Dorzolamide

Names

[ CAS No. ]:
120279-96-1

[ Name ]:
Dorzolamide

[Synonym ]:
(4S,6S)-4-(ethylamino)-6-methyl-7,7-dioxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide
(4S,6S)-4H-Thieno[2,3-b]thiopyran-2-sulfonamide (4-(ethylamino)-5,6-dihydro-6-methyl
1cil
Trusopt
MFCD00865636

Biological Activity

[Description]:

Dorzolamide(L671152; MK507) is an anti-glaucoma agent, which is a carbonic anhydrase inhibitor.Target: carbonic anhydrase (CA)Dorzolamide is a carbonic anhydrase inhibitor. It is an anti-glaucoma agent, and acts by decreasing the production of aqueous humour [1]. Glaucoma was induced in the right eye of adult Wistar rats by episcleral venous occlusion. One experimental group was administered dorzolamide 2%-timolol 0.5% combination eye drops, while the other experimental group was administered dorzolamide 2% eye drops. Control groups had surgery without drug administration. Drug application was initiated either 2 weeks before surgery (Group A), from the day of surgery (Group B), 2 weeks after surgery (Group C), or 4 weeks after surgery (Group D). RGCs were labeled by intratectal Fluorogold injections and counted from flat-mount preparations, and IOP was measured using Tonopen. Both dorzolamide-timolol combination and dorzolamide, when applied topically, significantly reduced IOP and improved RGC densities in experimental eyes when compared to control eyes. Earlier initiation, as well as longer duration of drug application, resulted in higher RGC densities [2].Clinical indications: Glaucoma; Ocular hypertensionFDA Approved Date: 1995Toxicity: Dizziness, headache, shortness of breath, slow heartbeat, severe asthma, cardiac arrest

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Carbonic Anhydrase

Research Areas >> Others

[References]

[1]. Rankin AJ, et al. Effects of ocular administration of ophthalmic 2% dorzolamide hydrochloride solution on aqueous humor flow rate and intraocular pressure in clinically normal cats. Am J Vet Res. 2012 Jul;73(7):1074-8.

[2]. Sarup V, et al. Dorzolamide and timolol saves retinal ganglion cells in glaucomatous adult rats. J Ocul Pharmacol Ther. 2005 Dec;21(6):454-62.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.53 g/cm3

[ Boiling Point ]:
575.8ºC at 760 mmHg

[ Molecular Formula ]:
C₁₀H₁₆N₂O₄S₃

[ Molecular Weight ]:
324.44

[ Flash Point ]:
302ºC

[ PSA ]:
151.33000

[ LogP ]:
4.66680

[ Index of Refraction ]:
1.626

[ Storage condition ]:
room temp

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38:Irritating to eyes, respiratory system and skin .

[ Safety Phrases ]:
S24/25-S37/39-S26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
1

[ RTECS ]:
UQ1355000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Dorzolamide synergizes the antitumor activity of mitomycin C against Ehrlich's carcinoma grown in mice: role of thioredoxin-interacting protein.

Naunyn Schmiedebergs Arch. Pharmacol. 388 , 1271-82, (2015)

The antitumor activity of carbonic anhydrase (CA) inhibitors is attributed to their ability to induce a state of intracellular acidification. In fact, acidic intracellular pH was demonstrated to upreg...

Synaptic pathology and therapeutic repair in adult retinoschisis mouse by AAV-RS1 transfer.

J. Clin. Invest. 125 , 2891-903, (2015)

Strategies aimed at invoking synaptic plasticity have therapeutic potential for several neurological conditions. The human retinal synaptic disease X-linked retinoschisis (XLRS) is characterized by im...

Bleb Analysis and Short-Term Results of Biodegradable Collagen Matrix-Augmented Ahmed Glaucoma Valve Implantation: 6-Month Follow-up.

Invest. Ophthalmol. Vis. Sci. 56 , 5896-903, (2015)

To evaluate the short-term efficacy of a biodegradable collagen matrix (BCM) as an adjuvant for Ahmed valve implantation surgery to prevent the hypertensive phase.This prospective study included 43 re...