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| Product Name: | Triamcinolone acetonide | | Synonyms: | 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;1,4-PREGNADIEN-9-ALPHA-FLUORO-11-BETA, 16-ALPHA, 17,21-TETROL-3,20-DIONE-16,17-ACETONIDE | | CAS: | 76-25-5 | | MF: | C24H31FO6 | | MW: | 434.5 | | EINECS: | 200-948-7 | | Product Categories: | NASACORT;Steroid and Hormone;Biochemistry;Steroids;Steroids (Others);Intermediates & Fine Chemicals;Pharmaceuticals;76-25-5 | | Mol File: | 76-25-5.mol |  |
| | Triamcinolone acetonide Chemical Properties |
| Melting point | 274-278°C (dec.) | | alpha | D23 +109° (c = 0.75 in chloroform) | | Boiling point | 576.9±50.0 °C(Predicted) | | density | 1.1517 (estimate) | | refractive index | 1.5980 (estimate) | | storage temp. | Refrigerator | | solubility | Practically insoluble in water, sparingly soluble in ethanol (96 per cent). | | form | neat | | pka | 12.87±0.10(Predicted) | | color | White to Off-White | | Water Solubility | Soluble in DMSO or ethanol. Slightly soluble in water. | | Merck | 9596 | | BCS Class | 4 | | Stability: | Combustible. Incompatible with strong oxidizing agents. | | InChIKey | YNDXUCZADRHECN-JNQJZLCISA-N | | NIST Chemistry Reference | Triamcinolone acetonide(76-25-5) | | EPA Substance Registry System | Triamcinolone acetonide (76-25-5) |
| 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.
The above information is edited by the Chemicalbook of Dai Xiongfeng.
| | 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. | | Description | Triamcinolone 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. | | Chemical Properties | White Solid | | Originator | Kenalog,Squibb,US,1958 | | Uses | antiinflammatory | | Uses | A glucocorticoid, antiasthmatic (inhalant); antiallergic (nasal). | | Uses | Triamcinolone acetonide is a topical and systemic corticosteroid belonging to the group-B (triamcinolone acetonide) type of steroids. | | Definition | ChEBI: A synthetic glucocorticoid that is the 16,17-acetonide of triamcinolone. Used to treat various skin infections. | | Indications | Triamcinolone acetonide (Aristocort, Kenalog) is a synthetic fluorinated corticosteroid. | | 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 | 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. | | 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. | | 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. |
| | Triamcinolone acetonide Preparation Products And Raw materials |
| Raw materials | Acetone-->Triamcinolone-->Pregn-4-ene-3,20-dione, 16,21-bis(acetyloxy)-9-fluoro-11,17-dihydroxy-, (11β,16α)- (9CI)-->21-hydroxypregna-4,9(11),16-triene-3,20-dione 21-acetate-->16alpha,17,21-trihydroxypregna-4,9(11)-diene-3,20-dione 21-acetate-->Pregn-4-ene-3,20-dione, 9-bromo-21-(formyloxy)-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (11β,16α)- (9CI)-->11beta,16alpha,17,21-tetrahydroxypregn-4-ene-3,20-dione-->9-Fluoro-16a,17-(isopropylidenedioxy)corticosterone-->11a,16b,17,21-Tetrahydroxy-pregna-1,4-diene-3,20-dione | | Preparation Products | Triamcinolone acetonide 21-acetate |
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