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Triamcinolone

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Name

Triamcinolone

EINECS 204-718-7
CAS No. 124-94-7 Density 1.42 g/cm3
PSA 115.06000 LogP 0.62050
Solubility 79.99mg/L(25 oC) Melting Point 262-263 °C(lit.)
Formula C21H27FO6 Boiling Point 587.5 °C at 760 mmHg
Molecular Weight 394.44 Flash Point 309.1 °C
Transport Information N/A Appearance N/A
Safety 22-36 Risk Codes 40
Molecular Structure Molecular Structure of 124-94-7 (Triamcinolone) Hazard Symbols HarmfulXn
Synonyms

11b,16a,17a,21-Tetrahydroxy-9a-fluoro-1,4-pregnadiene-3,20-dione;9-Fluoro-11b,16a,17,21-tetrahydroxypregna-1,4-diene-3,20-dione;9a-Fluoro-16a-hydroxyprednisolone;Adcortyl;CL 19823;Cinolone;Fluoxyprednisolone;Kenacort;Ledercort;Mycolog;NSC13397;Omicilon;Polcortolon;Rodinolone;Triamcinlon;Triamcinolone;Tricortale;Volon;

 

Triamcinolone Synthetic route

3859-65-2

(11β,16α)-21-acetyloxy-9-fluoro-11,16,17-trihydroxypegna-1,4-diene-3,20-dione

124-94-7

triamcinolone

Conditions
ConditionsYield
With sodium hydroxide In methanol; dichloromethane at -7 - -3℃; Inert atmosphere;85.29%

C28H38O9

124-94-7

triamcinolone

Conditions
ConditionsYield
Stage #1: C28H38O9 With hydrogen fluoride In chloroform; water at -40℃;
Stage #2: With toluene-4-sulfonic acid at 40℃;
81%
338-95-4

isoflupredone

124-94-7

triamcinolone

Conditions
ConditionsYield
mit Hilfe von Streptomyces roseochromogenus;
4001-36-9

16β,21-diacetoxy-9-fluoro-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione

124-94-7

triamcinolone

Conditions
ConditionsYield
With potassium hydroxide
67-78-7

triamcinolone diacetate

124-94-7

triamcinolone

Conditions
ConditionsYield
With potassium hydroxide
98422-57-2, 114417-77-5

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

124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: CH2Cl2; THF; HF
2: SeO2
3: methanol.KOH
View Scheme
2967-24-0

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

124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SeO2
2: methanol.KOH
View Scheme
98422-57-2, 114417-77-5

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

124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: CHCl3; HF
2: mit Hilfe von Nocardia corallina
3: methanol.KOH
View Scheme
1171-81-9

11β,16α,17,21-tetrahydroxy-pregn-4-ene-3,20-dione

124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: mit Hilfe von Corynebacterium simplex oder Nocardia corallina
2: pyridine
3: SOCl2; pyridine
4: aqueous HClO4; dioxane
5: potassium acetate; ethanol
6: CHCl3; HF
7: methanol.KOH
View Scheme
426-39-1

16α,21-Diacetoxy-9α-fluoro-11β,17α-dihydroxpregn-4-ene-3,20-dione

124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: mit Hilfe von Nocardia corallina
2: methanol.KOH
View Scheme

Triamcinolone Chemical Properties

Molecular Formula: C21H27FO6
Molar mass: 394.44 g/mol
EINECS: 204-718-7
Density: 1.42 g/cm3
Flash Point: 309.1 °C
Index of Refraction: 1.617
Boiling Point: 587.5 °C at 760 mmHg
Vapour Pressure: 3E-16 mmHg at 25°C
Melting point: 260-263 ºC (dec.)
Synonyms of Triamcinolone (124-94-7): (8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11,16,17-trihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one ;  (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one
Structure of Triamcinolone (124-94-7):

XLogP3-AA: 1.2
H-Bond Donor: 4
H-Bond Acceptor: 7
IUPAC Name: (8S,9R,10S,11S,13S,14S,16R,17S)-9-Fluoro-11,16,17-trihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
Canonical SMILES: CC12CC(C3(C(C1CC(C2(C(=O)CO)O)O)CCC4=CC(=O)C=CC43C)F)O
Isomeric SMILES: C[C@]12C[C@@H]([C@]3([C@H]([C@@H]1C[C@H]([C@@]2(C(=O)CO)O)O)CCC4=CC(=O)C=C[C@@]43C)F)O
InChI: InChI=1S/C21H27FO6/c1-18-6-5-12(24)7-11(18)3-4-13-14-8-15(25)21(28,
17(27)10-23)19(14,2)9-16(26)20(13,18)22/h5-7,13-16,23,25-26,28H,3-4,8-10H2,1-2H3/t13-,14-,15+,16-,18-,19-,20-,21-/m0/s1 
InChIKey: GFNANZIMVAIWHM-OBYCQNJPSA-N

Triamcinolone Uses

 Triamcinolone (124-94-7) is used in the post-operative period of certain cosmetic surgery procedures, notably rhinoplasty. Injected into the subcutaneous area, it may help to alleviate stubborn swelling, scar tissue, and inflamed sebaceous cysts.It is occasionally used to treat lichen planus and severe cases of hayfever, and may also be used to treat diabetic retinopathy.It is highly effective in the most severe cases of eczema, but may require a waiting period before subsequent treatments.Inaddition, it can be used in case of severe arthritis, Lumbago sciatica.

Triamcinolone Toxicity Data With Reference

1.    

oms-hmn-orl 428 µg/kg

    ARDEAC    Archives of Dermatology. 103 (1971),39.
2.    

scu-rat LD50:99 mg/kg

    TXAPA9    Toxicology and Applied Pharmacology. 8 (1966),250.

Triamcinolone Safety Profile

Poison by subcutaneous route. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of F. An anti-inflammatory and antiallergic agent.
 

Hazard Codes: Xn
Risk Statements:
40:  Limited evidence of a carcinogenic effect
Safety Statements:
22:  Do not breathe dust
36:  Wear suitable protective clothing

Triamcinolone Specification

Triamcinolone (124-94-7) (trade names Kenalog, Aristocort, Nasacort, Tri-Nasal, Triderm, Azmacort, Trilone, Volon A, Tristoject, Fougera, Tricortone,Triesence) is a synthetic corticosteroid given orally, by inhalation, injection, or as a topical ointment or cream.
Its side effects include nosebleeds, a sore throat, increased headache, coughing, and runny nose. White patches in the throat or nose indicates a serious side effect. Symptoms of an allergic reaction include itch, rash, severe dizziness, swelling, trouble breathing.

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