Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > Clobetasol propionate

Clobetasol propionate

pharmaceutical raw materials
Clobetasol propionate structure

Clobetasol propionate 

structure
  • CAS No:

    25122-46-7

  • Formula:

    C25H32ClFO5

  • Chemical Name:

    Clobetasol propionate

  • Synonyms:

    Pregna-1,4-diene-3,20-dione,21-chloro-9-fluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)-,(11β,16β)-;Pregna-1,4-diene-3,20-dione,21-chloro-9-fluoro-11β,17-dihydroxy-16β-methyl-,17-propionate;(11β,16β)-21-Chloro-9-fluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)pregna-1,4-diene-3,20-dione;21-Chloro-21-deoxybetamethasone 17-propionate;Dermovate;Clobetasol propionate;Clobetasol 17-propionate;CGP 9555;Clobesol;Temovate;Clobederm;GR 2/925;Dermoxin;Dermoxinale;Dermoval;CCl 4725;Karison;Clobex;Olux;Skin Cap;Olux-E;Tenovate

  • Categories:

    Active Pharmaceutical Ingredients  >  Hormones and the Endocrine System

Description

Clobetasol propionate is a anti-inflammatory corticosteroid used to treat various skin disorders.Target: Glucocorticoid ReceptorClobetasol propionate is a corticosteroid of the glucocorticoid class used to treat various skin disorders including eczema and psoriasis. It is also highly effective for contact dermatitis caused by exposure to poison ivy/oak. Clobetasol belongs to US Class I (Europe: class IV) of the corticosteroids, making it one of the most potent available. It comes in sham


Clobetasol propionate is the 17-O-propionate ester of clobetasol. A potent corticosteroid, it is used to treat various skin disorders, including exzema and psoriasis. It has a role as an anti-inflammatory drug. It is an 11beta-hydroxy steroid, a 20-oxo steroid, a glucocorticoid, a fluorinated steroid, a 3-oxo-Delta(1),Delta(4)-steroid and a chlorinated steroid. It derives from a clobetasol and a propionic acid.|Clobetasol propionate is a prednisolone derivative with higher specificity for glucocorticoid receptors than mineralocorticoid receptors. It has demonstrated superior activity compared to [fluocinonide] and was first described in the literature in 1974. Clobetasol Propionate was granted FDA approval on 27 December 1985.|Clobetasol Propionate is the propionate salt form of clobetasol, a topical synthetic corticosteroid with anti-inflammatory, anti-pruritic, and vasoconstrictive properties. Clobetasol propionate exerts its effect by binding to cytoplasmic glucocorticoid receptors and subsequently activates glucocorticoid receptor mediated gene expression. This results in synthesis of certain anti-inflammatory proteins, while inhibiting the synthesis of certain inflammatory mediators. Specifically, clobetasol propionate appears to induce phospholipase A2 inhibitory proteins, thereby controlling the release of the inflammatory precursor arachidonic acid from membrane phospholipids by phospholipase A2.|A derivative of PREDNISOLONE with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than FLUOCINONIDE, it is used topically in treatment of PSORIASIS but may cause marked adrenocortical suppression.

Clobetasol propionate Basic Attributes

466.97000

466.97

246-634-3

779619577M

DTXSID6045907

C28934

2937290090

Characteristics

80.67000

4.10310

White Crystalline Powder

1.28 g/cm3

195.5-197 °C

569ºC at 760 mmHg

297.9ºC

1.56

2.58E-15mmHg at 25°C

205.1 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

NONH for all modes of transport

2

R36/37/38

S26-S36

TU3725000

Xi

P201-P260-P280-P308 + P313

H360Df-H373-H413

|Danger|H315 (33.71%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P260, P261, P264, P271, P273, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 89 companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Data regarding acute overdoses of glucocorticoids are rare. Overdoses of clobetasol propionate can lead to reversible HPA axis suppression and glucocorticoid insufficiency. Chronic high doses of glucocorticoids can lead to the development of cataract, glaucoma, hypertension, water retention, hyperlipidemia, peptic ulcer, pancreatitis, myopathy, osteoporosis, mood changes, psychosis, dermal atrophy, allergy, acne, hypertrichosis, immune suppression, decreased resistance to infection, moon face, hyperglycemia, hypocalcemia, hypophosphatemia, metabolic acidosis, growth suppression, and secondary adrenal insufficiency. Overdose may be treated by adjusting the dose or stopping the corticosteroid as well as initiating symptomatic and supportive treatment.

Data regarding the protein binding of clobetasol propionate are not readily available. Corticosteroids are generally bound to corticosteroid binding globulin and serum albumin in plasma.

Drug Information

Clobetasol propionate is indicated to treat moderate to severe plaque psoriasis as well as inflammatory and pruritic manifestations of corticosteroid responsive dermatoses.|FDA Label

Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals. Clobetasol propionate is generally applied twice daily so the duration of action is long. 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.

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. (See all compounds classified as Glucocorticoids.)|Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

Twice daily application of clobetasol foam leads to a Cmax of 59±36pg/mL with a Tmax of 5 hours. Clobetasol cream showed an increase in clobetasol concentrations from 50.7±96.0pg/mL to 56.3±104.7pg/mL.|Corticosteroids are eliminated predominantly in the urine.|Data regarding the volume of distribution of clobetasole propionate are not readily available.|Data regarding the clearance of clobetasol propionate are not readily available.

The metabolism of clobetasol propionate is not well studied but it does induce metabolic enzymes, even when delivered topically. The metabolism of clobetasol propionate is predicted to follow similar metabolic pathways to other corticosteroids including the addition of oxygen, hydrogen, glucuronides, and sulfates to form water soluble metabolites.

Data regarding the half life of clobetasol propionate are not readily available.

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.

Clobetasol

Clobetasol propionate Use and Manufacturing

Uses

Topical corticosteroid. Glucocorticoid; anti-inflammatory

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals

Computed Properties

Molecular Weight:467.0
XLogP3:3.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:5
Exact Mass:466.1922300
Monoisotopic Mass:466.1922300
Topological Polar Surface Area:80.7
Heavy Atom Count:32
Complexity:929
Defined Atom Stereocenter Count:8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

A highly potent topical corticosteroid with capillary constriction and anti-inflammatory effects.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • RN LABORATORIES EUROPE BV

    United States United States
    Active
  • CURIA SPAIN SAU

    United States United States
    Active
  • FARMABIOS S.P.A.

    Italy Italy
    Active

Recommended Suppliers of Clobetasol propionate

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.