Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C27H36O8 |
Molecular Weight | 488.5699 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)O[C@@]1(CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@]12C)C(=O)COC(=O)CC
InChI
InChIKey=FNPXMHRZILFCKX-KAJVQRHHSA-N
InChI=1S/C27H36O8/c1-5-22(31)34-15-21(30)27(35-24(32)33-6-2)12-10-19-18-8-7-16-13-17(28)9-11-25(16,3)23(18)20(29)14-26(19,27)4/h9,11,13,18-20,23,29H,5-8,10,12,14-15H2,1-4H3/t18-,19-,20-,23+,25-,26-,27-/m0/s1
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12677094
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12677094
Prednicarbate is a relatively new topical corticosteroid drug. It is similar in potency to hydrocortisone. It has a favorable benefit-risk ratio, with an inflammatory action similar to that of a medium potency corticosteroid, but with a low potential to cause skin atrophy. DERMATOP Ointment (prednicarbate ointment) 0.1% is a medium potency corticosteroid indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid responsive dermatoses. Like other topical corticosteroids, prednicarbate has anti-inflammatory, anti-pruritic and vasoconstrictive properties. The mechanism of the anti-inflammatory activity of the topical steroids, in general, is unclear. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. Prednicarbate has a strong correlation between transactivation and glucocorticoid receptor binding.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2034 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12677094 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | DERMATOP Approved UseDERMATOP Ointment 0.1% is a medium potency corticosteroid indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid responsive dermatoses. Launch Date1991 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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158.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8274287/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
PREDNISOLONE 17-ETHYL CARBONATE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
43.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8274287/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
PREDNISOLONE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
402 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8274287/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
PREDNISOLONE 17-ETHYL CARBONATE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
251 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8274287/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
PREDNISOLONE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Investigation of the skin thinning effect of prednicarbate and other corticoids in mouse skin. | 1988 |
|
Contact allergies to topical corticosteroids: 10 cases of contact dermatitis. | 1991 Aug |
|
Small reduction of capsaicin-induced neurogenic inflammation in human forearm skin by the glucocorticoid prednicarbate. | 1993 |
Patents
Sample Use Guides
Apply a thin film of DERMATOP (prednicarbate) Ointment 0.1% to the affected skin areas twice daily
Route of Administration:
Transdermal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8722602
Prednicarbate (10(-5) M-10(-9) M) caused a comparable dose- and time-dependent inhibition of cytokine release from human leukemic mast (HMC-1) cells stimulated for 24 h with phorbol 12-myristate 13-acetate 25 ng/ml and calcium ionophore 2 x 10(-7) M.
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NDF-RT |
N0000175450
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NDF-RT |
N0000175576
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NCI_THESAURUS |
C28394
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WHO-VATC |
QD07AC18
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NCI_THESAURUS |
C521
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WHO-ATC |
D07AC18
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PREDNICARBATE
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6714002
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V901LV1K7D
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7605
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SUB10015MIG
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2243
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DB01130
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277-590-3
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1554909
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760042
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DTXSID9045502
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m9110
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Prednicarbate
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4968
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34369
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73771-04-7
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V901LV1K7D
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C035287
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CHEMBL1200386
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T-122
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100000081404
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C47684
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ACTIVE MOIETY