U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of DORZOLAMIDE

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

HIDE SMILES / InChI

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

7.8693119E11
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

7.8693119E11
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)
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)
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)
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%)
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)
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

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
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

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 Wed Jul 05 23:04:02 UTC 2023
Edited
by admin
on Wed Jul 05 23:04:02 UTC 2023
Record UNII
9JDX055TW1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DORZOLAMIDE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
DORZOLAMIDE, TRANS-(-)-
Common Name English
DORZOLAMIDE [VANDF]
Common Name English
(4S,6S)-4-(ETHYLAMINO)-5,6-DIHYDRO-6-METHYL-4H-THIENO(2,3-B)THIOPYRAN-2-SULFONAMIDE 7,7-DIOXIDE
Systematic Name English
DORZOLAMIDE [MI]
Common Name English
Dorzolamide [WHO-DD]
Common Name English
dorzolamide [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC S01EC03
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
NCI_THESAURUS C29577
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
NDF-RT N0000175517
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
WHO-VATC QS01EC03
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
NDF-RT N0000000235
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
Code System Code Type Description
SMS_ID
100000080767
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
PUBCHEM
5284549
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
DAILYMED
9JDX055TW1
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
ChEMBL
CHEMBL218490
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
IUPHAR
6810
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
MESH
C062765
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
DRUG CENTRAL
949
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
EPA CompTox
DTXSID7022960
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
FDA UNII
9JDX055TW1
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
NCI_THESAURUS
C62026
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
RXCUI
60207
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY RxNorm
CAS
120279-96-1
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
LACTMED
Dorzolamide
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
CHEBI
4702
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
INN
6960
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
DRUG BANK
DB00869
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
EVMPD
SUB06374MIG
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
MERCK INDEX
M4745
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
DORZOLAMIDE
Created by admin on Wed Jul 05 23:04:02 UTC 2023 , Edited by admin on Wed Jul 05 23:04:02 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Ki
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE LESS ACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY