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Triamcinolone

CAT: 0931-T0798-01Size: 500 mgDry Ice: NoHazardous: No
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CAT#:0931-T0798-01Size:500 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
124-94-7
Target
Interleukin, Glucocorticoid Receptor, COX
Related Pathways
Neuroscience, Immunology/Inflammation, Endocrinology/Hormones
Purity
0.996
Bioactivity
Triamcinolone (Aristocort) is a synthetic glucocorticoid with anti-inflammatory and immunomodulating properties. Upon cell entry, triamcinolone binds to and activates the glucocorticoid receptor, which leads to translocation of the ligand-receptor complex to the nucleus and induces expression of glucocorticoid-responsive genes such as lipocortins. Lipocortins inhibit phospholipase A2, thereby blocking the release of arachidonic acid from membrane phospholipids and preventing the synthesis of prostaglandins and leukotrienes, both mediators of inflammation. In addition, pro-inflammatory cytokine production, including interleukin (IL) -1and IL-6, and the activation of cytotoxic T-lymphocytes is also inhibited. T-cells are prevented from making IL-2 and proliferating. This agent also decreases the number of circulating lymphocytes, induces cell differentiation, and stimulates apoptosis through increasing Ikappa-B expression and curtailing activation of nuclear factor (NF) kappa-B.
Smiles
[H][C@@]12C[C@@H](O)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
Molecular Formula
C21H27FO6
Molecular Weight
394.43
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Triamcinolone

Triamcinolone is 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. Used in the form of its 16,17-acetonide to treat various skin infections. It has a role as an anti-inflammatory drug and an anti-allergic agent. It is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone, a 16alpha-hydroxy steroid, a glucocorticoid, a 17alpha-hydroxy steroid, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, a 3-oxo-Delta(4) steroid, a fluorinated steroid and a C21-steroid hormone. It derives from a hydride of a pregnane.

CAS Number124-94-7
PubChem CID31307
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
Molecular FormulaC21H27FO6
Molecular Weight394.4
XLogP1.2
Topological Polar Surface Area115
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Heavy Atom Count28
Formal Charge0
Complexity807
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
Chemical Structure
2D Structure
2D structure of Triamcinolone
CAS: 124-94-7
CID: 31307
Formula: C21H27FO6
MW: 394.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight394.4
XLogP31.2
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Exact Mass394.17916674
Monoisotopic Mass394.17916674
Topological Polar Surface Area115 Ų
Heavy Atom Count28
Formal Charge0
Complexity807
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
TRC-T767160-5GTriamcinolone
AR-T02914-01Triamcinolone Acetonide Impurity (Triamcinolone Base)
A8540-250Triamcinolone Acetonide

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