CAS 120279-95-0

4R,6R-Dorzolamide

Description:

4R,6R-Dorzolamide is a sulfonamide compound primarily used as a carbonic anhydrase inhibitor, which is effective in the treatment of glaucoma and ocular hypertension. This compound works by reducing the production of aqueous humor in the eye, thereby lowering intraocular pressure. Structurally, it features a bicyclic ring system with a sulfonamide functional group, contributing to its pharmacological activity. The stereochemistry of 4R,6R-Dorzolamide is crucial for its efficacy, as the specific configuration at the chiral centers enhances its binding affinity to the carbonic anhydrase enzyme. It is typically administered as a topical ophthalmic solution. In terms of solubility, dorzolamide is more soluble in aqueous solutions, which facilitates its absorption when applied to the eye. Common side effects may include ocular discomfort and a bitter taste, but it is generally well-tolerated. Overall, 4R,6R-Dorzolamide represents a significant advancement in the management of conditions associated with elevated intraocular pressure.

Synonyms:

• 4H-Thieno[2,3-b]thiopyran-2-sulfonamide, 4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide, (4R,6R)-
• 4H-Thieno[2,3-b]thiopyran-2-sulfonamide, 4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide, (4R-trans)-

DORZOLAMIDE IMPURITY A CRS

CAS: 120279-95-0

DORZOLAMIDE IMPURITY A CRS

Formula: C₁₀H₁₆N₂O₄S₃

Molecular weight: 324.44

Ref: 41-Y0000727

4R,6R)-4-(Ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-Dioxide ((4R,6R)-Dorzolamide)

CAS: 120279-95-0

Color and Shape: Neat

Ref: 86-MM0403.01

ent-Dorzolamide

Controlled Product

CAS: 120279-95-0

Impurity Dorzolamide EP Impurity A
Applications ent-Dorzolamide (Dorzolamide EP Impurity A) is an enantiomer of Dorzolamide (D535100), an carbonic anhydrase inhibitor and antiglaucoma agent.
References Temperini, C., et al.: Bioorg. Med. Chem. Lett., 17, 4866 (2007); Novak, T.J., et al.: J. Liq. Chroma. Rel. Technol., 21, 1883 (1998); Matuszewski, B.K., et al.: Pharma. Res., 11, 449 (1994);

Formula: C₁₀H₁₆N₂O₄S₃

Color and Shape: Off-White

Molecular weight: 324.44

Ref: TR-D535125

ent-Dorzolamide Maleate

Controlled Product

CAS: 120279-95-0

Applications ent-Dorzolamide Maleate is an enantiomer of Dorzolamide (D535100), an carbonic anhydrase inhibitor and antiglaucoma agent.
References Novak, T.J., et al.: J. Liq. Chroma. Rel. Technol., 21, 1883 (1998); Matuszewski, B.K., et al.: Pharma. Res., 11, 449 (1994);

Formula: C₁₄H₂₀N₂O₈S₃

Color and Shape: Neat

Molecular weight: 440.51

Ref: TR-D535140

ent-Dorzolamide L-Tartrate

Controlled Product

CAS: 120279-95-0

Applications ent-Dorzolamide L-Tartrate is an enantiomer of Dorzolamide (D535100), an carbonic anhydrase inhibitor and antiglaucoma agent.
References Novak, T.J., et al.: J. Liq. Chroma. Rel. Technol., 21, 1883 (1998); Matuszewski, B.K., et al.: Pharma. Res., 11, 449 (1994);

Formula: C₃₀H₃₄N₂O₁₂S₃

Color and Shape: Neat

Molecular weight: 710.79

Ref: TR-D535135

Ent-dorzolamide

CAS: 120279-95-0

Ent-dorzolamide is a carbonic anhydrase inhibitor that binds to the β-adrenergic receptor, which is a G protein-coupled receptor. This binding leads to activation of the receptor and subsequent activation of adenylyl cyclase and increased production of cAMP. It has been shown to have insulin sensitizing effects in animal models. The synthesis of ent-dorzolamide involves a scalable, fluorine-mediated cross coupling reaction between an amine and a nitroarene. Ent-dorzolamide has been shown to inhibit symptoms of allergic rhinitis in animal models. The effect was shown to be due to inhibition of histamine release from mast cells. Ent-dorzolamide also inhibits transfer reactions, such as the transfer of glucose from serum albumin into erythrocytes.

Formula: C₁₀H₁₆N₂O₄S₃

Purity: Min. 95%

Molecular weight: 324.4 g/mol

Ref: 3D-VEA27995