4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6,7-thieno[2,3-b][1λ6]thiopyran-6-sulfonamide

• ChemBase ID: 747
• Molecular Formular: C10H16N2O4S3
• Molecular Mass: 324.44004
• Monoisotopic Mass: 324.02722
• SMILES: S1(=O)(=O)C(CC(NCC)c2c1sc(S(=O)(=O)N)c2)C
• Canonical SMILES: CCNC1CC(C)S(=O)(=O)c2c1cc(s2)S(=O)(=O)N
• InChI: InChI=1S/C10H16N2O4S3/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)
• InChIKey: IAVUPMFITXYVAF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ^6,7-thieno[2,3-b][1λ^6]thiopyran-6-sulfonamide; 4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1$l^{6},7-thieno[2,3-b][1$l^{6}]thiopyran-6-sulfonamide
• IUPAC Traditional name: dorzolamide
• Brand Name: Trusopt
• Synonyms: Dorzolamide

Database IDs

• CAS Number: 120279-96-1; 130693-82-2
• PubChem SID: 160964210
• PubChem CID: 3154; 5284549
• CHEBI ID: 4702
• ATC CODE: S01EC03
• CHEMBL: 218490
• Chemspider ID: 4447604
• DrugBank ID: DB00869
• KEGG ID: D07871
• Unique Ingredient Identifier: 9JDX055TW1
• Wikipedia Title: Dorzolamide
• Medline Plus: a602022

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.1842785
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.5705113
• LogD (pH = 7.4): -0.15743962
• Log P: -0.15111351
• Molar Refractivity: 72.4611 cm^3
• Polarizability: 30.45586 Å^3
• Polar Surface Area: 106.33 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.5
• LOG S: -2.67
• Solubility (Water): 6.99e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -1

Pharmacology Properties

• Admin Routes: Topical (eye drops)
• Half Life: 4 months
• Protein Bound: ~33%
• Legal Status: Rx-only (US)
• Pregnancy Category: C (US)

DETAILS

DrugBank - DB00869

• Drug Groups: approved
• Description: Dorzolamide is a carbonic anhydrase (CA) inhibitor. It is used in ophthalmic solutions (Trusopt) to lower intraocular pressure (IOP) in open-angle glaucoma and ocular hypertension.
• Indication: For the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma. Also used prophylatically for the inhibition of perioperative IOP increase (before neodynium yttrium aluminum garnet laser posterior capsulotomy).
• Pharmacology: Dorzolamide is topical CA inhibitor that is indicated for the reduction of elevated IOP in patients with open-angle glaucoma or ocular hypertension who are insufficiently responsive to beta-blockers. Dorzolamide reduces IOP by approximately 17-23% in patients with elevater IOP.
• Toxicity: Dizziness, headache, shortness of breath, slow heartbeat, severe asthma, cardiac arrest
• Affected Organisms: Humans and other mammals
• Half Life: 4 months
• Protein Binding: ~33%
• Elimination: Dorzolamide is primarily excreted unchanged in the urine; the metabolite also is excreted in urine.
• References: Plummer CE, MacKay EO, Gelatt KN: Comparison of the effects of topical administration of a fixed combination of dorzolamide-timolol to monotherapy with timolol or dorzolamide on IOP, pupil size, and heart rate in glaucomatous dogs. Vet Ophthalmol. 2006 Jul-Aug;9(4):245-9. [Pubmed] ; Grover S, Apushkin MA, Fishman GA: Topical dorzolamide for the treatment of cystoid macular edema in patients with retinitis pigmentosa. Am J Ophthalmol. 2006 May;141(5):850-8. Epub 2006 Mar 20. [Pubmed] ; Almeida GC Jr, Faria e Souza SJ: Effect of topical dorzolamide on rabbit central corneal thickness. Braz J Med Biol Res. 2006 Feb;39(2):277-81. Epub 2006 Feb 2. [Pubmed] ; Martens-Lobenhoffer J, Banditt P: Clinical pharmacokinetics of dorzolamide. Clin Pharmacokinet. 2002;41(3):197-205. [Pubmed] ; Balfour JA, Wilde MI: Dorzolamide. A review of its pharmacology and therapeutic potential in the management of glaucoma and ocular hypertension. Drugs Aging. 1997 May;10(5):384-403. [Pubmed] ; Ponticello GS, Sugrue MF, Plazonnet B, Durand-Cavagna G: Dorzolamide, a 40-year wait. From an oral to a topical carbonic anhydrase inhibitor for the treatment of glaucoma. Pharm Biotechnol. 1998;11:555-74. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Plummer CE, MacKay EO, Gelatt KN: Comparison of the effects of topical administration of a fixed combination of dorzolamide-timolol to monotherapy with timolol or dorzolamide on IOP, pupil size, and heart rate in glaucomatous dogs. Vet Ophthalmol. 2006 Jul-Aug;9(4):245-9. Pubmed
• Grover S, Apushkin MA, Fishman GA: Topical dorzolamide for the treatment of cystoid macular edema in patients with retinitis pigmentosa. Am J Ophthalmol. 2006 May;141(5):850-8. Epub 2006 Mar 20. Pubmed
• Almeida GC Jr, Faria e Souza SJ: Effect of topical dorzolamide on rabbit central corneal thickness. Braz J Med Biol Res. 2006 Feb;39(2):277-81. Epub 2006 Feb 2. Pubmed
• Martens-Lobenhoffer J, Banditt P: Clinical pharmacokinetics of dorzolamide. Clin Pharmacokinet. 2002;41(3):197-205. Pubmed
• Balfour JA, Wilde MI: Dorzolamide. A review of its pharmacology and therapeutic potential in the management of glaucoma and ocular hypertension. Drugs Aging. 1997 May;10(5):384-403. Pubmed
• Ponticello GS, Sugrue MF, Plazonnet B, Durand-Cavagna G: Dorzolamide, a 40-year wait. From an oral to a topical carbonic anhydrase inhibitor for the treatment of glaucoma. Pharm Biotechnol. 1998;11:555-74. Pubmed