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Basic Information
CAS No.: 378-44-9
Name: Betamethasone
Article Data: 22
Molecular Structure:
Molecular Structure of 378-44-9 (Betamethasone)
Formula: C22H29FO5
Molecular Weight: 392.468
Synonyms: Celestene;Prestwick_703;9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one;Rinderon A;Cidoten;beta-Methasone alcohol;Betamethazone;Bedifos;Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17, 21-trihydroxy-16-methyl-, (11.beta.,16.beta.)-;9.alpha.-Fluoro-16.beta.-methylprednisolone;Desacort-beta;Betsolan;Sch 4831;.beta.-Methasone alcohol;Pregna-1,4-diene-3,20-dione,9-fluoro-11,17,- 21-trihydroxy-16-methyl-,(11a,16a)-;Becort;Betacortril;Prednisolone, 9-fluoro-16beta-methyl-;Betamamallet;Betamethasone (JP14/USP);9-alpha-Fluoro-16-beta-methylprednisolone;Betafluorene;9-Fluoro-11-beta,17,21-trihydroxy-16-beta-methylpregna-1,4-diene-3,20-dione;Betapredol;Visubeta;
EINECS: 206-825-4
Density: 1.32 g/cm3
Melting Point: 235-237 °C
Boiling Point: 568.2 °C at 760 mmHg
Flash Point: 297.5 °C
Solubility: 58mg/L(25 oC)
Appearance: white to off-white solid
Hazard Symbols: IrritantXi,HarmfulXn
Risk Codes: 40
Safety: 22-36
PSA: 94.83000
LogP: 1.89570
Synthetic route
987-24-6

betamethasone 21-acetate

378-44-9

betamethasone

Conditions
ConditionsYield
With methanol; sodium methylate at 25℃; for 4h;90%
981-34-0

17α,21-dihydroxy-9β,11β-epoxy-16β-methylpregna-1,4-diene-3,20-dione

378-44-9

betamethasone

Conditions
ConditionsYield
With hydrogen fluoride In water; N,N-dimethyl-formamide at -15℃;89%
With hydrogen fluoride

C24H31FO5

378-44-9

betamethasone

Conditions
ConditionsYield
Stage #1: C24H31FO5 In ethyl acetate at 0 - 10℃;
Stage #2: With hydrogenchloride In water at 30 - 35℃; for 1h;
45%
5593-20-4

betamethasone dipropionate

A

378-44-9

betamethasone

B

5534-13-4

Betamethasone propionate

C

24703-00-2

6β-hydroxybetamethasone

D

78144-00-0

6β-hydroxybetamethasone 17-propionate

Conditions
ConditionsYield
With phosphate buffer; air; plasma of 20 d pregnant Sprague-Dawley rat at 37℃; for 1h; Product distribution; metabolism with tissues (plasma, liver, brain, placenta) from mothers and fetuses of Sprague-Dawley rats sacrificed on day 20 of pregnancy and mice on day 17 of pregnancy, further in vivo;A 14.8 % Chromat.
B 67.8 % Chromat.
C 1.4 % Chromat.
D 2.3 % Chromat.
21-acetoxy-9-fluoro-11,17-dihydroxy-16-methyl-pregna-1,4-diene-3,20-dione/s

21-acetoxy-9-fluoro-11,17-dihydroxy-16-methyl-pregna-1,4-diene-3,20-dione/s

378-44-9

betamethasone

Conditions
ConditionsYield
With sodium methylate
5593-20-4

betamethasone dipropionate

A

378-44-9

betamethasone

B

5534-13-4

Betamethasone propionate

C

betamethasone 21-monopropionate

Conditions
ConditionsYield
With sulfuric acid In acetonitrile at 20℃; for 20h; Product distribution; Further Variations:; Temperatures;
884488-47-5

16α,17α-epoxy-3β-hydroxy-5α-pregn-9(11)-en-20-one

378-44-9

betamethasone

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 95 percent / pyridine / 20 °C
2.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C
3.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C
4.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating
4.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C
5.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling
5.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling
6.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C
7.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C
8.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating
9.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C
View Scheme
37413-99-3

16β-methyl-9β,11β-epoxy-17α-hydroxy-1,4-pregnadiene-3,20-dione

378-44-9

betamethasone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C
2: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C
3: 180 mg / acetic acid / acetone; H2O / 3 h / Heating
4: 90 percent / sodium methoxide; methanol / 4 h / 25 °C
View Scheme
884488-49-7

16β-methyl-3β,17α-dihydroxy-20,20-ethylenedioxy-5α-pregn-9(11)-ene

378-44-9

betamethasone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating
1.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C
2.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling
2.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling
3.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C
4.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C
5.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating
6.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C
View Scheme
884488-48-6

3β-acetoxy-16α,17α-epoxy-20,20-ethylenedioxy-5α-pregn-9(11)-ene

378-44-9

betamethasone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C
2.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating
2.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C
3.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling
3.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling
4.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C
5.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C
6.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating
7.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C
View Scheme
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Specification

The Betamethasone is an organic compound with the formula C22H29FO5. The IUPAC name of this chemical is (8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one. With the CAS registry number 378-44-9, it is also named as (11β,16α)-9-Fluor-11,17,21-trihydroxy-16-methylpregna-1,4-dien-3,20-dion. The product's categories are Biochemistry; Hydroxyketosteroids; Steroids; Intermediates & Fine Chemicals; Pharmaceuticals. Besides, it is a white to off-white solid.

The Betamethasone is a corticosteroid used as a topical cream to relieve skin irritation, such as itching and flaking from eczema. Betamethasone dipropionate and salicylic acid can be used as a treatment for local psoriasis. Betamethasone is also used to stimulate fetal lung maturation (prevention of IRDS), and to decrease the incidence and mortality from intracranial hemorrhage in premature infants.

Physical properties about Betamethasone are: (1)ACD/LogP: 1.87; (2)ACD/LogD (pH 5.5): 1.87; (3)ACD/LogD (pH 7.4): 1.87; (4)ACD/BCF (pH 5.5): 15.49; (5)ACD/BCF (pH 7.4): 15.49; (6)ACD/KOC (pH 5.5): 247.46; (7)ACD/KOC (pH 7.4): 247.45; (8)#H bond acceptors: 5; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 61.83 Å2; (12)Index of Refraction: 1.591; (13)Molar Refractivity: 100.23 cm3; (14)Molar Volume: 296.2 cm3; (15)Polarizability: 39.73×10-24cm3; (16)Surface Tension: 56.5 dyne/cm; (17)Density: 1.32 g/cm3; (18)Flash Point: 297.5 °C; (19)Enthalpy of Vaporization: 97.96 kJ/mol; (20)Boiling Point: 568.2 °C at 760 mmHg; (21)Vapour Pressure: 2.81E-15 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical has limited evidence of a carcinogenic effect. When you are using it, wear suitable protective clothing and do not breathe dust.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(CO)[C@]3(O)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)CC[C@H]4[C@@H]2C[C@H]3C)C)C
(2)InChI: InChI=1/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1
(3)InChIKey: UREBDLICKHMUKA-CXSFZGCWBM
(4)Std. InChI: InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1
(5)Std. InChIKey: UREBDLICKHMUKA-CXSFZGCWSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral > 4500mg/kg (4500mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 21, Pg. 2117, 1979.