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Dexamethasone structure
Dexamethasone structure

Dexamethasone

Iupac Name:(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
CAS No.:50-02-2
Molecular Weight:392.46
Introduction: Dexamethasone is an Anti-inflammatory glucocorticoid that is used to treat inflammatory and autoimmune conditions such as rheumatoid arthritis and bronchospasm. It is useful to study apoptosis, cell signaling pathways and gene expression. It is associated with marbofloxacin and clotrimazole and finds application in veterinary medicine to treat difficult ear infections in dogs. It is also used to treat horses with swelling of of distal limbs and general bruising in combination with trichlormethiazide.Dexamethasone induces the production of phospholipase A2 inhibitory protein (lipocortin). It also inhibits induction of nitric oxide synthase (IC50=5 nM). Dexamethasone has been shown to cause reduction in cyclin A and Cd k2 activity, inhibition of G1/S transition in osteoblasts and inhibition of phosphorylation of Rb protein in vitro. Dexamethasone has been observed to induce apoptosis in human thymocytes and eosinophils, but inhibits apoptosis in neutrophils in vitro. Dexamethasone is an activator of IDO.Dexamethasone Inhibits the expression of the inducible but not the constitutive nitric oxide synthase in vascular endothelial cells (IC50=5 nM). Dexamethasone regulates T cell survival, growth, and differentiation.Enhances active cation transport in aortic smooth muscle cells by stimulating the Na+-K+ pump. Has anti-inflammatory and anti-rheumatic properties. Induces apoptosis in human thymocytes. In general, 500-1000 nM of dexamethasone is sufficient to induce apoptosis following a 6-hour incubation at 37°C. View more+
1. Names and Identifiers
1.1 Name
Dexamethasone
1.2 Synonyms

(11B,16A)-9-FLUORO-11,17,21-TRIHYDROXY-16-METHYL-PREGNA-1,4-DIENE-3,20-DIONE (11b,16a)-9-fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione (11BETA,16ALPHA)-9-FLUORO-11,17,21-TRIHYDROXY-16-METHYLPREGNA-1,4-DIENE-3,20-DIONE (11Β,16α)-9-Fluoro-11,17,21-trihydroxy-16-methylp (11Β,16α)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione (8S,9R,10S,11S,13S,14S,16R,17R)-9-Fluor-11,17-dihydroxy-17-(hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-on (8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-17-(hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one (8S,9R,10S,11S,13S,14S,16R,17R)-9-Fluoro-17-glycoloyl-11,17-dihydroxy-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one 1,4-PREGNADIEN-9ALPHA-FLUORO-16ALPHA-METHYL-11BETA, 17ALPHA, 21-TRIOL 3,20-DIONE 16a-Methyl-9a-fluoro-1,4-pregnadiene-11b,17a,21-triol-3,20-dione 16a-Methyl-9a-fluoro-D1-hydrocortisone 16a-Methyl-9a-fluoroprednisolone 16α-Methyl-9α-fluoroprednisolone 1-Dehydro-16a-methyl-9a-fluorohydrocortisone 1-Dehydro-16α-methyl-9α-fluorohydrocortisone 9a-Fluoro-16a-methylprednisolone 9-Fluoro-11-Β,17,21-trihydroxy-16-α-methylpregna-1,4-diene-3,20-dione 9α-Fluoro-16α-methylprednisolone Adexone Aphthasolone Auxiron CALONAT Corson Decacort Dexa Dexa-Mamallet DEXAMETHASON DEXAMETHASONE BASE DEXAMETHASONUM Dexamonozon Dexone Dezone DXM Dxms EINECS 200-003-9 Hl-dex MFCD00064136 mk125 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-11,17,21-trihydroxy-16-methyl-, (11Β,16α)- Pregna-1,4-diene-3,20-dione, 9-fluoro-11Β,17,21-trihydroxy-16α-methyl-

1.3 CAS No.
50-02-2
1.4 CID
5743
1.5 EINECS(EC#)
200-003-9
1.6 Molecular Formula
C22H29FO5 (isomer)
1.7 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
1.8 InChkey
UREBDLICKHMUKA-CXSFZGCWSA-N
1.9 Canonical Smiles
CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)CO)O)C)O)F)C
1.10 Isomers Smiles
C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)F)C
2. Properties
3.1 Density
1.1283 (estimate)
3.1 Melting point
262-264 °C(lit.)
3.1 Boiling point
568.2oC at 760 mmHg
3.1 Refractive index
76 ° (C=1, Dioxane)
3.1 Flash Point
9℃
3.1 Precise Quality
392.20000
3.1 PSA
94.83000
3.1 logP
1.89570
3.1 Solubility
ethanol: 1?mg/mL
3.2 AnalyticLaboratory Methods
Determination of descamethasone using a HPLC equipped with an UV detection at an absorption of 254 nm. Flow rate of 2 ml/min.
3.3 Appearance
White crystalline solid
3.4 Chemical Properties
White or almost white, crystalline powder.
3.5 Color/Form
off-white
3.6 Decomposition
When heated to decomposition it emits toxic fumes of /hydrogen fluoride;/.
3.7 Ionization Potential
11.70 eV
3.8 Physical
PHYSICAL DESCRIPTION: Odorless white to off-white crystalline powder with a slightly bitter taste. (NTP, 1992)
3.9 pKa
12.13±0.70(Predicted)
3.10 Water Solubility
ethanol: 1 mg/mL
3.11 Spectral Properties
Specific optical rotation: +77.5 deg at 25 deg C/D (dioxane)
IR: u 5108 (Coblentz Society spectral collection) /spectra converted from micrometers to wavenumbers/
3.12 Stability
Stable. Combustible. Incompatible with strong oxidizing agents, strong bases, acid anhydrides, acid chlorides. May be light sensitive.
3.13 StorageTemp
2-8°C
3. Use and Manufacturing
4.1 Fire Hazard
Flash point data for Dexamethasone are not available; however, Dexamethasone is probably combustible.
4.2 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 124 companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 124 companies. For more detailed information, please visit ECHA C&L website

Of the 21 notification(s) provided by 123 of 124 companies with hazard statement code(s):

H315 (23.58%): Causes skin irritation [Warning Skin corrosion/irritation]
H317 (27.64%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H319 (23.58%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H334 (22.76%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]
H335 (22.76%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H360 (63.41%): May damage fertility or the unborn child [Danger Reproductive toxicity]
H373 (31.71%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
H410 (28.46%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P260, P261, P264, P271, P272, P273, P280, P281, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P308+P313, P312, P314, P321, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P391, P403+P233, P405, and P501
4.3 Methods of Manufacturing
Preparation: Muller et al., US 3007923 (1961 to Lab Franc Chimiother); Arth et al., DE 1113690 (1961 to Merck & Co.)
4.4 Purification Methods
Dexamethasone has been recrystallised from Et2O or small volumes of EtOAc. Its solubility in H2O is 10 mg/100mL at 25o; and is freely soluble in Me2CO, EtOH and CHCl3. [Arth et al. J Am Chem Soc 80 3161 1958; for the -methyl isomer see Taub et al. J Am Chem Soc 82 4025 1960, see Beilstein 8 IV 3501.] Dexamethasone Preparation Products And Raw materials Preparation Products
4.5 Safety Profile
Poison by intraperitoneal and subcutaneous routes. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of F-.
4.6 Storage
Light Sensitive. Ambient temperatures.
4.7 Usage
Glucocorticoid.
4. Safety and Handling
5.1 Symbol
GHS07, GHS08
5.1 Hazard Codes
F,T,Xi,Xn
5.1 Signal Word
Danger
5.1 Risk Statements
43-40-36/37/38-20/21/22-42/43-39/23/24/25-23/24/25-11
5.1 Safety Statements
36/37-45-36-26-22-16
5.1 Exposure Standards and Regulations
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl dexamethasone sodium phosphate approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Dexamethasone sodium phosphate/
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl dexamethasone, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Dexamethasone-21-isonicotinate is included on this list. /Dexamethasone-21-isonicotinate/
The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Dexamethasone sodium phosphate is included on this list. /Dexamethasone Sodium Phosphate/
The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Dexamethasone is included on this list.
Oral dosage form new animal drugs. ... Dexamethasone powder is indicated in cases where cattle and horses require additional steroid therapy following its parenteral administration. The drug is used as supportive therapy for management or inflammatory conditions such as acute arthritic lameness, and for various stress conditions where corticosteroids are required while the animal is being treated for a specific condition. ... Federal law restricts this drug to use by or on the order of a licensed veterinarian. A withdrawal period has not been established for this product in preruminating calves. Do not use in calves to be processed for veal.
Oral dosage form new animal drugs. ... Dexamethasone bolus is indicated in cases where cattle and horses require additional steroid therapy following its parenteral administration. The drug may be used as supportive therapy for management of inflammatory conditions such as acute arthritic lamenesses, and for various stress conditions where corticosteroids are required while the animal is being treated for a specific condition. ... In treatment of dogs and cats as an anti-inflammatory agent. ... Federal law restricts this drug to use by or on the order of a licensed veterinarian.
Oral dosage form new animal drugs. ... Dexamethasone chewable tablets. ... Indications for use. Supportive therapy in nonspecific dermatosis and inflammatory conditions in dogs. ... Federal law restricts this drug to use by or on the order of a licensed veterinarian.
Implantation or injectable dosage form new animal drugs. Dexamethasone injection. ... The drug is indicated: (A) For the treatment of primary bovine ketosis and as an anti-inflammatory agent in cattle and horses; (B) As an anti-inflammatory agent in dogs and cats. ... Federal law restricts this drug to use by or on the order of a licensed veterinarian.
5.2 Octanol/Water Partition Coefficient
log Kow = 1.83
5.3 Hazard Declaration
H315-H317-H319-H334-H335
5.3 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
5.4 RIDADR
UN1230 - class 3 - PG 2 - Methanol, solution
5.4 Caution Statement
P261-P280-P305 + P351 + P338-P342 + P311
5.4 Formulations/Preparations
Parenteral Injection, for IM or IV use: 4 mg (of dexamethasone phosphate) per mL Dexmethasone Sodium Phosphate Injection (with benzyl alcohol 1%), (Abraxis), Dexamethasone Sodium Phosphate Injection ( with benzyl alcohol 1%), American Regent 10 mg (of dexamethasone phosphate) per mL Dexmethasone Sodium Phosphate Injection (preservative-free), (Abraxis). /Dexamethasone sodium phosphate/
Oral: Elixir 0.5 mg/5 mL Dexamethasone Elixir (with alcohol 5%), (Actavis), Dexamethasone Elixir (with alcohol 5%), (Morton Grove Pharmaceuticals) Solution: 0.5 mg/5 mL Dexamethasone Oral Solution, (Roxane). Solution, concentrate: 0.5 mg/0.5 mL Dexamethasone Intensol (with alcohol 30%), (Roxane). Tablets: 0.25 mg 0.5 mg Decadron (scored), (Merck); 0.75 mg Decadron (scored), (Merck); 1 mg Dexamethasone Tablets, (Roxane); 1.5 mg Dexpak Taperpak (available as 13-day mnemonic pack of 51 tablets), (ECR), Dexamethasone Tablets, (Par), Dexamethasone Tablets, (Roxane), Dexamethasone Tablets, (Par), Dexamethasone Tablets, (Roxane); 2 mg Dexamethasone Tablets, (Roxane); 4 mg Dexamethasone Tablets, (Par), Dexamethasone Tablets, (Roxane); 6 mg Dexamethasone Tablets, (Par), Dexamethasone Tablets, (Roxane).
Ophthalmic: Solution: 0.1% (of dexamethasone phosphate) Dexamethasone Sodium Phosphate Ophthalmic Solution, Bausch & Lomb).
Ophthalmic Suspension: 0.1% Maxidex (with benzalkonium chloride; viscous), (Alcon).
5.5 WGK Germany
2
5.5 RTECS
TU3980000
5.5 Safety

Hazard Codes:?Xi,Xn
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.)

5.6 Specification

?Dexamethasone , its cas register number is 50-02-2. It also can be called 9alpha-Fluoro-11beta,17alpha,21-trihydroxy-16alpha-methylpregn-1,4-diene-3,20-dione .?It 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.

5.7 Toxicity

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.
?

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H360 May damage fertility or the unborn child

Precautionary statement(s)
Prevention

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P308+P313 IF exposed or concerned: Get medical advice/ attention.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

8. Precursor and Product
product :
382-67-2
382-67-2
9. Other Information
9.0 Merck
14,2943
9.1 BRN
2066651
9.2 Anti-inflammatory effects
Dexamethasone reduces and prevents the tissue response to inflammation, thereby reducing the manifestations of inflammation. Hormones inhibit the accumulation of inflammatory cells, including macrophages and leukocytes, at sites of inflammation, and inhibit phagocytosis, the release of lysosomal enzymes, and the synthesis and release of inflammatory chemical mediators.
9.3 Description
Dexamethasone is an Anti-inflammatory glucocorticoid that is used to treat inflammatory and autoimmune conditions such as rheumatoid arthritis and bronchospasm. It is useful to study apoptosis, cell signaling pathways and gene expression. It is associated with marbofloxacin and clotrimazole and finds application in veterinary medicine to treat difficult ear infections in dogs. It is also used to treat horses with swelling of of distal limbs and general bruising in combination with trichlormethiazide.
Dexamethasone induces the production of phospholipase A2 inhibitory protein (lipocortin). It also inhibits induction of nitric oxide synthase (IC50=5 nM). Dexamethasone has been shown to cause reduction in cyclin A and Cd k2 activity, inhibition of G1/S transition in osteoblasts and inhibition of phosphorylation of Rb protein in vitro. Dexamethasone has been observed to induce apoptosis in human thymocytes and eosinophils, but inhibits apoptosis in neutrophils in vitro. Dexamethasone is an activator of IDO.
Dexamethasone Inhibits the expression of the inducible but not the constitutive nitric oxide synthase in vascular endothelial cells (IC50=5 nM). Dexamethasone regulates T cell survival, growth, and differentiation.Enhances active cation transport in aortic smooth muscle cells by stimulating the Na+-K+ pump. Has anti-inflammatory and anti-rheumatic properties. Induces apoptosis in human thymocytes. In general, 500-1000 nM of dexamethasone is sufficient to induce apoptosis following a 6-hour incubation at 37°C.
9.4 Side Effects
Dexamethasone is a artificially synthetic glucocorticoid, belonging to a long-term glucocorticoid drugs. Glucocorticoids can promote the metabolism of the three major nutrients while preventing protein synthesis with long-term topical being able to causing more serious consequences. However, the adverse effects should be much smaller than oral medication. Common side effects of systemic corticosteroid include:
It can cause stomach discomfort and increased sensitivity to stomach ulcers.
It can Increase the appetite and results in a significant increase in body weight.
Potential patients with diabetes: glucose intolerance in patients with aggravating existing diabetes.
It can cause mental illness including personality changes, irritability, agitation, and mania.
It can be used for the long-term treatment of osteoporosis: pathological fractures (such as hip).
It can cause elevated liver enzymes, fatty liver degeneration (usually reversible).
For patients of nephrotic syndrome, applying long-term high-dose medication is likely to cause large side effects such as gastrointestinal ulcers and avascular necrosis. For treatment of nephrotic syndrome, it is better to apply prednisone acetate tablets.
Dexamethasone can be used for the treatment of high altitude cerebral edema and pulmonary edema. Upon climbing expeditions, people can apply it to alleviate altitude sickness.
Combination with marbofloxacin and clotrimazole, etc. can be used for treating the ear infection and allergies of a dog or a bird.
9.5 Drug Reactions
Dexamethasone is a corticosteroid known as a glucocorticoid. Corticosteroids are meant to resemble a naturally occurring hormone produced in the adrenal cortex, cortisol. Corticosteroids act on the immune system by blocking the production of substances that trigger inflammatory and immune responses.
Dexamethasone may react with these drugs:
Amphotericin
Aspirin
Cyclophosphamide
Cyclosporine
Digoxin
Daunorubicin HCl
Doxorubicin HCl
Insulin
Mitotane
Phenobarbital
Phenytoin sodium
Rifampin
Rimadyl
9.6 Description
The activity of dexamethasone, as measured by glycogen deposition, is 20 times greater than that of hydrocortisone. It has five times the anti-inflammatory activity of prednisolone. Clinical data indicate that this compound has seven times the antirheumatic potency of prednisolone. It is roughly 30 times more potent than hydrocortisone. Its pharmacokinetics are presented in Table 33.3. Routes of metabolism for dexamethasone are similar to those for prednisolone, with its primary 6β-hydroxy metabolite being recovered in urine. Dexamethasone sodium phosphate is the water-soluble sodium salt of the 21-phosphate ester, with an IV half-life of less than 10 minutes because of rapid hydrolysis by plasma phosphatases. Peak plasma levels for dexamethasone usually are attained in approximately 10 to 20 minutes following its IV administered dose. A similar reaction occurs when the phosphate ester is applied topically or by inhalation.
9.7 Chemical Properties
White or almost white, crystalline powder.
9.8 Originator
Dexacen,Central,US,1977
9.9 Uses
Glucocorticoid.
9.10 Uses
Dexamethasone is used for the same indications as all corticosteroids; however, it exhibits a significantly more powerful anti-inflammatory and anti-allergic action. It is used for circulatory collapse—shock during or after surgical operations, trauma, blood loss, myocardial infarction, and burns. It is also used in severe infections—toxemia, vascular collapse in meningococcosis, septicemia, diphtheria, typhoid fever, and peritonitis. It is used in severe allergic conditions—asthmatic status, laryngeal edema, severe anaphylactic reactions to medicinal drugs, and pyrogenic reactions.
9.11 Indications
Cushing’s disease is defined as hypercortisolism due to chronic overproduction of corticotrophin by a corticotroph adenoma. Cortisol’s lack of suppressibility during the administration of low doses of dexamethasone but suppressibility during high-dose dexamethasone is the key diagnostic finding in 99% of the patients with Cushing’s disease. This contrasts with the lack of glucocorticoid suppressibility typically found in patients with corticotrophin-independent hypercortisolism (Cushing’s syndrome). A judicious selection of the available tests may be necessary to obtain an accurate diagnosis in patients with Cushing’s syndrome.
9.12 Manufacturing Process
The preparation of dexamethasone acetate is described in US Patent 3,007,923 as follows. 1.5 cc of dimethylformamide and 1.5 cc of anhydrous hydrofluoric acid are admixed and treated with 480 mg of 9β,11β-epoxy-17αhydroxy-21-acetoxy-16α-methyl-?1,4-pregnadiene-3,20-dione (prepared according to E.P. Oliveto et al, J. Am. Chem. Soc., 80, 44331, 1958). The steroid dissolves in about 15 minutes. The reaction mixture is shaken for two hours at a temperature between 0 and +5°C, and then poured into 75 cc of
water containing in suspension, 7.5 grams of sodium bicarbonate. The mixture is vacuum filtered, the filter cake washed and then dried at 100°C, yielding 460 mg of crude hexadecadrol contaminated with a small amount of the starting material. A single recrystallization from methylene chloride yields 370 mg of the pure product having a melting point of 170°C and 229°C. The mother liquor yields 62 mg of the starting material, and a remainder constituting a mixture of starting and final materials with little other contamination.
9.13 Usage
Anti-inflammatory glucocorticoidDexamethasone is used to treat inflammatory and autoimmune conditions such as rheumatoid arthritis and bronchospasm. It is useful to study apoptosis, cell signaling pathways and gene expression. It is associated with marbofloxacin and clotrimazole and finds application in veterinary medicine to treat difficult ear infections in dogs. It is also used to treat horses with swelling of of distal limbs and general bruising in combination with trichlormethiazide. It is also an anti-inflammatory glucocorticoid.
9.14 Brand name
Aeroseb-Dex (Allergan); Decadron (Merck); Dexone (Solvay Pharmaceuticals); Hexadrol (Organon); Maxidex (Alcon); Mymethasone (Morton Grove).
9.15 Therapeutic Function
9-Fluoro-11β,17-dihydroxy-21-acetoxy-16α-methylpregna1,4-diene-3,20-dione
9.16 General Description
Dexamethasone, 9-fluoro-11β,17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione,is the 16 -isomer of betamethasone.
Dexamethasone acetate, USP (21-acetate)
Dexamethasone sodium phosphate, USP (21-sodiumphosphate).
9.17 General Description
Odorless white to off-white crystalline powder with a slightly bitter taste.
9.18 Air & Water Reactions
Insoluble in water.
9.19 Reactivity Profile
Dexamethasone may be sensitive to prolonged exposure to light. Dexamethasone is incompatible with strong oxidizers, strong acids, acid chlorides and acid anhydrides. Oxidation may occur with bases.
9.20 Fire Hazard
Flash point data for Dexamethasone are not available; however, Dexamethasone is probably combustible.
9.21 Biological Activity
Glucocorticoid; anti-inflammatory. Reduces levels of activated NF- κ B in immature dendritic cells (DCs) and inhibits differentiation into mature DCs.
9.22 Biochem/physiol Actions
Target IC50: 5 nM Inhibiting the expression of inducible but not constitutive nitric oxide synthase in vascular endothelial cells
9.23 Pharmacology
Dexamethasone is a corticosteroid with high glucocorticoid activity and virtually no mineralocorticoid activity. I ts mechanism of action as an antiemetic is unknown, but it is possible that either direct genomic or indirect non-genomic effects on 5-HT3 and GABAA receptors contribute to its antiemetic activity. Many of the original studies were carried out using 8– 10mg of dexamethasone phosphate, but smaller doses (2.5–4mg) provide equal antiemetic efficacy with minimal risk of adverse effects. Concerns relating to adrenal suppression and other steroid-induced adverse effects (including increased risk of bleeding) after a single dose of dexamethasone remain largely unfounded. O ne of the most unpleasant adverse effects of dexamethasone involves intense perineal stimulation after rapid i.v. injection.
9.24 Safety Profile
Poison by intraperitoneal and subcutaneous routes. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of F-.
9.25 Chemical Synthesis
Dexamethasone, 9α-fluoro-16α-methyl-11β,17,21-trihydroxypregna- 1,4-dien-3,20-dione (27.1.51), or simply 9α-fluoro-16α-methylprednisolone. The distinctive characteristic of dexamethasone is the presence of a fluorine atom at C9 of the steroid ring.
Dexamethasone is synthesized in a multistage process from 3α-acetoxy-16-pregnen- 11,20-dione, which is reacted with methylmagnesium bromide in the presence of lithium bromide to give 3α-hydroxy-16α-methylpregnan-11,20-dione (27.1.39), after which a 17α- hydroxyl group is added. This is done by a reaction with acetic anhydride in the presence of p-toluenesulfonic acid, forming the 3-acetoxy-17-enolacetate 27.1.40, which is epoxidized by perbenzoic acid 27.1.41, and the product is hydrolyzed by an alkali to give an oxyketone 27.1.42. Addition of another hydroxyl group at C21 is accomplished by subsequent bromination of a methyl group with molecular bromine, replacing the bromine atom with iodine, and reacting iodide with potassium acetate, which forms the corresponding acetoxyketone 27.1.43. The hydroxyl group at C3 is oxidized to a carbonyl by chromium(VI) oxide in pyridine, giving the 3,11,20-triketone 27.1.44, which again undergoes bromination by molecular bromine, but at position C4. Dehydrogenation of this compound is accomplished using semicarbazide, which results in the formation of an unsaturated triketone 27.1.45. In order to avoid formation of semicarbazones at the keto-groups at C3 and C20, the final product is treated with pyruvic acid. Semicarbazones are then specially formed at the keto-groups of C3 and C20, and the keto-group at C11 that does not take part in semicarbazone formation is reduced to hydroxyl group using sodium borohydride. After removing the protective semicarbzone groups, 21-O-acetoxy-16β-methylhydrocortisone (27.1.46) is formed. This is reacted with potassium acetate and transformed to the epoxide 27.1.49. Reacting this with hydrofluoric acid results in an opening of the epoxide ring, during which the fluorohydrin 27.1.50 is formed. Finally, microbiological dehydrogenation of this compound at C1–C2 and simultaneous deacetylation gives dexamethasone (27.1.51).

9.26 Veterinary Drugs and Treatments
Glucocorticoids have been used in an attempt to treat practically every malady that afflicts man or animal, but there are three broad uses and dosage ranges for use of these agents. 1) Replacement of glucocorticoid activity in patients with adrenal insufficiency, 2) as an antiinflammatory agent, and 3) as an immunosuppressive. Among some of the uses for glucocorticoids include treatment of: endocrine conditions (e.g., adrenal insufficiency), rheumatic diseases (e.g., rheumatoid arthritis), collagen diseases (e.g., systemic lupus), allergic states, respiratory diseases (e.g., asthma), dermatologic diseases (e.g., pemphigus, allergic dermatoses), hematologic disorders (e.g., thrombocytopenias, autoimmune hemolytic anemias), neoplasias, nervous system disorders (increased CSF pressure), GI diseases (e.g., ulcerative colitis exacerbations), and renal diseases (e.g., nephrotic syndrome). Some glucocorticoids are used topically in the eye and skin for various conditions or are injected intra-articularly or intralesionally. The above listing is certainly not complete. For specific dosages and indications refer to the Doses section.
High dose dexamethasone use for shock or CNS trauma is controversial; recent studies have not demonstrated significant benefit and it actually may cause increased deleterious effects.
9.27 Purification Methods
Dexamethasone has been recrystallised from Et2O or small volumes of EtOAc. Its solubility in H2O is 10 mg/100mL at 25o; and is freely soluble in Me2CO, EtOH and CHCl3. [Arth et al. J Am Chem Soc 80 3161 1958; for the -methyl isomer see Taub et al. J Am Chem Soc 82 4025 1960, see Beilstein 8 IV 3501.]
10. Computational chemical data
  • Molecular Weight:392.46g/mol
  • Molecular Formula:C22H29FO5
  • Compound Is Canonicalized:True
  • XLogP3-AA:
  • Exact Mass:392.19990218
  • Monoisotopic Mass:392.19990218
  • Complexity:805
  • Rotatable Bond Count:2
  • Hydrogen Bond Donor Count:3
  • Hydrogen Bond Acceptor Count:6
  • Topological Polar Surface Area:94.8
  • Heavy Atom Count:28
  • Defined Atom Stereocenter Count:8
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
11. Question & Answer
  • I am looking for a source for the radius of gyration of dexamethasone in aqueous solution. Does anyone know where I could get it from? Even better would be an estimation of the Stokes radius, but the radius of gyration will do.
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