New Release: Alpha testing version has been released.

Prednicarbate

D07A - Corticosteroids, plain ATC D07AC18 Small molecule approved 1991 Topical Prodrug Natural product

Active form: Prednisolone.

JFDA label: Peitel Cream 0.25%

Mechanism of Action

Agonist of Glucocorticoid receptor — Glucocorticoid receptor agonist

TargetActionGene / class
Glucocorticoid receptor efficacy AGONIST NR3C1

Indications

Approved

  • Dermatoses

Contraindications

Source: Lexicomp

  • Hypersensitivity to prednicarbate or any component of the formulation Documentation of allergenic cross-reactivity for corticosteroids is limited. However, because of similarities in chemical structure and/or pharmacologic actions, the possibility of cross-sensitivity cannot be ruled out with certainty Absolute

Adverse Reactions

Very Common >10%Common 1–10%Uncommon 0.1–1% Rare 0.01–0.1%Very Rare <0.01%Not Known

Other (3)

Common Dermatologic: Skin atrophy · taut and shiny skin · telangiectasia

Dosing

Source: Lexicomp

Steroid-responsive dermatoses: Topical: Cream, ointment: Apply a thin film to affected area twice daily. Therapy should be discontinued when control is achieved; if no improvement is seen within 2 weeks, reassessment of diagnosis may be necessary.
(For additional information see "Prednicarbate: Pediatric drug information") Steroid-responsive dermatoses: Topical: Cream: Children ≥1 year and Adolescents: Refer to adult dosing. Ointment: Children ≥10 year and Adolescents: Refer to adult dosing.
Refer to adult dosing.

Warnings & Precautions

Source: Lexicomp

Adrenal suppression

May cause hypercortisolism or suppression of hypothalamic-pituitary-adrenal (HPA) axis, particularly in younger children or in patients receiving high doses for prolonged periods. HPA axis suppression may lead to adrenal crisis.

Contact dermatitis

Allergic contact dermatitis can occur and it is usually diagnosed by failure to heal rather than clinical exacerbation.

Immunosuppression

Prolonged use of corticosteroids may result in fungal or bacterial superinfection; discontinue if dermatological infection persists despite appropriate antimicrobial therapy.

Kaposi sarcoma

Prolonged treatment with corticosteroids has been associated with the development of Kaposi sarcoma (case reports); if noted, discontinuation of therapy should be considered (Goedert, 2002).

Systemic effects

Topical corticosteroids may be absorbed percutaneously. Absorption of topical corticosteroids may cause manifestations of Cushing syndrome, hyperglycemia, or glycosuria. Absorption is increased by the use of occlusive dressings, application to denuded skin, or application to large surface areas. Disease-related concerns:

Diaper dermatitis

Do not use for diaper dermatitis. Special populations:

Pediatric

Children may absorb proportionally larger amounts after topical application and may be more prone to systemic effects. HPA axis suppression, intracranial hypertension, and Cushing's syndrome have been reported in children receiving topical corticosteroids. Prolonged use may affect growth velocity; growth should be routinely monitored in pediatric patients. Dosage form specific issues:

Petrolatum-based

Avoid contact with latex-containing products; may damage or reduce effectiveness of latex condoms or diaphragms. If contact occurs, throw away latex product. Do not use prednicarbate intravaginally. Other warnings/precautions:

Appropriate use

For topical use only; do not use intravaginally. Avoid contact with eyes, face, underarms, or groin area. Do not use occlusive dressings; discontinue use if irritation occurs.

Pregnancy & Lactation

Pregnancy

FDA category C

Adverse events have been observed in animal reproduction studies. Topical corticosteroids are not recommended for extensive use, in large quantities, or for long periods of time in pregnant women (Koutroulis, 2011; Leachman, 2006).

Lactation

Systemic corticosteroids are excreted in human milk. It is not known if sufficient quantities of prednicarbate are absorbed following topical administration to produce detectable amounts in breast milk. Do not apply topical corticosteroids to nipples; hypertension was noted in a nursing infant exposed to a topical corticosteroid while nursing (Leachman, 2006). The manufacturer recommends that caution be exercised when administering prednicarbate to nursing women.

Monitoring

Clinical pearlIf HPA axis suppression is suspected, evaluate patient using the following tests: ACTH stimulation test, AM plasma cortisol test, and urinary free cortisol test; growth in children.

Chemistry & Properties

2D structure
FormulaC27H36O8
Molecular weight488.58 g/mol
IUPAC name[2-[(8S,9S,10R,11S,13S,14S,17R)-17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] propanoate
CAS73771-04-7
PubChem CID6714002
InChIKeyFNPXMHRZILFCKX-KAJVQRHHSA-N
logP3.7 (XLogP 4.2)
Polar surface area116.2 Ų
H-bond acceptors / donors8 / 1
Drug-likeness (QED)0.56
Lipinski violations0
SMILESCCOC(=O)O[C@]1(C(=O)COC(=O)CC)CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C

Biology & Pharmacokinetics

Pharmacokinetics

BBB penetrantYes

Enzyme interactions

EnzymeRoleDetail
CYP2B6Inhibitor
CYP2C8Inhibitor
CYP3A4Substrate

Transporters

BCRP (Inhibitor)BSEP (Inhibitor)MRP1 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)P-gp (Inhibitor)P-gp (Substrate)

Registered Products (1)

BrandForm / strengthPackAgentCitizen (JOD)
Peitel Cream Cream 0.25 % 30 g tube Ibn Rushd Drug Store 4.150