| Candidate ID: | R1537 |
| Source ID: | DB14669 |
| Source Type: | approved; vet_approved |
| Compound Type: |
small molecule
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| Compound Name: |
Betamethasone phosphate
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| Synonyms: |
Betamethasone 21-(dihydrogen phosphate); Betamethasone 21-phosphate; Betamethasone dihydrogen phosphate
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| Molecular Formula: |
C22H30FO8P
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| SMILES: |
[H][C@@]12C[C@H](C)[C@](O)(C(=O)COP(O)(O)=O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
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| Structure: |
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| DrugBank Description: |
Betamethasone phosphate is a prodrug that is rapidly hydrolyzed, providing rapidly accessible to agonize glucocorticoid receptors. Betamethasone provides greater anti-inflammatory activity than with less sodium and water retention.
Betamethasone sodium phosphate was granted FDA approval on 3 March 1965.
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| CAS Number: |
360-63-4
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| Molecular Weight: |
472.446
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| DrugBank Indication: |
Betamethasone phosphate is indicated intramuscularly to treat allergic states, dermatologic diseases, endocrine disorders, gastrointestinal diseases, hematologic disorders, neoplastic diseases, nervous system conditions, ophthalmic diseases, renal diseases, respiratory diseases, rheumatic disorders, trichinosis with neurologic or myocardial involvement, and tuberculous meningitis with subarachnoid block or impending block. It is also used intra-articularly in the treatment of acute gouty arthritis, acute and subacute bursitis, acute nonspecific tenosynovitis, epicondylitis, rheumatoid arthritis, and synovitis of osteoarthritis. Intralesional betamethasone phospahte is indicated in the treatment of alopecia areata, discoid lupus erythematosus, keloids, lichen planus, lichen simplex chronicus, psoriatic plaques, necrobiosis lipoidica diabeticorum, and localized hypertrophic, infiltrated, inflammatory lesions of granuloma annulare.
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| DrugBank Pharmacology: |
Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals. Betamethasone phosphate has a short duration of action as it is rapidly hydrolyzed to betamethasone. Corticosteroids have a wide therapeutic window as patients may require doses that are multiples of what the body naturally produces. Patients taking corticosteroids should be counselled regarding the risk of hypothalamic-pituitary-adrenal axis suppression and increased susceptibility to infections.
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| DrugBank MoA: |
Betamethasone phosphate is a soluble ester prodrug of betamethasone. Betamethasone is rapidly de-esterified, allowing betamethasone to act as an agonist of the glucocorticoid receptor. The short term effects of corticosteroids are decreased vasodilation and permeability of capillaries, as well as decreased leukocyte migration to sites of inflammation. Corticosteroids binding to the glucocorticoid receptor mediates changes in gene expression that lead to multiple downstream effects over hours to days.
Glucocorticoids inhibit neutrophil apoptosis and demargination; they inhibit phospholipase A2, which decreases the formation of arachidonic acid derivatives; they inhibit NF-Kappa B and other inflammatory transcription factors; they promote anti-inflammatory genes like interleukin-10.
Lower doses of corticosteroids provide an anti-inflammatory effect, while higher doses are immunosuppressive. High doses of glucocorticoids for an extended period bind to the mineralocorticoid receptor, raising sodium levels and decreasing potassium levels.
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| Targets: |
Glucocorticoid receptor agonist; Annexin A1 agonist
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| Inclusion Criteria: |
Therapeutic strategy associated
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