Dorzolamide

Base Information

• Chemical Name: Dorzolamide
• CAS No.: 120279-96-1
• Molecular Formula: C10H16N2O4S3
• Molecular Weight: 324.446
• UNII: 9JDX055TW1
• DSSTox Substance ID: DTXSID7022960
• Nikkaji Number: J488.895B
• Wikipedia: Dorzolamide
• Wikidata: Q415401
• NCI Thesaurus Code: C62026
• RXCUI: 60207
• Pharos Ligand ID: LWVW9STSSBXL
• Metabolomics Workbench ID: 43145
• ChEMBL ID: CHEMBL218490
• Mol file: 120279-96-1.mol

Synonyms:4-ethylamino-5,6-dihydro-6-methyl-7,7-dioxide-4H-thieno(2,3-b)thiopyran-2-sulfonamide;5,6-dihydro-4-ethylamino-6-methyl-4H-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxide;dorzolamide;Dorzolamide Chibret;dorzolamide hydrochloride;dorzolamide, (trans)-isomer;L 671152;L-671,152;MK 507;MK-507;Trusopt

Chemical Property of Dorzolamide

Chemical Property:

• Appearance/Colour: White or almost white crystalline powder
• Refractive Index: 1.626
• Boiling Point: 575.8 °C at 760 mmHg
• PKA: pKa 6.35 (Uncertain);8.50 (Uncertain)
• Flash Point: 302 °C
• Density: 1.53 g/cm³
• Storage Temp.: room temp
• Solubility.: DMSO: soluble5mg/mL (clear solution, warmed)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 324.02722052
• Heavy Atom Count: 19
• Complexity: 534

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dorzolamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCNC1CC(S(=O)(=O)C2=C1C=C(S2)S(=O)(=O)N)C
• Isomeric SMILES: CCN[C@H]1C[C@@H](S(=O)(=O)C2=C1C=C(S2)S(=O)(=O)N)C
• Recent ClinicalTrials: Stop Retinal Ganglion Cell Dysfunction Study
• Recent EU Clinical Trials: Investigation of the efficacy and safety of preoperative IOP reduction with preservative-free COSOPT-S? (dorzolamide/timolol, MSD) eye drops versus oral acetazolamide and dexamethasone eye drops and assessment of the clinical outcome of trabeculectomy in glaucoma patients
• Recent NIPH Clinical Trials: The Clinical Efficacy of Carbonic Anhydrase Inhibitors and Steroids in the Management of Cystoid Macular Edema in Patients with Retinitis Pigmentosa
• Uses: Carbonic anhydrase inhibitor. Dorzolamide is an intermediate in synthesizing N-Acetyl Dorzolamide (A173640), a useful synthetic compound.

Technology Process of Dorzolamide

There total 16 articles about Dorzolamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(4S,6S)?4?acetamido?5,6?dihydro?6?methyl?4H?thieno[2,3?b]thiopyran?2?sulfonamide?7,7?dioxide (147200-03-1,120298-38-6) → dorzolamide (120279-96-1)

Guidance literature:

With zinc(II) tetrahydroborate; In methanol; at 90 ℃; for 3h; Temperature; Solvent; Green chemistry;

Reference yield: 66.0%

N-ethyl-N-[(4S,6S)-6-methyl-7,7-dioxo-2-sulfamoyl-4,5,6,7-tetrahydro-7λ6-thieno[2,3-b]thiopyran-4-yl]acetamide → dorzolamide (120279-96-1)

Guidance literature:

With hydrogenchloride; water; In methanol; for 72h; Heating / reflux;

Reference yield:

(6S)-4-ethylimino-5,6-dihydro-6-methyl-7,7-dioxo-thieno[2,3-b]thiopyran-2-sulfonamide → dorzolamide (120279-96-1)

Guidance literature:

With (1,5-cyclooctadiene)(hexafluoroacetylacetonato)iridium(I); hydrogen; (R)-(+)-1,1'-binaphthyl-2'-isopropoxy-2-diphenylphosphine; In water; iso-butanol; at 60 ℃; for 8h; under 7500.75 Torr; Solvent; Reagent/catalyst; Temperature; Autoclave; Large scale;

upstream raw materials:

4-(acetylamino)-5,6-dihydro-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-2-sulfonamide 7,7-dioxide

(S)-5,6-dihydro-6-methylthieno<2,3-b>thiopyran-4-one

5,6-dihydro-(R)-4-hydroxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran

(S)-3-(thien-2-ylthio)butyric acid

Downstream raw materials:

5,6-dihydro-4H-4-(R)-ethylamino-6-(R)-methylthieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide hydrochloride

Refernces

• 1、 -. "Synthetic process of dorzolamide Hydrochloride intermediate". Paragraph 0036; 0053; 0076-0083. . Retrieved 2020/06/20.
• 2、 -. "Process for preparing 5,6-dihydro-4-(S)-(ethylamino)-6-(S) methyl-4H-thieno[2,3b]thiopyran-2-sulphonamide-7,7-dioxide HCI". Page/Page column 10. . Retrieved 2008/06/13.