9-α-Fluor-11-β,21-dihydroxy-16-α,17-α-isopropylidendioxypregna-1,4-dien-3,20-dion

Triamcinolone Acetonide

HCID 6436

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

TRIAMCINOLONE ACETONIDE76-25-5AzmacortNasacortVetalogSolodelfTricinolonKenacort-AVolon AAristogelTramacinZilretta
Weitere Namen anzeigen
TRIAMCINOLONE ACETONIDE ACETATERefrigeratorTriamKENALOGTriamsinolone acetonideTriamcinolone acetonide CRSFluocinolone Acetonide EP Impurity HTrymexERIC-1
OraloneRinetonTriacetTridermNasacort AQTriacortTriatexTriesence

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

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparations
LogP2.53
Human Drugs · 2 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Animal Drugs · 2 Einträge

Active Ingredients (Triamcinolone Acetonide) -> FDA Greenbook

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section · 2 Einträge

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).

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

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

Regulatory InformationTriamcinolone acetonide: Non hazardous
Other Safety InformationIMAP assessments - Pregna-1,4-diene-3,20-dione, 9-fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (11.beta.,16.alpha.)-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (12.7%)

Sicherheitsdaten

wgk
3
tsca
TSCA listed
hs_code
29372290
RTECS-Nr.
TU3920000
risk_code
61
Toxizität
LD50 oral in mouse: 5gm/kg

Chemie und Industrie

Pharmakologische Informationen

FDA Pharmacological Classification · 6 Einträge

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 · 3 Einträge

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

UsesUse (kg; approx.) in Germany (2009): >100
Use Classification · 2 Einträge

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

General Manufacturing InformationPregna-1,4-diene-3,20-dione, 9-fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (11.beta.,16.alpha.)-: INACTIVE
Anwendungen · 1 Eintrag

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.

Anbieter100 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山东雨禾医药科技有限公司15263077727

Ergänzende Hinweise

DefinitionChEBI: A synthetic glucocorticoid that is the 16,17-acetonide of triamcinolone. Used to treat various skin infections.

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