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Record Information
Creation Date2006-05-18 08:41:17 UTC
Update Date2016-02-11 01:05:07 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameHydrochlorothiazide
DescriptionHydrochlorothiazide is 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. Hydrochlorothiazide (Apo-Hydro, Aquazide H, Microzide, Oretic), sometimes abbreviated HCT, HCTZ, or HZT is a popular diuretic drug that acts by inhibiting the kidney's ability to retain water. This reduces the volume of the blood, decreasing peripheral vascular resistance. Chlorothiazide, a carbonic anhydrase inhibitor. --Wikipedia.
  1. 3,4-Dihydrochlorothiazide
  2. Acuretic
  3. Aldactazide
  4. Aldoril
  5. Apresazide
  6. Aquarills
  7. Aquarius
  8. Bremil
  9. Caplaril
  10. Capozide
  11. Chlorosulthiadil
  12. Chlorothiazide
  13. Chlorsulfonamidodihydrobenzothiadiazine dioxide
  14. Chlorzide
  15. Cidrex
  16. Dichlorosal
  17. Dichlotiazid
  18. Dichlotride
  19. Diclotride
  20. Dihydrochlorothiazid
  21. Dihydrochlorothiazide
  22. Dihydrochlorothiazidum
  23. Dihydrochlorurit
  24. Dihydrochlorurite
  25. Dihydroxychlorothiazidum
  26. Direma
  27. Disalunil
  28. Diuril
  29. Drenol
  30. Dyazide
  31. Esidrex
  32. Esidrix
  33. Esimil
  34. Fluvin
  35. HCTZ
  36. HCZ
  37. Hidril
  38. Hidrochlortiazid
  39. Hidroronol
  40. Hidrotiazida
  41. Hydril
  42. Hydro-Aquil
  43. Hydro-D
  44. Hydro-Diuril
  45. Hydrochloro Thiazide
  46. Hydrochlorothiazid
  47. Hydrochlorothiazide
  48. Hydrochlorothiazide Intensol
  49. Hydrochlorthiazide
  50. Hydrodiuretic
  51. Hydrodiuril
  52. Hydropres
  53. Hydrosaluric
  54. Hydrothide
  55. Hydrozide
  56. Hypothiazid
  57. Hypothiazide
  58. Hyzaar
  59. Idrotiazide
  60. Inderide
  61. Ivaugan
  62. Jen-Diril
  63. Lopressor HCT
  64. Lotensin HCT
  65. Maschitt
  66. Maxzide
  67. Megadiuril
  68. Microzide
  69. Moduretic
  70. Nefrix
  71. Neo-codema
  72. Neoflumen
  73. Newtolide
  74. Oretic
  75. Panurin
  76. Prinzide
  77. Ro-hydrazide
  78. Ser-Ap-Es
  79. Servithiazid
  80. Thiaretic
  81. Thiuretic
  82. Thlaretic
  83. Timolide
  84. Unipres
  85. Urodiazin
  86. Vaseretic
  87. Vetidrex
  88. Ziac
  89. Zide
Chemical FormulaC7H8ClN3O4S2
Average Molecular Weight297.739
Monoisotopic Molecular Weight296.964474846
IUPAC Name6-chloro-1,1-dioxo-3,4-dihydro-2H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide
Traditional Namehydrochlorothiazide
CAS Registry Number58-93-5
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzothiadiazines. These are organic compounds containing a benzene fused to a thiadiazine ring (a six-member ring with two nitrogen atoms and a sulfur atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
Sub ClassBenzothiadiazines
Direct ParentBenzothiadiazines
Alternative Parents
  • Benzothiadiazine
  • Benzenesulfonamide
  • Secondary aliphatic/aromatic amine
  • Chlorobenzene
  • Benzenoid
  • Aryl halide
  • Aryl chloride
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Azacycle
  • Secondary amine
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
StatusDetected and Quantified
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
Experimental Properties
Melting Point274 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.722 mg/mL at 25 °CNot Available
LogP-0.07HANSCH,C ET AL. (1995)
Predicted Properties
Water Solubility2.24 mg/mLALOGPS
pKa (Strongest Acidic)9.09ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.36 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity63.11 m3·mol-1ChemAxon
Polarizability25.35 Å3ChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00z0000000-aaa48e4702874457ae26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0za0000000-b129acf72e7dde12441eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-4z00000000-67f803f38aed0bd12adeView in MoNA
MSMass Spectrum (Electron Ionization)splash10-qfz0000000-3f5d9320308b823c6489View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Adipose Tissue
  • Kidney
  • Platelet
Hydrochlorothiazide PathwaySMP00100Not Available
Normal Concentrations
BloodDetected and Quantified0.3 (0.00167-0.67) uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00999
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022745
KNApSAcK IDNot Available
Chemspider ID3513
KEGG Compound IDC07041
BiGG IDNot Available
Wikipedia LinkHydrochlorothiazide
NuGOwiki LinkHMDB01928
Metagene LinkHMDB01928
PubChem Compound3639
ChEBI ID102045
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Splendiani G, Condo S: [Diuretic therapy in heart failure] G Ital Nefrol. 2006 Jan-Feb;23 Suppl 34:S74-6. [16634001 ]
  2. Dimitriadis G, Tegos C, Golfinopoulou L, Roboti C, Raptis S: Furosemide-induced hyperglycaemia: the implication of glycolytic kinases. Horm Metab Res. 1993 Nov;25(11):557-9. [8288156 ]
  3. Vandenheuvel WJ, Gruber VF, Walker RW, Wolf FJ: GLC analysis of hydrochlorothiazide in blood and plasma. J Pharm Sci. 1975 Aug;64(8):1309-12. [1151702 ]
  4. Yamazaki M, Ito Y, Suzuka T, Yaginuma H, Itoh S, Kamada A, Orita Y, Nakahama H, Nakanishi T, Ando A: Biopharmaceutical studies of thiazide diuretics. II. High-performance liquid chromatographic method for determination of hydrochlorothiazide in plasma, urine, blood cells and bile. Chem Pharm Bull (Tokyo). 1984 Jun;32(6):2387-94. [6488407 ]
  5. Germano G, Sanguigni V, Pignatelli P, Caccese D, Lenti L, Ragazzo M, Lauro R, Violi F: Enhanced platelet release of superoxide anion in systemic hypertension: role of AT1 receptors. J Hypertens. 2004 Jun;22(6):1151-6. [15167450 ]
  6. Bernik MM, Heimann JC, Nakandakare ER, Cazita PM, Nunes VS, Rocha JC, Neves MQ, Quintao EC: Effects of hydrochlorothiazide and propranolol treatment on chylomicron metabolism in hypertensive objects. Can J Physiol Pharmacol. 2005 Jul;83(7):617-23. [16091787 ]
  7. Dornhorst A, Powell SH, Pensky J: Aggravation by propranolol of hyperglycaemic effect of hydrochlorothiazide in type II diabetics without alteration of insulin secretion. Lancet. 1985 Jan 19;1(8421):123-6. [2857210 ]
  8. Serradeil-Le Gal C, Lacour C, Valette G, Garcia G, Foulon L, Galindo G, Bankir L, Pouzet B, Guillon G, Barberis C, Chicot D, Jard S, Vilain P, Garcia C, Marty E, Raufaste D, Brossard G, Nisato D, Maffrand JP, Le Fur G: Characterization of SR 121463A, a highly potent and selective, orally active vasopressin V2 receptor antagonist. J Clin Invest. 1996 Dec 15;98(12):2729-38. [8981918 ]
  9. Kuo BS, Mandagere A, Osborne DR, Hwang KK: Column-switching high-performance liquid chromatographic (HPLC) determination of hydrochlorothiazide in rat, dog, and human plasma. Pharm Res. 1990 Dec;7(12):1257-61. [2095563 ]
  10. Cubeddu LX, Hoffmann IS, Davila S, Escontrelas C, Morales C, Rios A: Effects of propranolol, clonidine and hydrochlorothiazide treatment and abrupt discontinuation on central and peripheral noradrenergic activity in essential hypertension. Life Sci. 1986 Dec 22;39(25):2463-74. [3540504 ]
  11. Angelin B: Effect of thiazide treatment on biliary lipid composition in healthy volunteers. Eur J Clin Pharmacol. 1989;37(1):95-6. [2591472 ]
  12. Buttar HS: An overview of the influence of ACE inhibitors on fetal-placental circulation and perinatal development. Mol Cell Biochem. 1997 Nov;176(1-2):61-71. [9406146 ]
  13. Tisdall PA, Moyer TP, Anhalt JP: Liquid-chromatographic detection of thiazide diuretics in urine. Clin Chem. 1980 May;26(6):702-6. [7371146 ]
  14. Beermann B, Fahraeus L, Groschinsky-Grind M, Lindstrom B: Placental transfer of hydrochlorothiazide. Gynecol Obstet Invest. 1980;11(1):45-8. [7390276 ]
  15. Vonaparti A, Kazanis M, Panderi I: Development and validation of a liquid chromatographic/electrospray ionization mass spectrometric method for the determination of benazepril, benazeprilat and hydrochlorothiazide in human plasma. J Mass Spectrom. 2006 May;41(5):593-605. [16541390 ]


General function:
Involved in ion 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 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)
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General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:
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General function:
Involved in carbonate dehydratase activity
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 into the anterior chamber of the eye.
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General function:
Involved in transport
Specific function:
Electrically silent transporter system. Mediates sodium and chloride reabsorption
Gene Name:
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Molecular weight:
General function:
Involved in carbonate dehydratase activity
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 and retina epithelium, and acid release in the choriocapillaris in the choroid.
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