Paramethasone

Các tên gọi khác (1) :

Dillar

Thuốc Gốc

Small Molecule

CAS: 53-33-8

ATC: H02AB05

CTHH: C₂₂H₂₉FO₅

PTK: 392.4611

A glucocorticoid with the general properties of corticosteroids. It has been used by mouth in the treatment of all conditions in which corticosteroid therapy is indicated except adrenal-deficiency states for which its lack of sodium-retaining properties makes it less suitable than hydrocortisone with supplementary fludrocortisone. (From Martindale, The Extra Pharmacopoeia, 30th ed, p737)

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₂₂H₂₉FO₅

Phân tử khối

392.4611

Monoisotopic mass

392.199902243

InChI

InChI=1S/C22H29FO5/c1-11-6-14-13-8-16(23)15-7-12(25)4-5-20(15,2)19(13)17(26)9-21(14,3)22(11,28)18(27)10-24/h4-5,7,11,13-14,16-17,19,24,26,28H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19-,20+,21+,22+/m1/s1

InChI Key

InChIKey=MKPDWECBUAZOHP-AFYJWTTESA-N

IUPAC Name

(1S,2R,8S,10S,11S,13R,14R,15S,17S)-8-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one

Traditional IUPAC Name

paramethasone

SMILES

[H][C@@]12C[C@@H](C)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])C[C@]([H])(F)C2=CC(=O)C=C[C@]12C

Độ hòa tan

1.45e-01 g/l

logP

1.3

logS

-3.4

pKa (strongest acidic)

12.45

pKa (Strongest Basic)

-2.9

PSA

94.83 Å²

Refractivity

102.79 m³·mol^-1

Polarizability

40.84 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

Rule of Five

true

Ghose Filter

true

Dược Lực Học : Paramethasone is a glucocorticoid with the general properties of corticosteroids. Glucocorticoids are a class of steroid hormones characterised by an ability to bind with the cortisol receptor and trigger a variety of important cardiovascular, metabolic, immunologic and homeostatic effects. Glucocorticoids are distinguished from mineralocorticoids and sex steroids by having different receptors, target cells, and effects. Technically, the term corticosteroid refers to both glucocorticoids and mineralocorticoids, but is often used as a synonym for glucocorticoid. Glucocorticoids suppress cell-mediated immunity. They act by inhibiting genes that code for the cytokines IL-1, IL-2, IL-3, IL-4, IL-5, IL-6, IL-8 and TNF-alpha, the most important of which is the IL-2. Reduced cytokine production limits T cell proliferation. Glucocorticoids also suppress humoral immunity, causing B cells to express lower amounts of IL-2 and IL-2 receptors. This diminishes both B cell clonal expansion and antibody synthesis. The diminished amounts of IL-2 also leads to fewer T lymphocyte cells being activated.

Cơ Chế Tác Dụng : A glucocorticoid with the general properties of corticosteroids. It has been used by mouth in the treatment of all conditions in which corticosteroid therapy is indicated except adrenal-deficiency states for which its lack of sodium-retaining properties makes it less suitable than hydrocortisone with supplementary fludrocortisone. (From Martindale, The Extra Pharmacopoeia, 30th ed, p737) Glucocorticoids such as paramethasone can inhibit leukocyte infiltration at the site of inflammation, interfere with mediators of inflammatory response, and suppress humoral immune responses. The antiinflammatory actions of glucocorticoids are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes. Paramethasone reduces inflammatory reaction by limiting the capillary dilatation and permeability of the vascular structures. These compounds restrict the accumulation of polymorphonuclear leukocytes and macrophages and reduce the release of vasoactive kinins. Recent research suggests that corticosteroids may inhibit the release of arachidonic acid from phospholipids, thereby reducing the formation of prostaglandins. Prednisolone is a glucocorticoid receptor agonist. On binding, the corticoreceptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing an increase or decrease in expression of specific target genes, including suppression of IL2 (interleukin 2) expression.

Dược Động Học :

▧ Protein binding :
80%
▧ Metabolism :
Hepatic.
▧ Route of Elimination :
Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.

Độc Tính : Side effects include inhibition of bone formation, suppression of calcium absorption delayed wound healing, immune suppression, and hyperglycemia.

Chỉ Định : For the treatment of all conditions in which corticosteroid therapy is indicated except adrenal-deficiency states for which its lack of sodium-retaining properties makes it less suitable than hydrocortisone with supplementary fludrocortisone.

Tương Tác Thuốc :

Acetylsalicylic acid The corticosteroid, paramethasone, may decrease the effect of the salicylate, acetylsalicylic acid.
Fosphenytoin The enzyme inducer, fosphenytoin, may decrease the effect of the corticosteroid, paramethasone.
Midodrine Increased arterial pressure
Phenobarbital The barbiturate, phenobarbital, may decrease the effect of the corticosteroid, paramethasone.
Phenytoin The enzyme inducer, phenytoin, may decrease the effect of the corticosteroid, paramethasone.
Primidone The barbiturate, primidone, may decrease the effect of the corticosteroid, paramethasone.
Pyridostigmine The corticosteroid, paramethasone, may decrease the effect of the anticholinesterase, pyridostigmine.
Rifampicin The enzyme inducer, rifampin, may decrease the effect of the corticosteroid, paramethasone.

Liều Lượng & Cách Dùng : Tablet - Oral

Dữ Kiện Thương Mại

Nhà Sản Xuất

Công ty :

Sản phẩm biệt dược : Haldrone

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB01384

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5875

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46504651

KEGG Compound

http://www.genome.jp/dbget-bin/www_bget?cpd:C07413

ChemSpider

http://www.chemspider.com/Chemical-Structure.5664.html

PharmGKB

http://www.pharmgkb.org/drug/PA164777035

Wikipedia

http://en.wikipedia.org/wiki/Paramethasone

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