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Identification
Name Hydrochlorothiazide
Accession Number DB00999 (APRD00092)
Type small molecule
Groups approved
Description

A thiazide diuretic often considered the prototypical member of this class. It reduces the reabsorption of electrolytes from the renal tubules. This results in increased excretion of water and electrolytes, including sodium, potassium, chloride, and magnesium. It has been used in the treatment of several disorders including edema, hypertension, diabetes insipidus, and hypoparathyroidism. [PubChem]
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Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Dihydrochlorothiazid
Dihydrochlorothiazide
Dihydrochlorothiazidum
Dihydrochlorurit
Dihydrochlorurite
Dihydroxychlorothiazidum
HCTZ
HCZ
Hydrochlorothiazid
Hydrochlorthiazide
Salts Not Available
Brand names
Name Company
Apresazide
Aquarills
Aquarius
Bremil
Caplaril
Chlorosulthiadil
Chlorzide
Cidrex
Dichlorosal
Dichlorotride
Dichlotiazid
Dichlotride
Diclotride
Dicyclotride
Direma
Disalunil
Diu-Melusin
Drenol
Esidrex
Fluvin
Hidril
Hidrochlortiazid
Hidroronol
Hidrotiazida
Hydril
Hydro-Aquil
Hydrodiuretic
HydroDIURIL Merck
Hydropres
Hydrosaluric
Hydrothide
Hydrozide
Hypothiazid
Hypothiazide
Idrotiazide
Ivaugan
Jen-Diril
Maschitt
Megadiuril
Microzide Watson
Nefrix
Neo-Codema
Neoflumen
Newtolide
Panurin
Ro-Hydrazide
Servithiazid
Thiaretic
Thiuretic
Thlaretic
Timolide
Urodiazin
Vetidrex
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Brand mixtures
Brand Name Ingredients
Accuretic quinapril + hydrochlorothiazide
Aldactazide spironolactone + hydrochlorothiazide
Aldoril methyldopa + hydrochlorothiazide
Atacand HCT candesartan + hydrochlorothiazide
Avalide irbesartan + hydrochlorothiazide
Benicar HCT olmesartan + hydrochlorothiazide
Capozide captopril + hydrochlorothiazide
Diovan HCT valsartan + hydrochlorothiazide
Dyazide triamterene + hydrochlorothiazide
Hydra-Zide hydralazine + hydrochlorothiazide
Hyzaar losartan + hydrochlorothiazide
Inderide propranolol + hydrochlorothiazide
Lopressor HCT metoprolol + hydrochlorothiazide
Lotensin HCT benazepril + hydrochlorothiazide
Maxzide triamterene + hydrochlorothiazide
Micardis HCT telmisartan + hydrochlorothiazide
Moduretic amiloride + hydrochlorothiazide
Monopril-HCT fosinopril + hydrochlorothiazide
Prinzide lisinopril + hydrochlorothiazide
Teveten HCT eprosartan + hydrochlorothiazide
Timolide timolol + hydrochlorothiazide
Uniretic HCT moexipril + hydrochlorothiazide
Vaseretic enalapril + hydrochlorothiazide
Zestoretic lisinopril + hydrochlorothiazide
Ziac bisoprolol + hydrochlorothiazide
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Categories
  • Antihypertensive Agents
  • Diuretics
  • Sodium Chloride Symporter Inhibitors
CAS number 58-93-5
Weight Average: 297.739
Monoisotopic: 296.964474846
Chemical Formula C7H8ClN3O4S2
InChI Key InChIKey=JZUFKLXOESDKRF-UHFFFAOYSA-N
InChI
InChI=1S/C7H8ClN3O4S2/c8-4-1-5-7(2-6(4)16(9,12)13)17(14,15)11-3-10-5/h1-2,10-11H,3H2,(H2,9,12,13)
Plain Text
IUPAC Name
6-chloro-1,1-dioxo-3,4-dihydro-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide
SMILES
NS(=O)(=O)C1=C(Cl)C=C2NCNS(=O)(=O)C2=C1
Plain Text
Mass Spec show (11.5 KB)
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For the treatment of high blood pressure and management of edema.
Pharmacodynamics Thiazides such as hydrochlorothiazide promote water loss from the body (diuretics). They inhibit Na+/Cl- reabsorption from the distal convoluted tubules in the kidneys. Thiazides also cause loss of potassium and an increase in serum uric acid. Thiazides are often used to treat hypertension, but their hypotensive effects are not necessarily due to their diuretic activity. Thiazides have been shown to prevent hypertension-related morbidity and mortality although the mechanism is not fully understood. Thiazides cause vasodilation by activating calcium-activated potassium channels (large conductance) in vascular smooth muscles and inhibiting various carbonic anhydrases in vascular tissue.
Mechanism of action Hydrochlorothiazide, a thiazide diuretic, inhibits water reabsorption in the nephron by inhibiting the sodium-chloride symporter (SLC12A3) in the distal convoluted tubule, which is responsible for 5% of total sodium reabsorption. Normally, the sodium-chloride symporter transports sodium and chloride from the lumen into the epithelial cell lining the distal convoluted tubule. The energy for this is provided by a sodium gradient established by sodium-potassium ATPases on the basolateral membrane. Once sodium has entered the cell, it is transported out into the basolateral interstitium via the sodium-potassium ATPase, causing an increase in the osmolarity of the interstitium, thereby establishing an osmotic gradient for water reabsorption. By blocking the sodium-chloride symporter, hydrochlorothiazide effectively reduces the osmotic gradient and water reabsorption throughout the nephron.Hydrochlorothiazide, a thiazide diuretic, inhibits water reabsorption in the nephron by inhibiting the sodium-chloride symporter (SLC12A3) in the distal convoluted tubule, which is responsible for 5% of total sodium reabsorption. Normally, the sodium-chloride symporter transports sodium and chloride from the lumen into the epithelial cell lining the distal convoluted tubule. The energy for this is provided by a sodium gradient established by sodium-potassium ATPases on the basolateral membrane. Once sodium has entered the cell, it is transported out into the basolateral interstitium via the sodium-potassium ATPase, causing an increase in the osmolarity of the interstitium, thereby establishing an osmotic gradient for water reabsorption. By blocking the sodium-chloride symporter, hydrochlorothiazide effectively reduces the osmotic gradient and water reabsorption throughout the nephron.
Absorption 50-60%
Volume of distribution Not Available
Protein binding 67.9%
Metabolism Hydrochlorothiazide is not metabolized.
Route of elimination Hydrochlorothiazide is not metabolized but is eliminated rapidly by the kidney. Hydrochlorothiazide crosses the placental but not the blood-brain barrier and is excreted in breast milk.
Half life 5.6 and 14.8 hours
Clearance Not Available
Toxicity The most common signs and symptoms observed are those caused by electrolyte depletion (hypokalemia, hypochloremia, hyponatremia) and dehydration resulting from excessive diuresis. If digitalis has also been administered, hypokalemia may accentuate cardiac arrhythmias. The oral LD50 of hydrochlorothiazide is greater than 10 g/kg in the mouse and rat.
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00100 Hydrochlorothiazide Pathway SMP00100
Pharmacoeconomics
Manufacturers
  • Apotex inc
  • Aurobindo pharma ltd
  • Cadista pharmaceuticals inc
  • Ipca laboratories ltd
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mylan pharmaceuticals inc
  • Unichem laboratories ltd
  • Vintage pharmaceuticals inc
  • West ward pharmaceutical corp
  • Watson laboratories inc
  • Morton grove pharmaceuticals inc
  • Roxane laboratories inc
  • Novartis pharmaceuticals corp
  • Abc holding corp
  • Actavis elizabeth llc
  • Alra laboratories inc
  • Ascot hosp pharmaceuticals inc div travenol laboratories inc
  • Barr laboratories inc
  • Caraco pharmaceutical laboratories ltd
  • Dava pharmaceuticals inc
  • Elkins sinn div ah robins co inc
  • Excellium pharmaceutical inc
  • Heather drug co inc
  • Heritage pharmaceuticals inc
  • Impax laboratories inc
  • Inwood laboratories inc sub forest laboratories inc
  • Lannett holdings inc
  • Mm mast and co
  • Mutual pharmaceutical co inc
  • Private formulations inc
  • Sandoz inc
  • Solvay pharmaceuticals
  • Superpharm corp
  • Teva pharmaceuticals usa inc
  • Tg united labs llc
  • Usl pharma inc
  • Vangard laboratories inc div midway medical co
  • Warner chilcott div warner lambert co
  • Whiteworth towne paulsen inc
  • Halsey drug co inc
  • Merck and co inc
  • Abbott laboratories pharmaceutical products div
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Niferex-150 Forte 100 80-70 mg capsule Box 109.86 USD box
Niferex 100 mg/5ml Elixir 236ml Bottle 80.55 USD bottle
Niferex 100 40-20 mg capsule Box 77.99 USD box
Capozide 50-25 mg tablet 3.63 USD tablet
Ziac 10-6.25 mg tablet 3.6 USD tablet
Ziac 2.5-6.25 mg tablet 3.6 USD tablet
Ziac 5-6.25 mg tablet 3.6 USD tablet
Capozide 50-15 tablet 3.49 USD tablet
Capozide 50-25 tablet 3.49 USD tablet
Capozide 50-15 mg tablet 2.59 USD tablet
Lotensin 20 mg tablet 2.25 USD tablet
Lotensin 10 mg tablet 2.09 USD tablet
Lotensin 40 mg tablet 2.09 USD tablet
Lotensin 5 mg tablet 2.09 USD tablet
Accuretic 20-12.5 mg tablet 2.04 USD tablet
Capozide 25-15 tablet 2.03 USD tablet
Capozide 25-25 tablet 2.03 USD tablet
Accuretic 10-12.5 mg tablet 2.0 USD tablet
Accuretic 20-25 mg tablet 2.0 USD tablet
Lotensin HCT 20-12.5 mg tablet 1.97 USD tablet
Lotensin HCT 10-12.5 mg tablet 1.95 USD tablet
Lotensin HCT 20-25 mg tablet 1.94 USD tablet
Lotensin hct 10-12.5 tablet 1.9 USD tablet
Lotensin hct 20-12.5 tablet 1.9 USD tablet
Lotensin hct 20-25 tablet 1.9 USD tablet
Lotensin hct 5-6.25 tablet 1.9 USD tablet
Niferex-150 150-50-50 mg capsule 1.62 USD capsule
Capozide 25-15 mg tablet 1.51 USD tablet
Lotensin HCT 5-6.25 mg tablet 1.31 USD tablet
Hydrochlorothiazide powder 1.1 USD g
Hydrochlorothiazide 12.5 mg tablet 0.82 USD tablet
Moduretic 5-50 mg tablet 0.68 USD tablet
Hydrochlorothiazide 12.5 mg capsule 0.5 USD capsule
Hydrochlorothiazide 50 mg tablet 0.16 USD tablet
Apo-Hydro 100 mg Tablet 0.13 USD tablet
Hydrochlorothiazide 25 mg tablet 0.11 USD tablet
Apo-Hydro 50 mg Tablet 0.06 USD tablet
Novo-Hydrazide 50 mg Tablet 0.06 USD tablet
Apo-Hydro 25 mg Tablet 0.04 USD tablet
Novo-Hydrazide 25 mg Tablet 0.04 USD tablet
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 274 °C PhysProp
water solubility 722 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP -0.07 HANSCH,C ET AL. (1995)
logS -2.62 ADME Research, USCD
Caco2 permeability -6.06 ADME Research, USCD
pKa 7.9 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 2.24e+00 g/l ALOGPS
logP -0.16 ALOGPS
logP -0.58 ChemAxon
logS -2.1 ALOGPS
pKa (strongest acidic) 9.09 ChemAxon
pKa (strongest basic) -2.7 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 118.36 ChemAxon
rotatable bond count 1 ChemAxon
refractivity 63.11 ChemAxon
polarizability 25.35 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00340 Link_out
BindingDB 13076 Link_out
Therapeutic Targets Database DAP000750 Link_out
PharmGKB PA449899 Link_out
Drug Product Database 2247386 Link_out
RxList http://www.rxlist.com/cgi/generic/hctz.htm Link_out
Drugs.com http://www.drugs.com/hctz.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Hydrochlorothiazide Link_out
ATC Codes
  • C03AA03
AHFS Codes
  • 40:28.20
PDB Entries Not Available
FDA label Not Available
MSDS show (72.7 KB)
Interactions
Drug Interactions
Drug Interaction
Deslanoside Possible electrolyte variations and arrhythmias
Diazoxide Significant hyperglycemic effect
Digitoxin Possible electrolyte variations and arrhythmias
Digoxin Possible electrolyte variations and arrhythmias
Dofetilide Increased risk of cardiotoxicity and arrhythmias
Indacaterol Concomitant therapy may increase the risk of hypokalemia via intracellular shunting. Monitor for adverse effects and especially for cardiovascular effects associated with hypokalemia.
Lithium The thiazide diuretic, hydrochlorothiazide, may increase serum levels of lithium.
Tenoxicam Tenoxicam may antagonize the blood pressure lowering effect of Hydrochlorothiazide. Monitor for changes in the therapeutic effect of Hydrochlorothiazide if Tenoxicam is initiated, discontinued or dose changed.
Trandolapril The thiazide diuretic, Hydrochlorothiazide, may increase the hypotensive effect of Trandolapril. Hydrochlorothiazide may also increase the nephrotoxicity of Trandolapril. Monitor for postural hypotension at initiation of concomitant therapy and renal dysfunction during chronic therapy.
Treprostinil Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Food Interactions
  • Avoid alcohol.
  • Avoid excess salt/sodium unless otherwise instructed by your physician.
  • Avoid natural licorice.
  • Do not take calcium, aluminum, magnesium or Iron supplements within 2 hours of taking this medication.
  • Increase potassium intake; add a banana or orange juice; unless instructed otherwise.
  • Take with food.
Targets

1. Solute carrier family 12 member 3

Pharmacological action: yes
Actions: inhibitor

Electrically silent transporter system. Mediates sodium and chloride reabsorption

Organism class: human
UniProt ID: P55017 Link_out
Gene: SLC12A3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Ran XW, Wang C, Dai F, Jiang JJ, Tong NW, Li XJ, Liang JZ: [A case of Gitelman’s syndrome presenting with severe hypocalcaemia and hypokalemic periodic paralysis] Sichuan Da Xue Xue Bao Yi Xue Ban. 2005 Jul;36(4):583-7. Pubmed
  3. Turner ST, Schwartz GL, Chapman AB, Boerwinkle E: WNK1 kinase polymorphism and blood pressure response to a thiazide diuretic. Hypertension. 2005 Oct;46(4):758-65. Epub 2005 Sep 19. Pubmed
  4. Abuladze N, Yanagawa N, Lee I, Jo OD, Newman D, Hwang J, Uyemura K, Pushkin A, Modlin RL, Kurtz I: Peripheral blood mononuclear cells express mutated NCCT mRNA in Gitelman’s syndrome: evidence for abnormal thiazide-sensitive NaCl cotransport. J Am Soc Nephrol. 1998 May;9(5):819-26. Pubmed
  5. Barry EL, Gesek FA, Kaplan MR, Hebert SC, Friedman PA: Expression of the sodium-chloride cotransporter in osteoblast-like cells: effect of thiazide diuretics. Am J Physiol. 1997 Jan;272(1 Pt 1):C109-16. Pubmed
  6. Kurschat C, Heering P, Grabensee B: [Gitelman’s syndrome: an important differential diagnosis of hypokalemia] Dtsch Med Wochenschr. 2003 May 30;128(22):1225-8. Pubmed

2. Carbonic anhydrase 1

Pharmacological action: unknown
Actions: inhibitor

Reversible hydration of carbon dioxide

Organism class: human
UniProt ID: P00915 Link_out
Gene: CA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Puscas I, Coltau M, Baican M, Domuta G, Hecht A: Vasodilatory effect of diuretics is dependent on inhibition of vascular smooth muscle carbonic anhydrase by a direct mechanism of action. Drugs Exp Clin Res. 1999;25(6):271-9. Pubmed
  2. Couloigner V, Loiseau A, Sterkers O, Amiel C, Ferrary E: Effect of locally applied drugs on the endolymphatic sac potential. Laryngoscope. 1998 Apr;108(4 Pt 1):592-8. Pubmed
  3. Temperini C, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide, and furosemide X-ray crystal structures in adducts with isozyme II, when several water molecules make the difference. Bioorg Med Chem. 2009 Feb 1;17(3):1214-21. Epub 2008 Dec 24. Pubmed

3. Carbonic anhydrase 2

Pharmacological action: unknown
Actions: inhibitor

Reversible hydration of carbon dioxide

Organism class: human
UniProt ID: P00918 Link_out
Gene: CA2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Meyerson LR, Nesta D: [3H]acetazolamide binding to carbonic anhydrase in normal and transformed cells. Biochem Pharmacol. 1991 Mar 15-Apr 1;41(6-7):995-1000. Pubmed
  4. Schaeffer P, Vigne P, Frelin C, Lazdunski M: Identification and pharmacological properties of binding sites for the atypical thiazide diuretic, indapamide. Eur J Pharmacol. 1990 Jul 17;182(3):503-8. Pubmed
  5. Temperini C, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide, and furosemide X-ray crystal structures in adducts with isozyme II, when several water molecules make the difference. Bioorg Med Chem. 2009 Feb 1;17(3):1214-21. Epub 2008 Dec 24. Pubmed

4. Carbonic anhydrase 4

Pharmacological action: unknown
Actions: inhibitor

Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4

Organism class: human
UniProt ID: P22748 Link_out
Gene: CA4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Puscas I, Coltau M, Baican M, Domuta G, Hecht A: Vasodilatory effect of diuretics is dependent on inhibition of vascular smooth muscle carbonic anhydrase by a direct mechanism of action. Drugs Exp Clin Res. 1999;25(6):271-9. Pubmed
  2. Temperini C, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide, and furosemide X-ray crystal structures in adducts with isozyme II, when several water molecules make the difference. Bioorg Med Chem. 2009 Feb 1;17(3):1214-21. Epub 2008 Dec 24. Pubmed

5. Carbonic anhydrase 9

Pharmacological action: unknown
Actions: inhibitor

Reversible hydration of carbon dioxide. May be involved in the control of cell proliferation and transformation. Appears to be a novel specific biomarker for a cervical neoplasia

Organism class: human
UniProt ID: Q16790 Link_out
Gene: CA9
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Temperini C, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide, and furosemide X-ray crystal structures in adducts with isozyme II, when several water molecules make the difference. Bioorg Med Chem. 2009 Feb 1;17(3):1214-21. Epub 2008 Dec 24. Pubmed

6. Carbonic anhydrase 12

Pharmacological action: unknown
Actions: inhibitor

Reversible hydration of carbon dioxide

Organism class: human
UniProt ID: O43570 Link_out
Gene: CA12 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Temperini C, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide, and furosemide X-ray crystal structures in adducts with isozyme II, when several water molecules make the difference. Bioorg Med Chem. 2009 Feb 1;17(3):1214-21. Epub 2008 Dec 24. Pubmed

7. Calcium-activated potassium channel subunit alpha 1

Pharmacological action: unknown
Actions: other/unknown

Potassium channel activated by both membrane depolarization or increase in cytosolic Ca(2+) that mediates export of K(+). It is also activated by the concentration of cytosolic Mg(2+). Its activation dampens the excitatory events that elevate the cytosolic Ca(2+) concentration and/or depolarize the cell membrane. It therefore contributes to repolarization of the membrane potential. Plays a key role in controlling excitability in a number of systems, such as regulation of the contraction of smooth muscle, the tuning of hair cells in the cochlea, regulation of transmitter release, and innate immunity. In smooth muscles, its activation by high level of Ca(2+), caused by ryanodine receptors in the sarcoplasmic reticulum, regulates the membrane potential. In cochlea cells, its number and kinetic properties partly determine the characteristic frequency of each hair cell and thereby helps to establish a tonotopic map. Kinetics of KCNMA1 channels are determined by alternative splicing, phosphorylation status and its combination with modulating beta subunits. Highly sensitive to both iberiotoxin (IbTx) and charybdotoxin (CTX)

Organism class: human
UniProt ID: Q12791 Link_out
Gene: KCNMA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Tricarico D, Barbieri M, Mele A, Carbonara G, Camerino DC: Carbonic anhydrase inhibitors are specific openers of skeletal muscle BK channel of K+-deficient rats. FASEB J. 2004 Apr;18(6):760-1. Epub 2004 Feb 6. Pubmed
Transporters

1. Solute carrier family 22 member 6

Actions: inhibitor
UniProt ID: Q4U2R8 Link_out
Gene: hROAT1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Race JE, Grassl SM, Williams WJ, Holtzman EJ: Molecular cloning and characterization of two novel human renal organic anion transporters (hOAT1 and hOAT3). Biochem Biophys Res Commun. 1999 Feb 16;255(2):508-14. Pubmed
  2. Uwai Y, Saito H, Hashimoto Y, Inui KI: Interaction and transport of thiazide diuretics, loop diuretics, and acetazolamide via rat renal organic anion transporter rOAT1. J Pharmacol Exp Ther. 2000 Oct;295(1):261-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19