Synonym
Quinethazone; Chinethazonum; Quinethazon; Quinethazonum; Aquamox; Hydromox; quinethazone, (+)-isomer; quinethazone, (+-)-isomer; quinethazone, (-)-isomer;
IUPAC/Chemical Name
7-chloro-2-ethyl-4-oxo-2,3-dihydro-1H-quinazoline-6-sulfonamide
InChi Key
AGMMTXLNIQSRCG-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H12ClN3O3S/c1-2-9-13-7-4-6(11)8(18(12,16)17)3-5(7)10(15)14-9/h3-4,9,13H,2H2,1H3,(H,14,15)(H2,12,16,17)
SMILES Code
CCC1NC2=CC(=C(C=C2C(=O)N1)S(=O)(=O)N)Cl
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Quinethazone inhibits active chloride reabsorption at the early distal tubule via the Na-Cl cotransporter, resulting in an increase in the excretion of sodium, chloride, and water. Quinethazone also inhibits sodium ion transport across the renal tubular epithelium The antihypertensive mechanism of quinethazone is less well understood.
In vivo activity:
The additive natriuretic effects of single doses of quinethazone or bendroflumethiazide have been studied in patients with advanced congestive heart failure receiving longterm treatment with furosemide and spironolactone daily. Since the combined effects of all three drugs involve a tendency to development of hypokalaemia, hypochloraemia and alkalosis, it is recommended that quinethazone or bendroflumethiazide use is combined with the administration of potassium chloride.
Reference: Acta Medica Scandinavica, 190(3), 233–240. https://onlinelibrary.wiley.com/doi/abs/10.1111/j.0954-6820.1971.tb07423.x
Preparing Stock Solutions
The following data is based on the
product
molecular weight
289.74
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Zhang Z , Luo D , Xie J , Lin G , Zhou J , Liu W , Li H , Yi T , Su Z , Chen J . Octahydrocurcumin, a final hydrogenated metabolite of curcumin, possesses superior anti-tumor activity through induction of cellular apoptosis. Food Funct. 2018 Apr 25;9(4):2005-2014. doi: 10.1039/c7fo02048a. PMID: 29616245.
2. Olesen, K. H., & Sigurd, B. (1971). The supra-additive natriuretic effect addition of quinethazone or bendroflumethiazide during long-term treatment with furosemide and spironolactone. Permutation trial tests in patients with congestive heart failure. Acta Medica Scandinavica, 190(3), 233–240. https://doi.org/10.1111/j.0954-6820.1971.tb07423.x
In vivo protocol:
1. Zhang Z , Luo D , Xie J , Lin G , Zhou J , Liu W , Li H , Yi T , Su Z , Chen J . Octahydrocurcumin, a final hydrogenated metabolite of curcumin, possesses superior anti-tumor activity through induction of cellular apoptosis. Food Funct. 2018 Apr 25;9(4):2005-2014. doi: 10.1039/c7fo02048a. PMID: 29616245.
2. Olesen, K. H., & Sigurd, B. (1971). The supra-additive natriuretic effect addition of quinethazone or bendroflumethiazide during long-term treatment with furosemide and spironolactone. Permutation trial tests in patients with congestive heart failure. Acta Medica Scandinavica, 190(3), 233–240. https://doi.org/10.1111/j.0954-6820.1971.tb07423.x
1: Carta F, Supuran CT. Diuretics with carbonic anhydrase inhibitory action: a patent and literature review (2005 - 2013). Expert Opin Ther Pat. 2013;23(6):681-91. doi: 10.1517/13543776.2013.780598. Epub 2013 Mar 14. PMID: 23488823.
2: Temperini C, Cecchi A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Sulfonamide diuretics revisited--old leads for new applications? Org Biomol Chem. 2008 Jul 21;6(14):2499-506. doi: 10.1039/b800767e. Epub 2008 May 29. PMID: 18600270.
3: Temperini C, Cecchi A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for the indapamide-isozyme II adduct. Bioorg Med Chem Lett. 2008 Apr 15;18(8):2567-73. doi: 10.1016/j.bmcl.2008.03.051. Epub 2008 Mar 20. PMID: 18374572.
4: Supuran CT. Diuretics: from classical carbonic anhydrase inhibitors to novel applications of the sulfonamides. Curr Pharm Des. 2008;14(7):641-8. doi: 10.2174/138161208783877947. PMID: 18336309.
5: Takihi N, Zhang YP, Klopman G, Rosenkranz HS. An approach for evaluating and increasing the informational content of mutagenicity and clastogenicity data bases. Mutagenesis. 1993 May;8(3):257-64. doi: 10.1093/mutage/8.3.257. PMID: 8332089.
6: Lisi AM, Kazlauskas R, Trout GJ. Diuretic screening in human urine by gas chromatography-mass spectrometry: use of a macroreticular acrylic copolymer for the efficient removal of the coextracted phase-transfer reagent after derivatization by direct extractive alkylation. J Chromatogr. 1992 Oct 2;581(1):57-63. doi: 10.1016/0378-4347(92)80447-x. PMID: 1430008.
7: Cooper SF, Massé R, Dugal R. Comprehensive screening procedure for diuretics in urine by high-performance liquid chromatography. J Chromatogr. 1989 Apr 7;489(1):65-88. doi: 10.1016/s0378-4347(00)82884-4. PMID: 2745658.
8: Fullinfaw RO, Bury RW, Moulds RF. Liquid chromatographic screening of diuretics in urine. J Chromatogr. 1987 Apr 10;415(2):347-56. doi: 10.1016/s0378-4347(00)83226-0. PMID: 3584373.
9: Poulter NR, Sanderson JE. Reserpine versus beta-blocker as an additive to a diuretic in the treatment of Kenyan hypertensives. East Afr Med J. 1986 Jun;63(6):412-6. PMID: 3769850.
10: Chan PS, Poorvin D. Sequential method for combined screening antihypertensive and diuretic agents in the same spontaneously hypertensive rat (SHR). Clin Exp Hypertens (1978). 1979;1(6):817-30. doi: 10.3109/10641967909068641. PMID: 551899.
11: Clark DW, Goldberg LI. Guancydine: a new antihypertensive agent. Use with quinethazone and guanethidine or propranolol. Ann Intern Med. 1972 Apr;76(4):579-85. doi: 10.7326/0003-4819-76-4-579. PMID: 4565483.
12: Olesen KH, Sigurd B. The supra-additive natriuretic effect addition of quinethazone or bendroflumethiazide during long-term treatment with furosemide and spironolactone. Permutation trial tests in patients with congestive heart failure. Acta Med Scand. 1971 Sep;190(3):233-40. doi: 10.1111/j.0954-6820.1971.tb07423.x. PMID: 4941227.
13: Olesen KH. The natriuretic effect addition of quinethazone and furosemide in congestive heart failure. A permutation trial test. Acta Med Scand. 1971 Sep;190(3):229-32. doi: 10.1111/j.0954-6820.1971.tb07422.x. PMID: 4941226.
14: Pilewski RM, Scheib ET, Misage JR, Kessler E, Krifcher E, Shapiro AP. Technique of controlled drug assay in hypertension. V. Comparison of hydrochlorothiazide with a new quinethazone diuretic, metolazone. Clin Pharmacol Ther. 1971 Sep-Oct;12(5):843-8. doi: 10.1002/cpt1971125843. PMID: 4936150.
15: Zeneroli ML. Effetto antidiuretico del chinetazone del diabete insipido [Antidiuretic effect of quinethazone in diabetes insipidus]. Endocrinol Sci Cost. 1970 May;31(2):135-40. Italian. PMID: 5470189.
16: Olesen KH, Dupont B, Flensted-Jensen E. The combined diuretic action of quinethazone and furosemide in congestive heart failure. A permutation trial test. Acta Med Scand. 1970 Jan-Feb;187(1-2):33-40. doi: 10.1111/j.0954-6820.1970.tb02903.x. PMID: 4912468.
17: Parkes WE, Agarwal AP, Hunt LB. Treatment of hypertension with quinethazone alone or in combination with reserpine. Practitioner. 1969 Aug;203(214):194-8. PMID: 4896145.
18: Mathew TH, Kincaid-Smith P, Doyle AE, Baird CW. A comparison of the hyperuricaemic effect of chlorothiazide and quinethazone. Med J Aust. 1967 Mar 11;1(10):493-5. doi: 10.5694/j.1326-5377.1967.tb21409.x. PMID: 6022910.
19: Romero RL, Maljar L, Valdivia-Velarde H, Vives C, Toffoli de Matheos M. Quinetazona-K en la hipertensión arterial [Quinethazone-K in arterial hypertension]. Rev Clin Esp. 1967 Jan 31;104(2):139-47. Spanish. PMID: 5596061.
20: Ludwig HJ, Rahnema A. Zur Behandlung des Altershochdrucks mit Quinethazone- Reserpin-Kalium [On the treatment of hypertension in aged with quinethazone- reserpine-potassium]. Med Welt. 1966 Nov 19;47:2560-5. German. PMID: 5955414.
