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2D Structure
Also known as: 26921-17-5, (s)-timolol maleate, Timolol maleate salt, Blocadren, Timoptic, Timolol hydrogen maleate
Molecular Formula
C17H28N4O7S
Molecular Weight
432.5  g/mol
InChI Key
WLRMANUAADYWEA-NWASOUNVSA-N
FDA UNII
P8Y54F701R

A beta-adrenergic antagonist that is similar in action to PROPRANOLOL; the levo-isomer is more active. Timolol has been proposed as an anti-hypertensive, anti-arrhythmic, anti-angina, and anti-glaucoma agent. It is also used in the treatment of MIGRAINE DISORDERS and tremor.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(Z)-but-2-enedioic acid;(2S)-1-(tert-butylamino)-3-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol
2.1.2 InChI
InChI=1S/C13H24N4O3S.C4H4O4/c1-13(2,3)14-8-10(18)9-20-12-11(15-21-16-12)17-4-6-19-7-5-17;5-3(6)1-2-4(7)8/h10,14,18H,4-9H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t10-;/m0./s1
2.1.3 InChI Key
WLRMANUAADYWEA-NWASOUNVSA-N
2.1.4 Canonical SMILES
CC(C)(C)NCC(COC1=NSN=C1N2CCOCC2)O.C(=CC(=O)O)C(=O)O
2.1.5 Isomeric SMILES
CC(C)(C)NC[C@@H](COC1=NSN=C1N2CCOCC2)O.C(=C\C(=O)O)\C(=O)O
2.2 Other Identifiers
2.2.1 UNII
P8Y54F701R
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (s)-1-((1,1-dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadazol-3-yl)oxy)-2-propanol

2. 2-propanol, 1-((1,1-dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl)oxy)-, (s)-

3. Blocadren

4. L 714,465

5. L-714,465

6. L714,465

7. Mk 950

8. Mk-950

9. Mk950

10. Optimol

11. Timacar

12. Timolol

13. Timolol Hemihydrate

14. Timolol Maleate, (1:1) Salt

15. Timoptic

16. Timoptol

2.3.2 Depositor-Supplied Synonyms

1. 26921-17-5

2. (s)-timolol Maleate

3. Timolol Maleate Salt

4. Blocadren

5. Timoptic

6. Timolol Hydrogen Maleate

7. Istalol

8. (s)-timolol (maleate)

9. (s)-timolol Hydrogen Maleate

10. Timoptic-xe

11. Ophtamolol

12. Aquanil

13. Mk 950

14. Timolol (as Maleate)

15. Timolol Hydrogen Maleate Salt

16. Timolol Maleate, S-enantiomer

17. Wp-934

18. Mls000028539

19. Chebi:9600

20. 60469-65-0

21. P8y54f701r

22. (-)-1-(tert-butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)-2-propanol Maleate

23. Nsc-757351

24. (-)-1-(tert-butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)-2-propanol Maleate (1:1) (salt)

25. (z)-but-2-enedioic Acid;(2s)-1-(tert-butylamino)-3-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol

26. 2-propanol, 1-((1,1-dimethylethyl)amino)-3-((4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl)oxy)-, (s)-, (z)-2-butenedioate (1:1) (salt)

27. Smr000058305

28. Timacor

29. Betime

30. L-timolol Maleate

31. Timoptic In Ocudose

32. Mfcd00058356

33. 2-propanol, 1-[(1,1-dimethylethyl)amino]-3-[[4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl]oxy]-, (2s)-, (2z)-2-butenedioate (salt)

34. Ccris 1057

35. Einecs 248-111-5

36. Cas-26921-17-5

37. (s)-(-)-timolol Maleate

38. Timololmaleate

39. Timololi Maleas

40. Unii-p8y54f701r

41. S-timolol Maleate

42. Blocadren (tn)

43. Timolol Maleate [usan:usp:jan]

44. Timoptic (tn)

45. Einecs 262-251-4

46. Istalol (tn)

47. Bimatoprost / Timolol

48. Timolol Hydrogenmaleate

49. Opera_id_1256

50. Dsstox_cid_27504

51. Dsstox_rid_82384

52. Dsstox_gsid_47504

53. Schembl26233

54. Mls001076135

55. Timolol Maleate [jan]

56. Timolol Maleate (jp17/usp)

57. Timolol Maleate [usan]

58. L-714,465 (maleate)

59. Timolol Maleate [vandf]

60. Chembl1200870

61. Dtxsid3047504

62. Timolol Maleate [mart.]

63. Timolol Maleate [usp-rs]

64. Timolol Maleate [who-dd]

65. Timolol Maleate [who-ip]

66. Hms1570n18

67. Hms2097n18

68. Hms2230n19

69. Hms2234f03

70. Hms3411m12

71. Hms3675m12

72. Hms3714n18

73. Hms3885l05

74. Tox21_302468

75. S4123

76. Timolol Maleate [orange Book]

77. Akos024458595

78. Timolol Maleate [ep Monograph]

79. Timolol Maleate [usp Impurity]

80. Ccg-220948

81. Cosopt Component Timolol Maleate

82. Cs-1028

83. Nsc 757351

84. Timolol Maleate [usp Monograph]

85. Timololi Maleas [who-ip Latin]

86. (s)-3-(3-(tert-butylamino)-2-hydroxypropoxy)-4-morpholino-1,2,5-thiadiazole Maleate

87. Duotrav Component Timolol Maleate

88. Ganfort Component Timolol Maleate

89. Xalacom Component Timolol Maleate

90. Combigan Component Timolol Maleate

91. Ncgc00256737-01

92. 2-propanol, 1-(tert-butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)-, (-)-, Maleate (1:1) (salt)

93. 2-propanol, 1-[(1,1-dimethylethyl)amino]-3-[[4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl]oxy]-, (2s)-, (2z)-2-butenedioate (1:1) (salt)

94. As-18090

95. Bs164420

96. Hy-17380

97. Smr000653470

98. Timolol Hydrogen Maleate Salt [mi]

99. Timolol Maleate Component Of Cosopt

100. Timolol Maleate Component Of Duotrav

101. Timolol Maleate Component Of Ganfort

102. T2905

103. Timolol Maleate Component Of Combigan

104. Timolol Maleate Salt, >=98% (tlc), Powder

105. A13429

106. D00603

107. F20622

108. Timolol Maleate, S-enantiomer [who-dd]

109. 921t175

110. Sr-01000003102

111. Q-201836

112. Sr-01000003102-3

113. Q27108445

114. Timolol Maleate 1.0 Mg/ml In Methanol (as Free Base)

115. Timolol Maleate, British Pharmacopoeia (bp) Reference Standard

116. Timolol Maleate, European Pharmacopoeia (ep) Reference Standard

117. Timolol Maleate, United States Pharmacopeia (usp) Reference Standard

118. (s)-1-tert-butylamino-3-(4-morpholin-4-yl-[1,2,5]thiadiazol-3-yloxy)-propan-2-ol Maleate

119. 1-( Tert-butylamino)-3-[(4-morpholino-1,2,5-thiadiazol-3-yl)oxy]-2-propanol Maleate

120. Timolol For System Suitability, European Pharmacopoeia (ep) Reference Standard

121. (2s)-1-(tert-butylamino)-3-{[4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy}propan-2-ol (2z)-but-2-enedioate

122. (s)-1-[(1,1-dimethylethyl)amino]-3-[[4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl]oxy]-2-propanol Maleate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 432.5 g/mol
Molecular Formula C17H28N4O7S
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count12
Rotatable Bond Count9
Exact Mass432.16787042 g/mol
Monoisotopic Mass432.16787042 g/mol
Topological Polar Surface Area183 Ų
Heavy Atom Count29
Formal Charge0
Complexity429
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 8  
Drug NameTimoptic-xe
Drug LabelTIMOPTIC-XE (timolol maleate ophthalmic solution) is a non-selective beta-adrenergic receptor blocking agent. Its chemical name is (-)-1-(tert-butylamino)-3- [(4-morpholino-1, 2, 5-thiadiazol-3-yl)oxy]-2-propanol maleate (1:1) (salt). Timolol malea...
Active IngredientTimolol maleate
Dosage FormSolution, gel forming/drops
RouteOphthalmic
Strengtheq 0.25% base; eq 0.5% base
Market StatusPrescription
CompanyValeant Pharms

2 of 8  
Drug NameTimolol maleate
Active IngredientTimolol maleate
Dosage FormSolution/drops; Tablet; Solution, gel forming/drops
RouteOphthalmic; Oral
Strengtheq 0.25% base; 5mg; 10mg; eq 0.5% base; 20mg
Market StatusPrescription
CompanyWockhardt; Falcon Pharms; Pacific Pharma; Hi Tech Pharma; Bausch And Lomb; Fdc; Mylan; Akorn

3 of 8  
Drug NameTimoptic
Drug LabelTimolol Maleate Ophthalmic Gel Forming Solution is a non-selective beta-adrenergic receptor blocking agent. Its chemical name is (-)-1-(tert-butylamino)-3- [(4-morpholino-1, 2, 5-thiadiazol-3-yl)oxy]-2-propanol maleate (1:1) (salt). Timolol maleate p...
Active IngredientTimolol maleate
Dosage FormSolution/drops
RouteOphthalmic
Strengtheq 0.25% base; eq 0.5% base
Market StatusPrescription
CompanyAton

4 of 8  
Drug NameTimoptic in ocudose
PubMed HealthTimolol (Into the eye)
Drug ClassesAntiglaucoma
Drug LabelTIMOPTIC-XE (timolol maleate ophthalmic solution) is a non-selective beta-adrenergic receptor blocking agent. Its chemical name is (-)-1-(tert-butylamino)-3- [(4-morpholino-1, 2, 5-thiadiazol-3-yl)oxy]-2-propanol maleate (1:1) (salt). Timolol malea...
Active IngredientTimolol maleate
Dosage FormSolution/drops
RouteOphthalmic
Strengtheq 0.25% base; eq 0.5% base
Market StatusPrescription
CompanyAton

5 of 8  
Drug NameTimoptic-xe
Drug LabelTIMOPTIC-XE (timolol maleate ophthalmic solution) is a non-selective beta-adrenergic receptor blocking agent. Its chemical name is (-)-1-(tert-butylamino)-3- [(4-morpholino-1, 2, 5-thiadiazol-3-yl)oxy]-2-propanol maleate (1:1) (salt). Timolol malea...
Active IngredientTimolol maleate
Dosage FormSolution, gel forming/drops
RouteOphthalmic
Strengtheq 0.25% base; eq 0.5% base
Market StatusPrescription
CompanyValeant Pharms

6 of 8  
Drug NameTimolol maleate
Active IngredientTimolol maleate
Dosage FormSolution/drops; Tablet; Solution, gel forming/drops
RouteOphthalmic; Oral
Strengtheq 0.25% base; 5mg; 10mg; eq 0.5% base; 20mg
Market StatusPrescription
CompanyWockhardt; Falcon Pharms; Pacific Pharma; Hi Tech Pharma; Bausch And Lomb; Fdc; Mylan; Akorn

7 of 8  
Drug NameTimoptic
Drug LabelTimolol Maleate Ophthalmic Gel Forming Solution is a non-selective beta-adrenergic receptor blocking agent. Its chemical name is (-)-1-(tert-butylamino)-3- [(4-morpholino-1, 2, 5-thiadiazol-3-yl)oxy]-2-propanol maleate (1:1) (salt). Timolol maleate p...
Active IngredientTimolol maleate
Dosage FormSolution/drops
RouteOphthalmic
Strengtheq 0.25% base; eq 0.5% base
Market StatusPrescription
CompanyAton

8 of 8  
Drug NameTimoptic in ocudose
PubMed HealthTimolol (Into the eye)
Drug ClassesAntiglaucoma
Drug LabelTIMOPTIC-XE (timolol maleate ophthalmic solution) is a non-selective beta-adrenergic receptor blocking agent. Its chemical name is (-)-1-(tert-butylamino)-3- [(4-morpholino-1, 2, 5-thiadiazol-3-yl)oxy]-2-propanol maleate (1:1) (salt). Timolol malea...
Active IngredientTimolol maleate
Dosage FormSolution/drops
RouteOphthalmic
Strengtheq 0.25% base; eq 0.5% base
Market StatusPrescription
CompanyAton

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

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.)


Adrenergic beta-Antagonists

Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety. (See all compounds classified as Adrenergic beta-Antagonists.)


Anti-Arrhythmia Agents

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
beta-Adrenergic Blocker [EPC]; Adrenergic beta-Antagonists [MoA]