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Dexamethasone-17-acetate

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Name

Dexamethasone-17-acetate

EINECS 214-646-8
CAS No. 1177-87-3 Density 1.3 g/cm3
PSA 100.90000 LogP 2.46650
Solubility 5.47 mg/L at 25 ºC in water Melting Point 238-240 ºC(lit.)
Formula C24H31FO6 Boiling Point 579.4 ºC at 760 mmHg
Molecular Weight 434.505 Flash Point 304.2 ºC
Transport Information N/A Appearance White or almost white crystalline powder
Safety 36/37 Risk Codes 43
Molecular Structure Molecular Structure of 1177-87-3 (Dexamethasone-17-acetate) Hazard Symbols IrritantXi
Synonyms

Dex-Cortideltacetate;Dexa-Cortisyl;Fortecortin;Fortecortin (crystal suspension);Pregna-1,4-diene-3,20-dione,21-(acetyloxy)-9-fluoro-11,17-dihydroxy-16-methyl-, (11b,16a)-;Pregna-1,4-diene-3,20-dione,9-fluoro-11b,17,21-trihydroxy-16a-methyl-, 21-acetate (6CI,8CI);16a-Methyl-9a-fluoroprednisolone 21-acetate;Dalalone DP;Dalalone LA;Decadron LA;Decadronal;Dectancyl;Dexamethasone acetate;

Article Data 21

Dexamethasone-17-acetate Synthetic route

1524-94-3

21-acetoxy-9-fluoro-11β,17-dihydroxy-16α-methyl-pregn-4-ene-3,20-dione

1177-87-3

betamethasone

Conditions
ConditionsYield
With selenium(IV) oxide
912-38-9, 2884-51-7, 14622-51-6, 98573-86-5

21-acetoxy-9,11β-epoxy-17-hydroxy-16α-methyl-9β-pregna-1,4-diene-3,20-dione

1177-87-3

betamethasone

Conditions
ConditionsYield
With tetrahydrofuran; chloroform; hydrogen fluoride
2884-51-7

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

1177-87-3

betamethasone

Conditions
ConditionsYield
With hydrogen fluoride In N,N-dimethyl-formamide at -10℃; for 3h; Temperature;
With hydrogen fluoride In chloroform
34542-57-9

16β-methyl-17a,11β,21-trihydroxy-9-bromopregna-4-ene-3,20-dione-21-acetate

1177-87-3

betamethasone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium acetate; ethanol
2: THF; CHCl3; HF
3: SeO2
View Scheme
18769-18-1, 34542-58-0, 104111-24-2, 104527-32-4

21-acetoxy-9,11β-epoxy-17-hydroxy-16α-methyl-9β-pregn-4-ene-3,20-dione

1177-87-3

betamethasone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: THF; CHCl3; HF
2: SeO2
View Scheme
19784-87-3

17,21-dihydroxy-16α-methyl-pregna-1,4-diene-3,20-dione

1177-87-3

betamethasone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: mit Hilfe von Pestalotia foedans
4: sodium acetate; acetic acid
5: N-bromo-acetamide; dichloromethane; tert-butyl alcohol / Reagens 4: wss. Perchlorsaeure, Erwaermen des Reaktionsprodukts mit Kaliumacetat in Aceton
6: CHCl3; THF; HF
View Scheme
115606-30-9

21-acetoxy-17-hydroxy-16α-methyl-11α-(toluene-4-sulfonyloxy)-pregna-1,4-diene-3,20-dione

1177-87-3

betamethasone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium acetate; acetic acid
2: N-bromo-acetamide; dichloromethane; tert-butyl alcohol / Reagens 4: wss. Perchlorsaeure, Erwaermen des Reaktionsprodukts mit Kaliumacetat in Aceton
3: CHCl3; THF; HF
View Scheme
78761-59-8

11α,17,21-trihydroxy-16α-methyl-pregna-1,4-diene-3,20-dione

1177-87-3

betamethasone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
3: sodium acetate; acetic acid
4: N-bromo-acetamide; dichloromethane; tert-butyl alcohol / Reagens 4: wss. Perchlorsaeure, Erwaermen des Reaktionsprodukts mit Kaliumacetat in Aceton
5: CHCl3; THF; HF
View Scheme
6242-16-6

21-acetoxy-11α,17-dihydroxy-16α-methyl-pregna-1,4-diene-3,20-dione

1177-87-3

betamethasone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
2: sodium acetate; acetic acid
3: N-bromo-acetamide; dichloromethane; tert-butyl alcohol / Reagens 4: wss. Perchlorsaeure, Erwaermen des Reaktionsprodukts mit Kaliumacetat in Aceton
4: CHCl3; THF; HF
View Scheme
10106-41-9

17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate

1177-87-3

betamethasone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-bromo-acetamide; dichloromethane; tert-butyl alcohol / Reagens 4: wss. Perchlorsaeure, Erwaermen des Reaktionsprodukts mit Kaliumacetat in Aceton
2: CHCl3; THF; HF
View Scheme

Dexamethasone-17-acetate Chemical Properties


IUPAC Name: [2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-Fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
Molecular Weight: 434.497743 [g/mol]
Molecular Formula: C24H31FO6
XLogP3: 2.8
H-Bond Donor: 2
H-Bond Acceptor: 7 
EINECS: 214-646-8
Product Categories: Biochemistry; Hydroxyketosteroids; Steroids
refractive index: 87 ° (C=1, Dioxane)
storage temp.: 2-8 °C 
Index of Refraction: 1.571
Molar Refractivity: 109.82 cm3
Molar Volume: 334 cm3
Surface Tension: 52.9 dyne/cm
Density: 1.3 g/cm3
Flash Point: 304.2 °C
Enthalpy of Vaporization: 99.54 kJ/mol
Boiling Point: 579.4 °C at 760 mmHg
Vapour Pressure: 7.75E-16 mmHg at 25 °C 
Water Solubility: 5.47 mg/L at 25 °C
Melting Point: 238-240 °C(lit.)
Classification Code of Dexamethasone acetate (CAS NO.1177-87-3): Anti-Inflammatory Agents; Reproductive Effect

Dexamethasone-17-acetate Uses

1. Dexamethasone acetate (CAS NO.1177-87-3) is used to treat many inflammatory and autoimmune conditions, such as rheumatoid arthritis. It is useful to counteract allergic anaphylactic shock, if given in high doses. Dexamethasone acetate is used in transvenous screw-in cardiac pacing leads to minimize the inflammatory response of the myocardium.
2. In oncology, it is given to cancer patients undergoing chemotherapy, to counteract certain side-effects of their antitumor treatment. Dexamethasone can augment the antiemetic effect of 5-HT3 receptor antagonists like ondansetron. Dexamethasone acetate is also used in certain hematological malignancies, especially in the treatment of multiple myeloma, in which dexamethasone is given alone or together with thalidomide (thal-dex) or lenalidomide, or a combination of Adriamycin (doxorubicin) and vincristine (VAD). In brain tumours (primary or metastatic), Dexamethasone acetate is used to counteract the development of edema, which could eventually compress other brain structures. It is also given in cord compression where a tumor is compressing the spinal cord.
3. Dexamethasone acetate is the treatment for the very rare disorder of glucocorticoid resistance. In adrenal insufficiency and Addison's disease, it is prescribed when the person doesn't respond well to prednisone or methylprednisolone.
4. Dexamethasone acetate is used in the treatment of high altitude cerebral edema as well as pulmonary edema. It is commonly carried on mountain climbing expeditions to help climbers deal with altitude sickness.
5. Dexamethasone acetate has been used as an off-label pre-natal treatment for the symptoms of congenital adrenal hyperplasia (CAH) in female fetuses.  has also been used in the hope of enhancing sports performance. Dexamethasone acetate is also used in a diagnostic context, namely in its property to suppress the natural pituitary-adrenal axis.
6. Combined with marbofloxacin and clotrimazole, dDexamethasone acetate used to treat difficult ear infections, especially in dogs. It can also be combined with Trichlormethiazide to treat horses with swelling of distal limbs and general bruising.

Dexamethasone-17-acetate Consensus Reports

Reported in EPA TSCA Inventory.

Dexamethasone-17-acetate Safety Profile

Experimental teratogenic and reproductive effects. A steroid. When heated to decomposition it emits toxic fumes of F.
Hazard Codes: Xi
Risk Statements: 43
R43:May cause sensitization by skin contact ;
Safety Statements: 36/37
S36/37:Wear suitable protective clothing and gloves ;
WGK Germany: 3
RTECS: TU4050000

Dexamethasone-17-acetate Specification

  Dexamethasone acetate (CAS NO.1177-87-3), its Synonyms are 16alpha-Methyl-9alpha-fluoroprednisolone 21-acetate ; 9-Fluoro-11-beta,17,21-trihydroxy-16-alpha-methylpregna-1,4-diene-3,20-dione acetate ; 9alpha-Fluoro-16alpha-methylprednisolone acetate ; Decadron-LA ; Decadronal ; Dectan ; Dex-Cortidelt acetate ; Dexamethasone 21-acetate ; Fortecortin (VAN) ; Panasone ; Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-9-fluoro-11,17-dihydroxy-16-methyl-, (11beta,16alpha)- ; Pregna-1,4-diene-3,20-dione, 9-fluoro-11-beta,17,21-trihydroxy-16-alpha-methyl-, acetate Pregna-1,4-diene-3,20-dione, 9-fluoro-11beta,17,21-trihydroxy-16alpha-methyl-, 21-acetate (8CI) .

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