Dorzolamide hydrochloride

Base Information

• Chemical Name: Dorzolamide hydrochloride
• CAS No.: 130693-82-2
• Molecular Formula: C10H16N2O4S3^.HCl
• Molecular Weight: 360.907
• Hs Code.: 2935904000
• European Community (EC) Number: 620-304-2
• UNII: QZO5366EW7
• DSSTox Substance ID: DTXSID1045530
• Wikidata: Q27106441
• NCI Thesaurus Code: C29003
• RXCUI: 236065
• ChEMBL ID: CHEMBL1201162
• Mol file: 130693-82-2.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 hydrochloride

Chemical Property:

• Appearance/Colour: White off-white crystalline powder.
• Vapor Pressure: 2.93E-13mmHg at 25°C
• Melting Point: 265-267 °C
• Boiling Point: 575.8 °C at 760 mmHg
• Flash Point: 302 °C
• Density: 1.53 g/cm³
• Storage Temp.: Refrigerator
• Solubility.: Soluble in water, slightly soluble in methanol, very slightly soluble in anhydrous ethanol.
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 360.0038982
• Heavy Atom Count: 20
• Complexity: 534

Purity/Quality:

99%, ^*data from raw suppliers

Dorzolamide Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCNC1CC(S(=O)(=O)C2=C1C=C(S2)S(=O)(=O)N)C.Cl
• Isomeric SMILES: CCN[C@H]1C[C@@H](S(=O)(=O)C2=C1C=C(S2)S(=O)(=O)N)C.Cl
• Recent ClinicalTrials: Comparative Study of Dorzol Eye Drops, 20 mg/ml Versus Trusopt? Eye Drops, 20 mg/ml
• Recent EU Clinical Trials: A Randomized, Observer-blind, two Parallel Group, Multi-center, Clinical Trial for Comparing the Efficacy and Tolerability of Dorzo-Vision? sine Preservative-Free Eye Drops vs. Trusopt? Preservative-Free Eye Drops in Patients with Open Angle Glaucoma, or Ocular Hypertension, already on Treatment with IOP-lowering Drugs and Low Intraocular Pressure (IOP≤21 mmHg)
• Recent NIPH Clinical Trials: Evaluation of dorzolamide/timolol fixed-dose combination therapy for the patients who need more IOP (trough & peak) reduction under treatment of PG analogues, beta-blocker and CAI
• Description: Dorzolamide hydrochloride was introduced in the U.S.A. as eye drops for the treatment of open-angle glaucoma and ocular hypertension. Dorzolamide is a potent carbonic anhydrase inhibitor that, on topical administration, lowers intraocular pressure (IOP). In a clinical study in patients with bilateral primary open-angle glaucoma or ocular hypertension, dorzolamide (0.7-2%) was found to significantly lower IOP throughout the day. Dorzolamide has been shown to be effective as a single therapy or in combination with β-blockers. Dorzolamide (hydrochloride) (Item No. 26303) is an analytical reference standard categorized as a carbonic anhydrase inhibitor diuretic. Diuretics have been used in sports doping to reduce weight or anabolic androgenic steroid-induced water retention, or as masking agents. This product is intended for use in analytical forensic applications. This product is also available as a general research tool .
• Uses: Carbonic anhydrase inhibitor. Antiglaucoma agent. Antiglaucoma drug;Carbonic anhydrase inhibitor analgesic Dorzolamide HCl Ophthalmic Solution is indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma. An inhibitor of carbonic anhydrase.
• Therapeutic Function: Antiglaucoma

Technology Process of Dorzolamide hydrochloride

There total 22 articles about Dorzolamide hydrochloride 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: 100.0%

(4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno-[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide di-p-toluyl-L-tartate salt (1227941-29-8) → dorzolamide hydrochloride (130693-82-2,120279-37-0)

Guidance literature:

(4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno-[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide di-p-toluyl-L-tartate salt; With sodium hydrogencarbonate; In water; ethyl acetate; at 25 - 30 ℃; for 0.25h;

With hydrogenchloride; In ethyl acetate; isopropyl alcohol; at 25 - 85 ℃; for 12.5h; Product distribution / selectivity;

Reference yield: 99.2%

5,6-dihydro-(S)-4-(ethylamino)-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-2-sulfonamide 7,7-dioxide maleate salt → dorzolamide hydrochloride (130693-82-2,120279-37-0)

Guidance literature:

5,6-dihydro-(S)-4-(ethylamino)-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-2-sulfonamide 7,7-dioxide maleate salt; With hydrogenchloride; sodium hydroxide; In water; at 52 ℃; pH=7.7; Inert atmosphere;

With hydrogenchloride; In water; isopropyl alcohol; at 20 - 75 ℃;

Reference yield: 95.0%

dorzolamide (120279-96-1) → dorzolamide hydrochloride (130693-82-2,120279-37-0)

Guidance literature:

With hydrogenchloride; In ethyl acetate; pH=1;

upstream raw materials:

dorzolamide

(4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno-[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide di-p-toluyl-L-tartate salt

5,6-dihydro-4-hydroxy-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide

6-methyl-4-oxo-5,6-dihydro-4H-thieno[2.3-b]thiopyran-2-sulfonamide-7,7-dioxide

Refernces

• 1、 -. "Method for preparing dorzolamide hydrochloride and method for purifying intermediate". Paragraph 0105; 0106. . Retrieved 2021/08/28.
• 2、 -. "Process for Preparing Enantiomerically Enriched Oxamides". Paragraph 0066; 0067. . Retrieved 2015/07/15.