmed.ncbi.nlm.nih.gov/3286910 Page: p.3303	healthy, 33 n = 1 Health Status: healthy Age Group: 33 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/3286910 Page: p.3303	Disc. AE: Hypotension, Drowsiness... AEs leading to discontinuation/dose reduction: Hypotension Drowsiness Sources: https://pubmed.ncbi.nlm.nih.gov/3286910 Page: p.3303
50 mg 3 times / day multiple, oral (max) Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9074572 Page: p.750	unhealthy, 73 n = 370 Health Status: unhealthy Condition: Hypertension Age Group: 73 Sex: M+F Population Size: 370 Sources: https://pubmed.ncbi.nlm.nih.gov/9074572 Page: p.750	Disc. AE: Cough, Failure heart... AEs leading to discontinuation/dose reduction: Cough (3.8%) Failure heart (2.4%) Hyperkalaemia (1.6%) Taste perversion Decreased appetite Rash (1%) Hypotension (1.4%) Angio-oedema (0.8%) Arrhythmia (1%) Myocardial infarction (1%) Kidney dysfunction (0.8%) Stroke (0.8%) Angina (0.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/9074572 Page: p.750
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6753911 Page: 100S	unhealthy n = 81 Health Status: unhealthy Condition: Hypertension Sex: M Population Size: 81 Sources: https://pubmed.ncbi.nlm.nih.gov/6753911 Page: 100S	Disc. AE: Urticaria, Hypotension... AEs leading to discontinuation/dose reduction: Urticaria (1.2%) Hypotension (2.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/6753911 Page: 100S
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/018343s084lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Hypertension Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/018343s084lbl.pdf Page: p.1	Disc. AE: Disorder fetal... AEs leading to discontinuation/dose reduction: Disorder fetal Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/018343s084lbl.pdf Page: p.1

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 512 OAT1 599 MATE1 306 OCT2 647 P-gp 1461	OAT3 339 OAT1 326

Drug as perpetrator

Target	Modality	Activity
MATE1 308	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/20053795/	no
OCT1 543	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/20567254/	no
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23620485/	no
OAT1 603	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19953504/	yes
OCT2 648	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/20053795/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OAT1 326	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/28179375/\|https://pubmed.ncbi.nlm.nih.gov/23686349/	yes
OAT3 339	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/28179375/\|https://pubmed.ncbi.nlm.nih.gov/19953504/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3380	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3380
ChemicalBook	CB6206769	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6206769
MolPort	MolPort-001-794-639	https://www.molport.com/shop/molecule-link/MolPort-001-794-639
Selleck Chemicals	captopril-capoten	http://www.selleckchem.com/products/captopril-capoten.html
ZINC	ZINC000000057001	http://zinc15.docking.org/substances/ZINC000000057001
eMolecules	489049	https://www.emolecules.com/cgi-bin/more?vid=489049

PubMed

Title	Date	PubMed
Captopril disulfide conjugates may act as prodrugs: disposition of the disulfide dimer of captopril in the rat.	1984 Nov 15	6095854
Captopril and its dimer captopril disulfide: comparative structural and conformational studies.	2015 Mar	25734850

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:40:00 GMT 2023` Edited by `admin` on `Sat Dec 16 01:40:00 GMT 2023`
Record UNII	Y21D2C2453
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CAPTOPRIL DISULFIDE

Common Name

English

L-PROLINE, 1,1'-(DITHIOBIS(2-METHYL-1-OXO-3,1-PROPANEDIYL))BIS-, (S-(R*,R*))-

Common Name

English

SQ-14551

Code

English

CAPTOPRIL IMPURITY 2

Common Name

English

L-PROLINE, 1,1'-(DITHIOBIS((2S)-2-METHYL-1-OXO-3,1-PROPANEDIYL))BIS-

Systematic Name

English

CAPTOPRDS

Brand Name

English

CAPTOPRIL DISULFIDE [USP-RS]

Common Name

English

CAPTOPRIL IMPURITY A [EP IMPURITY]

Common Name

English

1,1'-(DISULFANEDIYLBIS((2S)-2-METHYL-1-OXOPROPANE-3,1-DIYL))BIS((2S)-PYRROLIDINE-2-CARBOXYLIC) ACID

Common Name

English

Code System Code Type Description

FDA UNII

Y21D2C2453