Dorzolamide

HCID 5284549

Basic information

CAS
120279-96-1
Standard SMILES
CCN[C@H]1C[C@H](C)S(=O)(=O)c2sc(S(N)(=O)=O)cc21
InChIKey
IAVUPMFITXYVAF-XPUUQOCRSA-N
Molecular formula
C10H16N2O4S3
Average molar mass
324.4 g/mol
Monoisotopic mass
324.02721999

Overview

Dorzolamide is 5,6-Dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide in which hydrogens at the 4 and 6 positions are substituted by ethylamino and methyl groups, respectively (4S, trans-configuration). A carbonic anhydrase inhibitor, it is used as the hydrochloride in ophthalmic solutions to lower increased intraocular pressure in the treatment of open-angle glaucoma and ocular hypertension. It has a role as an EC 4.2.1.1 (carbonic anhydrase) inhibitor, an antihypertensive agent and an antiglaucoma drug. It is a member of thiophenes and a sulfonamide.

Names & identifiers

Preferred name
Dorzolamide
IUPAC
(4S,6S)-4-(ethylamino)-6-methyl-7,7-dioxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide
English name
Dorzolamide
Molecular formula
C10H16N2O4S3
Molecular weight
324.44

Names & synonyms

dorzolamide120279-96-14S,6S-DorzolamideDorzolamidaDorzolamide, trans-(-)-9JDX055TW1CHEBI:4702DTXSID7022960(4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulfonic acid amide(4S,trans)-4-(ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulfonic acid amide4-ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulfonic acid amide
Show more names
(2r,4r)-2-ethylamino-4-methyl-5,5-dioxo-5,7-dithiabicyclo[4.3.0]nona-8,10-diene-8-sulfonamideC06969Dorzolamide-d5 MaleateDorzolamide >=98% (HPLC)Dorzalamide hydrochlorideDORZOLAMIDE(SUBJECTTOPATENTFREE)Dorzolamide Impurity A Hydrochloride(4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-7,
4H-Thieno(2,3-b)thiopyran-2-sulfonamide, 4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide, (4S-trans)-DorzolamidumDorzant4-ethylamino-6-methyl-7,7-dioxo-5,6-dihydro-4H-thieno(5,4-b)thiopyran-2-sulfonamide4-ethylamino-6-methyl-7,7-dioxo-5,6-dihydro-4H-thieno[5,4-b]thiopyran-2-sulfonamide(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1$l^(6),7-thieno(2,3-b)(1$l^(6))thiopyran-6-sulfonamide(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1$l^{6},7-thieno[2,3-b][1$l^{6}]thiopyran-6-sulfonamide(4S,6S)-4-ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno(2,3-b)thiopyran-2-sulfonic acid amide

Database identifiers

CAS
120279-96-1
PubChem CID
5284549
DTXSID
DTXSID7022960
ChEMBL
CHEMBL218490
ChEBI
CHEBI:4702
UNII
9JDX055TW1
EC Number
802-371-1

Properties

Computed structural properties

XLogP
0.4
Topological polar surface area
151 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
7
Rotatable bonds
3
Heavy atoms
19

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LogP · 2 items

-1

0.27

Solubility6.99e-01 g/L
Human Drugs · 2 items

Breast Feeding; Lactation; Antiglaucoma Agents; Carbonic Anhydrase Inhibitors

Pharmaceuticals

Melting Point283 - 285 °C
Physical DescriptionSolid

Physicochemical properties

Boiling point
575.8 · 575.8±60.0 °C(Predicted)
Density
1.53 · 1.53±0.1 g/cm3(Predicted)
storage temp.
room temp
solubility
5 mg/mL · DMSO: soluble5mg/mL (clear solution, warmed)
pka
6.35 · pKa 6.35 (Uncertain);8.50 (Uncertain)
form
powder

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (97.4%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicology

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

wgk
3
rtecs
XJ9095169
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi

Chemistry & industry

Pharmacology

ATC Code · 2 items

S - Sensory organs

QS - Sensory organs

Protein BindingDorzolamide is approximately 33% bound to plasma proteins.
Pharmacodynamics · 1 item

Dorzolamide is a carbonic anhydrase inhibitor that reduces elevated intraocular pressure in open-angle glaucoma or ocular hypertension. When used in combination with topic beta-adrenergic antagonists, dorzolamide has an additive effect of lowering intraocular pressure. The peak ocular hypotensive effect of dorzolamide is observed at about 2 hours following ophthalmic administration.

Mechanism of Action · 1 item

Elevated intraocular pressure is a characteristic manifestation of ocular hypertension or open-angle glaucoma. The level of intraocular pressure (IOP) is governed by the balance between the production of aqueous humour (by ocular ciliary processes) and its outflow from the anterior segment of the eye via trabecular (conventional) or uveoscleral (unconventional) pathways. When there is an increase in the resistance to the trabecular outflow of aqueous humour, the intraocular pressure is elevated. Subsequently, optic nerve damage can occur from blood flow restrictions and mechanical distortion of ocular structures. Optic nerve damage can further result in optic disc cupping and progressive visual field loss (and blindness in some cases). Carbonic anhydrase (CA) is a ubiquitous enzyme that catalyzes the reversible hydration of carbon dioxide to bicarbonate ions and dehydration of carbonic acid. In the ocular ciliary processes, the local production of bicarbonate by CAs promotes sodium and fluid transport. CA-II is a key isoenzyme found primarily in red blood cells (RBCs) that regulates aqueous humour production. Dorzolamide is a highly specific CA-II inhibitor, where it displays a 4000-fold higher affinity for carbonic anhydrase II than carbonic anhydrase I. The inhibition of CA-II in the ciliary process disrupts the formation of bicarbonate ions and reduces sodium and fluid transport, which leads to decreased aqueous humour secretion and reduced intraocular pressure.

Biological Half-Life · 1 item

As the drug administration is stopped, dorzolamide stored in RBCs is washed out of RBCs in a non-linear fashion, with the terminal elimination half-life of ≥120 days in RBCs. This initial rapid decline in drug concentrations is followed by the slow elimination phase, where the elimination half-life of the drug is about >4 months.

Metabolism/Metabolites · 1 item

Dorzolamide is slowly metabolised to N-desethyldorzolamide, which has a less potent pharmacological activity on CA-II and some inhibitory effect on CA-I. Like the parent drug, N-desethyldorzolamide is also stored in RBCs, where it binds to CA-I. The findings of an _in vitro_ study using liver microsomes from Sprague-Dawley rats suggest the involvement of CYP2B1, CYP2E1, and CYP3A2 in the metabolism of dorzolamide in rat liver.

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >250
Use ClassificationPharmaceuticals

Applications

UsesCarbonic anhydrase inhibitor.

UsesDorzolamide is an intermediate in synthesizing N-Acetyl Dorzolamide (A173640), a useful synthetic compound.

Upstream & downstream products

Downstream products

Suppliers63 total

北京华美互利生物化工010-56205725 · [email protected]
陕西缔都新材料有限公司81124267 17392282731 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
普善实业(陕西)有限公司029-81310890 18165209495 · [email protected]
苏州市森菲达化工有限公司18796480002 18796480002 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 5,6-Dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide in which hydrogens at the 4 and 6 positions are substituted by ethylamino and methyl groups, respectively (4S, trans-configuration . A carbonic anhydrase inhibitor, it is used as the hydrochloride in ophthalmic solutions to lower increased intraocular pressure in the treatment of open-angle glaucoma and ocular hypertension.

Related reactions

2 records

Compound notes

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