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Identification
- Summary
Captopril is an ACE inhibitor used for the management of essential or renovascular hypertension, congestive heart failure, left ventricular dysfunction following myocardial infarction, and nephropathy.
- Generic Name
- Captopril
- DrugBank Accession Number
- DB01197
- Background
Captopril is a potent, competitive inhibitor of angiotensin-converting enzyme (ACE), the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Captopril may be used in the treatment of hypertension.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Captopril (DB01197)
- Weight
- Average: 217.285
Monoisotopic: 217.077264041 - Chemical Formula
- C9H15NO3S
- Synonyms
- (2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid
- Captopril
- Captoprilum
- Captopryl
- CP
- D-2-methyl-3-mercaptopropanoyl-L-proline
- D-3-mercapto-2-methylpropanoyl-L-proline
- L-Captopril
- External IDs
- C09AA01
- SA-333
- SQ 14,225
- SQ-14225
Pharmacology
- Indication
For the treatment of essential or renovascular hypertension (usually administered with other drugs, particularly thiazide diuretics). May be used to treat congestive heart failure in combination with other drugs (e.g. cardiac glycosides, diuretics, β-adrenergic blockers). May improve survival in patients with left ventricular dysfunction following myocardial infarction. May be used to treat nephropathy, including diabetic nephropathy.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Diagnostic agent Aldosteronism ••• ••••• Diagnostic agent Anatomic renal artery stenosis ••• ••••• Management of Congestive heart failure •••••••••••• Management of Diabetic nephropathy •••••••••••• Prevention of Heart failure ••• ••••• - Contraindications & Blackbox Warnings
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Captopril, an ACE inhibitor, antagonizes the effect of the RAAS. The RAAS is a homeostatic mechanism for regulating hemodynamics, water and electrolyte balance. During sympathetic stimulation or when renal blood pressure or blood flow is reduced, renin is released from the granular cells of the juxtaglomerular apparatus in the kidneys. In the blood stream, renin cleaves circulating angiotensinogen to ATI, which is subsequently cleaved to ATII by ACE. ATII increases blood pressure using a number of mechanisms. First, it stimulates the secretion of aldosterone from the adrenal cortex. Aldosterone travels to the distal convoluted tubule (DCT) and collecting tubule of nephrons where it increases sodium and water reabsorption by increasing the number of sodium channels and sodium-potassium ATPases on cell membranes. Second, ATII stimulates the secretion of vasopressin (also known as antidiuretic hormone or ADH) from the posterior pituitary gland. ADH stimulates further water reabsorption from the kidneys via insertion of aquaporin-2 channels on the apical surface of cells of the DCT and collecting tubules. Third, ATII increases blood pressure through direct arterial vasoconstriction. Stimulation of the Type 1 ATII receptor on vascular smooth muscle cells leads to a cascade of events resulting in myocyte contraction and vasoconstriction. In addition to these major effects, ATII induces the thirst response via stimulation of hypothalamic neurons. ACE inhibitors inhibit the rapid conversion of ATI to ATII and antagonize RAAS-induced increases in blood pressure. ACE (also known as kininase II) is also involved in the enzymatic deactivation of bradykinin, a vasodilator. Inhibiting the deactivation of bradykinin increases bradykinin levels and may sustain its effects by causing increased vasodilation and decreased blood pressure.
- Mechanism of action
There are two isoforms of ACE: the somatic isoform, which exists as a glycoprotein comprised of a single polypeptide chain of 1277; and the testicular isoform, which has a lower molecular mass and is thought to play a role in sperm maturation and binding of sperm to the oviduct epithelium. Somatic ACE has two functionally active domains, N and C, which arise from tandem gene duplication. Although the two domains have high sequence similarity, they play distinct physiological roles. The C-domain is predominantly involved in blood pressure regulation while the N-domain plays a role in hematopoietic stem cell differentiation and proliferation. ACE inhibitors bind to and inhibit the activity of both domains, but have much greater affinity for and inhibitory activity against the C-domain. Captopril, one of the few ACE inhibitors that is not a prodrug, competes with ATI for binding to ACE and inhibits and enzymatic proteolysis of ATI to ATII. Decreasing ATII levels in the body decreases blood pressure by inhibiting the pressor effects of ATII as described in the Pharmacology section above. Captopril also causes an increase in plasma renin activity likely due to a loss of feedback inhibition mediated by ATII on the release of renin and/or stimulation of reflex mechanisms via baroreceptors. Captopril’s affinity for ACE is approximately 30,000 times greater than that of ATI.
Target Actions Organism AAngiotensin-converting enzyme inhibitorHumans U72 kDa type IV collagenase inhibitorHumans UMatrix metalloproteinase-9 inhibitorHumans ULeukotriene A-4 hydrolase inhibitorHumans UB1 bradykinin receptor Not Available Humans - Absorption
60-75% in fasting individuals; food decreases absorption by 25-40% (some evidence indicates that this is not clinically significant)
- Volume of distribution
Not Available
- Protein binding
25-30% bound to plasma proteins, primarily albumin
- Metabolism
Hepatic. Major metabolites are captopril-cysteine disulfide and the disulfide dimer of captopril. Metabolites may undergo reversible interconversion.
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
2 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms of overdose include emesis and decreased blood pressure. Side effects include dose-dependent rash (usually maculopapular), taste alterations, hypotension, gastric irritation, cough, and angioedema.
- Pathways
Pathway Category Captopril Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbaloparatide The risk or severity of adverse effects can be increased when Captopril is combined with Abaloparatide. Acamprosate The excretion of Acamprosate can be decreased when combined with Captopril. Acebutolol Acebutolol may increase the hypotensive activities of Captopril. Aceclofenac The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Aceclofenac is combined with Captopril. Acemetacin The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Acemetacin is combined with Captopril. - Food Interactions
- Avoid hypertensive herbs (e.g. bayberry, blue cohosh, cayenne, ephedra, and licorice).
- Avoid potassium-containing products. Potassium products increase the risk of hyperkalemia.
- Limit salt intake. Salt may attenuate the antihypertensive effect.
- Take separate from meals. The presence of food decreases absorption. Take one hour prior to meals.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- International/Other Brands
- Acepress (Bernofarm (Indonesia), BMS (Italy)) / Acepril (BMS (United Kingdom)) / Alopresin / Apopril / Captolane (Sanofi-Aventis (France)) / Captoril (Novopharm (Canada)) / Cesplon (Esteve (Spain)) / Dilabar (Qualigen (Spain)) / Garranil (Aristegui (Spain)) / Hipertil (Normal (Portugal)) / Hypertil (Normal (Portugal)) / Lopirin (BMS (Germany,Switzerland)) / Lopril (Orion (Finland), BMS (France)) / Tenosbon / Tensoprel (Rubio (Spain))
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bci Captopril Tablets Tablet 100 mg Oral Baker Cummins Inc Not applicable Not applicable Canada 
Bci Captopril Tablets Tablet 12.5 mg Oral Baker Cummins Inc Not applicable Not applicable Canada Bci Captopril Tablets Tablet 50 mg Oral Baker Cummins Inc Not applicable Not applicable Canada Bci Captopril Tablets Tablet 25 mg Oral Baker Cummins Inc Not applicable Not applicable Canada Capoten Tablet 50 mg/1 Oral Par Pharmaceutical 1981-04-06 2011-08-31 US 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-capto Tab 100mg Tablet 100 mg Oral Apotex Corporation 1990-12-31 Not applicable Canada Apo-capto Tab 12.5mg Tablet 12.5 mg Oral Apotex Corporation 1990-12-31 Not applicable Canada Apo-capto Tab 25mg Tablet 25 mg Oral Apotex Corporation 1990-12-31 Not applicable Canada Apo-capto Tab 50mg Tablet 50 mg Oral Apotex Corporation 1990-12-31 Not applicable Canada Apo-capto Tab 6.25mg Tablet 6.25 mg Oral Apotex Corporation 1992-12-31 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ACE HEMMER RATIO CO50/25 Captopril (50 mg) + Hydrochlorothiazide (25 mg) Tablet Oral 2010-09-01 Not applicable Germany 
ACEDIUR Captopril (50 MG) + Hydrochlorothiazide (25 MG) Tablet Oral A. Menarini Industrie Farmaceutiche Riunite s.r.l. 2014-07-08 Not applicable Italy 
ACEDIUR Captopril (50 MG) + Hydrochlorothiazide (15 MG) Tablet Oral A. Menarini Industrie Farmaceutiche Riunite s.r.l. 2014-07-08 Not applicable Italy Capozide Captopril (25 mg/1) + Hydrochlorothiazide (25 mg/1) Tablet Oral Par Pharmaceutical 2006-06-16 2008-06-16 US Capozide Captopril (50 mg/1) + Hydrochlorothiazide (25 mg/1) Tablet Oral Par Pharmaceutical 2006-06-16 2008-06-16 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Capozide Captopril (50 mg/1) + Hydrochlorothiazide (25 mg/1) Tablet Oral Physicians Total Care, Inc. 1997-01-03 2002-06-30 US Capozide Captopril (25 mg/1) + Hydrochlorothiazide (15 mg/1) Tablet Oral Physicians Total Care, Inc. 1996-05-14 2011-05-31 US
Categories
- ATC Codes
- C09AA01 — Captopril
- C09AA — ACE inhibitors, plain
- C09A — ACE INHIBITORS, PLAIN
- C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- ACE Inhibitors and Diuretics
- Agents Acting on the Renin-Angiotensin System
- Agents causing angioedema
- Agents causing hyperkalemia
- Agents Causing Muscle Toxicity
- Amino Acids
- Amino Acids, Cyclic
- Amino Acids, Peptides, and Proteins
- Angiotensin-Converting Enzyme Inhibitors
- Antihypertensive Agents
- Antihypertensive Agents Indicated for Hypertension
- Cardiovascular Agents
- Drugs causing inadvertant photosensitivity
- Enzyme Inhibitors
- Hypotensive Agents
- Imino Acids
- OAT1/SLC22A6 inhibitors
- OAT1/SLC22A6 Substrates
- OAT3/SLC22A8 Substrates
- P-glycoprotein inhibitors
- Photosensitizing Agents
- Protease Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Proline and derivatives
- Alternative Parents
- N-acyl-L-alpha-amino acids / Pyrrolidine carboxylic acids / N-acylpyrrolidines / Tertiary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Alkylthiols / Organopnictogen compounds / Organonitrogen compounds show 3 more
- Substituents
- Aliphatic heteromonocyclic compound / Alkylthiol / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid / Hydrocarbon derivative / Monocarboxylic acid or derivatives / N-acyl-alpha amino acid or derivatives / N-acyl-alpha-amino acid show 15 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- L-proline derivative, alkanethiol, pyrrolidinemonocarboxylic acid, N-acylpyrrolidine (CHEBI:3380)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 9G64RSX1XD
- CAS number
- 62571-86-2
- InChI Key
- FAKRSMQSSFJEIM-RQJHMYQMSA-N
- InChI
- InChI=1S/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7+/m1/s1
- IUPAC Name
- (2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid
- SMILES
- C[C@H](CS)C(=O)N1CCC[C@H]1C(O)=O
References
- Synthesis Reference
Charles M. Zepp, "Methods for preparing captopril and its analogues." U.S. Patent US5166361, issued July, 1981.
US5166361- General References
- Atkinson AB, Robertson JI: Captopril in the treatment of clinical hypertension and cardiac failure. Lancet. 1979 Oct 20;2(8147):836-9. [Article]
- Patchett AA, Harris E, Tristram EW, Wyvratt MJ, Wu MT, Taub D, Peterson ER, Ikeler TJ, ten Broeke J, Payne LG, Ondeyka DL, Thorsett ED, Greenlee WJ, Lohr NS, Hoffsommer RD, Joshua H, Ruyle WV, Rothrock JW, Aster SD, Maycock AL, Robinson FM, Hirschmann R, Sweet CS, Ulm EH, Gross DM, Vassil TC, Stone CA: A new class of angiotensin-converting enzyme inhibitors. Nature. 1980 Nov 20;288(5788):280-3. [Article]
- Smith CG, Vane JR: The discovery of captopril. FASEB J. 2003 May;17(8):788-9. [Article]
- External Links
- Human Metabolome Database
- HMDB0015328
- KEGG Drug
- D00251
- PubChem Compound
- 44093
- PubChem Substance
- 46506879
- ChemSpider
- 40130
- BindingDB
- 21642
- 1998
- ChEBI
- 3380
- ChEMBL
- CHEMBL1560
- ZINC
- ZINC000000057001
- Therapeutic Targets Database
- DAP000589
- PharmGKB
- PA448780
- PDBe Ligand
- X8Z
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Captopril
- PDB Entries
- 1j37 / 2x8z / 3lus / 4c1d / 4c1f / 4c1h / 4c2p / 4dpr / 4exs / 4pqa … show 5 more
- MSDS
- Download (37.6 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Coronavirus Disease 2019 (COVID‑19) / COVID / Hypertension 1 somestatus stop reason just information to hide Not Available Completed Prevention Type 1 Diabetes Mellitus 1 somestatus stop reason just information to hide Not Available Completed Treatment Atrial Fibrillation / Chronic Heart Failure (CHF) 1 somestatus stop reason just information to hide Not Available Completed Treatment Cardiomyopathy 1 somestatus stop reason just information to hide Not Available Completed Treatment Hypertension 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Advanced Pharmaceutical Services Inc.
- Amerisource Health Services Corp.
- Apotex Inc.
- Apotheca Inc.
- Apothecon
- AQ Pharmaceuticals Inc.
- A-S Medication Solutions LLC
- Bristol-Myers Squibb Co.
- Bryant Ranch Prepack
- Cardinal Health
- Caremark LLC
- Changzhou Pharmaceutical Factory
- Comprehensive Consultant Services Inc.
- Dept Health Central Pharmacy
- Direct Dispensing Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- E.R. Squibb and Sons LLC
- Egis Pharmaceuticals Public Ltd. Co.
- Eon Labs
- Heartland Repack Services LLC
- Innovative Manufacturing and Distribution Services Inc.
- Lake Erie Medical and Surgical Supply
- Legacy Pharmaceuticals Packaging LLC
- Liberty Pharmaceuticals
- Major Pharmaceuticals
- Medisca Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Neuman Distributors Inc.
- Novopharm Ltd.
- Nucare Pharmaceuticals Inc.
- Par Pharmaceuticals
- PCA LLC
- PD-Rx Pharmaceuticals Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmacy Service Center
- Pharmedix
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prepak Systems Inc.
- Prescript Pharmaceuticals
- Qualitest
- Rebel Distributors Corp.
- Remedy Repack
- Resource Optimization and Innovation LLC
- Sandhills Packaging Inc.
- Sandoz
- Southwood Pharmaceuticals
- Stason Pharmaceuticals Inc.
- Teva Pharmaceutical Industries Ltd.
- Tya Pharmaceuticals
- UDL Laboratories
- Vangard Labs Inc.
- West-Ward Pharmaceuticals
- Wockhardt Ltd.
- Dosage Forms
Form Route Strength Tablet Oral 100 mg Tablet Oral 6.25 mg Powder Not applicable 1 g/1g Tablet Oral 100 mg/1 Tablet Oral 12.5 mg/1 Tablet Oral 15 mg/1 Tablet Oral 25 mg/1 Tablet Oral 30 mg/1 Tablet Oral 50 mg/1 Tablet Oral 250 mg Tablet, film coated Oral 50 mg Tablet Oral Tablet Oral 2500 mg Tablet Oral 50.5 mg Tablet Oral 25.00 mg Solution Oral 25 mg / 5 mL Solution Oral 5 mg / 5 mL Tablet Oral 25.000 mg Tablet Oral 25.0000 mg Tablet Oral Tablet Oral 12.5 mg Tablet Oral 25 mg Tablet Oral 50 mg - Prices
Unit description Cost Unit Captopril powder 22.03USD g Capoten 100 mg tablet 4.53USD tablet Capoten 12.5 mg tablet 1.8USD tablet Captopril 100 mg tablet 1.53USD tablet Captopril 50 mg tablet 1.14USD tablet Capoten 25 mg tablet 1.13USD tablet Capoten 50 mg tablet 1.13USD tablet Apo-Capto 100 mg Tablet 1.09USD tablet Mylan-Captopril 100 mg Tablet 1.09USD tablet Novo-Captoril 100 mg Tablet 1.09USD tablet Nu-Capto 100 mg Tablet 1.09USD tablet Captopril 25 mg tablet 0.67USD tablet Captopril 12.5 mg tablet 0.62USD tablet Apo-Capto 50 mg Tablet 0.59USD tablet Mylan-Captopril 50 mg Tablet 0.59USD tablet Novo-Captoril 50 mg Tablet 0.59USD tablet Nu-Capto 50 mg Tablet 0.59USD tablet Apo-Capto 25 mg Tablet 0.31USD tablet Mylan-Captopril 25 mg Tablet 0.31USD tablet Novo-Captoril 25 mg Tablet 0.31USD tablet Nu-Capto 25 mg Tablet 0.31USD tablet Apo-Capto 12.5 mg Tablet 0.22USD tablet Mylan-Captopril 12.5 mg Tablet 0.22USD tablet Novo-Captoril 12.5 mg Tablet 0.22USD tablet Nu-Capto 12.5 mg Tablet 0.22USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5238924 No 1993-08-24 2010-08-24 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 103-104 Ondetti, M.A. and Cushman, D.W.; U.S. Patent 4,046,889; September 6, 1977; assigned t o E.R. Squibb & Sons, Inc. Ondetti, M.A. and Cushman, D.W.; U.S. Patent 4,105,776; August 8,1978; assigned to E.R. Squibb & Sons, Inc. Ondetti, M.A. and Cushman, D.W.; U.S. Patent 4,154,840; May 15,1979; assigned to E.R. Squibb & Sons, Inc. water solubility Freely soluble Not Available logP 0.34 RANADIVE,SA ET AL. (1992) - Predicted Properties
Property Value Source Water Solubility 4.52 mg/mL ALOGPS logP 1.02 ALOGPS logP 0.73 Chemaxon logS -1.7 ALOGPS pKa (Strongest Acidic) 4.02 Chemaxon pKa (Strongest Basic) -1.3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 57.61 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 54.63 m3·mol-1 Chemaxon Polarizability 21.72 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.97 Blood Brain Barrier + 0.6467 Caco-2 permeable + 0.8867 P-glycoprotein substrate Non-substrate 0.6276 P-glycoprotein inhibitor I Non-inhibitor 0.8448 P-glycoprotein inhibitor II Non-inhibitor 0.7415 Renal organic cation transporter Non-inhibitor 0.8073 CYP450 2C9 substrate Non-substrate 0.7898 CYP450 2D6 substrate Substrate 0.8918 CYP450 3A4 substrate Non-substrate 0.6293 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9102 CYP450 2D6 inhibitor Non-inhibitor 0.9537 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9049 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8975 Ames test Non AMES toxic 0.8164 Carcinogenicity Non-carcinogens 0.9434 Biodegradation Not ready biodegradable 0.6577 Rat acute toxicity 1.7403 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9604 hERG inhibition (predictor II) Non-inhibitor 0.9118
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 151.3452106 predictedDarkChem Lite v0.1.0 [M-H]- 152.2602106 predictedDarkChem Lite v0.1.0 [M-H]- 144.66211 predictedDeepCCS 1.0 (2019) [M+H]+ 150.6606106 predictedDarkChem Lite v0.1.0 [M+H]+ 152.6123106 predictedDarkChem Lite v0.1.0 [M+H]+ 147.02014 predictedDeepCCS 1.0 (2019) [M+Na]+ 151.6466106 predictedDarkChem Lite v0.1.0 [M+Na]+ 152.4599106 predictedDarkChem Lite v0.1.0 [M+Na]+ 153.4103 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dipeptidyl carboxypeptidase that removes dipeptides from the C-terminus of a variety of circulating hormones, such as angiotensin I, bradykinin or enkephalins, thereby playing a key role in the regulation of blood pressure, electrolyte homeostasis or synaptic plasticity (PubMed:15615692, PubMed:20826823, PubMed:2558109, PubMed:4322742, PubMed:7523412, PubMed:7683654). Composed of two similar catalytic domains, each possessing a functional active site, with different selectivity for substrates (PubMed:10913258, PubMed:1320019, PubMed:1851160, PubMed:19773553, PubMed:7683654, PubMed:7876104). Plays a major role in the angiotensin-renin system that regulates blood pressure and sodium retention by the kidney by converting angiotensin I to angiotensin II, resulting in an increase of the vasoconstrictor activity of angiotensin (PubMed:11432860, PubMed:1851160, PubMed:19773553, PubMed:23056909, PubMed:4322742). Also able to inactivate bradykinin, a potent vasodilator, and therefore enhance the blood pressure response (PubMed:15615692, PubMed:2558109, PubMed:4322742, PubMed:6055465, PubMed:6270633, PubMed:7683654). Acts as a regulator of synaptic transmission by mediating cleavage of neuropeptide hormones, such as substance P, neurotensin or enkephalins (PubMed:15615692, PubMed:6208535, PubMed:6270633, PubMed:656131). Catalyzes degradation of different enkephalin neuropeptides (Met-enkephalin, Leu-enkephalin, Met-enkephalin-Arg-Phe and possibly Met-enkephalin-Arg-Gly-Leu) (PubMed:2982830, PubMed:6270633, PubMed:656131). Acts as a regulator of synaptic plasticity in the nucleus accumbens of the brain by mediating cleavage of Met-enkephalin-Arg-Phe, a strong ligand of Mu-type opioid receptor OPRM1, into Met-enkephalin (By similarity). Met-enkephalin-Arg-Phe cleavage by ACE decreases activation of OPRM1, leading to long-term synaptic potentiation of glutamate release (By similarity). Also acts as a regulator of hematopoietic stem cell differentiation by mediating degradation of hemoregulatory peptide N-acetyl-SDKP (AcSDKP) (PubMed:26403559, PubMed:7876104, PubMed:8257427, PubMed:8609242). Acts as a regulator of cannabinoid signaling pathway by mediating degradation of hemopressin, an antagonist peptide of the cannabinoid receptor CNR1 (PubMed:18077343). Involved in amyloid-beta metabolism by catalyzing degradation of Amyloid-beta protein 40 and Amyloid-beta protein 42 peptides, thereby preventing plaque formation (PubMed:11604391, PubMed:16154999, PubMed:19773553). Catalyzes cleavage of cholecystokinin (maturation of Cholecystokinin-8 and Cholecystokinin-5) and Gonadoliberin-1 (both maturation and degradation) hormones (PubMed:10336644, PubMed:2983326, PubMed:7683654, PubMed:9371719). Degradation of hemoregulatory peptide N-acetyl-SDKP (AcSDKP) and amyloid-beta proteins is mediated by the N-terminal catalytic domain, while angiotensin I and cholecystokinin cleavage is mediated by the C-terminal catalytic region (PubMed:10336644, PubMed:19773553, PubMed:7876104)
- Specific Function
- actin binding
- Gene Name
- ACE
- Uniprot ID
- P12821
- Uniprot Name
- Angiotensin-converting enzyme
- Molecular Weight
- 149713.675 Da
References
- Andujar-Sanchez M, Jara-Perez V, Camara-Artigas A: Thermodynamic determination of the binding constants of angiotensin-converting enzyme inhibitors by a displacement method. FEBS Lett. 2007 Jul 24;581(18):3449-54. Epub 2007 Jun 27. [Article]
- Dalkas GA, Marchand D, Galleyrand JC, Martinez J, Spyroulias GA, Cordopatis P, Cavelier F: Study of a lipophilic captopril analogue binding to angiotensin I converting enzyme. J Pept Sci. 2010 Feb;16(2):91-7. doi: 10.1002/psc.1201. [Article]
- Natesh R, Schwager SL, Evans HR, Sturrock ED, Acharya KR: Structural details on the binding of antihypertensive drugs captopril and enalaprilat to human testicular angiotensin I-converting enzyme. Biochemistry. 2004 Jul 13;43(27):8718-24. [Article]
- Piepho RW: Overview of the angiotensin-converting-enzyme inhibitors. Am J Health Syst Pharm. 2000 Oct 1;57 Suppl 1:S3-7. [Article]
- Song JC, White CM: Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet. 2002;41(3):207-24. [Article]
- Tzakos AG, Naqvi N, Comporozos K, Pierattelli R, Theodorou V, Husain A, Gerothanassis IP: The molecular basis for the selection of captopril cis and trans conformations by angiotensin I converting enzyme. Bioorg Med Chem Lett. 2006 Oct 1;16(19):5084-7. Epub 2006 Aug 2. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Ubiquitinous metalloproteinase that is involved in diverse functions such as remodeling of the vasculature, angiogenesis, tissue repair, tumor invasion, inflammation, and atherosclerotic plaque rupture. As well as degrading extracellular matrix proteins, can also act on several nonmatrix proteins such as big endothelial 1 and beta-type CGRP promoting vasoconstriction. Also cleaves KISS at a Gly-|-Leu bond. Appears to have a role in myocardial cell death pathways. Contributes to myocardial oxidative stress by regulating the activity of GSK3beta. Cleaves GSK3beta in vitro. Involved in the formation of the fibrovascular tissues in association with MMP14
- Specific Function
- endopeptidase activity
- Gene Name
- MMP2
- Uniprot ID
- P08253
- Uniprot Name
- 72 kDa type IV collagenase
- Molecular Weight
- 73881.695 Da
References
- Brower GL, Levick SP, Janicki JS: Inhibition of matrix metalloproteinase activity by ACE inhibitors prevents left ventricular remodeling in a rat model of heart failure. Am J Physiol Heart Circ Physiol. 2007 Jun;292(6):H3057-64. Epub 2007 Feb 16. [Article]
- Okada M, Kikuzuki R, Harada T, Hori Y, Yamawaki H, Hara Y: Captopril attenuates matrix metalloproteinase-2 and -9 in monocrotaline-induced right ventricular hypertrophy in rats. J Pharmacol Sci. 2008 Dec;108(4):487-94. Epub 2008 Dec 5. [Article]
- Prontera C, Mariani B, Rossi C, Poggi A, Rotilio D: Inhibition of gelatinase A (MMP-2) by batimastat and captopril reduces tumor growth and lung metastases in mice bearing Lewis lung carcinoma. Int J Cancer. 1999 May 31;81(5):761-6. [Article]
- Reinhardt D, Sigusch HH, Hensse J, Tyagi SC, Korfer R, Figulla HR: Cardiac remodelling in end stage heart failure: upregulation of matrix metalloproteinase (MMP) irrespective of the underlying disease, and evidence for a direct inhibitory effect of ACE inhibitors on MMP. Heart. 2002 Nov;88(5):525-30. [Article]
- Williams RN, Parsons SL, Morris TM, Rowlands BJ, Watson SA: Inhibition of matrix metalloproteinase activity and growth of gastric adenocarcinoma cells by an angiotensin converting enzyme inhibitor in in vitro and murine models. Eur J Surg Oncol. 2005 Nov;31(9):1042-50. Epub 2005 Jul 1. [Article]
- Yamamoto D, Takai S, Hirahara I, Kusano E: Captopril directly inhibits matrix metalloproteinase-2 activity in continuous ambulatory peritoneal dialysis therapy. Clin Chim Acta. 2010 May 2;411(9-10):762-4. doi: 10.1016/j.cca.2010.02.059. Epub 2010 Feb 22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Matrix metalloproteinase that plays an essential role in local proteolysis of the extracellular matrix and in leukocyte migration (PubMed:12879005, PubMed:1480034, PubMed:2551898). Could play a role in bone osteoclastic resorption (By similarity). Cleaves KiSS1 at a Gly-|-Leu bond (PubMed:12879005). Cleaves NINJ1 to generate the Secreted ninjurin-1 form (PubMed:32883094). Cleaves type IV and type V collagen into large C-terminal three quarter fragments and shorter N-terminal one quarter fragments (PubMed:1480034). Degrades fibronectin but not laminin or Pz-peptide
- Specific Function
- collagen binding
- Gene Name
- MMP9
- Uniprot ID
- P14780
- Uniprot Name
- Matrix metalloproteinase-9
- Molecular Weight
- 78457.51 Da
References
- Okada M, Kikuzuki R, Harada T, Hori Y, Yamawaki H, Hara Y: Captopril attenuates matrix metalloproteinase-2 and -9 in monocrotaline-induced right ventricular hypertrophy in rats. J Pharmacol Sci. 2008 Dec;108(4):487-94. Epub 2008 Dec 5. [Article]
- Reinhardt D, Sigusch HH, Hensse J, Tyagi SC, Korfer R, Figulla HR: Cardiac remodelling in end stage heart failure: upregulation of matrix metalloproteinase (MMP) irrespective of the underlying disease, and evidence for a direct inhibitory effect of ACE inhibitors on MMP. Heart. 2002 Nov;88(5):525-30. [Article]
- Williams RN, Parsons SL, Morris TM, Rowlands BJ, Watson SA: Inhibition of matrix metalloproteinase activity and growth of gastric adenocarcinoma cells by an angiotensin converting enzyme inhibitor in in vitro and murine models. Eur J Surg Oncol. 2005 Nov;31(9):1042-50. Epub 2005 Jul 1. [Article]
- Yamamoto D, Takai S, Miyazaki M: Inhibitory profiles of captopril on matrix metalloproteinase-9 activity. Eur J Pharmacol. 2008 Jul 7;588(2-3):277-9. doi: 10.1016/j.ejphar.2008.04.031. Epub 2008 May 22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Bifunctional zinc metalloenzyme that comprises both epoxide hydrolase (EH) and aminopeptidase activities. Acts as an epoxide hydrolase to catalyze the conversion of LTA4 to the pro-inflammatory mediator leukotriene B4 (LTB4) (PubMed:11917124, PubMed:12207002, PubMed:15078870, PubMed:18804029, PubMed:1897988, PubMed:1975494, PubMed:2244921). Has also aminopeptidase activity, with high affinity for N-terminal arginines of various synthetic tripeptides (PubMed:18804029, PubMed:20813919). In addition to its pro-inflammatory EH activity, may also counteract inflammation by its aminopeptidase activity, which inactivates by cleavage another neutrophil attractant, the tripeptide Pro-Gly-Pro (PGP), a bioactive fragment of collagen generated by the action of matrix metalloproteinase-9 (MMP9) and prolylendopeptidase (PREPL) (PubMed:20813919, PubMed:24591641). Involved also in the biosynthesis of resolvin E1 and 18S-resolvin E1 from eicosapentaenoic acid, two lipid mediators that show potent anti-inflammatory and pro-resolving actions (PubMed:21206090)
- Specific Function
- aminopeptidase activity
- Gene Name
- LTA4H
- Uniprot ID
- P09960
- Uniprot Name
- Leukotriene A-4 hydrolase
- Molecular Weight
- 69284.64 Da
References
- Thunnissen MM, Andersson B, Samuelsson B, Wong CH, Haeggstrom J: Crystal structures of leukotriene A4 hydrolase in complex with captopril and two competitive tight-binding inhibitors. FASEB J. 2002 Oct;16(12):1648-50. Epub 2002 Aug 7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- This is a receptor for bradykinin. Could be a factor in chronic pain and inflammation
- Specific Function
- bradykinin receptor activity
- Gene Name
- BDKRB1
- Uniprot ID
- P46663
- Uniprot Name
- B1 bradykinin receptor
- Molecular Weight
- 40494.29 Da
References
- Ignjatovic T, Tan F, Brovkovych V, Skidgel RA, Erdos EG: Novel mode of action of angiotensin I converting enzyme inhibitors: direct activation of bradykinin B1 receptor. J Biol Chem. 2002 May 10;277(19):16847-52. Epub 2002 Mar 5. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Other/unknown
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- Keire DA, Mariappan SV, Peng J, Rabenstein DL: Nuclear magnetic resonance studies of the binding of captopril and penicillamine by serum albumin. Biochem Pharmacol. 1993 Sep 14;46(6):1059-69. [Article]
- Lin SY, Wei YS, Li MJ, Wang SL: Effect of ethanol or/and captopril on the secondary structure of human serum albumin before and after protein binding. Eur J Pharm Biopharm. 2004 May;57(3):457-64. [Article]
- Mariee AD, Al-Shabanah O: Protective ability and binding affinity of captopril towards serum albumin in an in vitro glycation model of diabetes mellitus. J Pharm Biomed Anal. 2006 May 3;41(2):571-5. Epub 2006 Feb 15. [Article]
- Narazaki R, Harada K, Sugii A, Otagiri M: Kinetic analysis of the covalent binding of captopril to human serum albumin. J Pharm Sci. 1997 Feb;86(2):215-9. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- Takara K, Kakumoto M, Tanigawara Y, Funakoshi J, Sakaeda T, Okumura K: Interaction of digoxin with antihypertensive drugs via MDR1. Life Sci. 2002 Feb 15;70(13):1491-500. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Electrogenic proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides. Transports neutral and monovalently charged peptides with a proton to peptide stoichiometry of 1:1 or 2:1 (By similarity) (PubMed:15521010, PubMed:18367661, PubMed:19685173, PubMed:26320580, PubMed:7896779, PubMed:8914574, PubMed:9835627). Primarily responsible for the absorption of dietary di- and tripeptides from the small intestinal lumen (By similarity). Mediates transepithelial transport of muramyl and N-formylated bacterial dipeptides contributing to recognition of pathogenic bacteria by the mucosal immune system (PubMed:15521010, PubMed:9835627)
- Specific Function
- dipeptide transmembrane transporter activity
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Watanabe K, Sawano T, Terada K, Endo T, Sakata M, Sato J: Studies on intestinal absorption of sulpiride (1): carrier-mediated uptake of sulpiride in the human intestinal cell line Caco-2. Biol Pharm Bull. 2002 Jul;25(7):885-90. [Article]
- Temple CS, Boyd CA: Proton-coupled oligopeptide transport by rat renal cortical brush border membrane vesicles: a functional analysis using ACE inhibitors to determine the isoform of the transporter. Biochim Biophys Acta. 1998 Aug 14;1373(1):277-81. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- Curator comments
- Substrate profile was determined in vitro using HEK293 cells.
- General Function
- Secondary active transporter that functions as a Na(+)-independent organic anion (OA)/dicarboxylate antiporter where the uptake of one molecule of OA into the cell is coupled with an efflux of one molecule of intracellular dicarboxylate such as 2-oxoglutarate or glutarate (PubMed:11669456, PubMed:11907186, PubMed:14675047, PubMed:22108572, PubMed:23832370, PubMed:28534121, PubMed:9950961). Mediates the uptake of OA across the basolateral side of proximal tubule epithelial cells, thereby contributing to the renal elimination of endogenous OA from the systemic circulation into the urine (PubMed:9887087). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). Transports prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may contribute to their renal excretion (PubMed:11907186). Also mediates the uptake of cyclic nucleotides such as cAMP and cGMP (PubMed:26377792). Involved in the transport of neuroactive tryptophan metabolites kynurenate (KYNA) and xanthurenate (XA) and may contribute to their secretion from the brain (PubMed:22108572, PubMed:23832370). May transport glutamate (PubMed:26377792). Also involved in the disposition of uremic toxins and potentially toxic xenobiotics by the renal organic anion secretory pathway, helping reduce their undesired toxicological effects on the body (PubMed:11669456, PubMed:14675047). Uremic toxins include the indoxyl sulfate (IS), hippurate/N-benzoylglycine (HA), indole acetate (IA), 3-carboxy-4- methyl-5-propyl-2-furanpropionate (CMPF) and urate (PubMed:14675047, PubMed:26377792). Xenobiotics include the mycotoxin ochratoxin (OTA) (PubMed:11669456). May also contribute to the transport of organic compounds in testes across the blood-testis-barrier (PubMed:35307651)
- Specific Function
- alpha-ketoglutarate transmembrane transporter activity
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Kuze K, Graves P, Leahy A, Wilson P, Stuhlmann H, You G: Heterologous expression and functional characterization of a mouse renal organic anion transporter in mammalian cells. J Biol Chem. 1999 Jan 15;274(3):1519-24. [Article]
- VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 06, 2024 08:03