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50-02-2

Basic Information
CAS No.: 50-02-2
Name: Dexamethasone
Article Data: 39
Cas Database
Molecular Structure:
Molecular Structure of 50-02-2 (Dexamethasone)
Formula: C22H29FO5
Molecular Weight: 392.468
Synonyms: Diodex;Etacortilen;Fluormone;Fluorocort;Gammacorten;HL-Dex;Hexadecadrol;Hexadrol;Isopto-Dex;Loverine;Luxazone;Millicorten;Oradexon;Pet-Derm III;Prednisolone F;Superprednol;Surodex;Visumetazone;Pregna-1,4-diene-3,20-dione,9-fluoro-11,17,21-trihydroxy-16-methyl-, (11b,16a)-;Pregna-1,4-diene-3,20-dione,9-fluoro-11b,17,21-trihydroxy-16a-methyl- (6CI,8CI);1-Dehydro-16a-methyl-9a-fluorohydrocortisone;16a-Methyl-9a-fluoro-D1-hydrocortisone;16a-Methyl-9a-fluoroprednisolone;9-Fluoro-11b,17,21-trihydroxy-16a-methylpregna-1,4-diene-3,20-dione;9a-Fluoro-16a-methyl-1,4-pregnadiene-11b,17a,21-triol-3,20-dione;9a-Fluoro-16a-methyl-11b,17,21-trihydroxypregna-1,4-diene-3,20-dione;9a-Fluoro-16a-methylprednisolone;Adexone;Aeroseb-Dex;Aphtasolon;Aphthasolone;Azium;Calonat;Corsone;Decacort;Decaderm;Decadron;Decadron A;Dekort;Delipos;Dergramin;Desameton;Dexa-Cortidelt;Dexa-Scheroson;Dexacortin;Dexalona;Dexamethasone alcohol;Dexapolcort;Dexaprol;Dexason;Dexinoral;Dexmethsone;Dexonium;Dinormon;
EINECS: 200-003-9
Density: 1.32 g/cm3
Melting Point: 262-264 °C(lit.)
Boiling Point: 568.2 °C at 760 mmHg
Flash Point: 297.5 °C
Solubility: 10 mg/100 mL (25 °C) in water
Appearance: White crystalline solid
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 43-40-36/37/38-20/21/22
Safety: 36/37-45-36-26-22
Transport Information: N/A
PSA: 94.83000
LogP: 1.89570
Synthetic route

C23H31FO4

50-02-2

dexamethasone

Conditions
ConditionsYield
Stage #1: C23H31FO4 In ethyl acetate at 0 - 10℃;
Stage #2: With hydrogenchloride In water at 30 - 35℃; for 1h;
40%
1177-87-3

betamethasone

50-02-2

dexamethasone

Conditions
ConditionsYield
In ethanol at 24 - 26℃; for 96h; Penicillium decumbens ATCC 10436, potato dextrose broth;5%
With methanol; sodium carbonate at 20℃; for 0.166667h; Temperature;
1966-25-2

16α-methyl-9β,11β-oxido-17α,20;20,21-bismethylenedioxy-pregna-1,4-diene-3-one

50-02-2

dexamethasone

Conditions
ConditionsYield
With hydrogen fluoride In tetrahydrofuran; ethanol at 0℃; for 20h;
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: 95 percent / 0.4M perchloric acid, N-bromoacetamide / dioxane / 15 h / Ambient temperature
3: 87 percent / potassium acetate / ethanol; dioxane / 19 h / Heating
4: 48percent hydrofluoric acid / ethanol; tetrahydrofuran / 20 h / 0 °C
View Scheme
14518-56-0

16α-methyl-17α,20;20,21-bismethylenedioxypregn-1,4,9(11)-triene-3-one

50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / 0.4M perchloric acid, N-bromoacetamide / dioxane / 15 h / Ambient temperature
2: 87 percent / potassium acetate / ethanol; dioxane / 19 h / Heating
3: 48percent hydrofluoric acid / ethanol; tetrahydrofuran / 20 h / 0 °C
View Scheme
88509-22-2

9α-bromo-11β-hydroxy-16α-methyl-17α,20;20,21-bismethylenedioxy-pregna-1,4-diene-3-one

50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 87 percent / potassium acetate / ethanol; dioxane / 19 h / Heating
2: 48percent hydrofluoric acid / ethanol; tetrahydrofuran / 20 h / 0 °C
View Scheme
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 63 percent / sodium metaperiodate / tetrahydrofuran; methanol; H2O / 2.5 h / Ambient temperature
2: 95 percent / 0.4M perchloric acid, N-bromoacetamide / dioxane / 15 h / Ambient temperature
3: 87 percent / potassium acetate / ethanol; dioxane / 19 h / Heating
4: 48percent hydrofluoric acid / ethanol; tetrahydrofuran / 20 h / 0 °C
View Scheme
80163-63-9, 88509-13-1, 88548-10-1

16α-methyl-17α,20;20,21-bismethylenedioxy-pregn-4,9(11)-diene-3-one

50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.) LDA / 1.) THF, -78 deg C, 1 h then 0 deg C, 5 h; 2.) THF, -78 deg C, 3.5 h
2: 63 percent / sodium metaperiodate / tetrahydrofuran; methanol; H2O / 2.5 h / Ambient temperature
3: 95 percent / 0.4M perchloric acid, N-bromoacetamide / dioxane / 15 h / Ambient temperature
4: 87 percent / potassium acetate / ethanol; dioxane / 19 h / Heating
5: 48percent hydrofluoric acid / ethanol; tetrahydrofuran / 20 h / 0 °C
View Scheme

2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl hydrogen (2-(2-(cyclooct-2-yn-1-yloxy)acetamido)ethyl)phosphoramidate

50-02-2

dexamethasone

Conditions
ConditionsYield
With rat liver lysosomes In water; dimethyl sulfoxide; acetonitrile at 37℃; for 6h; Enzymatic reaction;

C24H35FNO8P

50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 20 °C
2: rat liver lysosomes / water; acetonitrile; dimethyl sulfoxide / 6 h / 37 °C / Enzymatic reaction
View Scheme
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Specification

1. Introduction of Dexamethasone
Dexamethasone is a synthetic corticosteroid with approximately 25 times the anti-inflammatory potency of naturally occurring cortisol. The IUPAC Name of it is (8S,9R,10S,11S,13S,14S,16R,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. Dexamethasone commonly is used in both small- and large-animal veterinary medicine. It may be given by injection, inhalation orally or topically. Preparations for topical use may include other active ingredients such as antibiotics, antifungals or miticides.

2. Properties of Dexamethasone
Index of Refraction: 1.591 
Molar Refractivity: 100.23 cm3
Molar Volume: 296.2 cm3 
Surface Tension: 56.5 dyne/cm
Density: 1.32 g/cm3
Flash Point: 297.5 °C
Enthalpy of Vaporization: 97.96 kJ/mol
Boiling Point: 568.2 °C at 760 mmHg
Vapour Pressure: 2.81E-15 mmHg at 25 °C
Melting point: 262-264 °C(lit.)
Storage tempreture: 2-8 °C
Solubility: Ethanol: 1 mg/mL
Appearance: White crystalline solid

3. Toxicity of Dexamethasone

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 410mg/kg (410mg/kg)   Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 281, 1970.
mouse LD50 subcutaneous 4400mg/kg (4400mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 21, Pg. 2117, 1979.
rabbit LD50 subcutaneous 7200ug/kg (7.2mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 687, 1984.
rat LD50 intraperitoneal 54mg/kg (54mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 687, 1984.
rat LD50 oral > 3gm/kg (3000mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 687, 1984.
rat LD50 subcutaneous 14mg/kg (14mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 250, 1966.
women TDLo multiple routes 4759ug/kg/18D (4.759mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED Intensive Care Medicine. Vol. 21, Pg. 238, 1995.
 

4. Safety Information of Dexamethasone

Hazard Codes: IrritantXi,HarmfulXn
Risk Statements: 43-40-36/37/38-20/21/22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R40:Limited evidence of a carcinogenic effect. 
R43:May cause sensitization by skin contact.
Safety Statements: 36/37-45-36-26-22
S22:Do not breathe dust. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S36/37:Wear suitable protective clothing and gloves. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

5. Preparation of Dexamethasone
Dexamethasone is reacted with a source of hypobromite, such as basic N-bromosuccinimide, to form the 9α-bromo-11β-hydrin derivative, which is then ring-closed to an epoxide. A ring-opening reaction with hydrogen fluoride in tetrahydrofuran gives dexamethasone.


6. Use of Dexamethasone
Dexamethasone is used to treat many inflammatory and autoimmune conditions. If given in high doses, it is useful to counteract allergic anaphylactic shock. It is used in transvenous screw-in cardiac pacing leads to minimize the inflammatory response of the myocardium. In oncology, it is given to cancer patients undergoing chemotherapy to counteract certain side-effects of their antitumor treatment. It is also used in the treatment of high altitude cerebral edema as well as pulmonary edema. Dexamethasone is also used in a diagnostic context namely in its property to suppress the natural pituitary-adrenal axis.

7. Side effect of Dexamethasone
Dexamethasone may have such sife effects:
1)Stomach upset, increased sensitivity to stomach acid to the point of ulceration of esophagus, stomach, and duodenum.
2)Increased appetite leading to significant weight gain
3)A latent diabetes mellitus often becomes manifest, glucose intolerance is worsened in patients with pre-existing diabetes
4)Immunsuppressant action, particularly if given with other immunosuppressants, such as cyclosporine, may allow bacterial, viral, and fungal disease to progress more easily and can become life-threatening; fever as a warning symptom is often suppressed.
5)Psychiatric disturbances, including personality changes, irritability, euphoria, or mania and mood swings.

8. Other details of Dexamethasone
Dexamethasone is a potent synthetic member of the glucocorticoid class of steroid hormones, and acts as an anti-inflammatory and immunosuppressant. It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately.

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