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Namespace Prefixes

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Statements

Subject Item
n2:DB01197
rdf:type
n3:Drug
n3: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.
n3:dosage
n29:271B53D6-363D-11E5-9242-09173F13E4C5 n29:271B53D7-363D-11E5-9242-09173F13E4C5 n29:271B53D8-363D-11E5-9242-09173F13E4C5 n29:271B53D9-363D-11E5-9242-09173F13E4C5 n29:271B53DA-363D-11E5-9242-09173F13E4C5 n29:271B53DB-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Atkinson AB, Robertson JI: Captopril in the treatment of clinical hypertension and cardiac failure. Lancet. 1979 Oct 20;2(8147):836-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/90928 # 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":http://www.ncbi.nlm.nih.gov/pubmed/6253826 # Smith CG, Vane JR: The discovery of captopril. FASEB J. 2003 May;17(8):788-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12724335
n3:group
approved
n3:halfLife
2 hours
n3: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.
owl:sameAs
n9:DB01197 n16:DB01197
dcterms:title
Captopril
adms:identifier
n14:Captopril n18:D00251 n19:40130 n20:DB01197 n21:21642 n22:3380 n23:44093 n24:46506879 n25:0378-3007-01 n26:PA448780
n3:mechanismOfAction
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.
n3:packager
n7:271B53A7-363D-11E5-9242-09173F13E4C5 n7:271B53A8-363D-11E5-9242-09173F13E4C5 n7:271B5384-363D-11E5-9242-09173F13E4C5 n7:271B5385-363D-11E5-9242-09173F13E4C5 n7:271B53AB-363D-11E5-9242-09173F13E4C5 n7:271B53AC-363D-11E5-9242-09173F13E4C5 n7:271B53A9-363D-11E5-9242-09173F13E4C5 n7:271B53AA-363D-11E5-9242-09173F13E4C5 n7:271B53AF-363D-11E5-9242-09173F13E4C5 n7:271B53AD-363D-11E5-9242-09173F13E4C5 n7:271B53AE-363D-11E5-9242-09173F13E4C5 n7:271B53B9-363D-11E5-9242-09173F13E4C5 n7:271B53BA-363D-11E5-9242-09173F13E4C5 n7:271B53B7-363D-11E5-9242-09173F13E4C5 n7:271B53B8-363D-11E5-9242-09173F13E4C5 n7:271B53BB-363D-11E5-9242-09173F13E4C5 n7:271B53BC-363D-11E5-9242-09173F13E4C5 n7:271B53B1-363D-11E5-9242-09173F13E4C5 n7:271B53B2-363D-11E5-9242-09173F13E4C5 n7:271B53B0-363D-11E5-9242-09173F13E4C5 n7:271B53B5-363D-11E5-9242-09173F13E4C5 n7:271B53B6-363D-11E5-9242-09173F13E4C5 n7:271B53B3-363D-11E5-9242-09173F13E4C5 n7:271B53B4-363D-11E5-9242-09173F13E4C5 n7:271B538B-363D-11E5-9242-09173F13E4C5 n7:271B538C-363D-11E5-9242-09173F13E4C5 n7:271B538F-363D-11E5-9242-09173F13E4C5 n7:271B5390-363D-11E5-9242-09173F13E4C5 n7:271B538D-363D-11E5-9242-09173F13E4C5 n7:271B538E-363D-11E5-9242-09173F13E4C5 n7:271B539B-363D-11E5-9242-09173F13E4C5 n7:271B539C-363D-11E5-9242-09173F13E4C5 n7:271B5399-363D-11E5-9242-09173F13E4C5 n7:271B539A-363D-11E5-9242-09173F13E4C5 n7:271B539F-363D-11E5-9242-09173F13E4C5 n7:271B53A0-363D-11E5-9242-09173F13E4C5 n7:271B539D-363D-11E5-9242-09173F13E4C5 n7:271B539E-363D-11E5-9242-09173F13E4C5 n7:271B5393-363D-11E5-9242-09173F13E4C5 n7:271B5394-363D-11E5-9242-09173F13E4C5 n7:271B5391-363D-11E5-9242-09173F13E4C5 n7:271B5392-363D-11E5-9242-09173F13E4C5 n7:271B5397-363D-11E5-9242-09173F13E4C5 n7:271B5398-363D-11E5-9242-09173F13E4C5 n7:271B5395-363D-11E5-9242-09173F13E4C5 n7:271B5396-363D-11E5-9242-09173F13E4C5 n7:271B53A3-363D-11E5-9242-09173F13E4C5 n7:271B53A4-363D-11E5-9242-09173F13E4C5 n7:271B53A1-363D-11E5-9242-09173F13E4C5 n7:271B53A2-363D-11E5-9242-09173F13E4C5 n7:271B53A5-363D-11E5-9242-09173F13E4C5 n7:271B53A6-363D-11E5-9242-09173F13E4C5 n7:271B5388-363D-11E5-9242-09173F13E4C5 n7:271B5389-363D-11E5-9242-09173F13E4C5 n7:271B5386-363D-11E5-9242-09173F13E4C5 n7:271B5387-363D-11E5-9242-09173F13E4C5 n7:271B538A-363D-11E5-9242-09173F13E4C5
n3:patent
n15:5238924
n3:synonym
Captoril Acepress Captoprilum Hypertil Captopryl Apopril Lopirin D-2-Methyl-3-mercaptopropanoyl-L-proline (2S)-1-[(2S)-2-Methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid CP Dilabar Garranil Tenosbon L-Captopril Tensoprel Cesplon D-3-Mercapto-2-methylpropanoyl-L-proline Tensobon Captolane Capoten
n3: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.
n11:hasAHFSCode
n12:24-32-04
n3:foodInteraction
Captopril decreases the excretion of potassium. Salt substitutes containing potassium increase the risk of hyperkalemia. Herbs that may attenuate the antihypertensive effect of captopril include: bayberry, blue cohash, cayenne, ephedra, ginger, ginseng (American), kola and licorice. Food decreases absorption by 25 - 40%. Clinical significance is debatable. High salt intake may attenuate the antihypertensive effect of captopril.
n3:mixture
n17:271B5383-363D-11E5-9242-09173F13E4C5 n17:271B5381-363D-11E5-9242-09173F13E4C5 n17:271B5382-363D-11E5-9242-09173F13E4C5
n3:proteinBinding
25-30% bound to plasma proteins, primarily albumin
n3:synthesisReference
Charles M. Zepp, "Methods for preparing captopril and its analogues." U.S. Patent US5166361, issued July, 1981.
n31:hasConcept
n32:M0003319
foaf:page
n5:cap1064.shtml n27:captopril.html n28:captop.htm
n3:IUPAC-Name
n10:271B53E0-363D-11E5-9242-09173F13E4C5
n3:InChI
n10:271B53E6-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n10:271B53E5-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n10:271B53E2-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n10:271B53E3-363D-11E5-9242-09173F13E4C5
n3:SMILES
n10:271B53E4-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n10:271B53DE-363D-11E5-9242-09173F13E4C5 n10:271B53F6-363D-11E5-9242-09173F13E4C5
n3:logP
n10:271B53DC-363D-11E5-9242-09173F13E4C5 n10:271B53DF-363D-11E5-9242-09173F13E4C5 n10:271B53F8-363D-11E5-9242-09173F13E4C5
n3:logS
n10:271B53DD-363D-11E5-9242-09173F13E4C5
n11:hasATCCode
n30:C09AA01
n3:H-Bond-Acceptor-Count
n10:271B53EC-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n10:271B53ED-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n10:271B53E7-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n10:271B53E8-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n10:271B53EA-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n10:271B53E9-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n10:271B53EB-363D-11E5-9242-09173F13E4C5
n3:absorption
60-75% in fasting individuals; food decreases absorption by 25-40% (some evidence indicates that this is not clinically significant)
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
62571-86-2
n3:category
n3:containedIn
n6:271B53BE-363D-11E5-9242-09173F13E4C5 n6:271B53BF-363D-11E5-9242-09173F13E4C5 n6:271B53C8-363D-11E5-9242-09173F13E4C5 n6:271B53C9-363D-11E5-9242-09173F13E4C5 n6:271B53C6-363D-11E5-9242-09173F13E4C5 n6:271B53C7-363D-11E5-9242-09173F13E4C5 n6:271B53CC-363D-11E5-9242-09173F13E4C5 n6:271B53CD-363D-11E5-9242-09173F13E4C5 n6:271B53CA-363D-11E5-9242-09173F13E4C5 n6:271B53CB-363D-11E5-9242-09173F13E4C5 n6:271B53C0-363D-11E5-9242-09173F13E4C5 n6:271B53C1-363D-11E5-9242-09173F13E4C5 n6:271B53BD-363D-11E5-9242-09173F13E4C5 n6:271B53C4-363D-11E5-9242-09173F13E4C5 n6:271B53C5-363D-11E5-9242-09173F13E4C5 n6:271B53C2-363D-11E5-9242-09173F13E4C5 n6:271B53C3-363D-11E5-9242-09173F13E4C5 n6:271B53D0-363D-11E5-9242-09173F13E4C5 n6:271B53D1-363D-11E5-9242-09173F13E4C5 n6:271B53CE-363D-11E5-9242-09173F13E4C5 n6:271B53CF-363D-11E5-9242-09173F13E4C5 n6:271B53D4-363D-11E5-9242-09173F13E4C5 n6:271B53D5-363D-11E5-9242-09173F13E4C5 n6:271B53D2-363D-11E5-9242-09173F13E4C5 n6:271B53D3-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n10:271B53F2-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n10:271B53F4-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n10:271B53F5-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n10:271B53F7-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n10:271B53F1-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n10:271B53F0-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n10:271B53F3-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n10:271B53E1-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n10:271B53EE-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n10:271B53EF-363D-11E5-9242-09173F13E4C5