Basic information
- CAS
302-25-0- Standard SMILES
C[C@]12C=CC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)COP(=O)(O)O- InChIKey
JDOZJEUDSLGTLU-VWUMJDOOSA-N- Molecular formula
- C21H29O8P
- Average molar mass
- 440.4 g/mol
- Monoisotopic mass
- 440.16000488
Overview
Prednisolone sodium phosphate can cause developmental toxicity according to state or federal government labeling requirements.
Names & identifiers
- Preferred name
- Prednisolone Phosphate
- IUPAC
- [2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] dihydrogen phosphate
- English name
- 11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-(dihydrogen phosphate)
- Molecular formula
- C21H29O8P
- Molecular weight
- 440.42
Names & synonyms
Prednisolone phosphate302-25-0PREDNISOLONE 21-PHOSPHATEprednisolone 21-monophosphatePrednisolone 21-(dihydrogen phosphate)752SY38R6CDTXSID7047481CHEBI:145705{2-[(1R,3aS,3bS,9aR,9bS,10S,11aS)-1,10-dihydroxy-9a,11a-dimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]-2-oxoethoxy}phosphonic acid(2-((1R,3aS,3bS,9aR,9bS,10S,11aS)-1,10-dihydroxy-9a,11a-dimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta(a)phenanthren-1-yl)-2-oxoethoxy)phosphonic acidRefChem:868418DTXCID5027481
Show more names
PSLP11β,17-Dihydroxy-21-(phosphonooxy)pregna-1,4-diene-3,20-dione11β,17,21-Trihydroxypregna-1,4-diene-3,20-dione 21-phosphoric acidPregna-1,4-diene-3,20-dione, 11,17-dihydroxy-21-(phosphonooxy)-, (11β)-11β,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-(dihydrogen phosphate)[2-(11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl] dihydrogen phosphate
Properties
Computed structural properties
- XLogP
- 0
- Topological polar surface area
- 141 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 4
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 889
Experimental & physicochemical properties
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- FDA UNII
- 752 SY38R6C · 752SY38R6C
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 360 · H360
- REACH Registrations
- Active
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H360 (33.3%): May damage fertility or the unborn child [Danger Reproductive toxicity]
P203, P260, P280, P318, P319, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationREACH registered substance: 11β,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-(dihydrogen phosphate) (EC: 206-120-1)
Hazard Classes and CategoriesRepr. 1B (33.3%)
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- Hazard statements
- H360
- REACH Registrations
- Active
Chemistry & industry
Pharmacology
Protein BindingPrednisolone is 70-90% protein bound in plasma. Prednisolone typically binds to albumin and corticosteroid binding globulin.
Pharmacodynamics
Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals. Prednisolone has a short duration of action as the half life is 2-4 hours. Corticosteroids have a wide therapeutic window as patients make 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.
Mechanism of Action
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.
Biological Half-LifeThe half life of prednisolone is 2-4 hours.
Metabolism/MetabolitesPrednisolone phosphate undergoes ester hydrolysis to [prednisolone]. After this step, the drug undergoes the normal metabolism of prednisolone.
MeSH Pharmacological Classification
A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…