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124-94-7
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???(??):
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Triamcinolone
???(??):
Cinolone;(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;Volon;0-dione;Celeste;cl19823;omcilon;CL 19823;Kenacort;Omicilon
CBNumber:
CB1734678
???:
C21H27FO6
??? ??:
394.43
MOL ??:
124-94-7.mol

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???
262-263 °C(lit.)
?? ?
587.5±50.0 °C(Predicted)
??
69 º (c=2, DMF)
??
1.1703 (estimate)
?? ??
2-8°C
???
DMF: ???20mg/mL
?? ?? (pKa)
11.57±0.70(Predicted)
??? ??
Solid
??
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optical activity
[α]25/D +69°, c = 2 in DMF
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79.99mg/L(25℃)
Merck
9595
InChIKey
GFNANZIMVAIWHM-OBYCQNJPSA-N
CAS ??????
124-94-7(CAS DataBase Reference)
NIST
Triamcinolone(124-94-7)
EPA
Triamcinolone (124-94-7)
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  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
??? ?? Xn
?? ???? ?? 40
????? 22-36
WGK ?? 3
RTECS ?? TU3850000
HS ?? 2937220000
?? ?? ??? 124-94-7(Hazardous Substances Data)
?? LD50 subcutaneous in mouse: > 4gm/kg
????(GHS): GHS hazard pictograms
?? ?: Warning
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?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H351 ?? ??? ??? ??? (????? ?? ???? ???? ???? ??? ?? ????? ??? ???? ??) ??? ?? ?? 2 ?? P201, P202, P281, P308+P313, P405,P501
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P280 ????/???/???/?????? ?????.

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A natural extension of corticoid research involved examination of compounds containing both a 9α-fluoro group and a double bond between positions 1 and 2. Triamcinolone (9-fluoro-11β, 16α, 17, 21-tetrahydroxypregna- 1,4-diene-3,20-dione), introduced in 1958, combines the structural features of a ?1 -corticoid and a 9α-fluoro corticoid. As mentioned previously, the 9α-fluoro group increases the anti-inflammatory potency, but it also markedly increases the mineralocorticoid potency. This is undesirable if the drug is to be used internally for the treatment of rheumatoid arthritis. By inserting a 16α-hydroxy group into the molecule, one can decrease the mineralocorticoid activity.

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White, crystalline powder. Insoluble in water; slightly soluble in usual organic solvents; soluble in dimethylformamide.

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Triamcinolone is a glucocorticoid. Triamcinolone is used as an antiasthmatic (inhalant); antiallergic (nasal).

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ChEBI: A C21-steroid hormone that is 1,4-pregnadiene-3,20-dione carrying four hydroxy substituents at positions 11beta, 16alpha, 17alpha and 21 as well as a fluoro substituent at position 9. sed in the form of its 16,17-acetonide to treat various skin infections.

Indications

Intralesional bleomycin, a cytotoxic drug that inhibits DNA synthesis, is effective for all varieties of recalcitrant warts. Various concentrations of the drug have been used, although the total dose must be carefully tracked over time to avoid potential systemic toxicity.

Clinical Use

Triamcinolone to be used topically is generally dispensed as its more potent and lipophilic acetonide, a 16α,17α-methylenedioxy cyclic ketal or isopropylidene derivative. It is effective in the treatment of psoriasis and other corticoid-sensitive dermatologic conditions. Topically, triamcinolone acetonide is a more potent derivative of triamcinolone and is approximately eight times more active than prednisolone.

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Even though triamcinolone has an apparently decreased tendency to cause salt and water retention and edema and may induce sodium and water diuresis, it causes other unwanted side effects, including anorexia, weight loss, muscle weakness, leg cramps, nausea, dizziness, and a general toxic feeling.

Safety Profile

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

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