Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H16N2O4S3 |
Molecular Weight | 324.44 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O
InChI
InChIKey=IAVUPMFITXYVAF-XPUUQOCRSA-N
InChI=1S/C10H16N2O4S3/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16)/t6-,8-/m0/s1
Molecular Formula | C10H16N2O4S3 |
Molecular Weight | 324.44 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Dorzolamide is a sulfonamide and a highly specific carbonic anhydrase II (CA-II) inhibitor, which is the main CA isoenzyme involved in aqueous humor secretion. Dorzolamide is marketed under the trade name Trusopt, indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma. Carbonic anhydrase (CA) is an enzyme found in many tissues of the body including the eye. It
catalyzes the reversible reaction involving the hydration of carbon dioxide and the dehydration of carbonic
acid. In humans, carbonic anhydrase exists as a number of isoenzymes, the most active being carbonic
anhydrase II (CA-II), found primarily in red blood cells (RBCs), but also in other tissues. Inhibition of
carbonic anhydrase in the ciliary processes of the eye decreases aqueous humor secretion, presumably
by slowing the formation of bicarbonate ions with subsequent reduction in sodium and fluid transport. The
result is a reduction in intraocular pressure (IOP).
TRUSOPT Ophthalmic Solution contains dorzolamide hydrochloride, an inhibitor of human carbonic
anhydrase II. Following topical ocular administration, TRUSOPT reduces elevated intraocular pressure.
Elevated intraocular pressure is a major risk factor in the pathogenesis of optic nerve damage and
glaucomatous visual field loss.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
0.18 nM [IC50] | |||
Target ID: CHEMBL3729 |
31.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | TRUSOPT Approved UseTRUSOPT Ophthalmic Solution is indicated in the treatment of elevated intraocular pressure in
patients with ocular hypertension or open-angle glaucoma. Launch Date7.8693119E11 |
|||
Primary | TRUSOPT Approved UseTRUSOPT Ophthalmic Solution is indicated in the treatment of elevated intraocular pressure in
patients with ocular hypertension or open-angle glaucoma. Launch Date7.8693119E11 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
22667 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7720769 |
7.7 μg 4 times / day multiple, topical dose: 7.7 μg route of administration: Topical experiment type: MULTIPLE co-administered: |
DORZOLAMIDE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
133 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7720769 |
7.7 μg 4 times / day multiple, topical dose: 7.7 μg route of administration: Topical experiment type: MULTIPLE co-administered: |
DORZOLAMIDE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
1 drop 3 times / day multiple, ophthalmic Highest studied dose Dose: 1 drop, 3 times / day Route: ophthalmic Route: multiple Dose: 1 drop, 3 times / day Sources: |
unhealthy, 61.1 years (range: 23-83 years) n = 78 Health Status: unhealthy Condition: ocular hypertension | open-angle glaucoma | angle-closure glaucoma Age Group: 61.1 years (range: 23-83 years) Sex: M+F Population Size: 78 Sources: |
Other AEs: Application site irritation, Lacrimation... Other AEs: Application site irritation (8 patients) Sources: Lacrimation (1 patient) Foreign body sensation in eyes (1 patient) Conjunctival hyperemia (1 patient) Visual disturbance (1 patient) Throat pain (1 patient) Seborrheic dermatitis (1 patient) Sugar urinary (1 patient) |
1 drop 3 times / day multiple, ophthalmic Recommended Dose: 1 drop, 3 times / day Route: ophthalmic Route: multiple Dose: 1 drop, 3 times / day Sources: |
unhealthy, 62.1 years (range: 20-88 years) n = 148 Health Status: unhealthy Condition: ocular hypertension | open-angle glaucoma Age Group: 62.1 years (range: 20-88 years) Sex: M+F Population Size: 148 Sources: |
Other AEs: Ocular stinging, Conjunctival injection... Other AEs: Ocular stinging (22%) Sources: Conjunctival injection (12%) Headache (3%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Conjunctival hyperemia | 1 patient | 1 drop 3 times / day multiple, ophthalmic Highest studied dose Dose: 1 drop, 3 times / day Route: ophthalmic Route: multiple Dose: 1 drop, 3 times / day Sources: |
unhealthy, 61.1 years (range: 23-83 years) n = 78 Health Status: unhealthy Condition: ocular hypertension | open-angle glaucoma | angle-closure glaucoma Age Group: 61.1 years (range: 23-83 years) Sex: M+F Population Size: 78 Sources: |
Foreign body sensation in eyes | 1 patient | 1 drop 3 times / day multiple, ophthalmic Highest studied dose Dose: 1 drop, 3 times / day Route: ophthalmic Route: multiple Dose: 1 drop, 3 times / day Sources: |
unhealthy, 61.1 years (range: 23-83 years) n = 78 Health Status: unhealthy Condition: ocular hypertension | open-angle glaucoma | angle-closure glaucoma Age Group: 61.1 years (range: 23-83 years) Sex: M+F Population Size: 78 Sources: |
Lacrimation | 1 patient | 1 drop 3 times / day multiple, ophthalmic Highest studied dose Dose: 1 drop, 3 times / day Route: ophthalmic Route: multiple Dose: 1 drop, 3 times / day Sources: |
unhealthy, 61.1 years (range: 23-83 years) n = 78 Health Status: unhealthy Condition: ocular hypertension | open-angle glaucoma | angle-closure glaucoma Age Group: 61.1 years (range: 23-83 years) Sex: M+F Population Size: 78 Sources: |
Seborrheic dermatitis | 1 patient | 1 drop 3 times / day multiple, ophthalmic Highest studied dose Dose: 1 drop, 3 times / day Route: ophthalmic Route: multiple Dose: 1 drop, 3 times / day Sources: |
unhealthy, 61.1 years (range: 23-83 years) n = 78 Health Status: unhealthy Condition: ocular hypertension | open-angle glaucoma | angle-closure glaucoma Age Group: 61.1 years (range: 23-83 years) Sex: M+F Population Size: 78 Sources: |
Sugar urinary | 1 patient | 1 drop 3 times / day multiple, ophthalmic Highest studied dose Dose: 1 drop, 3 times / day Route: ophthalmic Route: multiple Dose: 1 drop, 3 times / day Sources: |
unhealthy, 61.1 years (range: 23-83 years) n = 78 Health Status: unhealthy Condition: ocular hypertension | open-angle glaucoma | angle-closure glaucoma Age Group: 61.1 years (range: 23-83 years) Sex: M+F Population Size: 78 Sources: |
Throat pain | 1 patient | 1 drop 3 times / day multiple, ophthalmic Highest studied dose Dose: 1 drop, 3 times / day Route: ophthalmic Route: multiple Dose: 1 drop, 3 times / day Sources: |
unhealthy, 61.1 years (range: 23-83 years) n = 78 Health Status: unhealthy Condition: ocular hypertension | open-angle glaucoma | angle-closure glaucoma Age Group: 61.1 years (range: 23-83 years) Sex: M+F Population Size: 78 Sources: |
Visual disturbance | 1 patient | 1 drop 3 times / day multiple, ophthalmic Highest studied dose Dose: 1 drop, 3 times / day Route: ophthalmic Route: multiple Dose: 1 drop, 3 times / day Sources: |
unhealthy, 61.1 years (range: 23-83 years) n = 78 Health Status: unhealthy Condition: ocular hypertension | open-angle glaucoma | angle-closure glaucoma Age Group: 61.1 years (range: 23-83 years) Sex: M+F Population Size: 78 Sources: |
Application site irritation | 8 patients | 1 drop 3 times / day multiple, ophthalmic Highest studied dose Dose: 1 drop, 3 times / day Route: ophthalmic Route: multiple Dose: 1 drop, 3 times / day Sources: |
unhealthy, 61.1 years (range: 23-83 years) n = 78 Health Status: unhealthy Condition: ocular hypertension | open-angle glaucoma | angle-closure glaucoma Age Group: 61.1 years (range: 23-83 years) Sex: M+F Population Size: 78 Sources: |
Conjunctival injection | 12% | 1 drop 3 times / day multiple, ophthalmic Recommended Dose: 1 drop, 3 times / day Route: ophthalmic Route: multiple Dose: 1 drop, 3 times / day Sources: |
unhealthy, 62.1 years (range: 20-88 years) n = 148 Health Status: unhealthy Condition: ocular hypertension | open-angle glaucoma Age Group: 62.1 years (range: 20-88 years) Sex: M+F Population Size: 148 Sources: |
Ocular stinging | 22% | 1 drop 3 times / day multiple, ophthalmic Recommended Dose: 1 drop, 3 times / day Route: ophthalmic Route: multiple Dose: 1 drop, 3 times / day Sources: |
unhealthy, 62.1 years (range: 20-88 years) n = 148 Health Status: unhealthy Condition: ocular hypertension | open-angle glaucoma Age Group: 62.1 years (range: 20-88 years) Sex: M+F Population Size: 148 Sources: |
Headache | 3% | 1 drop 3 times / day multiple, ophthalmic Recommended Dose: 1 drop, 3 times / day Route: ophthalmic Route: multiple Dose: 1 drop, 3 times / day Sources: |
unhealthy, 62.1 years (range: 20-88 years) n = 148 Health Status: unhealthy Condition: ocular hypertension | open-angle glaucoma Age Group: 62.1 years (range: 20-88 years) Sex: M+F Population Size: 148 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: (PMDA) 9 |
yes | |||
Page: (PMDA) 9 |
yes | |||
Page: (PMDA) 9 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Dorzolamide-induced immune thrombocytopenia: a case report and literature review. | 2001 Apr |
|
Comparison of topical brinzolamide 1% and dorzolamide 2% eye drops given twice daily in addition to timolol 0.5% in patients with primary open-angle glaucoma or ocular hypertension. | 2001 Aug |
|
Latanoprost versus combined therapy with timolol plus dorzolamide: IOP-lowering effect in open-angle glaucoma. | 2001 Feb |
|
Treatment of intraocular pressure elevation after photorefractive keratectomy. | 2001 Jul |
|
Effect of topical administration of 2% dorzlamide hydrochloride or 2% dorzlamide hydrochloride-0.5% timolol maleate on intraocular pressure in clinically normal horses. | 2001 May |
|
Comparisons of intraocular-pressure- lowering efficacy and side effects of 2% dorzolamide and 1% brinzolamide. | 2001 May-Jun |
|
[Innovative glaucoma therapy. Glaucoma therapy with topical carbonic anhydrase inhibitors]. | 2001 Oct |
|
The pulsatile ocular blood flow behaviour in open angle glaucoma patients after replacing timolol therapy with timolol and dorzolamide fixed combination: preliminary study. | 2002 |
|
Comparison of latanoprost, brimonidine and a fixed combination of timolol and dorzolamide on circadian intraocular pressure in patients with primary open-angle glaucoma and ocular hypertension. | 2002 |
|
Effect of brimonidine on patients undergoing uncontrolled IOP with beta-blockers. | 2002 |
|
[Weill-Marchesani syndrome. Late athalamia following antiglaucomatous surgery]. | 2002 Jul |
|
Inhibitors of NHE-1 Na+/H+ exchange reduce mouse intraocular pressure. | 2002 Jun |
|
Additive intraocular pressure lowering effect of various medications with latanoprost. | 2002 Jun |
|
Dorzolamide X apraclonidine in the prevention of the intraocular pressure spike after Nd : YAG laser posterior capsulotomy. | 2002 Oct |
|
Experience with COSOPT, the fixed combination of timolol and dorzolamide, gained in Swiss ophthalmologists' offices. | 2003 |
|
Comparison of the efficacy of the fixed-combination timolol/dorzolamide versus concomitant administration of timolol and dorzolamide. | 2003 Apr |
|
[Glaucoma: an ocular blood flow disorder?]. | 2003 Feb |
|
New topical drugs for open-angle glaucoma. | 2003 Feb |
|
Readability of ocular medication inserts. | 2003 Feb |
|
Timolol 0.5%/dorzolamide 2% fixed combination vs timolol maleate 0.5% and unoprostone 0.15% given twice daily to patients with primary open-angle glaucoma or ocular hypertension. | 2003 Feb |
|
The effect of topical glaucoma medications evaluated by perimetry. | 2003 Jun |
|
The effects of dorzolamide on choroidal and retinal perfusion in non-exudative age related macular degeneration. | 2003 Jun |
|
Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides. | 2003 Mar 24 |
|
Influence of dorzolamide on corneal endothelium. | 2003 Mar-Apr |
|
[Therapy of normal tension glaucoma: effect of brinzolamide on ocular haemodynamics]. | 2003 May |
|
Short-term effect of dorzolamide hydrochloride on central corneal thickness in humans with cornea guttata. | 2003 May |
Patents
Sample Use Guides
Usual Adult Dose for Intraocular Hypertension
One drop in the affected eye(s) three times a day
Usual Adult Dose for Glaucoma (Open Angle)
One drop in the affected eye(s) three times a day
Applies to the following strength(s): 2%
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10948564
Dorzolamide hydrochloride is a potent inhibitor of human CA isoenzyme II, with an IC50 value of 0.18 nM in vitro. In contrast, its inhibitory activity against human CA isozyme I is much weaker (IC50 value of 600 nM).
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:04:02 UTC 2023
by
admin
on
Wed Jul 05 23:04:02 UTC 2023
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Record UNII |
9JDX055TW1
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
S01EC03
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NCI_THESAURUS |
C29577
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N0000175517
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QS01EC03
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N0000000235
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Dorzolamide
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DORZOLAMIDE
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR |
Ki
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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR |
Related Record | Type | Details | ||
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METABOLITE LESS ACTIVE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |