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Metolazone

Metolazone

Synopsis, Chemistry

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Also known as: 17560-51-9, Zaroxolyn, Diulo, Mykrox, Oldren, Metenix

Molecular Formula

C₁₆H₁₆ClN₃O₃S

Molecular Weight

365.8 g/mol

InChI Key

AQCHWTWZEMGIFD-UHFFFAOYSA-N

FDA UNII

NN9U607695

A quinazoline-sulfonamide derived DIURETIC that functions by inhibiting SODIUM CHLORIDE SYMPORTERS.

Metolazone is a Thiazide-like Diuretic. The physiologic effect of metolazone is by means of Increased Diuresis.

1 2D Structure

Metolazone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

7-chloro-2-methyl-3-(2-methylphenyl)-4-oxo-1,2-dihydroquinazoline-6-sulfonamide

2.1.2 InChI

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)

2.1.3 InChI Key

AQCHWTWZEMGIFD-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1NC2=CC(=C(C=C2C(=O)N1C3=CC=CC=C3C)S(=O)(=O)N)Cl

2.2 Other Identifiers

2.2.1 UNII

NN9U607695

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Diulo

2. Microx

3. Mykrox

4. Sr 720 22

5. Sr-720-22

6. Sr72022

7. Zaroxolyn

2.3.2 Depositor-Supplied Synonyms

1. 17560-51-9

2. Zaroxolyn

3. Diulo

4. Mykrox

5. Oldren

6. Metenix

7. Microx

8. Metalozone

9. Metolazona

10. Metolazonum

11. 7-chloro-2-methyl-4-oxo-3-(o-tolyl)-1,2,3,4-tetrahydroquinazoline-6-sulfonamide

12. Metolazonum [inn-latin]

13. Metolazona [inn-spanish]

14. Sr-720-22

15. Metozalone

16. 7-chloro-1,2,3,4-tetrahydro-2-methyl-3-(2-methylphenyl)-4-oxo-6-quinazolinesulfonamide

17. Sr 720-22

18. 6-quinazolinesulfonamide, 7-chloro-1,2,3,4-tetrahydro-2-methyl-3-(2-methylphenyl)-4-oxo-

19. Metazoline

20. Metolazone (zaroxolyn)

21. Normelan

22. 7-chloro-1,2,3,4-tetrahydro-2-methyl-4-oxo-3-o-tolyl-6-quinazolinesulfonamide

23. 2-methyl-3-o-tolyl-6-sulfamyl-7-chloro-1,2,3,4-tetrahydro-4-quinazolinone

24. 7-chloro-2-methyl-3-(2-methylphenyl)-4-oxo-1,2-dihydroquinazoline-6-sulfonamide

25. Metolazone, (+)-

26. Metolazone, (-)-

27. Nsc-759581

28. Nm7v2y3g0u

29. Tz7v40x7vx

30. 7-chloro-2-methyl-3-(2-methylphenyl)-4-oxo-1,2,3,4-tetrahydroquinazoline-6-sulfonamide

31. Chebi:64354

32. 6-quinazolinesulfonamide, 7-chloro-1,2,3,4-tetrahydro-2-methyl-4-oxo-3-o-tolyl-

33. Nn9u607695

34. Ncgc00093985-07

35. Metalazone

36. Xuret

37. 6-quinazolinesulfonamide, 1,2,3,4-tetrahydro-7-chloro-2-methyl-4-oxo-3-o-tolyl-

38. Dsstox_cid_25167

39. Dsstox_rid_80717

40. Dsstox_gsid_45167

41. Zaroxolyn (tn)

42. 56436-31-8

43. 56436-32-9

44. 6-quinazolinesulfonamide, 7-chloro-1,2,3,4-tetrahydro-2-methyl-3-(2-methylphenyl)-4-oxo-, (+)-

45. 6-quinazolinesulfonamide, 7-chloro-1,2,3,4-tetrahydro-2-methyl-3-(2-methylphenyl)-4-oxo-, (-)-

46. Smr001230730

47. Hsdb 3367

48. Sr-05000001765

49. Einecs 241-539-3

50. Unii-tz7v40x7vx

51. Brn 0965506

52. Metolazone (jan/usp/inn)

53. Prestwick_333

54. Cas-17560-51-9

55. Mfcd00069304

56. Metolazone [usan:usp:inn:ban:jan]

57. Spectrum_000456

58. Metolazone [mi]

59. Metolazone [inn]

60. Metolazone [jan]

61. Prestwick0_000112

62. Prestwick1_000112

63. Prestwick2_000112

64. Prestwick3_000112

65. Spectrum2_001741

66. Spectrum4_000229

67. Spectrum5_001237

68. Metolazone [hsdb]

69. Metolazone [usan]

70. Metolazone [vandf]

71. Chembl878

72. Unii-nm7v2y3g0u

73. Metolazone [mart.]

74. (non-labelled)metolazone-d7

75. Metolazone [usp-rs]

76. Metolazone [who-dd]

77. Schembl40558

78. Bspbio_000124

79. Bspbio_002422

80. Kbiogr_000897

81. Kbioss_000936

82. 5-25-09-00212 (beilstein Handbook Reference)

83. Mls002153316

84. Mls002154200

85. Divk1c_000275

86. Spectrum2300325

87. Spbio_001842

88. Spbio_002063

89. Bpbio1_000138

90. Gtpl4838

91. Dtxsid6045167

92. Metolazone [ep Impurity]

93. Metolazone [orange Book]

94. Unii-nn9u607695

95. Bdbm25899

96. Hms500n17

97. Kbio1_000275

98. Kbio2_000936

99. Kbio2_003504

100. Kbio2_006072

101. Metolazone [ep Monograph]

102. Ninds_000275

103. Bcpp000166

104. Hms1568g06

105. Hms1922l16

106. Hms2093p14

107. Hms2095g06

108. Hms2230j15

109. Hms3261j22

110. Hms3373c11

111. Hms3655m09

112. Hms3712g06

113. Hms3744i19

114. Metolazone [usp Monograph]

115. Pharmakon1600-02300325

116. Bcp21574

117. Hy-b0209

118. Tox21_110186

119. Tox21_113526

120. Tox21_500610

121. Ccg-39450

122. Nsc759581

123. S1610

124. Akos015897109

125. Metolazone, >=98% (hplc), Solid

126. Tox21_110186_1

127. Bcp9000920

128. Db00524

129. Ks-5139

130. Lp00610

131. Nsc 759581

132. Sdccgsbi-0051460.p003

133. Idi1_000275

134. Ncgc00093985-01

135. Ncgc00093985-02

136. Ncgc00093985-03

137. Ncgc00093985-04

138. Ncgc00093985-05

139. Ncgc00093985-06

140. Ncgc00093985-08

141. Ncgc00093985-10

142. Ncgc00093985-11

143. Ncgc00093985-20

144. Ncgc00261295-01

145. As-13016

146. Sbi-0051460.p002

147. Db-044227

148. Ab00052055

149. Sw196612-3

150. D00431

151. 7-chloro-2-methyl-4-oxo-3-o-tolyl-1,2,3,4

152. Ab00052055-08

153. Ab00052055_09

154. Ab00052055_10

155. 560m519

156. Q-201399

157. Q1169561

158. Sr-05000001765-1

159. Sr-05000001765-4

160. Sr-05000001765-7

161. Brd-a61793559-001-05-7

162. Brd-a61793559-001-08-1

163. Metolazone, European Pharmacopoeia (ep) Reference Standard

164. Metolazone, United States Pharmacopeia (usp) Reference Standard

165. 7-chloro-2-methyl-3-(2-methylphenyl)-4-oxo-1,2,3,4-tetrahydro-6-quinazolinesulfonamide #

166. Metolazone For System Suitability, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₆ClN₃O₃S
Molecular Weight	365.8 g/mol
XLogP3	4.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	365.0600902 g/mol
Monoisotopic Mass	365.0600902 g/mol
Topological Polar Surface Area	101 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	594
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Metolazone
PubMed Health	Metolazone (By mouth)
Drug Classes	Cardiovascular Agent
Drug Label	ZAROXOLYN Tablets (metolazone tablets, USP) for oral administration contain 2 or 5 mg of metolazone, USP, a diuretic/saluretic/antihypertensive drug of the quinazoline class.Metolazone has the molecular formula C16H16ClN3S, the chemical name 7-chlo...
Active Ingredient	Metolazone
Dosage Form	Tablet
Route	oral; Oral
Strength	2.5mg; 5mg; 10mg
Market Status	Prescription
Company	Sandoz; Roxane; Mylan

2 of 4
Drug Name	Zaroxolyn
PubMed Health	Metolazone (By mouth)
Drug Classes	Cardiovascular Agent
Drug Label	ZAROXOLYN Tablets (metolazone tablets, USP) for oral administration contain 2 or 5 mg of metolazone, USP, a diuretic/saluretic/antihypertensive drug of the quinazoline class.Metolazone has the molecular formula C16H16ClN3S, the chemical name 7-chlo...
Active Ingredient	Metolazone
Dosage Form	Tablet
Route	Oral
Strength	2.5mg; 5mg; 10mg
Market Status	Prescription
Company	Ucb

3 of 4
Drug Name	Metolazone
PubMed Health	Metolazone (By mouth)
Drug Classes	Cardiovascular Agent
Drug Label	ZAROXOLYN Tablets (metolazone tablets, USP) for oral administration contain 2 or 5 mg of metolazone, USP, a diuretic/saluretic/antihypertensive drug of the quinazoline class.Metolazone has the molecular formula C16H16ClN3S, the chemical name 7-chlo...
Active Ingredient	Metolazone
Dosage Form	Tablet
Route	oral; Oral
Strength	2.5mg; 5mg; 10mg
Market Status	Prescription
Company	Sandoz; Roxane; Mylan

4 of 4
Drug Name	Zaroxolyn
PubMed Health	Metolazone (By mouth)
Drug Classes	Cardiovascular Agent
Drug Label	ZAROXOLYN Tablets (metolazone tablets, USP) for oral administration contain 2 or 5 mg of metolazone, USP, a diuretic/saluretic/antihypertensive drug of the quinazoline class.Metolazone has the molecular formula C16H16ClN3S, the chemical name 7-chlo...
Active Ingredient	Metolazone
Dosage Form	Tablet
Route	Oral
Strength	2.5mg; 5mg; 10mg
Market Status	Prescription
Company	Ucb

4.2 Therapeutic Uses

Antihypertensive Agents; Diuretics, Sulfamyl

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

DIURETIC & ANTIHYPERTENSIVE DRUG. ... METOLAZONE IS INDICATED FOR EDEMA ACCOMPANYING CONGESTIVE HEART FAILURE, RENAL DISEASE INCL NEPHROTIC SYNDROME, & OTHER CONDITIONS OF DIMINISHED RENAL FUNCTION.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 873

METOLAZONE MAY BE USEFUL IN PT WITH GLOMERULAR FILTRATION RATE LESS THAN 20 ML/MIN & IN UNRESPONSIVE PT, IF TREATED CONCURRENTLY WITH FUROSEMIDE.

Evaluations of Drug Interactions. 2nd ed. and supplements. Washington, DC: American Pharmaceutical Assn., 1976, 1978., p. 415

RANGE OF OPTIMALLY EFFECTIVE ORAL DIURETIC DOSE IN MAN: 25-100 MG/DAY; RELATIVE ORAL NATRIURETIC MAXIMAL RESPONSE IN MAN: 1.8. /FROM TABLE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 829

4.3 Drug Warning

IT IS CONTRAINDICATED IN ANURIA, HEPATIC COMA, KNOWN ALLERGY OR HYPERSENSITIVITY, PREGNANCY, & NURSING MOTHERS. ... MORE EXTENSIVE CLINICAL EXPERIENCE IS REQUIRED BEFORE DEFINITIVE EVALUATION CAN BE MADE.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 873

4.4 Drug Indication

For the treatment of hypertension, alone or in combination with other antihypertensive drugs of a different class.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Metolazone is a quinazoline diuretic, with properties generally similar to the thiazide diuretics. A proximal action of metolazone has been shown in humans by increased excretion of phosphate and magnesium ions and by a markedly increased fractional excretion of sodium in patients with severely compromised glomerular filtration. This action has been demonstrated in animals by micropuncture studies.

5.2 MeSH Pharmacological Classification

Diuretics

Agents that promote the excretion of urine through their effects on kidney function. (See all compounds classified as Diuretics.)

Sodium Chloride Symporter Inhibitors

Agents that inhibit SODIUM CHLORIDE SYMPORTERS. They act as DIURETICS. Excess use is associated with HYPOKALEMIA. (See all compounds classified as Sodium Chloride Symporter Inhibitors.)

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

METOLAZONE

5.3.2 FDA UNII

TZ7V40X7VX

5.3.3 Pharmacological Classes

Thiazide-like Diuretic [EPC]; Increased Diuresis [PE]

5.4 ATC Code

C - Cardiovascular system

C03 - Diuretics

C03B - Low-ceiling diuretics, excl. thiazides

C03BA - Sulfonamides, plain

C03BA08 - Metolazone

5.5 Absorption, Distribution and Excretion

Absorption

Peak blood levels are obtained within 2 to 4 hours of oral administration. The rate and extent of absorption are formulation dependent.

Route of Elimination

Most of the drug is excreted in the unconverted form in the urine.

75% OF DOSE /ADMIN TO DOGS/ ...EXCRETED IN URINE & 25% IN BILE. 60%...AS HYDROXYLATED DERIV...& FURTHER PRODUCTS OF OXIDN...& UNIDENTIFIED POLAR METABOLITES ARE ALSO PRESENT IN URINE.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 287

RENAL CLEARANCES OF.../THIAZIDE DIURETICS/ ARE...HIGH. MOST COMPOUNDS ARE RAPIDLY EXCRETED WITHIN 3-6 HR. BENDROFLUMETHIAZIDE & POLYTHIAZIDE HAVE LONGER DURATION OF ACTION THAT IS CORRELATED WITH SLOWER EXCRETION... SAME IS TRUE OF...METOLAZONE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 831

5.6 Metabolism/Metabolites

Not substantially metabolized. 70-95% is excreted unchanged in urine via glomerular filtration and active tubular secretion. Undergoes enterohepatic recycling.

SEVENTY-FIVE PER CENT OF DOSE /ADMIN TO DOGS/ IS EXCRETED IN URINE & 25% IN BILE. 60%...AS HYDROXYLATED DERIV...& FURTHER PRODUCTS OF OXIDN...& UNIDENTIFIED POLAR METABOLITES ARE ALSO PRESENT IN URINE.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 287

5.7 Biological Half-Life

Approximately 14 hours.

LONG T/2 VALUE...IN DOGS IS RELATED TO TRANSPORT MECHANISM IN BLOOD & PARTITION BETWEEN FORMED ELEMENTS & SERUM PROTEINS.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 287

...METOLAZONE IS EXCRETED BY GLOMERULAR FILTRATION & TUBULAR SECRETION IN DOGS, ALTHOUGH DRUG:CREATININE CLEARANCE RATIO IS LOWER THAN FOR MOST OTHER DIURETICS. T/2 IN DOGS OF 5-6 HR IS INFLUENCED BY EXTENSIVE BINDING TO ERYTHROCYTES & PLASMA PROTEINS, & POSSIBLY TO TISSUE PROTEINS.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 161

5.8 Mechanism of Action

The actions of metolazone result from interference with the renal tubular mechanism of electrolyte reabsorption. Metolazone acts primarily to inhibit sodium reabsorption at the cortical diluting site and to a lesser extent in the proximal convoluted tubule. Sodium and chloride ions are excreted in approximately equivalent amounts. The increased delivery of sodium to the distal tubular exchange site results in increased potassium excretion. Metolazone does not inhibit carbonic anhydrase. The antihypertensive mechanism of action of metolazone is not fully understood but is presumed to be related to its saluretic and diuretic properties.

IT ACTS PRIMARILY TO INHIBIT SODIUM REABSORPTION AT CORTICAL DILUTING SITE & IN PROXIMAL CONVOLUTED TUBULE. SODIUM & CHLORIDE IONS ARE EXCRETED IN APPROX EQUAL AMT; INCR POTASSIUM EXCRETION MAY ALSO OCCUR. DIURETIC POTENCY APPROXIMATES THAT OF THIAZIDES.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 873