Basic information
- CAS
76-25-5- Standard SMILES
CC1(C)O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO)O1- InChIKey
YNDXUCZADRHECN-JNQJZLCISA-N- Molecular formula
- C24H31FO6
- Average molar mass
- 434.5 g/mol
- Monoisotopic mass
- 434.21046693
Overview
Triamcinolone acetonide is a synthetic glucocorticoid that is the 16,17-acetonide of triamcinolone. Used 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 glucocorticoid, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, a 3-oxo-Delta(4) steroid, a fluorinated steroid and a cyclic ketal. It is functionally related to a triamcinolone. It derives from a hydride of a pregnane.
Names & identifiers
- Preferred name
- Triamcinolone Acetonide
- IUPAC
- (1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one
- English name
- Triamcinolone acetonide
- Molecular formula
- C24H31FO6
- Molecular weight
- 434.5
Names & synonyms
Show more names
Database identifiers
- CAS
76-25-5- PubChem CID
- 6436
- DTXSID
DTXSID6021371- ChEMBL
CHEMBL1504- ChEBI
CHEBI:71418- UNII
- F446C597KA
- EC Number
- 200-948-7
- Nikkaji
- J55.714E
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 93.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 2
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 925
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal Drugs
Active Ingredients (Triamcinolone Acetonide) -> FDA Greenbook
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Collision Cross Section
290.1 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID6021371]
197.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 274 · 274-278°C (dec.)
- alpha
- 23 · D23 +109° (c = 0.75 in chloroform)
- Boiling point
- 576.9 · 576.9±50.0 °C(Predicted)
- Density
- 1.1517 · 1.1517 (estimate)
- refractive index
- 1.598 · 1.5980 (estimate)
- storage temp.
- Refrigerator
- solubility
- Practically insoluble in water, sparingly soluble in ethanol (96 per cent).
- pka
- 12.87 · 12.87±0.10(Predicted)
- form
- Solid
- color
- White to Off-White
- Water Solubility
- Soluble in DMSO or ethanol. Slightly soluble in water.
- Merck
- 9596 · 9596
- BCS Class
- 4 · 4
- Stability
- Combustible. Incompatible with strong oxidizing agents.
- InChIKey
- YNDXUCZADRHECN-JNQJZLCISA-N
- FDA UNII
- 446 C597KA · F446C597KA
- NIST Chemistry Reference
- Triamcinolone acetonide(76-25-5)
- NCI Drug Dictionary
- Aristocort
- EPA Substance Registry System
- Triamcinolone acetonide (76-25-5)
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 302 · H302-H360
- Precautionary statements
- 201 · P201-P202-P264-P270-P301+P312-P308+P313
- Hazard Codes
- T
- Risk Statements
- 61 · 61
- Safety Statements
- 53 · 53-45
- WGK Germany
- 3 · 3
- RTECS
- 3920000 · TU3920000
- TSCA
- TSCA listed
- HS Code
- 29372290 · 29372290
- Toxicity
- 50 oral · LD50 oral in mouse: 5gm/kg
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.8% (1 of 55) of reports.
Danger
H302 (12.7%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P264, P270, P280, P301+P317, P318, P319, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 55 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- TU3920000
- hs_code
- 29372290
- Toxicity
- LD50 oral in mouse: 5gm/kg
- risk_code
- 61
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- T
- safety_code
- 53-45
- Hazard statements
- H302-H360
- Precautionary statements
- P201-P202-P264-P270-P301+P312-P308+P313
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
F446C597KA
TRIAMCINOLONE ACETONIDE
Established Pharmacologic Class [EPC] - Corticosteroid
Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists
Triamcinolone acetonide is a Corticosteroid. The mechanism of action of triamcinolone acetonide is as a Corticosteroid Hormone Receptor Agonist.
ALLERGY NASAL
MeSH Pharmacological Classification
Substances that reduce or suppress INFLAMMATION.
A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system.
Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.
Uses & manufacturing
Use Classification
Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Applications
UsesTriamcinolone acetonide is a topical and systemic corticosteroid belonging to the group B (triamcinolone acetonide) type of steroids. Triamcinolone acetonide is an adrenal cortex hormone drug. As an antiasthmatic (inhalant) and antiallergic (nasal), it could used for treating diseases such as neurodermatitis, eczema, psoriasis, joint pain, and asthma.
DescriptionTriamcinolone acetonide is a synthetic corticosteroid. It decreases cytokine levels, the firing rate of sensory neurons, and mechanical hypersensitivity in a rat spinal nerve ligation model when used at a dose of 1.5 mg/kg prior to and following surgery for three days. Triamcinolone acetonide also decreases outflow facility in a mouse model of steroid-induced glaucoma when 20 μl of a 40 mg/ml suspension is administered subconjunctivally. Formulations containing triamcinolone acetonide are used in the treatment of diabetic macular edema.
General DescriptionThe three main metabolitesof triamcinolone acetonide (Azmacort, Nasacort) are 6β-hydroxytriamcinolone acetonide, 21-carboxytriamcinoloneacetonide, and 6β-hydroxy-21-carboxytriamcinolone acetonide.All are much less active than the parent compound.The 6β-hydroxyl group and the 21-carboxy group are bothstructural features that greatly reduce GC action. The increasedwater solubility of these metabolites also facilitatesmore rapid excretion.
General DescriptionTriamcinolone acetonide is approximately 8 times morepotent than prednisone in animal inflammation models.Topically applied triamcinolone acetonide is a potent antiinflammatoryagent, about 10 times more sothan triamcinolone. The plasma half-life is approximately 90minutes, although the plasma half-life and biological halflivesfor GCs do not correlate well. The hexacetonide isslowly converted to the acetonide in vivo and is given onlyby intra-articular injection. Only triamcinolone and the diacetateare given orally. The acetonide and diacetate may begiven by intra-articular or intrasynovial injection. In addition,the acetonide may be given by intrabursal or, sometimes,IM or subcutaneous injection. A single IM dose of thediacetate or acetonide may last up to 3 or 4 weeks. Plasmalevels with IM doses of the acetonide are significantly higherthan with triamcinolone itself. The acetonide is also used totreat asthma and allergic rhinitis.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: A synthetic glucocorticoid that is the 16,17-acetonide of triamcinolone. Used to treat various skin infections.
Related reactions
Compound notes
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