Hydroflumethiazide

Identification

Summary

Hydroflumethiazide is a thiazide diuretic used to treat hypertension as well as edema due to congestive heart failure and liver cirrhosis.

Brand Names
Saluron
Generic Name
Hydroflumethiazide
DrugBank Accession Number
DB00774
Background

A thiazide diuretic with actions and uses similar to those of hydrochlorothiazide. (From Martindale, The Extra Pharmacopoeia, 30th ed, p822)

Type
Small Molecule
Groups
Approved, Investigational, Withdrawn
Structure
Weight
Average: 331.292
Monoisotopic: 330.990831754
Chemical Formula
C8H8F3N3O4S2
Synonyms
  • Dihydroflumethazide
  • Hidroflumetiazid
  • Hidroflumetiazida
  • Hydrofluméthiazide
  • Hydroflumethiazide
  • Hydroflumethiazidum
  • Idroflumetiazide
  • Metforylthiadiazin

Pharmacology

Indication

Used as adjunctive therapy in edema associated with congestive heart failure, hepatic cirrhosis, and corticosteroid and estrogen therapy. Also used in the management of hypertension either as the sole therapeutic agent or to enhance the effect of other antihypertensive drugs in the more severe forms of hypertension.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Adjunct therapy in treatment ofEdema••••••••••••••••••
Adjunct therapy in treatment ofEdema••••••••••••••••••
Adjunct therapy in treatment ofEdema••••••••••••••••••
Adjunct therapy in treatment ofEdema••••••••••••••••••
Adjunct therapy in treatment ofEdema••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Hydroflumethiazide is an oral thiazide used to treat hypertension and edema. High blood pressure adds to the workload of the heart and arteries. If it continues for a long time, the heart and arteries may not function properly. This can damage the blood vessels of the brain, heart, and kidneys, resulting in a stroke, heart failure, or kidney failure. High blood pressure may also increase the risk of heart attacks. Like other thiazides, Hydroflumethiazide promotes water loss from the body (diuretics). Thiazides 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

Hydroflumethiazide is a thiazide diuretic that 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, Hydroflumethiazide effectively reduces the osmotic gradient and water reabsorption throughout the nephron.

TargetActionsOrganism
ASolute carrier family 12 member 1
inhibitor
Humans
UCarbonic anhydrase 7
inhibitor
Humans
UCarbonic anhydrase 9
inhibitor
Humans
USodium/potassium-transporting ATPase subunit alpha-1
inducer
Humans
UCalcium-activated potassium channel subunit alpha-1
inducer
Humans
UCarbonic anhydrase 1
inhibitor
Humans
UCarbonic anhydrase 2
inhibitor
Humans
UCarbonic anhydrase 4
inhibitor
Humans
UCarbonic anhydrase 12
inhibitor
Humans
Absorption

Hydroflumethiazide is incompletely but fairly rapidly absorbed from the gastrointestinal tract

Volume of distribution

Not Available

Protein binding

74%

Metabolism

Essentially unchanged

Route of elimination

Not Available

Half-life

It appears to have a biphasic biological half-life with an estimated alpha-phase of about 2 hours and an estimated beta-phase of about 17 hours

Clearance

Not Available

Adverse Effects
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Toxicity

Overdoses lead to diuresis, lethargy progressing to coma, with minimal cardiorespiratory depression and with or without significant serum electrolyte changes or dehydration.

Pathways
PathwayCategory
Hydroflumethiazide Action PathwayDrug 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.
DrugInteraction
AbacavirHydroflumethiazide may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy.
AbaloparatideThe risk or severity of adverse effects can be increased when Hydroflumethiazide is combined with Abaloparatide.
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Hydroflumethiazide.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Hydroflumethiazide.
AcebutololThe therapeutic efficacy of Acebutolol can be increased when used in combination with Hydroflumethiazide.
Food Interactions
  • Increase consumption of potassium-rich foods. This medication may cause a loss of potassium.

Products

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International/Other Brands
Leodrine (Leo)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
SaluronTablet50 mg/1OralUNSPECIFIED2006-07-19Not applicableUS flag

Categories

ATC Codes
C03AA02 — HydroflumethiazideG01AE10 — Combinations of sulfonamidesC03AH02 — Hydroflumethiazide, combinationsC03AB02 — Hydroflumethiazide and potassium
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 1,2,4-benzothiadiazine-1,1-dioxides. These are aromatic heterocyclic compounds containing a 1,2,4-benzothiadiazine ring system with two S=O bonds at the 1-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Thiadiazines
Sub Class
Benzothiadiazines
Direct Parent
1,2,4-benzothiadiazine-1,1-dioxides
Alternative Parents
Secondary alkylarylamines / Organosulfonamides / Benzenoids / Aminosulfonyl compounds / Azacyclic compounds / Organopnictogen compounds / Organofluorides / Organic oxides / Hydrocarbon derivatives / Alkyl fluorides
Substituents
1,2,4-benzothiadiazine-1,1-dioxide / Alkyl fluoride / Alkyl halide / Amine / Aminosulfonyl compound / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Hydrocarbon derivative / Organic nitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
benzothiadiazine (CHEBI:5784)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
501CFL162R
CAS number
135-09-1
InChI Key
DMDGGSIALPNSEE-UHFFFAOYSA-N
InChI
InChI=1S/C8H8F3N3O4S2/c9-8(10,11)4-1-5-7(2-6(4)19(12,15)16)20(17,18)14-3-13-5/h1-2,13-14H,3H2,(H2,12,15,16)
IUPAC Name
1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-1lambda6,2,4-benzothiadiazine-7-sulfonamide
SMILES
NS(=O)(=O)C1=CC2=C(NCNS2(=O)=O)C=C1C(F)(F)F

References

Synthesis Reference

U.S. Patent 3,254,076.

General References
  1. Moser M, Feig PU: Fifty years of thiazide diuretic therapy for hypertension. Arch Intern Med. 2009 Nov 9;169(20):1851-6. doi: 10.1001/archinternmed.2009.342. [Article]
  2. FDA Approved Drug Products: Saluron Hydroflumethiazide Oral Tablets [Link]
Human Metabolome Database
HMDB0014912
KEGG Drug
D00654
KEGG Compound
C07763
PubChem Compound
3647
PubChem Substance
46505220
ChemSpider
3521
BindingDB
25897
RxNav
5495
ChEBI
5784
ChEMBL
CHEMBL1763
ZINC
ZINC000000897225
Therapeutic Targets Database
DAP000747
PharmGKB
PA164752557
PDBe Ligand
HFZ
RxList
RxList Drug Page
Wikipedia
Hydroflumethiazide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableWithdrawnNot AvailableHypertension1

Pharmacoeconomics

Manufacturers
  • Wyeth ayerst laboratories
  • Par pharmaceutical inc
  • Watson laboratories inc
  • Shire development inc
Packagers
  • Shire Inc.
Dosage Forms
FormRouteStrength
TabletOral50 mg/1
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)272-273U.S. Patent 3,254,076.
water solubility300 mg/L (at 25 °C)MERCK INDEX (1996)
logP0.36HANSCH,C ET AL. (1995)
pKa8.9BUDAVARI,S ET AL. (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.858 mg/mLALOGPS
logP0.44ALOGPS
logP-0.3Chemaxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9.07Chemaxon
pKa (Strongest Basic)-2.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area118.36 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity64.28 m3·mol-1Chemaxon
Polarizability25.68 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9636
Blood Brain Barrier-0.902
Caco-2 permeable-0.8221
P-glycoprotein substrateNon-substrate0.6668
P-glycoprotein inhibitor INon-inhibitor0.8016
P-glycoprotein inhibitor IINon-inhibitor0.787
Renal organic cation transporterNon-inhibitor0.8592
CYP450 2C9 substrateNon-substrate0.7732
CYP450 2D6 substrateNon-substrate0.8302
CYP450 3A4 substrateNon-substrate0.6442
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9232
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9544
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9324
Ames testNon AMES toxic0.8463
CarcinogenicityNon-carcinogens0.8011
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.1299 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9868
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0udi-1093000000-2f9f0c24bcd8d1681b17
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-03dr-0759000000-a0627a1596dc3c763f34
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03dr-0759000000-a0627a1596dc3c763f34
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-cdf24c9593ec77e14315
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-f6992761bd1e07df9802
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-07fc8797002c83ac7893
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001r-0982000000-413c1cd31be23b6fd234
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-3c2421daa5dd57180939
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-040r-9531000000-ab1cd46ce50d09a7bd68
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-165.1261879
predicted
DarkChem Lite v0.1.0
[M-H]-156.97116
predicted
DeepCCS 1.0 (2019)
[M+H]+165.8500879
predicted
DarkChem Lite v0.1.0
[M+H]+159.36671
predicted
DeepCCS 1.0 (2019)
[M+Na]+165.4522879
predicted
DarkChem Lite v0.1.0
[M+Na]+165.72784
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Sodium:potassium:chloride symporter activity
Specific Function
Electrically silent transporter system. Mediates sodium and chloride reabsorption. Plays a vital role in the regulation of ionic balance and cell volume.
Gene Name
SLC12A1
Uniprot ID
Q13621
Uniprot Name
Solute carrier family 12 member 1
Molecular Weight
121449.13 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide.
Gene Name
CA7
Uniprot ID
P43166
Uniprot Name
Carbonic anhydrase 7
Molecular Weight
29658.235 Da
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. doi: 10.1016/j.bmc.2008.12.023. Epub 2008 Dec 24. [Article]
Details
3. Carbonic anhydrase 9
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. Participates in pH regulation. May be involved in the control of cell proliferation and transformation. Appears to be a novel specific biomarker for a cervic...
Gene Name
CA9
Uniprot ID
Q16790
Uniprot Name
Carbonic anhydrase 9
Molecular Weight
49697.36 Da
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. doi: 10.1016/j.bmc.2008.12.023. Epub 2008 Dec 24. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hormone binding
Specific Function
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates th...
Gene Name
ATP1A1
Uniprot ID
P05023
Uniprot Name
Sodium/potassium-transporting ATPase subunit alpha-1
Molecular Weight
112895.01 Da
References
  1. Goldenberg K, Wergowske G, Chatterjee S, Kezdi P: Effects of thiazide on erythrocyte sodium and potassium concentrations and Na+K+ATPase in hypertensive patients. Clin Exp Hypertens A. 1988;10(1):91-103. doi: 10.3109/10641968809046801. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Voltage-gated potassium channel activity
Specific Function
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 activati...
Gene Name
KCNMA1
Uniprot ID
Q12791
Uniprot Name
Calcium-activated potassium channel subunit alpha-1
Molecular Weight
137558.115 Da
References
  1. Martin P, Moncada M, Kuntamallappanavar G, Dopico AM, Milesi V: Activation of human smooth muscle BK channels by hydrochlorothiazide requires cell integrity and the presence of BK beta1 subunit. Acta Pharmacol Sin. 2018 Mar;39(3):371-381. doi: 10.1038/aps.2017.133. Epub 2017 Nov 30. [Article]
Details
6. Carbonic anhydrase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name
CA1
Uniprot ID
P00915
Uniprot Name
Carbonic anhydrase 1
Molecular Weight
28870.0 Da
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. doi: 10.1016/j.bmc.2008.12.023. Epub 2008 Dec 24. [Article]
Details
7. Carbonic anhydrase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion in...
Gene Name
CA2
Uniprot ID
P00918
Uniprot Name
Carbonic anhydrase 2
Molecular Weight
29245.895 Da
References
  1. 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. [Article]
  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. doi: 10.1016/j.bmc.2008.12.023. Epub 2008 Dec 24. [Article]
Details
8. Carbonic anhydrase 4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina an...
Gene Name
CA4
Uniprot ID
P22748
Uniprot Name
Carbonic anhydrase 4
Molecular Weight
35032.075 Da
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. doi: 10.1016/j.bmc.2008.12.023. Epub 2008 Dec 24. [Article]
Details
9. Carbonic anhydrase 12
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide.
Gene Name
CA12
Uniprot ID
O43570
Uniprot Name
Carbonic anhydrase 12
Molecular Weight
39450.615 Da
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. doi: 10.1016/j.bmc.2008.12.023. Epub 2008 Dec 24. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Agren A, Back T: Complex formation between macromolecules and drugs. 8. Binding of saccharine, N-methyl saccharine, and the diuretic drugs hydroflumethiazide and bendroflumethiazide to human serum albumin. Acta Pharm Suec. 1973 Jun;10(3):223-8. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Vallon V, Rieg T, Ahn SY, Wu W, Eraly SA, Nigam SK: Overlapping in vitro and in vivo specificities of the organic anion transporters OAT1 and OAT3 for loop and thiazide diuretics. Am J Physiol Renal Physiol. 2008 Apr;294(4):F867-73. doi: 10.1152/ajprenal.00528.2007. Epub 2008 Jan 23. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Vallon V, Rieg T, Ahn SY, Wu W, Eraly SA, Nigam SK: Overlapping in vitro and in vivo specificities of the organic anion transporters OAT1 and OAT3 for loop and thiazide diuretics. Am J Physiol Renal Physiol. 2008 Apr;294(4):F867-73. doi: 10.1152/ajprenal.00528.2007. Epub 2008 Jan 23. [Article]

Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:55