PREDNICARBATE

First approved in 1991

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

Structure Search

SMILES

[H][C@@]12CC[C@](OC(=O)OCC)(C(=O)COC(=O)CC)[C@@]1(C)C[C@H](O)[C@@]3([H])[C@@]2([H])CCC4=CC(=O)C=C[C@]34C

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

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019568s014lbl.pdf
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucocorticoid receptor 172 Target ID: CHEMBL2034 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12677094	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dermatoses 23 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019568s014lbl.pdf	Palliative		Approved 8429	DERMATOP Approved Use DERMATOP Ointment 0.1% is a medium potency corticosteroid indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid responsive dermatoses. Launch Date 1991

C_max

Value	Dose	Co-administered	Analyte	Population
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
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

AUC

Value	Dose	Co-administered	Analyte	Population
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
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

Doses

Dose	Population	Adverse events
0.25 % 1 times / day multiple, topical Recommended Dose: 0.25 %, 1 times / day Route: topical Route: multiple Dose: 0.25 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3705676/	unhealthy, 10-90 n = 665 Health Status: unhealthy Condition: dermatitis Age Group: 10-90 Sex: M+F Population Size: 665 Sources: https://pubmed.ncbi.nlm.nih.gov/3705676/	Sources: https://pubmed.ncbi.nlm.nih.gov/3705676/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	esterase 72

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
esterase 72	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8274287/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY427012	https://www.001chemical.com/chem/73771-04-7
3B Scientific (Wuhan) Corp	3B2-1403	http://www.3bsc.com/index/pro_info.php?id=55119
AA Blocks	AA005KLF	https://www.aablocks.com/goods/Goods/detail?id=AA005KLF
AHH Chemical co.,ltd	MT-58141	http://www.ahhchemical.com/product/MT-58141.html
Alfa Chemistry	AP73771047	https://reagents.alfa-chemistry.com/product/prednicarbate-cas-73771-04-7-15762.html
Ambinter	Amb13889636	http://www.ambinter.com/reference/13889636
Angene	AGN-PC-00J0T5	http://www.angenechemical.com/productshow/AGN-PC-00J0T5.html
AvaChem Scientific	3061	http://www.avachem.com/productSearch.asp?3061
BioChemPartner	BCP33443	http://www.biochempartner.com/73771-04-7-BCP33443
BioSynth	Q-101379	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-101379.html
Boerchem	BC226387	http://www.boerchem.com/?product_38107.html
ChemMol	30109770	http://www.chemmol.com/chemmol/30109770.html
ChemMol	44007688	http://www.chemmol.com/chemmol/44007688.html
ChemMol	49401283	http://www.chemmol.com/chemmol/49401283.html
Chemspace	CSSB00020617558	https://chem-space.com/CSSB00020617558
Chemspace	CSSB00025740742	https://chem-space.com/CSSB00025740742
Clearsynth	CS-T-84441	https://www.clearsynth.com/en/CST84441.html
DC Chemicals	DC31818	http://www.dcchemicals.com//product_show-Prednicarbate.html
Debye Scientific	DB-055800	http://www.debyesci.com/cas_73771-04-7.html
Finetech	FT-0630823	http://www.finetechnology-ind.com/prod/detail/pub/73771-04-7.html
Glentham Life Sciences	GP5901	http://www.glentham.com/products/product/GP5901/
Hairui	HR131659	http://www.hairuichem.com/en/product/73771-04-7.html
LGC Standards	DRE-C16286450	https://www.lgcstandards.com/US/en/p/DRE-C16286450
LGC Standards	MM3382.00	https://www.lgcstandards.com/US/en/p/MM3382.00
Lab Network	LN01312356	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01312356
MolPort	MolPort-006-167-713	https://www.molport.com/shop/molecule-link/MolPort-006-167-713
Molcore	MC427012	https://www.molcore.com/product/73771-04-7
MuseChem	R050882	https://www.musechem.com/product/R050882.html
OChem	21003	http://www.ocheminc.com/index.php?act=psearch&pid=771P047
Smolecule	S540140	http://www.smolecule.com/products/s540140
THE BioTek	bt-279675	https://www.thebiotek.com/product/inhibitors/bt-279675
TripleBond	CP0118	http://www.triplebond-canada.com/prod/1534/
Yuhao Chemical	LL1308	http://www.chemyuhao.com/73771-04-7.html
eNovation Chemicals	D674667	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674667
iChemical	EBD43463	http://www.ichemical.com/products/73771-04-7.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Investigation of the skin thinning effect of prednicarbate and other corticoids in mouse skin.	1988	3272751
[Eczema diseases and erythemato-squamous dermatoses of aging skin--studies of the effectiveness and tolerance of Prednicarbate in various vehicles].	1989 Nov 15	2692325
Contact allergies to topical corticosteroids: 10 cases of contact dermatitis.	1991 Aug	1834432
0.25% prednicarbate cream and the corresponding vehicle induce less skin atrophy than 0.1% betamethasone-17-valerate cream and 0.05% clobetasol-17-propionate cream.	1992	1618247
Topical glucocorticoids of the non-fluorinated double-ester type. Lack of atrophogenicity in normal skin as assessed by high-frequency ultrasound.	1992	1357864
Small reduction of capsaicin-induced neurogenic inflammation in human forearm skin by the glucocorticoid prednicarbate.	1993	8317318
Targeting keratinocyte apoptosis in the treatment of atopic dermatitis and allergic contact dermatitis.	2001 Nov	11692113
A review of prednicarbate (Dermatop).	2004 Dec-2005 Jan	15657633

Patents

Sample Use Guides

In Vivo Use Guide

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

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.

Name

Type

Language

PREDNICARBATE

Official Name

English

PREDNICARBATE [MI]

Common Name

English

PREDNICARBATE [MART.]

Common Name

English

S-77-0777

Code

English

HOE-777

Code

English

DERMATOP

Brand Name

English

PREDNICARBATE [ORANGE BOOK]

Common Name

English

PREDNICARBATE [EP MONOGRAPH]

Common Name

English

S-770777

Code

English

PREGNA-1,4-DIENE-3,20-DIONE, 17-((ETHOXYCARBONYL)OXY)-11-HYDROXY-21-(1-OXOPROPOXY)-, (11.BETA.)-

Systematic Name

English

PREDNICARBATE [USP-RS]

Common Name

English

PREDNICARBATE [USP MONOGRAPH]

Common Name

English

LAS-189961

Code

English

PREDNICARBATE [VANDF]

Common Name

English

LAS-41003 COMPONENT PREDNICARBATE

Code

English

11β,17,21-Trihydroxypregna-1,4-diene-3,20-dione 17-(ethyl carbonate) 21-propionate

Common Name

English

PREDNICARBATE [USAN]

Common Name

English

Prednicarbate [WHO-DD]

Common Name

English

HOE 777

Code

English

prednicarbate [INN]

Common Name

English

S 77 0777

Code

English

S-77 0777

Code

English

NSC-760042

Code

English

LAS189961

Code

English

Classification Tree Code System Code

NDF-RT

N0000175450