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Identification
NameTimolol
Accession NumberDB00373  (APRD00229, DB08625)
TypeSmall Molecule
GroupsApproved
Description

A beta-adrenergic antagonist similar in action to propranolol. The levo-isomer is the more active. Timolol has been proposed as an antihypertensive, antiarrhythmic, antiangina, and antiglaucoma agent. It is also used in the treatment of migraine disorders and tremor. [PubChem]

Structure
Thumb
Synonyms
(S)-1-(tert-butylamino)-3-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol
Timolol
Timolol anhydrous
Timololo
Timololum
External Identifiers
  • MK 950
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Beta-tim - 0.25% Liqliquid0.25 %ophthalmicCiba Vision Canada Inc1994-12-311998-07-16Canada
Beta-tim - 0.5% Liqliquid0.5 %ophthalmicCiba Vision Canada Inc1994-12-311998-07-16Canada
Betimolsolution2.5 mg/mLophthalmicVistakon Pharmaceuticals LLC2000-10-01Not applicableUs
Betimolsolution5 mg/mLophthalmicVistakon Pharmaceuticals LLC2000-10-01Not applicableUs
Betimolsolution/ drops5.12 mg/mLophthalmicOak Pharmaceuticals, Inc. (Subsidiary of Akorn, Inc.) (968937719)2014-01-02Not applicableUs
Betimolsolution/ drops2.56 mg/mLophthalmicOak Pharmaceuticals, Inc. (Subsidiary of Akorn, Inc.) (968937719)2014-01-02Not applicableUs
Blocadren Tab 10mgtablet10 mgoralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1977-12-312000-08-03Canada
Blocadren Tab 20mgtablet20 mgoralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1980-12-311999-03-02Canada
Blocadren Tab 5mgtablet5 mgoralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1978-12-312000-08-03Canada
Dom-timololliquid0.5 %ophthalmicDominion Pharmacal1999-03-08Not applicableCanada
Dom-timololliquid0.25 %ophthalmicDominion Pharmacal1999-03-08Not applicableCanada
Istalolsolution5 mg/mLophthalmicISTA Pharmaceuticals, Inc.2004-08-01Not applicableUs
Istalolsolution/ drops5 mg/mLophthalmicBausch & Lomb Incorporated2004-08-02Not applicableUs
Jamp-timololsolution5 mgophthalmicJamp Pharma Corporation2015-11-20Not applicableCanada
Med Timolol Liq Oph 0.25%liquid0.25 %ophthalmicMedican Pharma Incorporated1995-12-312011-03-29Canada
Med Timolol Liq Oph 0.5%liquid0.5 %ophthalmicMedican Pharma Incorporated1995-12-312011-03-29Canada
Mylan-timololsolution0.5 %ophthalmicMylan Pharmaceuticals Ulc1992-12-312012-10-19Canada
Mylan-timololsolution0.25 %ophthalmicMylan Pharmaceuticals Ulc1992-12-312012-10-19Canada
Novo-timol Liq 0.25%liquid0.25 %ophthalmicNovopharm Limited1993-12-312015-10-26Canada
Novo-timol Liq 0.5%liquid0.5 %ophthalmicNovopharm Limited1993-12-312015-10-26Canada
Nu-timolol Tab 10mgtablet10 mgoralNu Pharm Inc1993-12-312012-09-04Canada
Nu-timolol Tab 20mgtablet20 mgoralNu Pharm Inc1993-12-312012-09-04Canada
Nu-timolol Tab 5mgtablet5 mgoralNu Pharm Inc1993-12-312012-09-04Canada
Odan-timololliquid0.5 %ophthalmicOdan Laboratories Ltd1994-12-31Not applicableCanada
Odan-timololliquid0.25 %ophthalmicOdan Laboratories Ltd1994-12-31Not applicableCanada
PMS-timololliquid0.25 %ophthalmicPharmascience Inc1997-11-13Not applicableCanada
PMS-timololliquid0.5 %ophthalmicPharmascience Inc1997-11-13Not applicableCanada
Ratio-timolol Maleate 0.25%solution0.25 %ophthalmicRatiopharm Inc Division Of Teva Canada Limited2001-08-242006-08-04Canada
Ratio-timolol Maleate 0.5%solution0.5 %ophthalmicRatiopharm Inc Division Of Teva Canada Limited2001-08-242006-08-04Canada
Rhoxal-timolol 0.25%liquid0.25 %ophthalmicRhoxalpharma Inc2000-05-022009-11-24Canada
Rhoxal-timolol 0.5%liquid0.5 %ophthalmicRhoxalpharma Inc2000-05-022009-11-24Canada
Sandoz Timololsolution0.5 %ophthalmicSandoz Canada Incorporated1995-12-31Not applicableCanada
Sandoz Timololsolution0.25 %ophthalmicSandoz Canada Incorporated1995-12-31Not applicableCanada
T-LO - Liq Oph 0.25%liquid0.25 %ophthalmicAlcon Canada IncNot applicableNot applicableCanada
T-LO - Liq Oph 0.5%liquid0.5 %ophthalmicAlcon Canada IncNot applicableNot applicableCanada
Teva-timololtablet5 mgoralTeva Canada Limited1992-12-31Not applicableCanada
Teva-timololtablet10 mgoralTeva Canada Limited1992-12-31Not applicableCanada
Teva-timololtablet20 mgoralTeva Canada Limited1992-12-31Not applicableCanada
Timolol Gfssolution, gel forming, extended release5 mg/mLophthalmicSandoz Inc1998-12-24Not applicableUs
Timolol Gfssolution, gel forming, extended release2.5 mg/mLophthalmicSandoz Inc1998-12-24Not applicableUs
Timolol Maleatesolution6.8 mg/mLophthalmicPhysicians Total Care, Inc.2002-10-16Not applicableUs
Timolol Maleatesolution6.8 mg/mLophthalmicREMEDYREPACK INC.2013-12-03Not applicableUs
Timolol Maleatesolution5 mg/mLophthalmicAton Pharma, Inc.1993-11-14Not applicableUs
Timolol Maleatesolution2.5 mg/mLophthalmicAton Pharma, Inc.2009-10-15Not applicableUs
Timolol Maleate-EXsolution0.50 %ophthalmicAlcon Canada Inc2003-04-30Not applicableCanada
Timolol Maleate-EXsolution0.25 %ophthalmicAlcon Canada Inc2003-04-30Not applicableCanada
Timolol Solution - 0.25%solution.25 %ophthalmicBdh Inc.1998-10-132000-08-03Canada
Timolol Solution - 0.5%solution0.5 %ophthalmicBdh Inc.1998-10-132000-08-03Canada
Timolol-10 Tab 10mgtablet10 mgoralPro Doc Limitee1989-12-312011-07-27Canada
Timolol-20 Tab 20mgtablet20 mgoralPro Doc Limitee1989-12-312009-07-23Canada
Timolol-5 Tab 5mgtablet5 mgoralPro Doc Limitee1989-12-312011-07-27Canada
Timopticsolution5 mg/mLophthalmicAton Pharma, Inc.1986-11-05Not applicableUs
Timopticsolution6.8 mg/mLophthalmicValeant Pharmaceuticals North America LLC1986-11-05Not applicableUs
Timopticsolution2.5 mg/mLophthalmicAton Pharma, Inc.1986-11-05Not applicableUs
Timopticsolution5 mg/mLophthalmicAton Pharma, Inc.1978-08-17Not applicableUs
Timopticsolution2.5 mg/mLophthalmicAton Pharma, Inc.1978-08-17Not applicableUs
Timopticsolution0.25 %ophthalmicMerck Canada Inc1979-12-312006-11-22Canada
Timopticsolution0.5 %ophthalmicMerck Canada Inc1979-12-31Not applicableCanada
Timopticsolution3.4 mg/mLophthalmicValeant Pharmaceuticals North America LLC1986-11-05Not applicableUs
Timoptic-XEsolution (long-acting)0.5 %ophthalmicMerck Canada Inc1995-12-31Not applicableCanada
Timoptic-XEsolution (long-acting)0.25 %ophthalmicMerck Canada Inc1995-12-31Not applicableCanada
Timoptic-XEsolution5 mg/mLophthalmicAton Pharma, Inc.1993-11-14Not applicableUs
Timoptic-XEsolution2.5 mg/mLophthalmicAton Pharma, Inc.1993-11-14Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-timol Tablets 10mgtablet10 mgoralApotex Inc1988-12-31Not applicableCanada
Apo-timol Tablets 20mgtablet20 mgoralApotex Inc1988-12-31Not applicableCanada
Apo-timol Tablets 5mgtablet5 mgoralApotex Inc1988-12-31Not applicableCanada
Apo-timop Gelsolution0.25 %ophthalmicApotex IncNot applicableNot applicableCanada
Apo-timop Gelsolution0.5 %ophthalmicApotex Inc2008-02-20Not applicableCanada
Apo-timop Liq 0.5%liquid0.5 %ophthalmicApotex Inc1988-12-31Not applicableCanada
Apo-timop Oph Soln 0.25%liquid0.25 %ophthalmicApotex Inc1988-12-31Not applicableCanada
Timolol Maleatesolution5 mg/mLophthalmicAscend Laboratories, LLC2011-03-09Not applicableUs
Timolol Maleatesolution/ drops5 mg/mLophthalmicApotex Corp.2011-07-15Not applicableUs
Timolol Maleatesolution/ drops5 mg/mLophthalmicPacific Pharma, Inc.1997-05-20Not applicableUs
Timolol Maleatesolution/ drops2.5 mg/mLophthalmicBausch & Lomb Incorporated1997-03-25Not applicableUs
Timolol Maleatetablet5 mg/1oralMylan Pharmaceuticals Inc.1990-06-08Not applicableUs
Timolol Maleatesolution/ drops5 mg/mLophthalmicRising Pharmaceuticals, Inc.2014-12-15Not applicableUs
Timolol Maleatesolution/ drops2.5 mg/mLophthalmicApotex Corp.2011-07-15Not applicableUs
Timolol Maleatesolution/ drops5 mg/mLophthalmicBausch & Lomb Incorporated1997-03-25Not applicableUs
Timolol Maleatesolution/ drops2.5 mg/mLophthalmicRising Pharmaceuticals, Inc.2014-12-15Not applicableUs
Timolol Maleatesolution/ drops5 mg/mLophthalmicFdc Limited2014-12-15Not applicableUs
Timolol Maleatesolution/ drops2.5 mg/mLophthalmicAkorn, Inc.2012-03-26Not applicableUs
Timolol Maleatesolution/ drops2.5 mg/mLophthalmicREMEDYREPACK INC.2015-11-17Not applicableUs
Timolol Maleatesolution/ drops2.5 mg/mLophthalmicFdc Limited2014-12-15Not applicableUs
Timolol Maleatesolution/ drops5 mg/mLophthalmicAkorn, Inc.2012-03-26Not applicableUs
Timolol Maleatesolution/ drops2.5 mg/mLophthalmicREMEDYREPACK INC.2015-06-16Not applicableUs
Timolol Maleatesolution5 mg/mLophthalmicPhysicians Total Care, Inc.1995-01-26Not applicableUs
Timolol Maleatesolution/ drops5 mg/mLophthalmicPack Pharmaceuticals LLC2009-02-162016-01-23Us
Timolol Maleatesolution5 mg/mLophthalmicSandoz Inc1996-01-15Not applicableUs
Timolol Maleatesolution2.5 mg/mLophthalmicPhysicians Total Care, Inc.1996-01-26Not applicableUs
Timolol Maleatesolution/ drops2.5 mg/mLophthalmicPack Pharmaceuticals LLC2009-02-162016-01-23Us
Timolol Maleatesolution2.5 mg/mLophthalmicSandoz Inc1996-01-15Not applicableUs
Timolol Maleatesolution/ drops5 mg/mLophthalmicREMEDYREPACK INC.2013-12-03Not applicableUs
Timolol Maleatetablet20 mg/1oralMylan Pharmaceuticals Inc.1990-06-08Not applicableUs
Timolol Maleatesolution/ drops2.5 mg/mLophthalmicPacific Pharma, Inc.1997-05-20Not applicableUs
Timolol Maleatesolution/ drops5 mg/mLophthalmicHi Tech Pharmacal Co., Inc.2002-09-10Not applicableUs
Timolol Maleatetablet10 mg/1oralMylan Pharmaceuticals Inc.1990-06-08Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BlocadrenMerck
ProflaxSidus
TenoptSigma
Timacar DepotMSD
TimacorGerda
TimoptolMerck
Brand mixtures
NameLabellerIngredients
Act DorzotimololActavis Pharma Company
Act Latanoprost/timololActavis Pharma Company
Apo-brimonidine-timopApotex Inc
Apo-dorzo-timopApotex Inc
Apo-latanoprost-timopApotex Inc
Apo-travoprost-timopApotex Inc
AzargaAlcon Canada Inc
CombiganAllergan, Inc.
CosoptMerck Sharp & Dohme Corp.
Cosopt PFMerck Sharp & Dohme Corp.
Dorzolamide HCl /timolol MaleateREMEDYREPACK INC.
Dorzolamide HCl and Timolol MaleateActavis Pharma, Inc.
Dorzolamide Hydrochloride and Timolol MaleateBausch & Lomb Incorporated
Dorzolamide Hydrochloride and Timolol Maleate Ophthalmic SolutionBausch & Lomb Inc
Dorzolamide Hydrochloride-timolol MaleateLannett Company, Inc.
Dorzolamide Hydrochloride-timolol Maleate Ophthalmic Solution Sterile Ophthalmic SolutionAlvogen Inc.
Duotrav PqAlcon Canada Inc
Gd-latanoprost/timololGenmed A Division Of Pfizer Canada Inc
Jamp-latanoprost/timololJamp Pharma Corporation
Med-dorzolamide-timololGeneric Medical Partners Inc
Med-latanoprost-timololGeneric Medical Partners Inc
Mint-dorzolamide/timololMint Pharmaceuticals Inc
Mint-latanoprost/timololMint Pharmaceuticals Inc
Mylan-dorzolamide/timololMylan Pharmaceuticals Ulc
Mylan-latanoprost/timololMylan Pharmaceuticals Ulc
PMS-dorzolamide-timololPharmascience Inc
PMS-latanoprost-timololPharmascience Inc
Preservative-free CosoptMerck Canada Inc
Riva-dorzolamide/timololLaboratoire Riva Inc
Sandoz Dorzolamide/timololSandoz Canada Incorporated
Sandoz Latanoprost/timololSandoz Canada Incorporated
Sandoz Travoprost / Timolol PqSandoz Canada Incorporated
Teva-dorzotimolTeva Canada Limited
Teva-latanoprost/timololTeva Canada Limited
Timolide TabMerck Frosst Canada & Cie, Merck Frosst Canada & Co.
Timpilo 2Merck Canada Inc
Timpilo 4Merck Canada Inc
Van-dorzolamide-timololVanc Pharmaceuticals Inc
XalacomPfizer Canada Inc
Salts
Name/CASStructureProperties
Timolol hemihydrate
91524-16-2
Thumb
  • InChI Key: TWBNMYSKRDRHAT-RCWTXCDDSA-N
  • Monoisotopic Mass: 650.32438833
  • Average Mass: 650.86
DBSALT000990
Timolol maleate
26921-17-5
Thumb
  • InChI Key: WLRMANUAADYWEA-NWASOUNVSA-N
  • Monoisotopic Mass: 432.167870432
  • Average Mass: 432.49
DBSALT000989
Categories
UNII5JKY92S7BR
CAS number26839-75-8
WeightAverage: 316.42
Monoisotopic: 316.156911344
Chemical FormulaC13H24N4O3S
InChI KeyInChIKey=BLJRIMJGRPQVNF-UHFFFAOYSA-N
InChI
InChI=1S/C13H24N4O3S/c1-13(2,3)14-8-10(18)9-20-12-11(15-21-16-12)17-4-6-19-7-5-17/h10,14,18H,4-9H2,1-3H3
IUPAC Name
1-(tert-butylamino)-3-{[4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy}propan-2-ol
SMILES
CC(C)(C)NCC(O)COC1=NSN=C1N1CCOCC1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassTertiary amines
Direct ParentDialkylarylamines
Alternative Parents
Substituents
  • Dialkylarylamine
  • Alkyl aryl ether
  • Imidolactam
  • Oxazinane
  • Morpholine
  • 3-amino-1,2,5-thiadiazole
  • Heteroaromatic compound
  • Thiadiazole
  • Azole
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationIn its oral form it is used to treat high blood pressure and prevent heart attacks, and occasionally to prevent migraine headaches. In its opthalmic form it is used to treat open-angle and occasionally secondary glaucoma.
PharmacodynamicsSimilar to propranolol and nadolol, timolol is a non-selective, beta-adrenergic receptor antagonist. Timolol does not have significant intrinsic sympathomimetic, direct myocardial depressant, or local anesthetic (membrane-stabilizing) activity, but does possess a relatively high degree of lipid solubility. Timolol, when applied topically to the eye, has the action of reducing elevated, as well as normal, intraocular pressure, whether or not accompanied by glaucoma. Elevated intraocular pressure is a major risk factor in the pathogenesis of glaucomatous visual field loss and optic nerve damage.
Mechanism of actionLike propranolol and nadolol, timolol competes with adrenergic neurotransmitters such as catecholamines for binding at beta(1)-adrenergic receptors in the heart and vascular smooth muscle and beta(2)-receptors in the bronchial and vascular smooth muscle. Beta(1)-receptor blockade results in a decrease in resting and exercise heart rate and cardiac output, a decrease in both systolic and diastolic blood pressure, and, possibly, a reduction in reflex orthostatic hypotension. Beta(2)-blockade results in an increase in peripheral vascular resistance. The exact mechanism whereby timolol reduces ocular pressure is still not known. The most likely action is by decreasing the secretion of aqueous humor.
Related Articles
AbsorptionBioavailability is about 60%
Volume of distributionNot Available
Protein binding~10%
Metabolism

Primarily hepatic (80%) via the cytochrome P450 2D6 isoenzyme.

Route of eliminationTimolol and its metabolites are primarily excreted in the urine.
Half life2.5-5 hours
ClearanceNot Available
ToxicityLD50=1190 mg/kg (oral, mice), LD50=900 mg/kg (oral, rat). Symptoms of overdose include drowsiness, vertigo, headache, and atriventricular block.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Timolol Action PathwayDrug actionSMP00659
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9958
Blood Brain Barrier-0.6467
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.8522
P-glycoprotein inhibitor INon-inhibitor0.6567
P-glycoprotein inhibitor IINon-inhibitor0.9552
Renal organic cation transporterNon-inhibitor0.9105
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.5389
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8678
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.7338
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6096 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9214
hERG inhibition (predictor II)Non-inhibitor0.7334
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Santen oy
  • Falcon pharmaceuticals ltd
  • Aton pharma inc
  • Ista pharmaceuticals
  • Akorn inc
  • Bausch and lomb pharmaceuticals inc
  • Bausch and lomb inc
  • Falcon pharmaceuticals inc
  • Fdc ltd
  • E fougera div altana inc
  • Hi tech pharmacal co inc
  • Novex pharma
  • Pacific pharma inc
  • Pacific pharma
  • Wockhardt ltd
  • Merck research laboratories div merck co inc
  • Mylan pharmaceuticals inc
  • Quantum pharmics ltd
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Usl pharma inc
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
Suspensionophthalmic
Solution/ dropsophthalmic2.56 mg/mL
Solution/ dropsophthalmic5.12 mg/mL
Solution/ dropsophthalmic
Solutionophthalmic
Solutionophthalmic5 mg
Liquidophthalmic0.25 %
Liquidophthalmic0.5 %
Solutionophthalmic0.25 %
Solutionophthalmic0.5 %
Tabletoral10 mg
Tabletoral20 mg
Tabletoral5 mg
Tabletoral
Solution, gel forming, extended releaseophthalmic2.5 mg/mL
Solution, gel forming, extended releaseophthalmic5 mg/mL
Solution/ dropsophthalmic2.5 mg/mL
Solution/ dropsophthalmic5 mg/mL
Tabletoral10 mg/1
Tabletoral20 mg/1
Tabletoral5 mg/1
Solutionophthalmic0.50 %
Solutionophthalmic.25 %
Solutionophthalmic3.4 mg/mL
Solutionophthalmic6.8 mg/mL
Solutionophthalmic2.5 mg/mL
Solutionophthalmic5 mg/mL
Solution (long-acting)ophthalmic0.25 %
Solution (long-acting)ophthalmic0.5 %
Prices
Unit descriptionCostUnit
Betimol 0.5% Solution 15ml Bottle152.24USD bottle
Timolol maleate powder107.1USD g
Betimol 0.5% Solution 10ml Bottle106.88USD bottle
Betimol 0.25% Solution 15ml Bottle93.56USD bottle
Timoptic-XE 0.5% Gel Forming Solution 5ml Bottle85.09USD bottle
Timoptic 0.5% Solution 10ml Bottle83.2USD bottle
Timoptic-XE 0.25% Gel Forming Solution 5ml Bottle65.37USD bottle
Betimol 0.5% Solution 5ml Bottle63.43USD bottle
Timolol Maleate 0.5% Gel Forming Solution 5ml Bottle60.84USD bottle
Timoptic 0.5% Solution 5ml Bottle59.8USD bottle
Timolol Maleate 0.25% Gel Forming Solution 5ml Bottle59.71USD bottle
Betimol 0.25% Solution 5ml Bottle55.56USD bottle
Timolol Maleate 0.5% Solution 15ml Bottle50.7USD bottle
Betimol 0.25% Solution 10ml Bottle49.99USD bottle
Timolol Maleate 0.5% Gel Forming Solution 2.5ml Bottle46.74USD bottle
Timolol Maleate 0.25% Solution 15ml Bottle43.68USD bottle
Timoptic 0.25% Solution 5ml Bottle43.06USD bottle
Istalol 0.5% eye drops36.43USD ml
Timolol Maleate 0.5% Solution 10ml Bottle33.58USD bottle
Timolol Maleate 0.25% Solution 10ml Bottle28.87USD bottle
Timoptic-XE 0.25% Gel Forming Solution 2.5ml Bottle23.99USD bottle
Timolol Maleate 0.5% Solution 5ml Bottle17.68USD bottle
Timolol Maleate 0.25% Solution 5ml Bottle15.6USD bottle
Timoptic-xe 0.5% eye solution13.6USD ml
Timoptic-xe 0.25% eye solution11.51USD ml
Betimol 0.5% eye drops10.15USD ml
Betimol 0.25% eye drops9.19USD ml
Timoptic 0.5% eye drops8.63USD ml
Timoptic 0.25% eye drops7.32USD ml
Timoptic-Xe 0.5 % Long Acting Gellan Solution4.64USD ml
Timoptic 0.5% ocudose drops4.57USD each
Timoptic-Xe 0.25 % Long Acting Gellan Solution3.88USD ml
Timoptic 0.25% ocudose drops3.8USD each
Timoptic 0.5 % Solution3.63USD ml
Timolol 0.5% eye drops3.24USD ml
Timolol 0.25% eye drops2.78USD ml
Apo-Timop 0.5 % Solution1.95USD ml
Mylan-Timolol 0.5 % Solution1.95USD ml
Pms-Timolol 0.5 % Solution1.95USD ml
Sandoz Timolol Maleate 0.5 % Solution1.95USD ml
Apo-Timop 0.25 % Solution1.62USD ml
Mylan-Timolol 0.25 % Solution1.62USD ml
Pms-Timolol 0.25 % Solution1.62USD ml
Sandoz Timolol Maleate 0.25 % Solution1.62USD ml
Timolol maleate 20 mg tablet0.94USD tablet
Hydrocortisone 2.5% lotion0.6USD ml
Apo-Timol 20 mg Tablet0.59USD tablet
Novo-Timol 20 mg Tablet0.59USD tablet
Timolol maleate 10 mg tablet0.51USD tablet
Timolol maleate 5 mg tablet0.41USD tablet
Apo-Timol 10 mg Tablet0.3USD tablet
Novo-Timol 10 mg Tablet0.3USD tablet
Nu-Timolol 10 mg Tablet0.3USD tablet
Apo-Timol 5 mg Tablet0.19USD tablet
Novo-Timol 5 mg Tablet0.19USD tablet
Nu-Timolol 5 mg Tablet0.19USD tablet
Aquanil hc 1% lotion0.12USD ml
Aquanil cleanser0.03USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5231095 No1993-07-272010-07-27Us
US6174524 Yes1999-09-262019-09-26Us
US6335335 No1998-11-022018-11-02Us
US6645963 No1998-11-162018-11-16Us
US7030149 No2002-04-192022-04-19Us
US7320976 No2002-04-192022-04-19Us
US7323463 No2003-01-192023-01-19Us
US7642258 No2002-04-192022-04-19Us
US8133890 No2002-04-192022-04-19Us
US8354409 No2002-04-192022-04-19Us
US8748425 No2002-04-192022-04-19Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point202 °CPhysProp
water solubility2.74 mg/mLNot Available
logP1.83HANSCH,C ET AL. (1995)
Caco2 permeability-4.85ADME Research, USCD
pKa9.21KONTTURI,K & MURTOMAKI,L (1992)
Predicted Properties
PropertyValueSource
Water Solubility0.269 mg/mLALOGPS
logP1.44ALOGPS
logP1.34ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)14.08ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.74 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity83.92 m3·mol-1ChemAxon
Polarizability33.99 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Markku Per alampi, “S-timolol hemihydrate composition and method of preparation therefor.” U.S. Patent US5574035, issued October, 1986.

US5574035
General References
  1. Link [Link]
External Links
ATC CodesC07AA06C07BA06C07DA06S01ED01S01ED51
AHFS Codes
  • 24:24.00
  • 52:92.00
PDB EntriesNot Available
FDA labelDownload (471 KB)
MSDSDownload (73.5 KB)
Interactions
Drug Interactions
Drug
AbirateroneThe serum concentration of Timolol can be increased when it is combined with Abiraterone.
AcepromazineAcepromazine may increase the hypotensive activities of Timolol.
AcetylcholineThe risk or severity of adverse effects can be increased when Timolol is combined with Acetylcholine.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Timolol.
AlfuzosinTimolol may increase the orthostatic hypotensive activities of Alfuzosin.
AmifostineTimolol may increase the hypotensive activities of Amifostine.
AmiodaroneAmiodarone may increase the bradycardic activities of Timolol.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Timolol.
BretyliumBretylium may increase the bradycardic activities of Timolol.
BrimonidineBrimonidine may increase the antihypertensive activities of Timolol.
BupivacaineThe serum concentration of Bupivacaine can be increased when it is combined with Timolol.
ButabarbitalThe serum concentration of Timolol can be decreased when it is combined with Butabarbital.
ButethalThe serum concentration of Timolol can be decreased when it is combined with Butethal.
CabergolineTimolol may increase the vasoconstricting activities of Cabergoline.
CarbacholThe risk or severity of adverse effects can be increased when Timolol is combined with Carbachol.
CeritinibTimolol may increase the bradycardic activities of Ceritinib.
ChloroquineThe metabolism of Timolol can be decreased when combined with Chloroquine.
ChlorpropamideTimolol may increase the hypoglycemic activities of Chlorpropamide.
CobicistatThe serum concentration of Timolol can be increased when it is combined with Cobicistat.
DarunavirThe serum concentration of Timolol can be increased when it is combined with Darunavir.
DiazoxideDiazoxide may increase the hypotensive activities of Timolol.
DigoxinTimolol may increase the bradycardic activities of Digoxin.
DipivefrinDipivefrin may increase the atrioventricular blocking (AV block) activities of Timolol.
DipyridamoleDipyridamole may increase the bradycardic activities of Timolol.
DisopyramideDisopyramide may increase the bradycardic activities of Timolol.
DronedaroneDronedarone may increase the bradycardic activities of Timolol.
DuloxetineTimolol may increase the orthostatic hypotensive activities of Duloxetine.
EsmololEsmolol may increase the bradycardic activities of Timolol.
FingolimodTimolol may increase the bradycardic activities of Fingolimod.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Timolol.
FluoxetineThe metabolism of Timolol can be decreased when combined with Fluoxetine.
HeptabarbitalThe serum concentration of Timolol can be decreased when it is combined with Heptabarbital.
HexobarbitalThe serum concentration of Timolol can be decreased when it is combined with Hexobarbital.
InfliximabInfliximab may decrease the antihypertensive activities of Timolol.
IvabradineTimolol may increase the bradycardic activities of Ivabradine.
LacosamideTimolol may increase the atrioventricular blocking (AV block) activities of Lacosamide.
LevodopaTimolol may increase the orthostatic hypotensive activities of Levodopa.
LidocaineThe serum concentration of Lidocaine can be increased when it is combined with Timolol.
MepivacaineThe serum concentration of Mepivacaine can be increased when it is combined with Timolol.
MethacholineThe risk or severity of adverse effects can be increased when Timolol is combined with Methacholine.
MethohexitalThe serum concentration of Timolol can be decreased when it is combined with Methohexital.
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Timolol.
MidodrineTimolol may increase the bradycardic activities of Midodrine.
MolsidomineMolsidomine may increase the hypotensive activities of Timolol.
MoxonidineMoxonidine may increase the hypotensive activities of Timolol.
NicorandilNicorandil may increase the hypotensive activities of Timolol.
NifedipineNifedipine may increase the hypotensive activities of Timolol.
ObinutuzumabTimolol may increase the hypotensive activities of Obinutuzumab.
OctreotideOctreotide may increase the bradycardic activities of Timolol.
OrciprenalineTimolol may decrease the activities of Orciprenaline.
PanobinostatThe serum concentration of Timolol can be increased when it is combined with Panobinostat.
ParoxetineThe serum concentration of Timolol can be increased when it is combined with Paroxetine.
Peginterferon alfa-2bThe serum concentration of Timolol can be decreased when it is combined with Peginterferon alfa-2b.
PentobarbitalThe serum concentration of Timolol can be decreased when it is combined with Pentobarbital.
PentoxifyllinePentoxifylline may increase the hypotensive activities of Timolol.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Timolol.
PrazosinTimolol may increase the orthostatic hypotensive activities of Prazosin.
PrimidoneThe serum concentration of Timolol can be decreased when it is combined with Primidone.
PropafenoneThe serum concentration of Timolol can be increased when it is combined with Propafenone.
QuinineQuinine may increase the hypotensive activities of Timolol.
RegorafenibRegorafenib may increase the bradycardic activities of Timolol.
ReserpineReserpine may increase the hypotensive activities of Timolol.
RisperidoneTimolol may increase the hypotensive activities of Risperidone.
RitonavirThe metabolism of Timolol can be decreased when combined with Ritonavir.
RituximabTimolol may increase the hypotensive activities of Rituximab.
RivastigmineRivastigmine may increase the bradycardic activities of Timolol.
RuxolitinibRuxolitinib may increase the bradycardic activities of Timolol.
SecobarbitalThe serum concentration of Timolol can be decreased when it is combined with Secobarbital.
SufentanilSufentanil may increase the bradycardic activities of Timolol.
TacrineTacrine may increase the bradycardic activities of Timolol.
TadalafilTadalafil may increase the antihypertensive activities of Timolol.
TheophyllineTimolol may decrease the activities of Theophylline.
TiclopidineThe metabolism of Timolol can be decreased when combined with Ticlopidine.
TofacitinibTofacitinib may increase the bradycardic activities of Timolol.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Timolol.
TreprostinilTreprostinil may increase the hypotensive activities of Timolol.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Timolol.
VardenafilVardenafil may increase the antihypertensive activities of Timolol.
YohimbineYohimbine may decrease the antihypertensive activities of Timolol.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Receptor signaling protein activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular Weight:
51322.1 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Nieminen T, Uusitalo H, Maenpaa J, Turjanmaa V, Rane A, Lundgren S, Ropo A, Rontu R, Lehtimaki T, Kahonen M: Polymorphisms of genes CYP2D6, ADRB1 and GNAS1 in pharmacokinetics and systemic effects of ophthalmic timolol. A pilot study. Eur J Clin Pharmacol. 2005 Dec;61(11):811-9. Epub 2005 Nov 17. [PubMed:16315032 ]
  3. Varma DR, Shen H, Deng XF, Peri KG, Chemtob S, Mulay S: Inverse agonist activities of beta-adrenoceptor antagonists in rat myocardium. Br J Pharmacol. 1999 Jun;127(4):895-902. [PubMed:10433496 ]
  4. Hirooka K, Kelly ME, Baldridge WH, Barnes S: Suppressive actions of betaxolol on ionic currents in retinal ganglion cells may explain its neuroprotective effects. Exp Eye Res. 2000 May;70(5):611-21. [PubMed:10870519 ]
  5. Bhattacharyya BJ, Lee E, Krupin D, Hockberger P, Krupin T: (-)-Isoproterenol modulation of maxi-K(+) channel in nonpigmented ciliary epithelial cells through a G-protein gated pathway. Curr Eye Res. 2002 Mar;24(3):173-81. [PubMed:12221524 ]
  6. Wang T, Kaumann AJ, Brown MJ: (--)-Timolol is a more potent antagonist of the positive inotropic effects of (--)-adrenaline than of those of (--)-noradrenaline in human atrium. Br J Clin Pharmacol. 1996 Aug;42(2):217-23. [PubMed:8864321 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Protein homodimerization activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular Weight:
46458.32 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Fuchsjager-Mayrl G, Markovic O, Losert D, Lucas T, Wachek V, Muller M, Schmetterer L: Polymorphism of the beta-2 adrenoceptor and IOP lowering potency of topical timolol in healthy subjects. Mol Vis. 2005 Sep 23;11:811-5. [PubMed:16205624 ]
  3. Rotmensch HH, Vlasses PH, Feinberg JA, Abrams WB, Ferguson RK: Comparisons of beta-adrenergic blocking properties of S- and R-timolol in humans. J Clin Pharmacol. 1993 Jun;33(6):544-8. [PubMed:8103526 ]
  4. Borger P, Hoekstra Y, Esselink MT, Postma DS, Zaagsma J, Vellenga E, Kauffman HF: Beta-adrenoceptor-mediated inhibition of IFN-gamma, IL-3, and GM-CSF mRNA accumulation in activated human T lymphocytes is solely mediated by the beta2-adrenoceptor subtype. Am J Respir Cell Mol Biol. 1998 Sep;19(3):400-7. [PubMed:9730867 ]
  5. Van der Graaf PH, Saxena PR, Shankley NP, Black JW: Exposure and characterization of the action of noradrenaline at dopamine receptors mediating endothelium-independent relaxation of rat isolated small mesenteric arteries. Br J Pharmacol. 1995 Dec;116(8):3237-42. [PubMed:8719802 ]
  6. Ferro A, Hall JA, Dickerson JE, Brown MJ: A prospective study of the effects of prolonged timolol therapy on alpha- and beta-adrenoceptor and angiotensin II receptor mediated responses in normal subjects. Br J Clin Pharmacol. 1997 Mar;43(3):301-8. [PubMed:9088585 ]
  7. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Enterobacteria phage T4
Pharmacological action
unknown
General Function:
Lysozyme activity
Specific Function:
Endolysin with lysozyme activity that degrades host peptidoglycans and participates with the holin and spanin proteins in the sequential events which lead to the programmed host cell lysis releasing the mature viral particles. Once the holin has permeabilized the host cell membrane, the endolysin can reach the periplasm and break down the peptidoglycan layer.
Gene Name:
E
Uniprot ID:
P00720
Molecular Weight:
18691.385 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Terao T, Hisanaga E, Sai Y, Tamai I, Tsuji A: Active secretion of drugs from the small intestinal epithelium in rats by P-glycoprotein functioning as an absorption barrier. J Pharm Pharmacol. 1996 Oct;48(10):1083-9. [PubMed:8953513 ]
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Drug created on June 13, 2005 07:24 / Updated on June 29, 2016 03:04