3426. Dorzolamide

Nomenclature

CAS number: 120279-96-1
(4S,6S)-4-(Ethylamino)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide.
C10H16N2O4S3; mol wt 324.44.
C 37.02%, H 4.97%, N 8.63%, O 19.73%, S 29.65%.

Description and references

Carbonic anhydrase inhibitor. Prepn: J. J. Baldwin et al., EP 296879; eidem, US 4797413 (1988, 1989 both to Merck & Co.). Mechanism of action study: R.-F. Wang et al., Arch. Ophthalmol. 109, 1297 (1991). HPLC determn in plasma and urine: B. K. Matuszewski, M. L. Constanzer, Chirality 4, 515 (1992). Clinical evaluations in glaucoma and ocular hypertension: E. A. Lippa et al., Ophthalmology 98, 308 (1991); E. A. Lippa et al., Arch. Ophthalmol. 110, 495 (1992). Review of clinical pharmacokinetics: J. Martens-Lobenhoffer, P. Banditt, Clin. Pharmacokinet. 41, 197-205 (2002).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 130693-82-2
MK-507; Trusopt (Merck & Co.).
C10H16N2O4S3.HCl; mol wt 360.90.
C 33.28%, H 4.75%, N 7.76%, O 17.73%, S 26.65%, Cl 9.82%.

Properties

White to off-white crystalline powder, mp 283-285°. [α]D24 -8.34° (c = 1 in methanol). [α]40525 ≈-17° (c = 1 in water). Sol in water; slightly sol in methanol and ethanol.

Derivative

Mixture of hydrochloride with timolol maleate.

Nomenclature

Cosopt (Merck & Co.).

Description and references

HPLC determn in commercial formulation: N. Erk, Pharmazie 58, 491 (2003). Review of clinical experience in glaucoma and ocular hypertension: J. E. Frampton, C. M. Perry, Drugs Aging 23, 977-995 (2006).

Therapeutic Category

Antiglaucoma agent.

Keywords

Antiglaucoma; Carbonic Anhydrase Inhibitor