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

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
MOL RATIO 1 MOL RATIO (average)
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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
0.18 nM [IC50]
31.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRUSOPT
Primary
TRUSOPT

AUC

ValueDoseCo-administeredAnalytePopulation
22667 μM × h
7.7 μg 4 times / day multiple, topical
DORZOLAMIDE blood
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
133 day
7.7 μg 4 times / day multiple, topical
DORZOLAMIDE blood
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Tox targets

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
QZO5366EW7
Record Status Validated (UNII)
Record Version