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Dorzolamide
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Name

Dorzolamide

 EINECS 1533716-785-6
CAS No. 120279-96-1 Density 1.53 g/cm3
PSA N/A LogP N/A
Solubility N/A Melting Point N/A
Formula C10H16N2O4S3 Boiling Point 575.8 °C at 760 mmHg
Molecular Weight 324.446 Flash Point 302 °C
Transport Information N/A Appearance White or almost white crystalline powder
Safety 26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 120279-96-1 (Dorzolamide) Hazard Symbols Xi
Synonyms

Dorzolamide HCl;4H-Thieno[2,3-b]thiopyran-2-sulfonamide,4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide, (4S-trans)-;4S,6S-Dorzolamide;

Article Data 6

Dorzolamide Synthetic route

147200-03-1

(4S,6S)‑4‑acetamido‑5,6‑dihydro‑6‑methyl‑4H‑thieno[2,3‑b]thiopyran‑2‑sulfonamide‑7,7‑dioxide

120279-96-1

dorzolamide

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

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

120279-96-1

dorzolamide

Conditions
ConditionsYield
With hydrogenchloride; water In methanol for 72h; Heating / reflux;66%

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

120279-96-1

dorzolamide

Conditions
ConditionsYield
With dimethylsulfide borane complex; sulfuric acid 1) THF, r.t.; Yield given. Multistep reaction;
147086-79-1

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

120279-96-1

dorzolamide

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C
2: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h
3: 95 percent / pyridine / tetrahydrofuran / 48 h / 25 - 30 °C
4: 89.6 percent / H2SO4 / 20 - 25 °C
5: chlorosulfonic acid / 12 h / 50 °C
6: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
7: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme
Multi-step reaction with 7 steps
1: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C
2: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h
3: H2SO4 / -5 °C
4: H2SO4 / -5 °C
5: chlorosulfonic acid / 12 h / 50 °C
6: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
7: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme
Multi-step reaction with 6 steps
1: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C
2: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h
3: 1) conc. H2SO4 / 1) THF, 48 h, r.t., 2) overnight
4: chlorosulfonic acid / 12 h / 50 °C
5: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
6: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme
147086-80-4

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

120279-96-1

dorzolamide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h
2: 95 percent / pyridine / tetrahydrofuran / 48 h / 25 - 30 °C
3: 89.6 percent / H2SO4 / 20 - 25 °C
4: chlorosulfonic acid / 12 h / 50 °C
5: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
6: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme
Multi-step reaction with 6 steps
1: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h
2: H2SO4 / -5 °C
3: H2SO4 / -5 °C
4: chlorosulfonic acid / 12 h / 50 °C
5: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
6: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme
Multi-step reaction with 5 steps
1: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h
2: 1) conc. H2SO4 / 1) THF, 48 h, r.t., 2) overnight
3: chlorosulfonic acid / 12 h / 50 °C
4: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
5: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme
133359-80-5

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

120279-96-1

dorzolamide

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: trifluoroacetic anhydride / toluene / 1 h / 25 °C
2: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C
3: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h
4: 95 percent / pyridine / tetrahydrofuran / 48 h / 25 - 30 °C
5: 89.6 percent / H2SO4 / 20 - 25 °C
6: chlorosulfonic acid / 12 h / 50 °C
7: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
8: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme
Multi-step reaction with 8 steps
1: trifluoroacetic anhydride / toluene / 1 h / 25 °C
2: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C
3: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h
4: H2SO4 / -5 °C
5: H2SO4 / -5 °C
6: chlorosulfonic acid / 12 h / 50 °C
7: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
8: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme
Multi-step reaction with 7 steps
1: trifluoroacetic anhydride / toluene / 1 h / 25 °C
2: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C
3: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h
4: 1) conc. H2SO4 / 1) THF, 48 h, r.t., 2) overnight
5: chlorosulfonic acid / 12 h / 50 °C
6: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
7: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme
147086-84-8

(S)-6-Methyl-6H-thieno[2,3-b]thiopyran 7,7-dioxide

120279-96-1

dorzolamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: H2SO4 / -5 °C
2: chlorosulfonic acid / 12 h / 50 °C
3: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
4: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme
133359-79-2

methyl (S)-3-(thiophen-2-ylthio)butyrate

120279-96-1

dorzolamide

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 45 g / 12 N HCl / H2O / 3 h / Heating
2: trifluoroacetic anhydride / toluene / 1 h / 25 °C
3: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C
4: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h
5: 95 percent / pyridine / tetrahydrofuran / 48 h / 25 - 30 °C
6: 89.6 percent / H2SO4 / 20 - 25 °C
7: chlorosulfonic acid / 12 h / 50 °C
8: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
9: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme
Multi-step reaction with 9 steps
1: 45 g / 12 N HCl / H2O / 3 h / Heating
2: trifluoroacetic anhydride / toluene / 1 h / 25 °C
3: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C
4: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h
5: H2SO4 / -5 °C
6: H2SO4 / -5 °C
7: chlorosulfonic acid / 12 h / 50 °C
8: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
9: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme
Multi-step reaction with 8 steps
1: 45 g / 12 N HCl / H2O / 3 h / Heating
2: trifluoroacetic anhydride / toluene / 1 h / 25 °C
3: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C
4: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h
5: 1) conc. H2SO4 / 1) THF, 48 h, r.t., 2) overnight
6: chlorosulfonic acid / 12 h / 50 °C
7: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
8: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme
1034290-08-8

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

120279-96-1

dorzolamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 95 percent / pyridine / tetrahydrofuran / 48 h / 25 - 30 °C
2: 89.6 percent / H2SO4 / 20 - 25 °C
3: chlorosulfonic acid / 12 h / 50 °C
4: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
5: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme
Multi-step reaction with 5 steps
1: H2SO4 / -5 °C
2: H2SO4 / -5 °C
3: chlorosulfonic acid / 12 h / 50 °C
4: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
5: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme
Multi-step reaction with 4 steps
1: 1) conc. H2SO4 / 1) THF, 48 h, r.t., 2) overnight
2: chlorosulfonic acid / 12 h / 50 °C
3: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
4: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme

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

120279-96-1

dorzolamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C
2: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t.
View Scheme

Dorzolamide Chemical Properties

IUPAC Name: (4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-5,6-dihydro-4H-thieno[5,4-b]thiopyran-2-sulfonamide
Synonyms of Dorzolamide (CAS NO.120279-96-1) : 4S,6S-Dorzolamide ; 4H-Thieno(2,3-b)thiopyran-2-sulfonamide, 4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide, (4S,6S)- ; 4H-Thieno(2,3-b)thiopyran-2-sulfonamide, 4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide, (4S-trans)-
InChI: InChI=1/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)/t6-,8-/m0/s1
CAS NO:120279-96-1
Molecular Formula:C10H16N2O4S3
Molecular Weight :324.44
Molecular Structure :
H bond acceptors: 6
H bond donors: 3
Freely Rotating Bonds: 3
Polar Surface Area: 119.76 Å2
Index of Refraction: 1.634
Molar Refractivity: 75.48 cm3
Molar Volume: 211 cm3
Surface Tension: 69.4 dyne/cm
Density: 1.53 g/cm3
Flash Point: 302 °C
Enthalpy of Vaporization: 86.23 kJ/mol
Boiling Point: 575.8 °C at 760 mmHg
Vapour Pressure: 2.93E-13 mmHg at 25°C
SMILES: O=S(=O)(c1sc2c(c1)C(NCC)CC(C)S2(=O)=O)N
InChI: InChI=1/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-UHFFFAOYAE
Std. 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)
Std. InChIKey: IAVUPMFITXYVAF-UHFFFAOYSA-N

Dorzolamide Uses

 Dorzolamide (CAS NO.120279-96-1) is a carbonic anhydrase inhibitor. It is an anti-glaucoma agent and topically applied in the form of eye drops.

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