Triancinolone Acetanide - API Active Pharmaceutical Ingredient

Triancinolone Acetanide

Name	Triancinolone Acetanide
Synonyms	KENALOG; ARISTODERM; 9ALPHA-FLUORO-11BETA,21-DIHYDROXY-16ALPHA,17-ISOPROPYLIDENEDIOXY-1,4-PREGNADIENE-3,20-DIONE; 9ALPHA-FLUORO-16ALPHA-HYDROXYPREDNISOLONE 16ALPHA,17ALPHA-ACETONIDE; 9ALPHA-FLUORO-11BETA,16ALPHA,17ALPHA,21-TETRAHYDROXY-1,4-PREGNADIENE-3,20-DIONE 16,17-ACETONIDE; 9a-fluoro-11b,16a,17a,21-tetrahydroxy-1,4-pregnadiene-3,20-dione 16,17-acetonide; 9a-fluoro-16a-hydroxyprednisolone 16a,17a-acetonide; ALPHA-FLUORO-11BETA,16ALPHA,17,21-TETRA-HYDROXYPREGNA-1,4-DIENE-3,20-DIONE TAC-3 Triam ERIC1 ERIC-1 TAC-40 Trymex Vetalog Volon A Triacet Flutone KENALOG RINETON Coupe-A Azmacort Adcortyl Kenalone Nasacort Tramacin Tramasin Solodelf Triaceton Ftorocort Extracort Omcilon A Respicort Acetospan Aristogel Volonimat TRICINOLON Polcortoon Delphicort Adcortyl A Aristocort ARISTODERM Kenacort-A Volon A 40 Nasacort AQ Polcortolon Triam-Injekt Aristocort A Triamonide 40 Ledercort cream iene,3,20-dione Queyanshusong A Panolog ointment component of Mytrex aristocortacetonide Aristcort acetonide component of Panolog Aristocort acetonide TriaMcinolon Acetonide TriaMcinolone acetonid triamsinoloneacetonide TRIAMCINOLONE ACETONIDE Triamcinoione acetonide component of Mycolog ii Triamsinolone acetonide Triamcincolone acetonide Triamcinolone acetonaide TriaMcinolone Acetonide USP triamcinolone16,17-acetonide component of Myco-triacet ii (11beta,16alpha)-e)bis(oxy)] Triamcinolone 16,17-acetonide Triamcinolone acetonide,>=99% TriaMcinolon-6-d1 Acetonide-d6 TRIAMCINOLONE ACETONIDE ACETATE Triamcinolone Acetonide (500 mg) TRIAMCINOLONEACETONIDE,POWDER,USP Triamcinolone acetonide Solution, 100ppm Triamcinolone acetonide for system suitability 9alpha-Fluoro-16-hydroxyprednisolone acetonide 9-alpha-fluoro-16-hydroxyprednisoloneacetonide Anti-TACC3, C-Terminal antibody produced in rabbit 9α-Fluoro-16α-hydroxyprednisolone 16α,17α-acetonide 9a-fluoro-16a-hydroxyprednisolone 16a,17a-acetonide 16alpha-Hydroxy-9alpha-fluoroprednisolone acetonide Transforming acidic coiled-coil-containing protein 3 9a-Fluoro-16a,17a-isopropylidenedihydroxyprednisolone 17-alpha-isopropylidenedioxypregna-1,4-diene-3,20-dione 9alpha-Fluoro-16alpha-17alpha-isopropyledenedioxyprednisolone 9-alpha-fluoro-16-alpha-17-alpha-isopropyledenedioxyprednisolone 9ALPHA-FLUORO-16ALPHA-HYDROXYPREDNISOLONE 16ALPHA,17ALPHA-ACETONIDE 9alpha-Fluoro-16alpha-17alpha-isopropylidenedioxy-delta -1-hydrocortisone ALPHA-FLUORO-11BETA,16ALPHA,17,21-TETRA-HYDROXYPREGNA-1,4-DIENE-3,20-DIONE 9-alpha-fluoro-16-alpha-17-alpha-isopropylidenedioxy-delta-1-hydrocortisone 9-alpha-fluoro-11-beta,21-dihydroxy-16-alpha-isopropylidenedioxy-1,4-pregnad pregna-1,4-diene-3,20-dione,9-fluoro-11,21-dihydroxy-16,17-[(1-methylethyliden 11,16a-dihydroxy-16,17-isopropylidenedioxy-9-fluoro pregna-1,4-dien-3,20-dione 9α-fluoro-11β,16α,17α,21-tetrahydroxy-1,4-pregnadiene-3,20-dione 16,17-acetonide 9a-fluoro-11b,16a,17a,21-tetrahydroxy-1,4-pregnadiene-3,20-dione 16,17-acetonide 9-Fluoro-11β,21-dihydroxy-16α,17-[isopropylidenebis(oxy)]pregna-1,4-diene-3,20-dione 9-a-fluoro-11-b,21-dihydroxy-16-a,17-a-isopropylidenedioxypregna-1,4-diene-3,20-dione 1,4-PREGNADIEN-9-ALPHA-FLUORO-11-BETA, 16-ALPHA, 17,21-TETROL-3,20-DIONE-16,17-ACETONIDE 1,4-PREGNADIEN-9ALPHA-FLUORO-11BETA,16ALPHA,17ALPHA,21-TETROL 3,20-DIONE 16,17-ACETONIDE 9ALPHA-FLUORO-11BETA,21-DIHYDROXY-16ALPHA,17-ISOPROPYLIDENEDIOXY-1,4-PREGNADIENE-3,20-DIONE Pregna-1,4-diene-3,20-dione, 9-fluoro-11beta,21-dihydroxy-16alpha,17-(isopropylidenedioxy)- 9ALPHA-FLUORO-11BETA,16ALPHA,17ALPHA,21-TETRAHYDROXY-1,4-PREGNADIENE-3,20-DIONE 16,17-ACETONIDE (11,16a)-9-Fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione (11β,16α)-9-Fluoro-11,21-dihydroxy-16,17-[(1-Methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione 9-alpha-fluoro-11-beta,21-dihydroxy-16-alpha,17-alpha-isopropylidenedioxypregna-1,4-diene-3,20-dione 9-Fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone (11beta,16alpha)-9-Fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione Pregna-1,4-diene-3,20-dione, 9-fluoro-11beta,16alpha,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone Pregna-1,4-diene-3,20-dione, 9-fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (11beta,16alpha)- Pregna-1,4-diene-3,20-dione, 9-fluoro-11,21-dihydroxy-16,17-(1-methylethylidene)bis(oxy)-, (11.beta.,16.alpha.)- Adcortyl, Azmacort, Delphicort, Extracort, Ftorocort, Kenacort-A, Tramacin, Triam, Tricinolon, Vetalog, Volon A, Volonimat, 9α-Fluoro-11β,16α,17α,21-tetrahydroxy-1,4-pregnadiene-3,20-dione 16,17-acetonide 9α-Fluoro-16α-hydroxyprednisolone 16α,17α-acetonide 9α-Fluoro-16α-hydroxyprednisolone 16α,17α-acetonide, 9α-Fluoro-11β,16α,17α,21-tetrahydroxy-1,4-pregnadiene-3,20-dione 16,17-acetonide 4b-Fluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one
CAS NO	76-25-5
EINECS	200-948-7
Molecular Weight	434.5
Molecular Formula	C24H31FO6
Product Categories	NASACORT; Steroid and Hormone; Biochemistry; Steroids; Steroids (Others); Intermediates & Fine Chemicals; Pharmaceuticals
Mol File	76-25-5.mol

Triamcinolone acetonide Chemical Properties
Melting point	274-278°C (dec.)
density	1.1517 (estimate)
Boiling point	576.9±50.0 °C(Predicted)
refractive index	1.5980 (estimate)
storage temp	Refrigerator
solubility	Practically insoluble in water, sparingly soluble in ethanol (96 per cent).
form	neat
alpha	D23 +109° (c = 0.75 in chloroform)
Stability	Combustible. Incompatible with strong oxidizing agents
Water Solubility	Soluble in DMSO or ethanol. Slightly soluble in water.
Merck	9596
NIST Chemistry Reference	Triamcinolone acetonide (76-25-5)
InChIKey	YNDXUCZADRHECN-JNQJZLCISA-N
EPA Substance Registry System	Triamcinolone acetonide (76-25-5)

Safety Information
Hazard Codes	T
Risk Statements	61
Safety Statements	53-45
WGK Germany	3
RTECS	TU3920000
TSCA	Yes
HS Code	29372290
Toxicity	LD50 oral in mouse: 5gm/kg

Triamcinolone acetonide Usage And Synthesis
Appearance and properties	Triamcinolone acetonide, its acetate form appears to be white or white-like crystalline powder. The drug is odorless, with bitter taste. It is hardly soluble in water, slightly soluble in ethanol, soluble in chloroform, and slightly soluble in acetone.
Glucocorticoid drugs	Triamcinolone acetonide is a kind of long-term glucocorticoid drugs which is now widely used in clinical Dermatology of China. It belongs to adrenocorticotropic hormone drugs. It is the derivative of Triamcinolone, and with the same function as Triamcinolone. Triamcinolone acetonide functions in anti-inflammatory, anti-allergic, anti-itching and shrinking capillaries. What’s more, besides its weak water-sodium retention, the effect of Triamcinolone acetonide for anti-inflammatory, anti-allergic is much stronger and more durable than hydrocortisone (10 to 30 folds), and prednisone. It can also treat bronchial asthma by aerosol inhalation with very strong and durable effect. Triamcinolone acetonide has better efficacy on local treatment compared with triamcinolone. It is Oral absorbed easily. Taking orally 5mg of the drug yields a bioavailability of about 23%. Its plasma concentration reaches peak (105 ng/mL) within one hour with the half-life is being 2 hours; It has a slow intramuscular absorption rate which takes effect within hours, and gives maximal effect within 1 to 2 days. The effect can be maintained for 2~3 weeks; the absorption rate of intradermal and intra-articular injection of the drug is low, but has a long-lasting effect; generally the efficacy can be maintained for more than 1-2 week per injection. This product has a low binding rate with plasma albumin protein, and is metabolized into non-active product in the liver, kidneys and tissues which is then further excreted by the kidneys. It also has a long-lasting effect upon local injection. Moreover, topical ointments can also produce a good effect. Clinically triamcinolone acetonide is used for treatment of various skin diseases such as atopic dermatitis, contact dermatitis, seborrheic dermatitis, neurodermatitis, eczema, psoriasis, psoriasis, lichen planus and skin pruritus, as well as bronchial asthma, rheumatoid arthritis, acute sprains, chronic ache in back and legs, frozen shoulder, tenosynovitis, ophthalmic inflammation, oral mucosal congestion, erosion, ulcers, granulomatous cheilitis, and oral mucosa chronic infectious diseases, Furthermore, it can also be used for local injection treatment in keloid, cystic acne, discoid lupus erythematosus, alopecia areata and other small area of damages. Triamcinolone acetonide nasal spray can be used for the prevention and treatment of perennial, seasonal allergic rhinitis, and vasomotor rhinitis. Intra-articular injection of this drug can eliminate inflammation and pain, swelling or can alleviate, pain, stiffness and swelling feeling.
Uses	It is adrenal cortex hormones drugs used for treating diseases such as neurodermatitis, eczema, psoriasis, joint pain, and asthma.
Category	Toxic Substances.
Toxicity grading	Highly toxic.
Acute toxicity	Subcutaneous-rat LD50: 13.1 mg/kg; intraperitoneal-Mouse LD50: 105 mg/kg.
Flammability hazard characteristics	Combustible; combustion produces toxic fumes of fluoride.
Storage Characteristics Treasury	ventilation, low-temperature and dry; store separately from food raw materials.
Extinguishing agent	Dry powder, foam, sand, carbon dioxide, water spray.
Chemical Properties	White Solid
Originator	Kenalog,Squibb,US,1958
Uses	A glucocorticoid, antiasthmatic (inhalant); antiallergic (nasal).
Uses	antiinflammatory
Uses	Triamcinolone acetonide is a topical and systemic corticosteroid belonging to the group-B (triamcinolone acetonide) type of steroids.
Indications	Triamcinolone acetonide (Aristocort, Kenalog) is a synthetic fluorinated corticosteroid.
Definition	ChEBI: A synthetic glucocorticoid that is the 16,17-acetonide of triamcinolone. Used to treat various skin infections.
Manufacturing Process	A solution of 250 mg of 9α-fluoro-11β,16α,17α,21-tetrahydroxy-1,4- pregnadiene-3,20-dione in 70 ml of hot acetone and 7 drops of concentrated hydrochloric acid is boiled for 3 minutes. After standing at room temperature for 17 hours, the reaction mixture is poured into dilute sodium bicarbonate and extracted with ethyl acetate. The extract is washed with saturated saline solution, dried and evaporated to a colorless glass. The residue is crystallized from acetone-petroleum ether to afford 166 mg of the acetonide, MP 270° to 274°C, decomposition, (with previous softening and browning). Three recrystallizations from acetone-petroleum ether give 113 mg of 9α-fluoro- 11β,21-dihydroxy-16α,17α-isopropylidenedioxy-1,4-pregnadiene-3,20-dione, MP 274° to 279°C, decomposition, (with previous softening and browning).
Therapeutic Function	Glucocorticoid
General Description	The 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 Description	Triamcinolone 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.
Clinical Use	Triamcinolone acetonide frequently is used by inhalation for the treatment of lung diseases (e.g., asthma).
Safety Profile	Poison by subcutaneous and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and toxic fumes of F-.
Veterinary Drugs and Treatments	The systemic veterinary labeled product (Vetalog? Injection) is labeled as “indicated for the treatment of inflammation and related disorders in dogs, cats, and horses. It is also indicated for use in dogs and cats for the management and treatment of acute arthritis, allergic and dermatologic disorders.” Glucocorticoids have been used in an attempt to treat practically every malady that afflicts man or animal, but there are three broad uses and dosage ranges for use of these agents. 1) Replacement of glucocorticoid activity in patients with adrenal insufficiency, 2) as an antiinflammatory agent, and 3) as an immunosuppressive. Among some of the uses for glucocorticoids include treatment of: endocrine conditions (e.g., adrenal insufficiency), rheumatic diseases (e.g., rheumatoid arthritis), collagen diseases (e.g., systemic lupus), allergic states, respiratory diseases (e.g., asthma), dermatologic diseases (e.g., pemphigus, allergic dermatoses), hematologic disorders (e.g., thrombocytopenias, autoimmune hemolytic anemias), neoplasias, nervous system disorders (increased CSF pressure), GI diseases (e.g., ulcerative colitis exacerbations), and renal diseases (e.g., nephrotic syndrome). Some glucocorticoids are used topically in the eye and skin for various conditions or are injected intra-articularly or intra-lesionally. The above listing is certainly not complete.
Metabolism	Triamcinolone acetonide frequently is used by inhalation for the treatment of lung diseases (e.g., asthma). After inhalation, triamcinolone acetonide can become systemically available when the inhaled formulation is swallowed and absorbed unchanged from the GI tract, causing undesirable systemic effects. Triamcinolone acetonide that is swallowed is metabolized to 6β-hydroxytriamcinolone acetonide, 21-carboxytriamcinolone acetonide, and 21-carboxy-6β-hydroxytriamcinolone acetonide, all of which are more hydrophilic than their parent drug. Only approximately 1% of the dose was recovered from the urine as triamcinolone acetonide. Triamcinolone is not a major metabolite of triamcinolone acetonide in humans, suggesting that acetonide is resistant to hydrolytic cleavage. Triamcinolone acetonide is approximately eight times more potent than prednisolone.