9-α-Fluor-11-β,21-dihydroxy-16-α,17-α-isopropylidendioxypregna-1,4-dien-3,20-dion
Triamcinolone Acetonide
Grundinformationen
- 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- Summenformel
- C24H31FO6
- Durchschnittliche Molmasse
- 434,5 g/mol
- Monoisotopische Masse
- 434,21046693
Überblick
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.
Namen und Bezeichner
- Bevorzugter 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
- Lokaler Name
- 9-α-Fluor-11-β,21-dihydroxy-16-α,17-α-isopropylidendioxypregna-1,4-dien-3,20-dion
- Englischer Name
- Triamcinolone acetonide
- Summenformel
- C24H31FO6
- Molmasse
- 434.5
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
76-25-5- PubChem CID
- 6436
- DTXSID
DTXSID6021371- ChEMBL
CHEMBL1504- ChEBI
CHEBI:71418- UNII
- F446C597KA
- EC Number
- 200-948-7
- Nikkaji
- J55.714E
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,5
- Polarare Oberfläche (TPSA)
- 93,1 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 31
- Formalladung
- 0
- Komplexität
- 925
Experimentelle und physikochemische Eigenschaften
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]
Physikochemische Eigenschaften
- Schmelzpunkt
- 274 · 274-278°C (dec.)
- Siedepunkt
- 576.9 · 576.9±50.0 °C(Predicted)
- Dichte
- 1.1517 · 1.1517 (estimate)
- Brechungsindex
- 1.598 · 1.5980 (estimate)
- storage temp.
- Refrigerator
- Löslichkeit
- Practically insoluble in water, sparingly soluble in ethanol (96 per cent).
- pka
- 12.87 · 12.87±0.10(Predicted)
- Aggregatzustand
- Solid
- Farbe
- White to Off-White
- Wasserlöslichkeit
- Soluble in DMSO or ethanol. Slightly soluble in water.
- Merck
- 9596 · 9596
- BCS Class
- 4 · 4
- Stabilität
- Combustible. Incompatible with strong oxidizing agents.
- InChIKey
- YNDXUCZADRHECN-JNQJZLCISA-N
- NIST chemische Informationen
- Triamcinolone acetonide(76-25-5)
- EPA chemische Informationen
- Triamcinolone acetonide (76-25-5)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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.
Gefahrenhinweise
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29372290
- RTECS-Nr.
- TU3920000
- risk_code
- 61
- Toxizität
- LD50 oral in mouse: 5gm/kg
- hazard_code
- T
- safety_code
- 53-45
Chemie und Industrie
Pharmakologische Informationen
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.
Verwendung und Herstellung
Use Classification
Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Anwendungen
BeschreibungTriamcinolone 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.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter100 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A synthetic glucocorticoid that is the 16,17-acetonide of triamcinolone. Used to treat various skin infections.
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