Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | 2C13H24N4O3S.H2O |
| Molecular Weight | 650.855 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N2CCOCC2.CC(C)(C)NC[C@H](O)COC3=NSN=C3N4CCOCC4
InChI
InChIKey=TWBNMYSKRDRHAT-RCWTXCDDSA-N
InChI=1S/2C13H24N4O3S.H2O/c2*1-13(2,3)14-8-10(18)9-20-12-11(15-21-16-12)17-4-6-19-7-5-17;/h2*10,14,18H,4-9H2,1-3H3;1H2/t2*10-;/m00./s1
| Molecular Formula | C13H24N4O3S |
| Molecular Weight | 316.42 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugs.com/cdi/timolol-drops.html | https://www.drugbank.ca/drugs/DB00373 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021398s007lbl.pdf | https://www.drugs.com/pro/timolol-gfs.html
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/cdi/timolol-drops.html | https://www.drugbank.ca/drugs/DB00373 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021398s007lbl.pdf | https://www.drugs.com/pro/timolol-gfs.html
Timolol is the non-selective Beta antagonist used as eye drops to treat increased pressure inside the eye such as in ocular hypertension and glaucoma. Timolol is also used for high blood pressure, chest pain due to insufficient blood flow to the heart, to prevent further complications after a heart attack, and to prevent migraines. Timolol is a beta1 and beta2 (non-selective) adrenergic receptor antagonist that does not have significant intrinsic sympathomimetic, direct myocardial depressant, or local anesthetic (membrane-stabilizing) activity. Timolol, when applied topically on 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. The precise mechanism of the ocular hypotensive action of Timolol is not clearly established at this time. Tonography and fluorophotometry studies of the timolol maleate ophthalmic solution in man suggest that its predominant action may be related to the reduced aqueous formation. However, in some studies, a slight increase in outflow facility was also observed. In a study of plasma drug concentration in six subjects, the systemic exposure to timolol was determined following once daily administration of Timolol Maleate Ophthalmic Gel Forming Solution 0.5% in the morning. The mean peak plasma concentration following this morning dose was 0.28 ng/mL. Side effects, when given in the eye, include burning sensation, eye redness, superficial punctate keratopathy, corneal numbness.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2903243 |
0.2 nM [Kd] | ||
Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2903243 |
7.9 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | BETIMOL Approved UseBetimol® is indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma. Launch Date1995 |
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| Primary | BETIMOL Approved UseBetimol® is indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma. Launch Date1995 |
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| Primary | BETIMOL Approved UseBetimol® is indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma. Launch Date1995 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
26 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18201139/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIMOLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
110 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18201139/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIMOLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18201139/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIMOLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1 drop 2 times / day steady, ophthalmic Dose: 1 drop, 2 times / day Route: ophthalmic Route: steady Dose: 1 drop, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Stinging... Other AEs: Stinging (1 patient) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Stinging | 1 patient | 1 drop 2 times / day steady, ophthalmic Dose: 1 drop, 2 times / day Route: ophthalmic Route: steady Dose: 1 drop, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021516s000_Istalol_BioPharmr.pdf Page: 5.0 |
likely | |||
Page: 7, 8, 19 |
likely | likely Comment: potentiated systemic beta-blockade has been reported during combined treatment with quinidine and timolol, possibly because quinidine inhibits the metabolism of timolol via CYP2D6 Page: 7, 8, 19 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of timolol-related ophthalmic solutions on cultured human conjunctival cells. | 2010-11 |
|
| Toxicity of antiglaucoma drugs with and without benzalkonium chloride to cultured human corneal endothelial cells. | 2010-10-21 |
|
| Association of CYP2D6 single-nucleotide polymorphism with response to ophthalmic timolol in primary open-angle Glaucoma--a pilot study. | 2010-10 |
|
| Factors which influenced the decentralisation of leprosy control activities in the municipality of Betim, Minas Gerais State, Brazil. | 2010-09 |
|
| Decentralisation of leprosy control activities in the municipality of Betim, Minas Gerais State, Brazil. | 2010-09 |
|
| Incidence, severity and factors related to drug-induced keratoepitheliopathy with glaucoma medications. | 2010-04-26 |
|
| Cytochrome P450 2D6 enzyme neuroprotects against 1-methyl-4-phenylpyridinium toxicity in SH-SY5Y neuronal cells. | 2010-04 |
|
| Short-term tolerability of once-daily timolol hemihydrate 0.5%, timolol maleate in sorbate 0.5%, and generic timolol maleate gel-forming solution 0.5% in glaucoma and/or ocular hypertension: a prospective, randomized, double-masked, active-controlled, three-period crossover pilot study. | 2009-10 |
|
| Cytochrome oxidase 2D6 gene polymorphism in primary open-angle glaucoma with various effects to ophthalmic timolol. | 2009-04 |
|
| Effect of latanoprost and timolol on the histopathology of the human conjunctiva. | 2009-02 |
|
| Role of fixed-combination brinzolamide 1%/timolol 0.5% in the treatment of elevated intraocular pressure in open-angle glaucoma and ocular hypertension. | 2009 |
|
| Oral versus topical carbonic anhydrase inhibitors in ocular hypertension after scleral tunnel cataract surgery. | 2009 |
|
| Role of endogenous RGS proteins on endothelial ERK 1/2 activation. | 2008-12 |
|
| Efficacy and safety of latanoprost versus pilocarpine/timolol maleate fixed combination in patients with primary open-angle glaucoma or ocular hypertension. | 2008-12 |
|
| A case of melancholic depression induced by beta-blocker antiglaucoma agents. | 2008-10-06 |
|
| Recent advances in pharmacotherapy of glaucoma. | 2008-10 |
|
| Evaluation of aqueous humor concentrations of Istalol and Betimol following a single ocular instillation in rabbit eyes. | 2008-10 |
|
| A patient preference comparison of Azarga (brinzolamide/timolol fixed combination) vs Cosopt (dorzolamide/timolol fixed combination) in patients with open-angle glaucoma or ocular hypertension. | 2008-09 |
|
| [Influence on tear film after instillation of timolol maleate ophthalmic gel-forming solution examination by a tear film stability analysis system]. | 2008-06 |
|
| Optic atrophy, necrotizing anterior scleritis and keratitis presenting in association with Streptococcal Toxic Shock Syndrome: a case report. | 2008-02-29 |
|
| Comparison of the 24-hour intraocular pressure-lowering effects of latanoprost and dorzolamide/timolol fixed combination after 2 and 6 months of treatment. | 2008-01 |
|
| Cost analysis of glaucoma medications. | 2008-01 |
|
| [Late postoperative choroidal detachment]. | 2008 |
|
| Comparison of the effects of bimatoprost and a fixed combination of latanoprost and timolol on circadian intraocular pressure. | 2007-12 |
|
| A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling. | 2007-10-16 |
|
| Effects of topical antiglaucoma medications on corneal epithelium as evaluated by gene expression patterns. | 2007-10 |
|
| [Effect of the mixture of timoptol and amino acid taurine in the bioregulation of the intraocular pressure in rabbits]. | 2007-07 |
|
| Hypotony and choroidal detachment as a complication of topical combined timolol and dorzolamide. | 2007-04 |
|
| Sinoatrial block induced by timolol eyedrops. | 2007-02 |
|
| 24-Hour control with a latanoprost-timolol fixed combination vs timolol alone. | 2006-11 |
|
| [The effect of glycine with timoptol on the rabbit IOP physiological values]. | 2006-07 |
|
| Atishoo! Atishoo! we all fall down! | 2006-07 |
|
| Prospective comparative switch study from timolol 0.5% and latanoprost 0.005% to bimatoprost 0.03%. | 2006-04-29 |
|
| Syncope and falls due to timolol eye drops. | 2006-04-22 |
|
| [Reduction of the physiologic IOP value after instilation of the mixture of the 2 amino acid's (L-lysine and L-arginine) in timoptol--experiment on rabbit's]. | 2006-01 |
|
| On call. The top of my tongue has taken on a dark brown color and a fuzzy look. I don't have a sore throat and I can taste everything, but I'm a bit worried. I am 67, and my only medications are Timoptic and Xalatan-drops for glaucoma. Can you tell me what's wrong and what to do about it? | 2005-04 |
|
| Polymorphism of the bm86 gene in South American strains of the cattle tick Boophilus microplus. | 2005 |
|
| Cardiovascular and intraocular pressure effects and plasma concentrations of apraclonidine. | 1990-09 |
|
| Complete heart block after topical timolol. | 1990-08 |
|
| [Raynaud syndrome following timolol-containing eyedrops]. | 1990 |
|
| Apraclonidine hydrochloride: an evaluation of plasma concentrations, and a comparison of its intraocular pressure lowering and cardiovascular effects to timolol maleate. | 1990 |
|
| Depression associated with diltiazem. | 1989-09-23 |
|
| [Timolol: adverse cardiorespiratory effects]. | 1989-05 |
|
| [Timolol ophthalmic solution and atrio-ventricular block syncope]. | 1989-01 |
|
| Topical beta-blocker therapy and central nervous system side effects. A preliminary study comparing betaxolol and timolol. | 1988-07 |
|
| Severe bradycardia due to interaction of timolol eye drops and verapamil. | 1987-01-17 |
|
| Regulation of diamine oxidase expression by beta 2-adrenoceptors in normal and hypertrophic rat kidney. | 1985-06-30 |
|
| Randomised study of six beta-blockers and a thiazide diuretic in essential hypertension. | 1978-08-05 |
|
| Amelioration of bendrofluazide-induced hypokalemia by timolol. | 1977-07 |
|
| Attenuation of hydrochlorothiazide-induced hypokalemia in dogs by a beta-adrenergic blocking drug, timolol. | 1975-06-01 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/timolol-gfs.html
Timolol Maleate Ophthalmic Gel Forming Solution is available in concentrations of 0.25% and 0.5%. The dose is one drop of Timolol Maleate Ophthalmic Gel Forming Solution (either 0.25% or 0.5%) in the affected eye(s) once a day.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28476050
Immortalized human meibomian gland epithelial cells (HMGECs) (n = 2-3 wells/treatment/experiment) were cultured with multiple concentrations of pilocarpine or timolol for up to 7 days. Experiments included positive controls for proliferation (epidermal growth factor and bovine pituitary extract) and differentiation (azithromycin). Cells were enumerated using a hemocytometer and evaluated for morphology, neutral lipid staining, and lysosome accumulation. Timolol cause a dose-dependent decrease in the survival of IHMGECs.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:00:54 GMT 2025
by
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on
Mon Mar 31 18:00:54 GMT 2025
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| Record UNII |
817W3C6175
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| Record Status |
Validated (UNII)
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WHO-ATC |
C07BA06
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C07DA06
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S01ED51
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QS01ED51
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N0000175556
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S01ED01
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QS01ED01
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WHO-ESSENTIAL MEDICINES LIST |
21.4
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C07AA06
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QC07AA06
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LIVERTOX |
NBK548254
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NCI_THESAURUS |
C29576
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WHO-VATC |
QC07BA06
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91524-16-2
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DB00373
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TIMOLOL
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10600
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817W3C6175
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W-130
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100000087971
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Timolol
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CHEMBL499
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565
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60787
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9599
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221172
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C47757
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SUB22330
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4061
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817W3C6175
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D013999
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62933
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| Related Record | Type | Details | ||
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ANHYDROUS->SOLVATE |
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PARENT -> SALT/SOLVATE |
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| Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
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