4-(Ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[3,2-e]thiazine-6-sulfonamide

Base Information

• Chemical Name: 4-(Ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[3,2-e]thiazine-6-sulfonamide
• CAS No.: 138890-62-7
• Molecular Formula: C12H21N3O5S3
• Molecular Weight: 383.514
• Hs Code.: 2935904000
• NSC Number: 760050
• DSSTox Substance ID: DTXSID70861347
• ChEMBL ID: CHEMBL6750
• Mol file: 138890-62-7.mol

Synonyms:CHEMBL6750;4-(ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[3,2-e]thiazine-6-sulfonamide;Birnzolamide;(S)-Brinzolamide;2H-Thieno[3,2-e]-1,2-thiazine-6-sulfonamide,4-(ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-, 1,1-dioxide, (S)- (9CI);MFCD08067749;SCHEMBL7509691;DTXSID70861347;HMS3371K11;HMS3652G09;Pharmakon1600-01502418;BDBM50481823;NSC760050;STL454172;CCG-213079;SY009759;AB01562979_01;A807453;B0464-467726;(R)-4-(Ethylamino)-2-(3-methoxypropyl)-3,4-dihydro-1,1-dioxo-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide;4-(Ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-1,2,3,4-tetrahydro-1lambda~6~-thieno[3,2-e][1,2]thiazine-6-sulfonamide;4-(ethylamino)-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide;AGN-190342;AL-4862;AL 4862;AL4862;UK-14304;(R)-4-(Ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide(R)-4-Ethylamino-2-(3-methoxypropyl)-1,1-dioxo-1,2,3,4-tetrahydro-1|E6-thieno[3,2-e][1,2]thiazine-6-sulfonic acid amide

Chemical Property of 4-(Ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[3,2-e]thiazine-6-sulfonamide

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 1.03E-13mmHg at 25°C
• Melting Point: 130.0 to 134.0 °C
• Refractive Index: 1.625
• Boiling Point: 586 °C at 760mmHg
• PKA: 9.62±0.40(Predicted)
• Flash Point: 308.2 °C
• PSA: 163.80000
• Density: 1.5 g/cm³
• LogP: 3.27760
• Storage Temp.: ?20°C
• Solubility.: DMSO: ≥10mg/mL
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 383.06433430
• Heavy Atom Count: 23
• Complexity: 598

Purity/Quality:

99% ^*data from raw suppliers

GAGE12I ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCNC1CN(S(=O)(=O)C2=C1C=C(S2)S(=O)(=O)N)CCCOC
• Description: Brinzolamide is a carbonic anhydrase inhibitor developed by Alcon (now Novartis) as a treatment for primary and open-angle glaucoma and ocular hypertension. It was First approval in the United States in 1998 under the trade name Azopt. It is the second of this class after dorzolamide (1995). Brinzolamide was approved as a generic medication in the United States in November 2020.Brinzolamide is a white powder commercially formulated as a 1% ophthalmic suspension to reduce intraocular pressure (IOP). In patients with primary open-angle glaucoma or ocular hypertension, brinzolamide produced significant reductions in IOP and showed less ocular discomfort than dorzolamide.
• Uses: Brinzolamide is a sulfonamide and carbonic anhydrase inhibitor with specific affinity for carbonic anhydrase II. Following topical ocular administration, brinzolamide inhibits carbonic anhydrase II, an enzyme that is responsible for the movement of sodium and fluid transport in the eye. This inhibition leads to a decrease in aqueous humor secretion, probably by slowing the formation of bicarbonate ions, and results in a reduction in intraocular pressure. Brinzolamide is used to treat increased pressure in the eye caused by open-angle glaucoma. Brinzolamide has been used as a melanin binding compound or drug in melanin binding assays. It has also been used as a carbonic anhydrase inhibitor (CAI).
• Indications: Brinzolamide, a heterocyclic sulfonamide, is a topical CAI suspension that has a high affinity for the carbonic anhydrase II isoenzyme.Because the ocular hypotensive effect of the drug is equivalent whether dosed twice or three times daily, brinzolamide 1% may be administered twice daily.
• Therapeutic Function: Antiglaucoma
• Clinical Use: Brinzolamide is indicated for the treatment of elevated IOP in patients with ocular hypertension or open-angle glaucoma.The drug is commercially available as a sterile 1.0% aqueous suspension with a pH of approximately 7.5. BAC 0.01% is added as a preservative. The efficacy and safety of brinzolamide 1%, either two or three times daily, were evaluated in 572 patients with open-angle glaucoma or ocular hypertension against timolol 0.5% twice daily and dorzolamide 2.0% three times daily. Mean IOP changes were -3.8 to -5.7 mm Hg, -4.2 to -5.6 mm Hg, and-4.3 to-5.9 mm Hg for two- and three-times-daily brinzolamide and dorzolamide dosing, respectively. The mean IOP changes for timolol 0.5% ranged from -5.6 to -6.3 mm Hg (Figure 10-15). Brinzolamide was well tolerated, with 1.8% (twice daily) and 3% (three times daily) of patients reporting ocular discomfort versus 16.4% with dorzolamide. Complaints of blurred vision were higher with brinzolamide (5–6%) than dorzolamide (1%) or timolol (0%). A meta-analysis of randomized clinical trials reported peak ocular hypotensive effect on IOP of 17% (19% to 15%) and trough effect of 17% (19% to 15%).

Technology Process of 4-(Ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[3,2-e]thiazine-6-sulfonamide

There total 25 articles about 4-(Ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[3,2-e]thiazine-6-sulfonamide 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: 83.0%

C21H29N3O8S4 → brinzolamide (138890-62-7,138890-50-3)

Guidance literature:

With sodium thiomethoxide; In methanol; at 0 - 25 ℃; for 12h; Reagent/catalyst;

Reference yield: 81.0%

C21H29N5O9S4 → brinzolamide (138890-62-7,138890-50-3)

Guidance literature:

With sodium tetradecyl mercaptan; In methanol; at 0 - 25 ℃; Reagent/catalyst;

Reference yield: 66.3%

C11H18N2O8S4 + ethylamine (75-04-7,85404-22-4) → brinzolamide (138890-62-7,138890-50-3)

Guidance literature:

In tetrahydrofuran; water; at 0 - 30 ℃;

upstream raw materials:

(R)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide

ethylamine

(S)-3,4-dihydro-4-hydroxy-2(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide

(R)-3,4-dihydro-4-(N-ethylamino)-2-(3-methoxy)propyl-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide

Downstream raw materials:

(R)-4-(ethylamino)-2-(3-hydroxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide1,1-dioxide

Refernces

• 1、 -. "Preparation methods of brinzolamide and an intermediate thereof". . . Retrieved 2018/03/24.
• 2、 -. "PHARMACEUTICALLY ACCEPTABLE SALT OF BRINZOLAMIDE AND COMPOSITION THEREOF". Page/Page column 7; 10. . Retrieved 2013/08/15.