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CAS No.: | 66734-13-2 |
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Name: | Alclometasone-17,21-dipropionate |
Article Data: | 5 |
Molecular Structure: | |
Formula: | C28H37ClO7 |
Molecular Weight: | 521.051 |
Synonyms: | Aclovate;Alclometasone dipropionate;Almeta;Delonal;Sch 22219;Vaderm; |
EINECS: | 266-464-3 |
Density: | 1.26 g/cm3 |
Melting Point: | 212-216° |
Boiling Point: | 636 °C at 760 mmHg |
Flash Point: | 338.4 °C |
PSA: | 106.97000 |
LogP: | 3.94270 |
alclometasone dipropionate
Conditions | Yield |
---|---|
With pyridine; phosphorus trichloride In toluene at 40 - 45℃; Solvent; Reagent/catalyst; Green chemistry; | 64.2% |
With pyridine; phosphorus trichloride In toluene at 40 - 45℃; Solvent; Reagent/catalyst; | 64.2 g |
alclometasone dipropionate
Conditions | Yield |
---|---|
With pyridine; phosphorus trichloride In toluene at 40 - 45℃; Solvent; Reagent/catalyst; | 64.2% |
16α-methyl-11β,17α,21-trihydroxy-1,4,6-pregnatriene-3,20-dione 17,21-dipropionate
alclometasone dipropionate
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane for 16h; Ambient temperature; | 15% |
16α-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione 21-acetate
alclometasone dipropionate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 21 percent / HCl, DDQ / dioxane / 24 h / Ambient temperature 2: 53 percent / sat. aq. NaHCO3 / methanol / 2 h / Ambient temperature 3: TsOH*H2O / dimethylsulfoxide / 2 h / Ambient temperature 4: 1.) aq. AcOH, 2.) pyridine / 1.) RT, 1 h, 2.) RT, 3.5 h 5: 15 percent / HCl / dioxane / 16 h / Ambient temperature View Scheme |
16α-methyl-11β,17α,21-trihydroxy-1,4,6-pregnatriene-3,20-dione
alclometasone dipropionate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: TsOH*H2O / dimethylsulfoxide / 2 h / Ambient temperature 2: 1.) aq. AcOH, 2.) pyridine / 1.) RT, 1 h, 2.) RT, 3.5 h 3: 15 percent / HCl / dioxane / 16 h / Ambient temperature View Scheme |
16α-methyl-11β,17α,21-trihydroxy-1,4,6-pregnatriene-3,20-dione 21-acetate
alclometasone dipropionate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 53 percent / sat. aq. NaHCO3 / methanol / 2 h / Ambient temperature 2: TsOH*H2O / dimethylsulfoxide / 2 h / Ambient temperature 3: 1.) aq. AcOH, 2.) pyridine / 1.) RT, 1 h, 2.) RT, 3.5 h 4: 15 percent / HCl / dioxane / 16 h / Ambient temperature View Scheme |
16α-methyl-11β,17α,21-trihydroxy-1,4,6-pregnatriene-3,20-dione 17α,21-ethylorthopropionate
alclometasone dipropionate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) aq. AcOH, 2.) pyridine / 1.) RT, 1 h, 2.) RT, 3.5 h 2: 15 percent / HCl / dioxane / 16 h / Ambient temperature View Scheme |
alclometasone dipropionate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / methanol / 25 - 30 °C / Green chemistry 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C / Green chemistry 3: pyridine; phosphorus trichloride / toluene / 40 - 45 °C / Green chemistry View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate / methanol / 25 - 30 °C 1.2: 25 - 30 °C / pH 2 - 3 2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C 3.1: pyridine; phosphorus trichloride / toluene / 40 - 45 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; methanol / 25 - 30 °C 1.2: 25 - 30 °C / pH 2 - 3 2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C 3.1: pyridine; phosphorus trichloride / toluene / 40 - 45 °C View Scheme |
alclometasone dipropionate
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: toluene-4-sulfonic acid / 20 - 25 °C / Green chemistry 2: acetic acid; chromium(VI) oxide / chloroform; water / 20 - 25 °C / Green chemistry 3: toluene-4-sulfonic acid / 30 - 35 °C / Green chemistry 4: toluene-4-sulfonic acid / dichloromethane / 20 - 25 °C / Green chemistry 5: sodium tetrahydroborate / methanol / 25 - 30 °C / Green chemistry 6: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C / Green chemistry 7: pyridine; phosphorus trichloride / toluene / 40 - 45 °C / Green chemistry View Scheme | |
Multi-step reaction with 7 steps 1.1: toluene-4-sulfonic acid / propionic acid / 20 - 25 °C 2.1: chromium(VI) oxide; water / chloroform / 20 - 25 °C 3.1: toluene-4-sulfonic acid / propionic acid / 30 - 35 °C 4.1: toluene-4-sulfonic acid / dichloromethane / 20 - 25 °C 5.1: sodium tetrahydroborate / methanol / 25 - 30 °C 5.2: 25 - 30 °C / pH 2 - 3 6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C 7.1: pyridine; phosphorus trichloride / toluene / 40 - 45 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: toluene-4-sulfonic acid / 20 - 25 °C 2.1: acetic acid; chromium(VI) oxide / water / 20 - 25 °C 3.1: toluene-4-sulfonic acid / 30 - 35 °C 4.1: toluene-4-sulfonic acid / dichloromethane / 20 - 25 °C 5.1: sodium tetrahydroborate; methanol / 25 - 30 °C 5.2: 25 - 30 °C / pH 2 - 3 6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C 7.1: pyridine; phosphorus trichloride / toluene / 40 - 45 °C View Scheme |
alclometasone dipropionate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: acetic acid; chromium(VI) oxide / chloroform; water / 20 - 25 °C / Green chemistry 2: toluene-4-sulfonic acid / 30 - 35 °C / Green chemistry 3: toluene-4-sulfonic acid / dichloromethane / 20 - 25 °C / Green chemistry 4: sodium tetrahydroborate / methanol / 25 - 30 °C / Green chemistry 5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C / Green chemistry 6: pyridine; phosphorus trichloride / toluene / 40 - 45 °C / Green chemistry View Scheme | |
Multi-step reaction with 6 steps 1.1: chromium(VI) oxide; water / chloroform / 20 - 25 °C 2.1: toluene-4-sulfonic acid / propionic acid / 30 - 35 °C 3.1: toluene-4-sulfonic acid / dichloromethane / 20 - 25 °C 4.1: sodium tetrahydroborate / methanol / 25 - 30 °C 4.2: 25 - 30 °C / pH 2 - 3 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C 6.1: pyridine; phosphorus trichloride / toluene / 40 - 45 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: acetic acid; chromium(VI) oxide / water / 20 - 25 °C 2.1: toluene-4-sulfonic acid / 30 - 35 °C 3.1: toluene-4-sulfonic acid / dichloromethane / 20 - 25 °C 4.1: sodium tetrahydroborate; methanol / 25 - 30 °C 4.2: 25 - 30 °C / pH 2 - 3 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C 6.1: pyridine; phosphorus trichloride / toluene / 40 - 45 °C View Scheme |
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Molecular Formula: C28H37ClO7
Molar mass: 521.04 g/mol
EINECS: 266-464-3
Density: 1.26 g/cm3
Flash Point: 338.4 °C
Index of Refraction: 1.562
Boiling Point: 636 °C at 760 mmHg
Vapour Pressure: 7.55E-19 mmHg at 25°C
Structure of Alclometasone-17,21-dipropionate (66734-13-2):
XLogP3-AA: 3.2
H-Bond Donor: 1
H-Bond Acceptor: 7
Systematic Name: [(7R,8S,9S,10R,11S,13S,14S,16R,17R)-7-Chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(2-propanoyloxyacetyl)-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl] propanoate
SMILES: O=C(OCC(=O)[C@@]1(OC(=O)CC)[C@@H](C[C@H]2[C@H]4[C@H]([C@@H](O)C[C@]12C)[C@]/3(/C=C\C(=O)\C=C\3C[C@H]4Cl)C)C)CC
InChI: InChI=1/C28H37ClO7/c1-6-22(33)35-14-21(32)28(36-23(34)7-2)15(3)10-18-24-19(29)12-16-11-17(30)8-9-26(16,4)25(24)20(31)13-27(18,28)5/h8-9,11,15,18-20,24-25,31H,6-7,10,12-14H2,1-5H3/t15-,18+,19-,20+,24-,25+,26+,27+,28+/m1/s1
InChIKey: DJHCCTTVDRAMEH-DUUJBDRPBB
Std. InChI: InChI=1S/C28H37ClO7/c1-6-22(33)35-14-21(32)28(36-23(34)7-2)15(3)10-18-24-19(29)12-16-11-17(30)8-9-26(16,4)25(24)20(31)13-27(18,28)5/h8-9,11,15,18-20,24-25,31H,6-7,10,12-14H2,1-5H3/t15-,18+,19-,20+,24-,25+,26+,27+,28+/m1/s1
Std. InChIKey: DJHCCTTVDRAMEH-DUUJBDRPSA-N
Alclometasone-17,21-dipropionate(66734-13-2) is used of topical cortical steroid hormone, and has potent local anti-inflammatory, anti-itch and shrinking blood vessels.It has been used for eczema, atopic dermatitis, psoriasis and other skin diseases.
Under the action of 2,3 - Dichloro-5,6 - dicyano-benzoquinone (DDQ) to give one H2O to get compound (Ⅱ) .With Sodium bicarbonate for ester hydrolysis of 21, and then has the original acid Triethyl reaction, the 17-bit and 21-OH to form a ring of the original ester (Ⅳ).Then, with C anhydride to have the reaction to get Double-propionate (Ⅵ). Final with Hydrogen chloride for addition to get: Alclometasone-17,21-dipropionate(66734-13-2). The total yield was 2.678 percent.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD | oral | > 15mg/kg (15mg/kg) | Drugs in Japan Vol. -, Pg. 70, 1990. | |
dog | LD50 | skin | > 15mg/kg (15mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 735, 1988. | |
mouse | LD50 | oral | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. -, Pg. 70, 1990. | |
mouse | LD50 | subcutaneous | 2506mg/kg (2506mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 1253, 1987. |
rat | LD50 | oral | 3593mg/kg (3593mg/kg) | Drugs in Japan Vol. -, Pg. 70, 1990. | |
rat | LD50 | skin | > 75mg/kg (75mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 735, 1988. | |
rat | LD50 | subcutaneous | 3593mg/kg (3593mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 1253, 1987. |
Moderately toxic by subcutaneous route. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of HCl.
Alclometasone-17,21-dipropionate (66734-13-2) also can be called Delonal ; Aclosone ; Modrasone ; Aclovate ; 7alpha-Chloro-11beta,17,21-trihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 17,21-dipropionate and (7R,8S,9S,10R,11S,13S,14S,16R,17R)-7-Chlor-11-hydroxy-10,13,16-trimethyl-3-oxo-17-[(propanoyloxy)acetyl]-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-ylpropanoat .