Clocortolone is a medium potency corticosteroid that is often used as a topical cream for the relief of inflammatory oand pruritic (itching) arising from steroid-responsive dermatoses of the scalp.

Structure

Similar Structures

Synonyms

9-chloro-6alpha-Fluoro-11beta,21-dihydroxy-16alpha-methyl-1,4-pregnadien-3,20-dione
9-chloro-6alpha-Fluoro-16alpha-methyl-1,4-pregnadiene-11beta,21-diol-3,20-dione
Clocortolon
Clocortolona
Clocortolone
Clocortolonum

External IDs

SH 863

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Clocortolone pivalate	QBL8IZH14X	34097-16-0	SXYZQZLHAIHKKY-GSTUPEFVSA-N

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Cloderm	Cream	0.001 g/1g	Topical	Promius Pharma, LLC	1977-08-22	Not applicable
Cloderm	Cream	0.001 g/1g	Topical	Coria Laboratories	1977-08-22	2016-05-01
Cloderm	Cream	1 mg/1g	Topical	Epi Health, Inc	2018-10-30	Not applicable

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Application Number

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Product Code

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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Clocortolone Pivalate	Cream	0.001 g/1g	Topical	Dr. Reddy's Laboratories Inc	2014-02-17	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

UNII

N8ZUB7XE0H

CAS number

4828-27-7

Weight

Average: 410.907
Monoisotopic: 410.166015296

Chemical Formula

C₂₂H₂₈ClFO₄

InChI Key

YMTMADLUXIRMGX-RFPWEZLHSA-N

InChI

InChI=1S/C22H28ClFO4/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-21(15,3)22(14,23)18(28)9-20(13,2)19(11)17(27)10-25/h4-5,7,11,13-14,16,18-19,25,28H,6,8-10H2,1-3H3/t11-,13+,14+,16+,18+,19-,20+,21+,22+/m1/s1

IUPAC Name

(1R,2S,8S,10S,11S,13R,14S,15S,17S)-1-chloro-8-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one

SMILES

[H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(Cl)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C

Pharmacology

Indication

For short-term topical treatment of the inflammatory and pruritic manifestations of moderate to severe corticosteroid-responsive dermatoses of the scalp.

Associated Conditions

Dermatosis

Pharmacodynamics

Like other topical corticosteroids, clocortolone has anti-inflammatory, antipruritic, and vasoconstrictive properties. Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Clocortolone is a moderate potency topical corticosteroid that should not be used with occlusive dressings. It is recommended that treatment should be limited to 2 consecutive weeks and therapy should be discontinued when adequate results have been achieved.

Mechanism of action

The precise mechanism of the antiinflammatory activity of topical steroids in the treatment of steroid-responsive dermatoses, in general, is uncertain. 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. These enzyme transcriptional changes are mediated by the drug binding first to the glucocorticoid receptor. This complex can migrate to the cell nucleus which then binds to DNA initiating genetic activation and repression of various genes.

Target	Actions	Organism
AGlucocorticoid receptor	agonist	Humans

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Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Topical corticosteroids can be absorbed from intact healthy skin. The extent of percutaneous absorption of topical corticosteroids is determined by many factors, including the vehicle and the integrity of the epidermal barrier. Occlusion, inflammation and/or other disease processes in the skin may also increase percutaneous absorption.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Metabolized, primarily in the liver, and then excreted by the kidneys.

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Topically applied clocortolone can be absorbed in sufficient amounts to produce systemic effects. Symptoms of overdose include thinning of skin and suppression of adrenal cortex (decreased ability to respond to stress).

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
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Tacrolimus	Tacrolimus may increase the immunosuppressive activities of Clocortolone.
Trastuzumab	Trastuzumab may increase the neutropenic activities of Clocortolone.

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Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

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Food Interactions

Not Available

References

General References

Not Available

External Links

Human Metabolome Database: HMDB0014976
KEGG Drug: D07719
PubChem Compound: 5311052
PubChem Substance: 46505290
ChemSpider: 4470589
ChEBI: 59582
Therapeutic Targets Database: DAP001190
PharmGKB: PA164744013
Wikipedia: Clocortolone

ATC Codes

D07AB21 — Clocortolone

FDA label

Download (167 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Psoriasis	1

Pharmacoeconomics

Manufacturers

Dow pharmaceutical sciences inc

Packagers

Coria Laboratories
DPT Laboratories Ltd.
Valeant Ltd.

Dosage forms

Form	Route	Strength
Cream	Topical	0.001 g/1g
Cream	Topical	1 mg/1g

Prices

Unit description	Cost	Unit
Cloderm 0.1% Cream 45 gm Tube	140.98USD	tube
Cloderm 0.1% cream	3.64USD	g

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
logP	3.8	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.015 mg/mL	ALOGPS
logP	2.73	ALOGPS
logP	2.47	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.53	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	105.74 m³·mol^-1	ChemAxon
Polarizability	41.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9737
Caco-2 permeable	+	0.8054
P-glycoprotein substrate	Substrate	0.7404
P-glycoprotein inhibitor I	Non-inhibitor	0.7095
P-glycoprotein inhibitor II	Non-inhibitor	0.8814
Renal organic cation transporter	Non-inhibitor	0.8141
CYP450 2C9 substrate	Non-substrate	0.8412
CYP450 2D6 substrate	Non-substrate	0.8977
CYP450 3A4 substrate	Substrate	0.7374
CYP450 1A2 substrate	Non-inhibitor	0.9164
CYP450 2C9 inhibitor	Non-inhibitor	0.9119
CYP450 2D6 inhibitor	Non-inhibitor	0.9061
CYP450 2C19 inhibitor	Non-inhibitor	0.9182
CYP450 3A4 inhibitor	Inhibitor	0.6251
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.857
Ames test	Non AMES toxic	0.8537
Carcinogenicity	Non-carcinogens	0.8855
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	1.9732 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9619
hERG inhibition (predictor II)	Non-inhibitor	0.5411

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Taxonomy

Description: This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
Kingdom: Organic compounds
Super Class: Lipids and lipid-like molecules
Class: Steroids and steroid derivatives
Sub Class: Hydroxysteroids
Direct Parent: 21-hydroxysteroids
Alternative Parents: Gluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 11-beta-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Alpha-hydroxy ketones / Secondary alcohols / Chlorohydrins / Cyclic ketones
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Substituents: 21-hydroxysteroid / Progestogin-skeleton / 20-oxosteroid / Pregnane-skeleton / 6-halo-steroid / Halo-steroid / 3-oxo-delta-1,4-steroid / 9-halo-steroid / 3-oxosteroid / Oxosteroid
show 24 more
Molecular Framework: Aliphatic homopolycyclic compounds
External Descriptors: 11beta-hydroxy steroid, glucocorticoid, 20-oxo steroid, fluorinated steroid, 3-oxo-Delta(1),Delta(4)-steroid, chlorinated steroid, 21-hydroxy steroid (CHEBI:59582)

Targets

Details1. Glucocorticoid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Zinc ion binding
Specific Function: Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name: NR3C1
Uniprot ID: P04150
Uniprot Name: Glucocorticoid receptor
Molecular Weight: 85658.57 Da

References

Ali A, Balkovec JM, Greenlee M, Hammond ML, Rouen G, Taylor G, Einstein M, Ge L, Harris G, Kelly TM, Mazur P, Pandit S, Santoro J, Sitlani A, Wang C, Williamson J, Forrest MJ, Carballo-Jane E, Luell S, Lowitz K, Visco D: Discovery of betamethasone 17alpha-carbamates as dissociated glucocorticoid receptor modulators in the rat. Bioorg Med Chem. 2008 Aug 15;16(16):7535-42. doi: 10.1016/j.bmc.2008.07.037. Epub 2008 Jul 20. [PubMed:18691892]
Buchwald P: Glucocorticoid receptor binding: a biphasic dependence on molecular size as revealed by the bilinear LinBiExp model. Steroids. 2008 Feb;73(2):193-208. Epub 2007 Oct 11. [PubMed:18022656]
Tanigawa K, Nagase H, Ohmori K, Tanaka K, Miyake H, Kiniwa M, Ikizawa K: Species-specific differences in the glucocorticoid receptor transactivation function upon binding with betamethasone-esters. Int Immunopharmacol. 2002 Jun;2(7):941-50. [PubMed:12188035]

Drug created on June 13, 2005 07:24 / Updated on July 13, 2019 00:34

Clocortolone

Identification

Structure for Clocortolone (DB00838)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References