U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of CAPTOPRIL DISULFIDE

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
230 ng/mL
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
260 ng × h/mL
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
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
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
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)
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)
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)
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.66 h
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
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
69.4%
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

Doses

DosePopulationAdverse events​
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
healthy, 22
n = 1
Health Status: healthy
Age Group: 22
Sex: M
Population Size: 1
Sources:
Disc. AE: Hypotension, Loss of consciousness...
AEs leading to
discontinuation/dose reduction:
Hypotension
Loss of consciousness
Sources:
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: Page: p.3303
healthy, 33
n = 1
Health Status: healthy
Age Group: 33
Sex: F
Population Size: 1
Sources: Page: p.3303
Disc. AE: Hypotension, Drowsiness...
AEs leading to
discontinuation/dose reduction:
Hypotension
Drowsiness
Sources: 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: Page: p.750
unhealthy, 73
n = 370
Health Status: unhealthy
Condition: Hypertension
Age Group: 73
Sex: M+F
Population Size: 370
Sources: 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: 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: Page: 100S
unhealthy
n = 81
Health Status: unhealthy
Condition: Hypertension
Sex: M
Population Size: 81
Sources: Page: 100S
Disc. AE: Urticaria, Hypotension...
AEs leading to
discontinuation/dose reduction:
Urticaria (1.2%)
Hypotension (2.5%)
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Hypertension
Sources: Page: p.1
Disc. AE: Disorder fetal...
AEs leading to
discontinuation/dose reduction:
Disorder fetal
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Hypotension Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
healthy, 22
n = 1
Health Status: healthy
Age Group: 22
Sex: M
Population Size: 1
Sources:
Loss of consciousness Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
healthy, 22
n = 1
Health Status: healthy
Age Group: 22
Sex: M
Population Size: 1
Sources:
Drowsiness Disc. AE
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: Page: p.3303
healthy, 33
n = 1
Health Status: healthy
Age Group: 33
Sex: F
Population Size: 1
Sources: Page: p.3303
Hypotension Disc. AE
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: Page: p.3303
healthy, 33
n = 1
Health Status: healthy
Age Group: 33
Sex: F
Population Size: 1
Sources: Page: p.3303
Angina 0.5%
Disc. AE
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: Page: p.750
unhealthy, 73
n = 370
Health Status: unhealthy
Condition: Hypertension
Age Group: 73
Sex: M+F
Population Size: 370
Sources: Page: p.750
Angio-oedema 0.8%
Disc. AE
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: Page: p.750
unhealthy, 73
n = 370
Health Status: unhealthy
Condition: Hypertension
Age Group: 73
Sex: M+F
Population Size: 370
Sources: Page: p.750
Kidney dysfunction 0.8%
Disc. AE
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: Page: p.750
unhealthy, 73
n = 370
Health Status: unhealthy
Condition: Hypertension
Age Group: 73
Sex: M+F
Population Size: 370
Sources: Page: p.750
Stroke 0.8%
Disc. AE
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: Page: p.750
unhealthy, 73
n = 370
Health Status: unhealthy
Condition: Hypertension
Age Group: 73
Sex: M+F
Population Size: 370
Sources: Page: p.750
Arrhythmia 1%
Disc. AE
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: Page: p.750
unhealthy, 73
n = 370
Health Status: unhealthy
Condition: Hypertension
Age Group: 73
Sex: M+F
Population Size: 370
Sources: Page: p.750
Myocardial infarction 1%
Disc. AE
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: Page: p.750
unhealthy, 73
n = 370
Health Status: unhealthy
Condition: Hypertension
Age Group: 73
Sex: M+F
Population Size: 370
Sources: Page: p.750
Rash 1%
Disc. AE
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: Page: p.750
unhealthy, 73
n = 370
Health Status: unhealthy
Condition: Hypertension
Age Group: 73
Sex: M+F
Population Size: 370
Sources: Page: p.750
Hypotension 1.4%
Disc. AE
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: Page: p.750
unhealthy, 73
n = 370
Health Status: unhealthy
Condition: Hypertension
Age Group: 73
Sex: M+F
Population Size: 370
Sources: Page: p.750
Hyperkalaemia 1.6%
Disc. AE
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: Page: p.750
unhealthy, 73
n = 370
Health Status: unhealthy
Condition: Hypertension
Age Group: 73
Sex: M+F
Population Size: 370
Sources: Page: p.750
Failure heart 2.4%
Disc. AE
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: Page: p.750
unhealthy, 73
n = 370
Health Status: unhealthy
Condition: Hypertension
Age Group: 73
Sex: M+F
Population Size: 370
Sources: Page: p.750
Cough 3.8%
Disc. AE
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: Page: p.750
unhealthy, 73
n = 370
Health Status: unhealthy
Condition: Hypertension
Age Group: 73
Sex: M+F
Population Size: 370
Sources: Page: p.750
Decreased appetite Disc. AE
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: Page: p.750
unhealthy, 73
n = 370
Health Status: unhealthy
Condition: Hypertension
Age Group: 73
Sex: M+F
Population Size: 370
Sources: Page: p.750
Taste perversion Disc. AE
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: Page: p.750
unhealthy, 73
n = 370
Health Status: unhealthy
Condition: Hypertension
Age Group: 73
Sex: M+F
Population Size: 370
Sources: Page: p.750
Urticaria 1.2%
Disc. AE
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: Page: 100S
unhealthy
n = 81
Health Status: unhealthy
Condition: Hypertension
Sex: M
Population Size: 81
Sources: Page: 100S
Hypotension 2.5%
Disc. AE
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: Page: 100S
unhealthy
n = 81
Health Status: unhealthy
Condition: Hypertension
Sex: M
Population Size: 81
Sources: Page: 100S
Disorder fetal Disc. AE
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Hypertension
Sources: Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Captopril disulfide conjugates may act as prodrugs: disposition of the disulfide dimer of captopril in the rat.
1984 Nov 15
Captopril and its dimer captopril disulfide: comparative structural and conformational studies.
2015 Mar
Patents

Patents

Name Type Language
CAPTOPRIL DISULFIDE
USP-RS  
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
Created by admin on Sat Dec 16 01:40:00 GMT 2023 , Edited by admin on Sat Dec 16 01:40:00 GMT 2023
PRIMARY
RS_ITEM_NUM
1091221
Created by admin on Sat Dec 16 01:40:00 GMT 2023 , Edited by admin on Sat Dec 16 01:40:00 GMT 2023
PRIMARY
PUBCHEM
10002934
Created by admin on Sat Dec 16 01:40:00 GMT 2023 , Edited by admin on Sat Dec 16 01:40:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID801024324
Created by admin on Sat Dec 16 01:40:00 GMT 2023 , Edited by admin on Sat Dec 16 01:40:00 GMT 2023
PRIMARY
CAS
64806-05-9
Created by admin on Sat Dec 16 01:40:00 GMT 2023 , Edited by admin on Sat Dec 16 01:40:00 GMT 2023
PRIMARY