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| CAS No.: | 138890-62-7 |
|---|---|
| Name: | Brinzolamide |
| Molecular Structure: | |
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|
|
| Formula: | C12H21N3O5S3 |
| Molecular Weight: | 383.514 |
| Synonyms: | 2H-Thieno[3,2-e]-1,2-thiazine-6-sulfonamide,4-(ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-, 1,1-dioxide, (R)-;AL 4862;2H-Thieno[3,2-e]-1,2-thiazine-6-sulfonamide,4-(ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-, 1,1-dioxide, (4R)-;Brinzolamide (JAN/USP); |
| EINECS: | 620-511-8 |
| Density: | 1.5 g/cm3 |
| Melting Point: | 130.0 to 134.0 °C |
| Boiling Point: | 586 °C at 760mmHg |
| Flash Point: | 308.2 °C |
| Appearance: | crystalline solid |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | R36/37/38 |
| PSA: | 163.80000 |
| LogP: | 3.27760 |
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- 138890-62-7
brinzolamide
| Conditions | Yield |
|---|---|
| With sodium thiomethoxide In methanol at 0 - 25℃; for 12h; Reagent/catalyst; | 83% |
- 138890-62-7
brinzolamide
| Conditions | Yield |
|---|---|
| With sodium tetradecyl mercaptan In methanol at 0 - 25℃; Reagent/catalyst; | 81% |
| Conditions | Yield |
|---|---|
| In tetrahydrofuran; water at 0 - 30℃; | 66.3% |
- 138890-62-7
brinzolamide
| Conditions | Yield |
|---|---|
| Stage #1: (R)-3,4-dihydro-4-ethylamino-6-chloro-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide hydrochloride With sodium hydrogencarbonate Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 1h; | 63% |
| Conditions | Yield |
|---|---|
| In water at 11 - 20℃; for 15h; enantioselective reaction; | 61% |
| Stage #1: C20H26N2O9S4; ethylamine In water at 10 - 12℃; for 15h; Stage #2: With hydrogenchloride In water at 20℃; for 1h; Temperature; | 2.4 g |
- 165117-54-4
(R)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide
- 75-04-7
ethylamine
- 138890-62-7
brinzolamide
| Conditions | Yield |
|---|---|
| Stage #1: (R)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide With zinc(II) tosylate; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20 - 80℃; for 8h; Stage #2: ethylamine In tetrahydrofuran at 0 - 20℃; for 36h; Product distribution / selectivity; | 49% |
| Stage #1: (R)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide With zinc(II) tosylate; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20 - 80℃; Stage #2: ethylamine In tetrahydrofuran at 0 - 20℃; |
- 154127-42-1
(S)-3,4-dihydro-4-hydroxy-2(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide
- 75-04-7
ethylamine
- 138890-62-7
brinzolamide
| Conditions | Yield |
|---|---|
| Stage #1: (S)-3,4-dihydro-4-hydroxy-2(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide With toluene-4-sulfonic acid; triethylamine In tetrahydrofuran at 0 - 20℃; for 18h; Stage #2: ethylamine In tetrahydrofuran at 0 - 20℃; for 36h; | |
| Stage #1: (S)-3,4-dihydro-4-hydroxy-2(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide With triethylamine; p-toluenesulfonyl chloride In tetrahydrofuran at 0 - 20℃; for 18h; Stage #2: ethylamine In tetrahydrofuran at 0 - 20℃; |
- 138890-62-7
brinzolamide
| Conditions | Yield |
|---|---|
| With sodium acetate; hydroxylamine-O-sulfonic acid In hexane at 0 - 20℃; Product distribution / selectivity; |
- 1029324-92-2
(R)-3,4-dihydro-4-(N-ethylamino)-2-(3-methoxy)propyl-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide
- 138890-62-7
brinzolamide
| Conditions | Yield |
|---|---|
| Stage #1: (R)-3,4-dihydro-4-(N-ethylamino)-2-(3-methoxy)propyl-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide With n-butyllithium In tetrahydrofuran; hexane at -60℃; for 8.75h; Inert atmosphere; Stage #2: With sulfur dioxide In tetrahydrofuran; hexane at -65 - 20℃; Stage #3: With sodium acetate trihydrate; hydroxylamine-O-sulfonic acid In ethyl acetate at 0 - 20℃; |
- 138890-62-7
brinzolamide
| Conditions | Yield |
|---|---|
| With chiral-prep-HPLC (Chiralpak IA0.46x15 cm, 5 umChiral-A (IA)002IA00CD-LF007) Resolution of racemate; |
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Chemistry
Molecule structure of Brinzolamide (CAS NO.138890-62-7):
IUPAC Name: (4R)-4-(Ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[3,2-e]thiazine-6-sulfonamide
Molecular Weight: 383.50724 g/mol
Molecular Formula: C12H21N3O5S3
Density: 1.5 g/cm3
Boiling Point: 586 °C at 760 mmHg
Flash Point: 308.2 °C
Index of Refraction: 1.625
Molar Refractivity: 90.39 cm3
Molar Volume: 255.3 cm3
Surface Tension: 69.7 dyne/cm
Enthalpy of Vaporization: 87.53 kJ/mol
Vapour Pressure: 1.03E-13 mmHg at 25 °C
XLogP3-AA: -0.3
H-Bond Donor: 2
H-Bond Acceptor: 8
Rotatable Bond Count: 7
Exact Mass: 383.064333
MonoIsotopic Mass: 383.064333
Topological Polar Surface Area: 119
Heavy Atom Count: 23
Canonical SMILES: CCNC1CN(S(=O)(=O)C2=C1C=C(S2)S(=O)(=O)N)CCCOC
Isomeric SMILES: CCN[C@H]1CN(S(=O)(=O)C2=C1C=C(S2)S(=O)(=O)N)CCCOC
InChI: InChI=1S/C12H21N3O5S3/c1-3-14-10-8-15(5-4-6-20-2)23(18,19)12-9(10)7-11(21-12)22(13,16)17/h7,10,14H,3-6,8H2,1-2H3,(H2,13,16,17)/t10-/m0/s1
InChIKey: HCRKCZRJWPKOAR-JTQLQIEISA-N
Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
Uses
Brinzolamide (CAS NO.138890-62-7) is used to lower intraocular pressure in patients with open-angle glaucoma or ocular hypertension.
Specification
Brinzolamide (CAS NO.138890-62-7) is also named as (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)-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno(3,2-e)-1,2-thiazine-6-sulfonamide ; 2H-Thieno(3,2-e)-1,2-thiazine-6-sulfonamide, 4-(ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-, 1,1-dioxide, (R)- ; AL 4862 ; Azopt ; UNII-9451Z89515 . Brinzolamide (CAS NO.138890-62-7) is crystalline solid. It is a carbonic anhydrase inhibitor.