Triamcinolon

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

https://huagongshe.com/de/chemical/31307

Identifikatoren & physikalische Daten

CAS No.	124-94-7
Summenformel	C21H27FO6
Durchschnittliche Molmasse	394,4 g/mol
Monoisotopische Masse	394,1791668 g/mol
SMILES	C[C@]12C=CC(=O)C=C1CC[C@H]1[C@@H]3C[C@@H](O)[C@](O)(C(=O)CO)[C@@]3(C)C[C@H](O)[C@@]12F
InChIKey	GFNANZIMVAIWHM-OBYCQNJPSA-N
PubChem CID	31307
ChEMBL	CHEMBL1451
ChEBI	CHEBI:9667
EC No.	204-718-7
DTXSID	DTXSID1040742
Lokaler Name	Triamcinolon

Chemische & physikalische Eigenschaften

XLogP	1,2
Polarare Oberfläche (TPSA)	115
H-Brücken-Donoren	4
H-Brücken-Akzeptoren	7
Frei drehbare Bindungen	2
Schwere Atome	28
Formalladung	0
Komplexität	807
Arzneimittel	Pharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparationsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Cortico-adrenal hormones
LogP (Verteilungskoeffizient)	log Kow = 1.160.2
Color/Form	CrystalsFINE, WHITE OR PRACTICALLY WHITE, CRYSTALLINE POWDERPOLYMORPHIC
Löslichkeit	FINE, WHITE OR SLIGHTLY OFF-WHITE CRYSTALS. SLIGHT, BITTER TASTESLIGHT ODORPRACTICALLY INSOL IN WATER. SOL IN CHLOROFORMSLIGHTLY SOL IN ETHERSPARINGLY SOL IN ALC & METHANOL. HYDRATED FORM MP 145-158 °CANHYDROUS FORM MP 170-185 °C /DIACETATE/WHITE TO CREAM-COLORED CRYSTALLINE POWDER. ODORLESS & TASTELESS TO SLIGHTLY BITTER TASTINGDECOMP @ ABOUT 295 °C. PRACTICALLY INSOL IN WATER1 G SOL IN 167 ML METHANOL, LESS THAN 20 ML CHLOROFORM. /HEXACETONIDE/WHITE TO CREAM-COLORED CRYSTALLINE POWDER. SLIGHT ODORPRACTICALLY INSOL IN WATER. VERY SOL IN DEHYDRATED ALC, CHLOROFORM, METHANOLSLIGHTLY SOL IN ALCSPARINGLY SOL IN ACETONE & ETHYL ACETATE /ACETONIDE/1 G SOL IN 5000 ML WATER, 70 ML PROPYLENE GLYCOL, LESS THAN 20 ML DIMETHYL SULFOXIDESLIGHTLY SOL IN ALC & CHLOROFORMSlightly sol in usual organic solventssol in dimethylformamideIn water, 80 mg/L at 25 °CDMF: soluble20 mg/mL79.99mg/L(25 ºC)
Human Drugs	Breast FeedingLactationMilk, HumanCorticosteroids, TopicalGlucocorticoidsAnti-Inflammatory AgentsCorticosteroids, SystemicFDA approved drugs -> Active ingredient
Animal Drugs	Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Endocrine Disruptors	Potential endocrine disrupting compound
Schmelzpunkt	269-271 °C274 - 278 °C262-263 °C(lit.)
Dampfdruck	7.20X10-15 mm Hg at 25 °C
Optical Rotation	Crystals, mp 268-270 °C. Specific optical rotation at 23 °C: +92 deg (c= 0.59 chloroform). /21-Acetate/SPECIFIC OPTICAL ROTATION: +75 DEG @ 25 °C/D (ACETONE)MAX ABSORPTION: 238 NM (E= 15,800)
Physical Description	Solid
Stability/Shelf Life	Commercially available oral and parenteral preparations of triamcinolone should be stored at a temperature less than 40 °C, preferably between 15-30 °Cfreezing of the sterile suspensions should be avoided. Exposure of sterile suspensions of the drug to freezing temperatures can result in irreversible clumping or agglomeration (granular appearance)such suspensions should not be used. Triamcinolone tablets should be stored in well-closed containers. Triamcinolone acetonide sterile suspension should be protected from light. Triamcinolone acetonide oral inhaler should be stored at controlled room temperature (20-25 °C). Because the contents of the oral inhaler are under pressure, the aerosol container should not be punctured, used or stored near heat or an open flame, exposed to temperatures greater than 49 °C, or placed into a fire or incinerator for disposal.
Siedepunkt	587.5±50.0 °C(Predicted)
Dichte	1.1703 (estimate)
Lagerbedingungen	2-8°C
pKa (Säurekonstante)	11.57±0.70(Predicted)
Aggregatzustand	Solid
Farbe	Crystals
Merck	9595
InChIKey	GFNANZIMVAIWHM-OBYCQNJPSA-N
CAS Datenbank	124-94-7(CAS DataBase Reference)
NIST chemische Informationen	Triamcinolone(124-94-7)
EPA chemische Informationen	Triamcinolone (124-94-7)

Sicherheit & Vorschriften

GHS-Einstufung	WarningH351 (63.3%): Suspected of causing cancer [Warning Carcinogenicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 60 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Weitere Sicherheitsinformationen	IMAP assessments - Pregna-1,4-diene-3,20-dione, 9-fluoro-11,16,17,21-tetrahydroxy-, (11.beta.,16.alpha.)-: Environment tier I assessment
FDA-Anforderungen	The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl triamcinolone hexacetonide approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Triamcinolone hexacetonide/The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl triamcinolone acetonide approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Triamcinolone acetonide/The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies discontinued drug products, incl triamcinolone.The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Triamcinolone acetonide is included on this list. /Triamcinolone acetonide/For more FDA Requirements (Complete) data for TRIAMCINOLONE (9 total), please visit the HSDB record page.
Hazard Classes and Categories	Carc. 2 (63.3%)
Entsorgungsverfahren	SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Wechselwirkungen	Intranasal triamcinolone acetonide should be used with caution in patients receiving other inhaled or systemic corticosteroids (e.g., prednisone in an alternate-day regimen) for any disease, since concomitant use of the drugs could increase the likelihood of hypothalamic-pituitary-adrenal (HPA)-axis suppression compared with therapeutic dosages of either drug alone. /Triamcinolone acetonide/

Anwendungen & Verwendung

Beschreibung

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.

Verwenden

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