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MedKoo Cat#: 318259 | Name: Metolazone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Metolazone is a thiazide-like diuretic. It is primarily used to treat congestive heart failure and high blood pressure. Metolazone indirectly decreases the amount of water reabsorbed into the bloodstream by the kidney, so that blood volume decreases and urine volume increases. This lowers blood pressure and prevents excess fluid accumulation in heart failure. Metolazone is sometimes used together with loop diuretics such as furosemide or bumetanide, but these highly effective combinations can lead to dehydration and electrolyte abnormalities.

Chemical Structure

Metolazone
Metolazone
CAS#17560-51-9

Theoretical Analysis

MedKoo Cat#: 318259

Name: Metolazone

CAS#: 17560-51-9

Chemical Formula: C16H16ClN3O3S

Exact Mass: 365.0601

Molecular Weight: 365.83

Elemental Analysis: C, 52.53; H, 4.41; Cl, 9.69; N, 11.49; O, 13.12; S, 8.76

Price and Availability

Size Price Availability Quantity
25mg USD 250.00 2 Weeks
100mg USD 550.00 2 Weeks
250mg USD 850.00 2 Weeks
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Related CAS #
50869-23-3 (sodium) 17560-51-9
Synonym
Metolazone, Zytanix, Zaroxolyn, Mykrox, Diulo, Oldren
IUPAC/Chemical Name
7-chloro-2-methyl-3-(2-methylphenyl)-4-oxo-1,2-dihydroquinazoline-6-sulfonamide
InChi Key
AQCHWTWZEMGIFD-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H16ClN3O3S/c1-9-5-3-4-6-14(9)20-10(2)19-13-8-12(17)15(24(18,22)23)7-11(13)16(20)21/h3-8,10,19H,1-2H3,(H2,18,22,23)
SMILES Code
O=S(C1=CC2=C(NC(C)N(C3=CC=CC=C3C)C2=O)C=C1Cl)(N)=O
Appearance
Solid powder
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).
Solubility
Soluble in DMSO, not in water
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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Metolazone (SR-720-22) is primarily used to treat congestive heart failure and high blood pressure.
In vitro activity:
These data showed that metolazone activated hPXR-mediated expression of CYP3A4 and MDR1 in human hepatocytes and intestine cells and increased CYP3A4 promoter activity in various cell lines. Mammalian two-hybrid assays showed that hPXR recruits its co-activator SRC-1 upon metolazone binding in HepG2 cells, explaining the mechanism of hPXR activation. Reference: Biochem Pharmacol. 2014 Nov 15;92(2):389-402. https://pubmed.ncbi.nlm.nih.gov/25181459/
In vivo activity:
This study administered the drug in nondiuretic doses in a rat model of preeclampsia previously developed in this laboratory. The drug reduced BP without an accompanying natriuresis. Metolazone, in low dosage, is an effective antihypertensive in this rat model. Reference: J Pharmacol Exp Ther. 2006 Sep;318(3):1027-32. https://pubmed.ncbi.nlm.nih.gov/16717105/
Solvent mg/mL mM comments
Solubility
DMF 25.0 68.34
DMSO 66.0 180.41
DMSO:PBS (pH 7.2) (1:1) 0.5 1.37
Ethanol 4.2 11.34
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 365.83 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.

Recalculate based on batch purity %
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. Ito A, Zhao Q, Tanaka Y, Yasui M, Katayama R, Sun S, Tanimoto Y, Nishikawa Y, Kage-Nakadai E. Metolazone upregulates mitochondrial chaperones and extends lifespan in Caenorhabditis elegans. Biogerontology. 2021 Feb;22(1):119-131. doi: 10.1007/s10522-020-09907-6. Epub 2020 Nov 20. PMID: 33216250. 2. Banerjee M, Chen T. Thiazide-like diuretic drug metolazone activates human pregnane X receptor to induce cytochrome 3A4 and multidrug-resistance protein 1. Biochem Pharmacol. 2014 Nov 15;92(2):389-402. doi: 10.1016/j.bcp.2014.08.025. Epub 2014 Aug 30. PMID: 25181459; PMCID: PMC4252478. 3. Pridjian G, Pridjian C, Danchuk S, Ianosi-Irimie M, Vu HV, Puschett JB. Beneficial effects of metolazone in a rat model of preeclampsia. J Pharmacol Exp Ther. 2006 Sep;318(3):1027-32. doi: 10.1124/jpet.106.104901. Epub 2006 May 22. PMID: 16717105.
In vitro protocol:
1. Ito A, Zhao Q, Tanaka Y, Yasui M, Katayama R, Sun S, Tanimoto Y, Nishikawa Y, Kage-Nakadai E. Metolazone upregulates mitochondrial chaperones and extends lifespan in Caenorhabditis elegans. Biogerontology. 2021 Feb;22(1):119-131. doi: 10.1007/s10522-020-09907-6. Epub 2020 Nov 20. PMID: 33216250. 2. Banerjee M, Chen T. Thiazide-like diuretic drug metolazone activates human pregnane X receptor to induce cytochrome 3A4 and multidrug-resistance protein 1. Biochem Pharmacol. 2014 Nov 15;92(2):389-402. doi: 10.1016/j.bcp.2014.08.025. Epub 2014 Aug 30. PMID: 25181459; PMCID: PMC4252478.
In vivo protocol:
1. Pridjian G, Pridjian C, Danchuk S, Ianosi-Irimie M, Vu HV, Puschett JB. Beneficial effects of metolazone in a rat model of preeclampsia. J Pharmacol Exp Ther. 2006 Sep;318(3):1027-32. doi: 10.1124/jpet.106.104901. Epub 2006 May 22. PMID: 16717105.
1: Dubey R, Ghosh M, Sinha BN, Muthukrishnan V. Simultaneous Determination and Pharmacokinetics of Metolazone, Losartan and Losartan Carboxylic Acid in Rat Plasma by HPLC-ESI-MS-MS. J Chromatogr Sci. 2015 Oct;53(9):1520-7. doi: 10.1093/chromsci/bmv047. Epub 2015 May 6. PubMed PMID: 25947361. 2: Moranville MP, Choi S, Hogg J, Anderson AS, Rich JD. Comparison of metolazone versus chlorothiazide in acute decompensated heart failure with diuretic resistance. Cardiovasc Ther. 2015 Apr;33(2):42-9. doi: 10.1111/1755-5922.12109. PubMed PMID: 25712736. 3: Banerjee M, Chen T. Thiazide-like diuretic drug metolazone activates human pregnane X receptor to induce cytochrome 3A4 and multidrug-resistance protein 1. Biochem Pharmacol. 2014 Nov 15;92(2):389-402. doi: 10.1016/j.bcp.2014.08.025. Epub 2014 Aug 30. PubMed PMID: 25181459; PubMed Central PMCID: PMC4252478. 4: Walash MI, El-Enany NM, Eid MI, Fathy ME. Simultaneous determination of metolazone and losartan potassium in their binary mixtures using high-performance liquid chromatography with fluorimetric detection: application to combined tablets and spiked human plasma. Luminescence. 2014 Aug;29(5):462-70. doi: 10.1002/bio.2570. Epub 2013 Sep 2. PubMed PMID: 23996979. 5: Cheng HW, Sham MK, Chan KY, Li CW, Au HY, Yip T. Combination therapy with low-dose metolazone and furosemide: a "needleless" approach in managing refractory fluid overload in elderly renal failure patients under palliative care. Int Urol Nephrol. 2014 Sep;46(9):1809-13. doi: 10.1007/s11255-014-0724-z. Epub 2014 May 14. PubMed PMID: 24824145. 6: Walash MI, El-Enany N, Eid MI, Fathy ME. Stability-Indicating Spectrofluorimetric Methods for the Determination of Metolazone and Xipamide in Their Tablets. Application to Content Uniformity Testing. J Fluoresc. 2013 Oct 4. [Epub ahead of print] PubMed PMID: 24091803. 7: Ng TM, Konopka E, Hyderi AF, Hshieh S, Tsuji Y, Kim BJ, Han SY, Phan DH, Jeng AI, Lou M, Elkayam U. Comparison of bumetanide- and metolazone-based diuretic regimens to furosemide in acute heart failure. J Cardiovasc Pharmacol Ther. 2013 Jul;18(4):345-53. doi: 10.1177/1074248413482755. Epub 2013 Mar 27. PubMed PMID: 23538300. 8: Jia Y, Zhang Y, Wang C, Wang Z, Liu Y, Wang J, Wen A. An improved LC-MS/MS method for quantitative determination of metolazone in human plasma and its application to a pharmacokinetic study. Biomed Chromatogr. 2011 Oct;25(10):1138-43. doi: 10.1002/bmc.1583. Epub 2011 Mar 9. PubMed PMID: 21387350. 9: Dubey R, Bhusari VK, Dhaneshwar SR. Validated RP-HPLC Method for Simultaneous Quantitation of Losartan Potassium and Metolazone in Bulk Drug and Formulation. Sci Pharm. 2011 Sep;79(3):545-54. doi: 10.3797/scipharm.1105-13. Epub 2011 Jun 26. PubMed PMID: 21886902; PubMed Central PMCID: PMC3163373. 10: Wei G, Xiao S, Liu C. Determination of metolazone in human blood by liquid chromatography with electrospray ionization tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Jan 1;845(1):169-73. Epub 2006 Aug 14. PubMed PMID: 16908225. 11: Pridjian G, Pridjian C, Danchuk S, Ianosi-Irimie M, Vu HV, Puschett JB. Beneficial effects of metolazone in a rat model of preeclampsia. J Pharmacol Exp Ther. 2006 Sep;318(3):1027-32. Epub 2006 May 22. PubMed PMID: 16717105. 12: Lorenz RA, Elwell RJ. Pre-dosing metolazone with loop diuretic combination regimens. Nephrol Nurs J. 2006 Jan-Feb;33(1):78-9. Review. PubMed PMID: 16538931. 13: Rosenberg J, Gustafsson F, Galatius S, Hildebrandt PR. Combination therapy with metolazone and loop diuretics in outpatients with refractory heart failure: an observational study and review of the literature. Cardiovasc Drugs Ther. 2005 Aug;19(4):301-6. PubMed PMID: 16189620. 14: Gabrielli M, Gasbarrini A, Santoliquido A, Flore R, Gaetani E, Flex A, Pola P. Metolazone-induced cholestatic liver disease. Dig Liver Dis. 2001 Aug-Sep;33(6):501. PubMed PMID: 11572578. 15: Chan P, Tomlinson B, Huang TY, Ko JT, Lin TS, Lee YS. Double-blind comparison of losartan, lisinopril, and metolazone in elderly hypertensive patients with previous angiotensin-converting enzyme inhibitor-induced cough. J Clin Pharmacol. 1997 Mar;37(3):253-7. PubMed PMID: 9089428. 16: Segar JL, Robillard JE, Johnson KJ, Bell EF, Chemtob S. Addition of metolazone to overcome tolerance to furosemide in infants with bronchopulmonary dysplasia. J Pediatr. 1992 Jun;120(6):966-73. PubMed PMID: 1593359. 17: Cox NH, Hodkin P. Vasculitis due to metolazone. Postgrad Med J. 1991 Sep;67(791):860. PubMed PMID: 1946137; PubMed Central PMCID: PMC2399120. 18: Cachero SD, Lofland G, Springate JE, Feld LG. Combination of metolazone and furosemide in the treatment of edema in the first month of life. Child Nephrol Urol. 1990;10(3):161-3. PubMed PMID: 2285924. 19: Kirancumar, Loureiro PA, Correia JM. [Metolazone in the treatment of refractory heart insufficiency. Experience of 10 cases]. Rev Port Cardiol. 1989 Nov;8(11):775-8. Portuguese. PubMed PMID: 2631826. 20: Fuchs JE Jr, Keith MR, Galanos AN. Probable metolazone-induced pancreatitis. DICP. 1989 Sep;23(9):711. PubMed PMID: 2800588.

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Metochalcone