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Compound Detail

CHEMBL1560

CAPTOPRIL
💊 Approved Drug
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💊 Approved Drug
C[C@H](CS)C(=O)N1CCC[C@H]1C(=O)O

Basic Information

ChEMBL ID CHEMBL1560
Name CAPTOPRIL
Phase Approved
Structure Type MOL
InChI Key FAKRSMQSSFJEIM-RQJHMYQMSA-N
Therapeutic ✓ Yes

Known Names

Acepril Apopril C09AA01 Capoten Captomax Captomex Captopril Captoprilum Ecopace Farcopril Garranil Hypopress +15 more
24
Targets
162
Activities
4
Assay Types
17
PK Parameters
20
Publications
27
Known Names
20
Indications
1
Mechanisms

Molecular Properties

217.3
MW (Da)
0.63
ALogP
3
HBA
2
HBD
57.6
PSA (Ų)
0.68
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1981
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -pril
USAN Year 1978

Extended Properties

Molecular Formula C9H15NO3S
MW 217.29
Aromatic Rings 0
Heavy Atoms 14
NP-Likeness 0.11

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Angiotensin-converting enzyme inhibitor INHIBITOR Angiotensin-converting enzyme

Indications

Cardiovascular Diseases Collagen Diseases Diabetic Nephropathies Diabetic Retinopathy Heart Failure Heart Failure Hypertension Myocardial Infarction Renal Insufficiency Ventricular Dysfunction, Left Diabetes Mellitus, Type 1 Essential Hypertension Severe Acute Respiratory Syndrome Heart Diseases Pneumonia Diabetes Mellitus, Type 2 Glioblastoma Hypertension, Pulmonary Neoplasms Primary Myelofibrosis

ATC Classification

C09AA01
captopril
Level 1: CARDIOVASCULAR SYSTEM
Level 2: AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM

Drug Warnings

Black Box Warning
teratogenicity
Country: United States

Activity Summary

IC50 124 meas. best 9.92
Ki 22 meas. best 8.77
EC50 8 meas. best 5.03
Kd 8 meas. best 6.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Angiotensin-converting enzyme
CHEMBL1808
IC50 9.92 7.7064 0.1 33
Angiotensin-converting enzyme
CHEMBL4074
Ki 8.77 8.77 1.7 1
Renin
CHEMBL286
Ki 8.77 8.77 1.7 1
Angiotensin-converting enzyme
CHEMBL1808
Ki 8.7 8.7 2.0 1
Angiotensin-converting enzyme
CHEMBL2625
Ki 8.7 8.7 2.0 1
Angiotensin-converting enzyme
CHEMBL4074
IC50 8.64 7.671 2.3 20
Angiotensin-converting enzyme
CHEMBL2625
IC50 8.52 7.619 3.0 10
Unchecked
CHEMBL612545
IC50 8.11 4.9804 7.7 24
Angiotensin-converting enzyme
CHEMBL2096989
IC50 8.05 8.05 9.0 1
Prothrombin
CHEMBL204
Ki 7.32 7.32 48.0 1
Leukotriene A-4 hydrolase
CHEMBL4618
IC50 7.16 5.6125 70.0 4
Unchecked
CHEMBL612545
Ki 7.15 5.6467 71.5 9
Beta-lactamase VIM-2
CHEMBL5798
Kd 6.22 6.22 600.0 1
Succinyl-diaminopimelate desuccinylase
CHEMBL1075192
Ki 5.74 5.74 1820.0 1
Beta-lactamase
CHEMBL1293244
Ki 5.62 5.62 2400.0 1
Succinyl-diaminopimelate desuccinylase
CHEMBL1075192
IC50 5.48 5.48 3300.0 1
Beta-lactamase VIM-2
CHEMBL5798
IC50 5.46 5.46 3500.0 1
Leukotriene A-4 hydrolase
CHEMBL4618
Ki 5.43 5.43 3700.0 1
No relevant target
CHEMBL2362975
IC50 5.36 4.995 4400.0 2
Beta-lactamase
CHEMBL1293244
IC50 5.3 5.3 5000.0 1
Leukotriene A-4 hydrolase
CHEMBL4618
Kd 5.2 5.1567 6250.0 3
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.19 5.17 6500.0 2
Beta-lactamase NDM-1
CHEMBL4295540
IC50 5.16 5.16 7000.0 1
Leishmania donovani
CHEMBL367
EC50 5.03 5.03 9410.0 1
Prostaglandin G/H synthase 2
CHEMBL230
Ki 4.92 4.92 12000.0 1
Unchecked
CHEMBL612545
Kd 4.92 4.92 12000.0 1
Leishmania major
CHEMBL612879
EC50 4.91 4.91 12400.0 1
Metallo-beta-lactamase type 2
CHEMBL1667695
Kd 4.85 4.85 14000.0 2
Prostaglandin G/H synthase 1
CHEMBL221
Ki 4.77 4.77 17000.0 1
Beta-lactamase II
CHEMBL2079847
Ki 4.75 4.75 17900.0 1
Angiotensin-converting enzyme
CHEMBL1808
EC50 4.73 4.7 18539.6 2
Trypanosoma brucei
CHEMBL612849
EC50 4.64 4.64 22900.0 1
Xaa-Pro dipeptidase
CHEMBL4185
Ki 4.6 4.6 25000.0 1
Beta-lactamase II
CHEMBL2079847
IC50 4.59 4.59 25800.0 1
Trypanosoma cruzi
CHEMBL368
EC50 4.52 4.52 30100.0 1
Radical scavenging activity
CHEMBL613712
IC50 4.37 4.37 43000.0 1
Metallo-beta-lactamase type 2
CHEMBL1667695
IC50 4.3 4.3 49800.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 275.7 - Chlorocebus sabaeus
CL 12.0 mL.min-1.kg-1 Homo sapiens
CL 12.0 mL.min-1.kg-1 Homo sapiens
CL - mL.min-1.kg-1 Homo sapiens
CL 10.0 mL.min-1.kg-1 Canis lupus familiaris
CL 12.0 mL.min-1.kg-1 Homo sapiens
CL 12.0 mL.min-1.kg-1 Homo sapiens
CL 13.0 mL.min-1.kg-1 Rattus norvegicus
CL 19.0 mL.min-1.kg-1 Macaca
CL 57.11 uL.min-1.(10^6cells)-1 Homo sapiens
F 79.0 % Homo sapiens
Fu 0.73 - Homo sapiens
Fu 0.73 - Homo sapiens
Ka 4.2 10'4/M/s Pseudomonas aeruginosa
MRT 1.0 hr Homo sapiens
T1/2 1.0 hr Homo sapiens
T1/2 2.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Angiotensin-converting enzyme IC50 = 0.12 nM 9.92 Inhibition of human recombinant ACE by fluorimetry 19596577
Angiotensin-converting enzyme IC50 = 0.63 nM 9.2 Inhibition of human ACE 18588282
Angiotensin-converting enzyme IC50 = 1.61 nM 8.79 Inhibition of ACE (unknown origin) using 3-Hydroxybutylyl-Gly-Gly-Gly substrate ... 25922884
Angiotensin-converting enzyme Ki = 1.7 nM 8.77 Inhibitory activity against rabbit lung angiotensin-1 converting enzyme 2836590
Renin Ki = 1.7 nM 8.77 Antihypertensive activity against human renin 6267277
Angiotensin-converting enzyme Ki = 2.0 nM 8.7 Inhibition of Angiotensin I converting enzyme (ACE) 11906289
Angiotensin-converting enzyme Ki = 2.0 nM 8.7 Inhibition of ACE (unknown origin) assessed as 3-Hydroxybutyril-glycil-glycil-gl... 24088053
Angiotensin-converting enzyme IC50 = 2.3 nM 8.64 In vitro inhibitory activity was evaluated against angiotensin converting enzyme... -
Angiotensin-converting enzyme IC50 = 3.0 nM 8.52 In vitro inhibitory activity against rat serum angiotensin I converting enzyme u... 8459398
Angiotensin-converting enzyme IC50 = 3.23 nM 8.49 Inhibition of Wistar rat plasma angiotensin 1-converting enzyme using H-hippuryl... 28810191
Angiotensin-converting enzyme IC50 = 3.6 nM 8.44 In vitro inhibitory activity was evaluated against angiotensin converting enzyme... -
Angiotensin-converting enzyme IC50 = 5.0 nM 8.3 Inhibition of ACE by fluorometric assay 3379417
Angiotensin-converting enzyme IC50 = 6.3 nM 8.2 Inhibition of human ACE using Hip-His-Leu-OH as substrate after 1 hr by fluorime... 29039662
Angiotensin-converting enzyme IC50 = 6.3 nM 8.2 Inhibition of ACE (unknown origin) using tripeptide Hip-His-Leu-OH as substrate ... 36096342
Unchecked IC50 = 7.7 nM 8.11 Inhibition of ACE 18096385
Angiotensin-converting enzyme IC50 = 9.0 nM 8.05 Inhibition of guinea pig serum Angiotensin I converting enzyme 6292422
Angiotensin-converting enzyme IC50 = 9.0 nM 8.05 Concentration required to inhibit the activity of Angiotensin I converting enzym... 6173481
Angiotensin-converting enzyme IC50 = 10.0 nM 8.0 Evaluation of in vitro inhibitory activity against Angiotensin I converting enzy... 8544178
Angiotensin-converting enzyme IC50 = 10.0 nM 8.0 In vitro inhibitory concentration against angiotensin-converting enzyme -
Angiotensin-converting enzyme IC50 = 11.0 nM 7.96 Inhibition of human ACE-mediated amyloid beta hydrolysis 24735644

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1469
- 10.6019/CHEMBL3885881 Rattus norvegicus 455
16472241 10.2174/1570163043334794 Hepatotoxicity 18
32940035 10.1021/acs.jmedchem.0c01541 No relevant target 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
2831364 10.1021/jm00398a012 Rattus norvegicus 13
6173481 10.1021/jm00140a010 Rattus norvegicus 12
31269398 10.1021/acs.jmedchem.9b00735 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
6620309 10.1021/jm00364a027 Rattus norvegicus 11
2836590 10.1021/jm00401a014 Rattus norvegicus 10
38242072 10.1016/j.ejmech.2024.116140 Escherichia coli 9
8544178 10.1021/jm00026a009 Angiotensin-converting enzyme 9
15920768 10.1002/jps.20373 ADMET 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
19233642 10.1016/j.bmcl.2008.12.102 Unchecked 8
20070106 10.1021/jm901371v Homo sapiens 8
2160536 10.1021/jm00168a013 Angiotensin-converting enzyme 8
6292422 10.1021/jm00353a005 Rattus norvegicus 7
27651294 10.1016/j.bmc.2016.08.047 Leukotriene A-4 hydrolase 7

Data from ChEMBL 36 via Core Engine