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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H16N2O4S3.ClH
Molecular Weight 360.901
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DORZOLAMIDE HYDROCHLORIDE

SMILES

Cl.CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O

InChI

InChIKey=OSRUSFPMRGDLAG-QMGYSKNISA-N
InChI=1S/C10H16N2O4S3.ClH/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);1H/t6-,8-;/m0./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRUSOPT

Approved Use

TRUSOPT Ophthalmic Solution is indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma.

Launch Date

1994
Primary
TRUSOPT

Approved Use

TRUSOPT Ophthalmic Solution is indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma.

Launch Date

1994
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
22667 μM × h
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

T1/2

ValueDoseCo-administeredAnalytePopulation
133 day
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

Doses

DosePopulationAdverse 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)
Health Status: unhealthy
Age Group: 61.1 years (range: 23-83 years)
Sex: M+F
Sources:
Other AEs: Application site irritation, Lacrimation...
Other AEs:
Application site irritation (8 patients)
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)
Sources:
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)
Health Status: unhealthy
Age Group: 62.1 years (range: 20-88 years)
Sex: M+F
Sources:
Other AEs: Ocular stinging, Conjunctival injection...
Other AEs:
Ocular stinging (22%)
Conjunctival injection (12%)
Headache (3%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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)
Health Status: unhealthy
Age Group: 61.1 years (range: 23-83 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 61.1 years (range: 23-83 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 61.1 years (range: 23-83 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 61.1 years (range: 23-83 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 61.1 years (range: 23-83 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 61.1 years (range: 23-83 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 61.1 years (range: 23-83 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 61.1 years (range: 23-83 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 62.1 years (range: 20-88 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 62.1 years (range: 20-88 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 62.1 years (range: 20-88 years)
Sex: M+F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Effects of commercial antiglaucoma drugs to glutamate-induced [Ca2+)]i increase in cultured neuroblastoma cells.
2003-06
The effect of topical glaucoma medications evaluated by perimetry.
2003-06
The effects of dorzolamide on choroidal and retinal perfusion in non-exudative age related macular degeneration.
2003-06
Effects of twice daily application of 2% dorzolamide on intraocular pressure in normal cats.
2003-06
Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives.
2003-05-22
Influence of dorzolamide on corneal endothelium.
2003-05-10
[Therapy of normal tension glaucoma: effect of brinzolamide on ocular haemodynamics].
2003-05
Short-term effect of dorzolamide hydrochloride on central corneal thickness in humans with cornea guttata.
2003-05
Unoprostone as adjunctive therapy to timolol: a double masked randomised study versus brimonidine and dorzolamide.
2003-05
Comparison of the efficacy of the fixed-combination timolol/dorzolamide versus concomitant administration of timolol and dorzolamide.
2003-04
The effect of latanoprost, brimonidine, and a fixed combination of timolol and dorzolamide on circadian intraocular pressure in patients with glaucoma or ocular hypertension.
2003-04
Acute and chronic ocular symptoms of dorzolamide 2% compared with placebo.
2003-04
Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides.
2003-03-24
Comparative analysis of the effects of dorzolamide and latanoprost on ocular hemodynamics in normal tension glaucoma patients.
2003-03-15
Four years later: a clinical update on latanoprost.
2003-03
Dorzolamide/timolol combination versus concomitant administration of brimonidine and timolol: six-month comparison of efficacy and tolerability.
2003-03
[Glaucoma: an ocular blood flow disorder?].
2003-02
New topical drugs for open-angle glaucoma.
2003-02
Blockers of carbonic anhydrase can cause increase of retinal capillary diameter, decrease of extracellular and increase of intracellular pH in rat retinal organ culture.
2003-02
Readability of ocular medication inserts.
2003-02
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.
2003-02
The efficacy and safety of the timolol/dorzolamide fixed combination vs latanoprost in exfoliation glaucoma.
2003-01
Latanoprost : an update of its use in glaucoma and ocular hypertension.
2003
Experience with COSOPT, the fixed combination of timolol and dorzolamide, gained in Swiss ophthalmologists' offices.
2003
Cost-minimisation study of dorzolamide versus brinzolamide in the treatment of ocular hypertension and primary open-angle glaucoma: in four European countries.
2003
Evaluation of the intraocular pressure-reducing effect of latanoprost as monotherapy in open-angle glaucoma.
2002-12
A comparison of the effects on intraocular pressure of latanoprost 0.005% and the fixed combination of dorzolamide 2% and timolol 0.5% in patients with open-angle glaucoma.
2002-12
The short-term IOP-lowering effect of brimonidine 0.2% and dorzolomide 2% combination in primary open-angle glaucoma.
2002-12
An update on bimatoprost in glaucoma therapy.
2002-12
Choroidal detachment induced by dorzolamide 20 years after cataract surgery.
2002-12
Acetazolamide: future perspective in topical glaucoma therapeutics.
2002-11-06
Functional analysis of retinal vessel diameter reaction to artificially raised intraocular pressure in glaucoma patients with and without dorzolamide therapy.
2002-11
Primary glaucoma in Burmese cats.
2002-11
Dorzolamide X apraclonidine in the prevention of the intraocular pressure spike after Nd : YAG laser posterior capsulotomy.
2002-10
Inhibition of carbonic anhydrase activity in cultured bovine corneal endothelial cells by dorzolamide.
2002-10
Gateways to clinical trials.
2002-09-13
Reappraising first-line treatment in glaucoma management.
2002-09
Effects of anti-glaucoma medications on ganglion cell survival: the DBA/2J mouse model.
2002-09
The European glaucoma prevention study design and baseline description of the participants.
2002-09
Latanoprost versus combined timolol and dorzolamide.
2002-08
The effect of latanoprost on circadian intraocular pressure.
2002-08
Cost analysis of glaucoma medications: a 3-year review.
2002-08
[Weill-Marchesani syndrome. Late athalamia following antiglaucomatous surgery].
2002-07
[Comparison of latanoprost monotherapy with timolol-dorzolamide combination in patients with open-angle glaucoma or ocular hypertension].
2002-06
Tolerability and efficacy of dorzolamide versus acetazolamide added to timolol.
2002-06
Inhibitors of NHE-1 Na+/H+ exchange reduce mouse intraocular pressure.
2002-06
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
Choroidal effusion and shallowing of the anterior chamber after adjunctive therapy with latanoprost in a trabeculectomized patient with angle closure glaucoma.
2001
Patents

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
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 Mon Mar 31 17:58:33 GMT 2025
Edited
by admin
on Mon Mar 31 17:58:33 GMT 2025
Record UNII
QZO5366EW7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
COSOPT COMPONENT DORZOLAMIDE HYDROCHLORIDE
Preferred Name English
DORZOLAMIDE HYDROCHLORIDE
EP   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
DORZOLAMIDE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
MK-507
Code English
DORZOLAMIDE HYDROCHLORIDE [JAN]
Common Name English
DORZOLAMIDE HYDROCHLORIDE [MI]
Common Name English
DORZOLAMIDE HYDROCHLORIDE [USAN]
Common Name English
DORZOLAMIDE HYDROCHLORIDE [USP IMPURITY]
Common Name English
DORZOLAMIDE HYDROCHLORIDE [VANDF]
Common Name English
DORZOLAMIDE HCL
Common Name English
DORZOLAMIDE (AS HYDROCHLORIDE)
Common Name English
TRUSOPT
Brand Name English
4H-THIENO(2,3-B)THIOPYRAN-2-SULFONAMIDE, 4-(ETHYLAMINO)-5,6-DIHYDRO-6-METHYL-, 7,7-DIOXIDE, MONOHYDROCHLORIDE, (4S-TRANS)-
Common Name English
DORZOLAMIDE HYDROCHLORIDE, TRANS-(-)-
Common Name English
DORZOLAMIDE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
DORZOLAMIDE HYDROCHLORIDE [MART.]
Common Name English
(4S,6S)-4-(Ethylamino)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide, monohydrochloride
Common Name English
Dorzolamide hydrochloride [WHO-DD]
Common Name English
DORZOLAMIDE HYDROCHLORIDE [USP-RS]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29577
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
Code System Code Type Description
USAN
DD-31
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
PRIMARY
DAILYMED
QZO5366EW7
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
PRIMARY
EVMPD
SUB01820MIG
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
PRIMARY
RS_ITEM_NUM
1225281
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
PRIMARY
SMS_ID
100000090313
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
PRIMARY
PUBCHEM
6918132
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
PRIMARY
CAS
130693-82-2
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
PRIMARY
MERCK INDEX
m4745
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID1045530
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
PRIMARY
CHEBI
4703
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
PRIMARY
CAS
122028-16-4
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
NON-SPECIFIC STEREOCHEMISTRY
RXCUI
236065
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
PRIMARY RxNorm
ChEMBL
CHEMBL218490
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
PRIMARY
FDA UNII
QZO5366EW7
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
PRIMARY
DRUG BANK
DBSALT000931
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
PRIMARY
NCI_THESAURUS
C29003
Created by admin on Mon Mar 31 17:58:33 GMT 2025 , Edited by admin on Mon Mar 31 17:58:33 GMT 2025
PRIMARY
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