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Identification
NameCaptopril
Accession NumberDB01197  (APRD00164)
TypeSmall Molecule
GroupsApproved
Description

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.

Structure
Thumb
Synonyms
SynonymLanguageCode
(2S)-1-[(2S)-2-Methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acidNot AvailableNot Available
AcepressNot AvailableNot Available
ApoprilNot AvailableNot Available
CapotenNot AvailableNot Available
CaptolaneNot AvailableNot Available
CaptoprilumLatinINN
CaptoprylNot AvailableNot Available
CaptorilNot AvailableNot Available
CesplonNot AvailableNot Available
CPNot AvailableNot Available
D-2-Methyl-3-mercaptopropanoyl-L-prolineNot AvailableNot Available
D-3-Mercapto-2-methylpropanoyl-L-prolineNot AvailableNot Available
DilabarNot AvailableNot Available
GarranilNot AvailableNot Available
HypertilNot AvailableNot Available
L-CaptoprilNot AvailableNot Available
LopirinNot AvailableNot Available
TenosbonNot AvailableNot Available
TensobonNot AvailableNot Available
TensoprelNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Captopriltablet12.5 mgoralWest ward Pharmaceutical Corp1996-02-13Not AvailableUs
Captopriltablet25 mgoralWest ward Pharmaceutical Corp1996-02-13Not AvailableUs
Captopriltablet50 mgoralWest ward Pharmaceutical Corp1996-02-13Not AvailableUs
Captopriltablet100 mgoralWest ward Pharmaceutical Corp1996-02-13Not AvailableUs
Captopriltablet12.5 mgoralMylan Pharmaceuticals Inc.1996-02-13Not AvailableUs
Captopriltablet25 mgoralMylan Pharmaceuticals Inc.1996-02-13Not AvailableUs
Captopriltablet50 mgoralMylan Pharmaceuticals Inc.1996-02-13Not AvailableUs
Captopriltablet100 mgoralMylan Pharmaceuticals Inc.1996-02-13Not AvailableUs
Captopriltablet12.5 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs1997-03-28Not AvailableUs
Captopriltablet25 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs1997-03-28Not AvailableUs
Captopriltablet50 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs1997-03-28Not AvailableUs
Captopriltablet12.5 mgoralMajor Pharmaceuticals2004-02-16Not AvailableUs
Captopriltablet25 mgoralMajor Pharmaceuticals2004-02-16Not AvailableUs
Captopriltablet50 mgoralMajor Pharmaceuticals2004-02-16Not AvailableUs
Captopriltablet25 mgoralRebel Distributors Corp1996-02-13Not AvailableUs
Captopriltablet50 mgoralRebel Distributors Corp1996-02-13Not AvailableUs
Captopriltablet50 mgoralAidarex Pharmaceuticals LLC1997-03-28Not AvailableUs
Captopriltablet100 mgoralAidarex Pharmaceuticals LLC1997-03-28Not AvailableUs
Captopriltablet25 mgoralAidarex Pharmaceuticals LLC1997-03-28Not AvailableUs
Captopriltablet25 mgoralRebel Distributors Corp1997-03-28Not AvailableUs
Captopriltablet50 mgoralRebel Distributors Corp1997-03-28Not AvailableUs
Captopriltablet12.5 mgoralPd Rx Pharmaceuticals, Inc.2011-05-04Not AvailableUs
Captopriltablet50 mgoralREMEDYREPACK INC.2011-06-16Not AvailableUs
Captopriltablet30 mgoralREMEDYREPACK INC.2013-02-28Not AvailableUs
Captopriltablet50 mgoralUnit Dose Services1996-02-13Not AvailableUs
Captopriltablet12.5 mgoralUnit Dose Services1997-03-28Not AvailableUs
Captopriltablet25 mgoralUnit Dose Services1996-02-13Not AvailableUs
Captopriltablet12.5 mgoralMylan Institutional Inc.1996-02-14Not AvailableUs
Captopriltablet25 mgoralMylan Institutional Inc.1996-02-14Not AvailableUs
Captopriltablet25 mgoralREMEDYREPACK INC.2014-01-30Not AvailableUs
Captopriltablet12.5 mgoralAidarex Pharmaceuticals LLC1997-03-28Not AvailableUs
Captopriltablet50 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Captopriltablet100 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Captopriltablet100 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Captopriltablet25 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Captopriltablet50 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Captopriltablet25 mgoralPhysicians Total Care, Inc.1996-04-25Not AvailableUs
Captopriltablet50 mgoralPhysicians Total Care, Inc.1996-08-05Not AvailableUs
Captopriltablet12.5 mgoralCardinal Health2004-02-16Not AvailableUs
Captopriltablet50 mgoralCardinal Health2004-02-16Not AvailableUs
Captopriltablet25 mgoralCardinal Health2004-02-16Not AvailableUs
Captopriltablet25 mgoralCardinal Health2011-04-29Not AvailableUs
Captopriltablet12.5 mgoralCardinal Health2011-04-29Not AvailableUs
Captopriltablet25 mgoralPd Rx Pharmaceuticals, Inc.1996-02-13Not AvailableUs
Captopriltablet12.5 mgoralWockhardt Limited1997-03-28Not AvailableUs
Captopriltablet25 mgoralWockhardt Limited1997-03-28Not AvailableUs
Captopriltablet50 mgoralWockhardt Limited1997-03-28Not AvailableUs
Captopriltablet100 mgoralWockhardt Limited1997-03-28Not AvailableUs
Captopriltablet12.5 mgoralGolden State Medical Supply, Inc.1996-02-132017-03-30Us
Captopriltablet25 mgoralGolden State Medical Supply, Inc.1996-02-13Not AvailableUs
Captopriltablet50 mgoralGolden State Medical Supply, Inc.1996-02-13Not AvailableUs
Captopriltablet100 mgoralGolden State Medical Supply, Inc.1996-02-13Not AvailableUs
Captopriltablet12.5 mgoralApotex Corp.2005-12-07Not AvailableUs
Captopriltablet25 mgoralApotex Corp.2005-12-07Not AvailableUs
Captopriltablet50 mgoralApotex Corp.2005-12-07Not AvailableUs
Captopriltablet100 mgoralApotex Corp.2005-12-07Not AvailableUs
Captopriltablet12.5 mgoralSt Marys Medical Park Pharmacy2014-04-21Not AvailableUs
Captopriltablet50 mgoralSt Marys Medical Park Pharmacy2014-01-16Not AvailableUs
Captopriltablet25 mgoralSt Marys Medical Park Pharmacy2014-04-21Not AvailableUs
Captopriltablet25 mgoralREMEDYREPACK INC.2014-09-15Not AvailableUs
Captopriltablet25 mgoralbryant ranch prepack1996-02-13Not AvailableUs
Captopriltablet100 mgoralbryant ranch prepack1996-02-13Not AvailableUs
Captopriltablet50 mgoralbryant ranch prepack2009-09-11Not AvailableUs
Captopriltablet12.5 mgoralbryant ranch prepack1996-02-13Not AvailableUs
Captopriltablet12.5 mgoralWockhardt USA LLC.1997-03-28Not AvailableUs
Captopriltablet25 mgoralWockhardt USA LLC.1997-03-28Not AvailableUs
Captopriltablet50 mgoralWockhardt USA LLC.1997-03-28Not AvailableUs
Captopriltablet100 mgoralWockhardt USA LLC.1997-03-28Not AvailableUs
Captopriltablet15 mgoralRed Pharm Drug Inc.1996-02-13Not AvailableUs
Captopriltablet50 mgoralRed Pharm Drug Inc.1996-02-13Not AvailableUs
Captopriltablet12.5 mgoralLegacy Pharmaceutical Packaging2009-09-11Not AvailableUs
Captopriltablet25 mgoralLegacy Pharmaceutical Packaging2009-09-11Not AvailableUs
Captopriltablet50 mgoralLegacy Pharmaceutical Packaging2009-09-11Not AvailableUs
Captopriltablet100 mgoralLegacy Pharmaceutical Packaging2009-09-11Not AvailableUs
Captopriltablet50 mgoralPreferred Pharmaceuticals, Inc.2012-12-13Not AvailableUs
Captopriltablet25 mgoralPreferred Pharmaceuticals, Inc.2012-12-13Not AvailableUs
Captopriltablet50 mgoralPreferred Pharmaceuticals, Inc.1996-02-13Not AvailableUs
Captopriltablet25 mgoralPreferred Pharmaceuticals, Inc.2012-03-29Not AvailableUs
Captopriltablet12.5 mgoralGLENVIEW PHARMA INC.1997-03-28Not AvailableUs
Captopriltablet25 mgoralGLENVIEW PHARMA INC.1997-03-28Not AvailableUs
Captopriltablet50 mgoralGLENVIEW PHARMA INC.1997-03-28Not AvailableUs
Captopriltablet12.5 mgoralPharmel IncNot AvailableNot AvailableCanada
Captopriltablet25 mgoralPharmel IncNot AvailableNot AvailableCanada
Captopriltablet50 mgoralPharmel IncNot AvailableNot AvailableCanada
Captopriltablet100 mgoralPharmel IncNot AvailableNot AvailableCanada
Over the Counter ProductsNot Available
International Brands
NameCompany
AcepressBernofarm (Indonesia), BMS (Italy)
AceprilBMS (United Kingdom)
AlopresinNot Available
ApoprilNot Available
CapotenBristol-Myers Squibb, Par
CaptolaneSanofi-Aventis (France)
CaptorilNovopharm (Canada)
CesplonEsteve (Spain)
DilabarQualigen (Spain)
GarranilAristegui (Spain)
HipertilNormal (Portugal)
HypertilNormal (Portugal)
LopirinBMS (Germany,Switzerland)
LoprilOrion (Finland), BMS (France)
TenosbonNot Available
TensoprelRubio (Spain)
Brand mixtures
Brand NameIngredients
Acediurcaptopril + hydrochlorothiazide
Acepluscaptopril + hydrochlorothiazide
Capozidecaptopril + hydrochlorothiazide
SaltsNot Available
Categories
CAS number62571-86-2
WeightAverage: 217.285
Monoisotopic: 217.077264041
Chemical FormulaC9H15NO3S
InChI KeyFAKRSMQSSFJEIM-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • N-acylpyrrolidine
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Tertiary amine
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Alkylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor 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.
PharmacodynamicsCaptopril, 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 actionThere 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.
Absorption60-75% in fasting individuals; food decreases absorption by 25-40% (some evidence indicates that this is not clinically significant)
Volume of distributionNot Available
Protein binding25-30% 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.

SubstrateEnzymesProduct
Captopril
Not Available
captopril-cysteine disulfideDetails
Route of eliminationNot Available
Half life2 hours
ClearanceNot Available
ToxicitySymptoms of overdose include emesis and decreased blood pressure. Side effects include dose-dependent rash (usually maculopapular), taste alterations, hypotension, gastric irritation, cough, and angioedema.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Captopril Action PathwayDrug actionSMP00146
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.97
Blood Brain Barrier+0.6467
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.6276
P-glycoprotein inhibitor INon-inhibitor0.8448
P-glycoprotein inhibitor IINon-inhibitor0.7415
Renal organic cation transporterNon-inhibitor0.8073
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.6293
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.9102
CYP450 2D6 substrateNon-inhibitor0.9537
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-inhibitor0.9049
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8975
Ames testNon AMES toxic0.8164
CarcinogenicityNon-carcinogens0.9434
BiodegradationNot ready biodegradable0.6577
Rat acute toxicity1.7403 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9604
hERG inhibition (predictor II)Non-inhibitor0.9118
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral100 mg
Tabletoral12.5 mg
Tabletoral15 mg
Tabletoral25 mg
Tabletoral30 mg
Tabletoral50 mg
Prices
Unit descriptionCostUnit
Captopril powder22.03USD g
Capoten 100 mg tablet4.53USD tablet
Capoten 12.5 mg tablet1.8USD tablet
Captopril 100 mg tablet1.53USD tablet
Captopril 50 mg tablet1.14USD tablet
Capoten 25 mg tablet1.13USD tablet
Capoten 50 mg tablet1.13USD tablet
Apo-Capto 100 mg Tablet1.09USD tablet
Mylan-Captopril 100 mg Tablet1.09USD tablet
Novo-Captoril 100 mg Tablet1.09USD tablet
Nu-Capto 100 mg Tablet1.09USD tablet
Captopril 25 mg tablet0.67USD tablet
Captopril 12.5 mg tablet0.62USD tablet
Apo-Capto 50 mg Tablet0.59USD tablet
Mylan-Captopril 50 mg Tablet0.59USD tablet
Novo-Captoril 50 mg Tablet0.59USD tablet
Nu-Capto 50 mg Tablet0.59USD tablet
Apo-Capto 25 mg Tablet0.31USD tablet
Mylan-Captopril 25 mg Tablet0.31USD tablet
Novo-Captoril 25 mg Tablet0.31USD tablet
Nu-Capto 25 mg Tablet0.31USD tablet
Apo-Capto 12.5 mg Tablet0.22USD tablet
Mylan-Captopril 12.5 mg Tablet0.22USD tablet
Novo-Captoril 12.5 mg Tablet0.22USD tablet
Nu-Capto 12.5 mg Tablet0.22USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States52389241993-08-242010-08-24
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point103-104Ondetti, 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 solubilityFreely solubleNot Available
logP0.34RANADIVE,SA ET AL. (1992)
Predicted Properties
PropertyValueSource
Water Solubility4.52 mg/mLALOGPS
logP1.02ALOGPS
logP0.73ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.61 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.63 m3·mol-1ChemAxon
Polarizability21.72 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Charles M. Zepp, “Methods for preparing captopril and its analogues.” U.S. Patent US5166361, issued July, 1981.

US5166361
General Reference
  1. Atkinson AB, Robertson JI: Captopril in the treatment of clinical hypertension and cardiac failure. Lancet. 1979 Oct 20;2(8147):836-9. Pubmed
  2. 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. Pubmed
  3. Smith CG, Vane JR: The discovery of captopril. FASEB J. 2003 May;17(8):788-9. Pubmed
External Links
ATC CodesC09AA01
AHFS Codes
  • 24:32.04
PDB Entries
FDA labelNot Available
MSDSDownload (37.6 KB)
Interactions
Drug Interactions
Drug
AmilorideIncreased risk of hyperkalemia
AprotininIn study of nine patients with untreated hypertension, aprotinin infused intravenously in a dose of 2 million KIU over two hours blocked the acute hypotensive effect of 100mg of captopril.
Azilsartan medoxomilPharmacodynamic synergism: dual blockade of renin-angiotensin system. Increases risks of hypotension, hyperkalemia, renal impairment.
DrospirenoneIncreased risk of hyperkalemia
IcatibantIcatibant may attenuate the antihypertensive effect of ACE inhibitors by pharmacodynamic antagonism. Monitor concomitant therapy closely.
LithiumThe ACE inhibitor increases serum levels of lithium
PotassiumIncreased risk of hyperkalemia
SpironolactoneIncreased risk of hyperkalemia
TerbinafineTerbinafine may reduce the metabolism and clearance of Captopril. Consider alternate therapy or monitor for therapeutic/adverse effects of Captopril if Terbinafine is initiated, discontinued or dose changed.
TizanidineTizanidine increases the risk of hypotension with the ACE inhibitor
TobramycinIncreased risk of nephrotoxicity
TreprostinilAdditive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
TriamtereneIncreased risk of hyperkalemia
Food Interactions
  • Captopril decreases the excretion of potassium. Salt substitutes containing potassium increase the risk of hyperkalemia.
  • Food decreases absorption by 25 - 40%. Clinical significance is debatable.
  • Herbs that may attenuate the antihypertensive effect of captopril include: bayberry, blue cohash, cayenne, ephedra, ginger, ginseng (American), kola and licorice.
  • High salt intake may attenuate the antihypertensive effect of captopril.

Targets

1. Angiotensin-converting enzyme

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Angiotensin-converting enzyme P12821 Details

References:

  1. 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. Pubmed
  2. 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. Pubmed
  3. 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. Pubmed
  4. Piepho RW: Overview of the angiotensin-converting-enzyme inhibitors. Am J Health Syst Pharm. 2000 Oct 1;57 Suppl 1:S3-7. Pubmed
  5. Song JC, White CM: Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet. 2002;41(3):207-24. Pubmed
  6. 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. Pubmed
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. 72 kDa type IV collagenase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
72 kDa type IV collagenase P08253 Details

References:

  1. 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. Pubmed
  2. 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. Pubmed
  3. 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. Pubmed
  4. 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. Pubmed
  5. 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. Pubmed
  6. 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. Epub 2010 Feb 22. Pubmed

3. Matrix metalloproteinase-9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Matrix metalloproteinase-9 P14780 Details

References:

  1. 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. Pubmed
  2. 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. Pubmed
  3. 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. Pubmed
  4. 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. Epub 2008 May 22. Pubmed

4. Leukotriene A-4 hydrolase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Leukotriene A-4 hydrolase P09960 Details

References:

  1. 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. Pubmed

Enzymes

1. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Carriers

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: no

Actions: other/unknown

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. 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. Pubmed
  2. 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. Pubmed
  3. 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. Pubmed
  4. 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. Pubmed

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. 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. Pubmed

2. Solute carrier family 15 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 15 member 1 P46059 Details

References:

  1. 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. Pubmed
  2. 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. Pubmed

3. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

References:

  1. 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. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13