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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 of PREDNICARBATE

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

Molecular Formula C27H36O8
Molecular Weight 488.5699
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
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

6.8558402E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
43.1 ng/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
251 ng × h/mL
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
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

Doses

DosePopulationAdverse 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:
unhealthy, 10-90
n = 665
Health Status: unhealthy
Condition: dermatitis
Age Group: 10-90
Sex: M+F
Population Size: 665
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Investigation of the skin thinning effect of prednicarbate and other corticoids in mouse skin.
1988
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
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 14:59:12 UTC 2023
Edited
by admin
on Fri Dec 15 14:59:12 UTC 2023
Record UNII
V901LV1K7D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PREDNICARBATE
EP   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
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
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
NDF-RT N0000175576
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
NCI_THESAURUS C28394
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
WHO-VATC QD07AC18
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
NCI_THESAURUS C521
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
WHO-ATC D07AC18
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
Code System Code Type Description
WIKIPEDIA
PREDNICARBATE
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
PUBCHEM
6714002
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
FDA UNII
V901LV1K7D
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
IUPHAR
7605
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
EVMPD
SUB10015MIG
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
DRUG CENTRAL
2243
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
DRUG BANK
DB01130
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
ECHA (EC/EINECS)
277-590-3
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
RS_ITEM_NUM
1554909
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
NSC
760042
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
EPA CompTox
DTXSID9045502
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
MERCK INDEX
m9110
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY Merck Index
LACTMED
Prednicarbate
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
INN
4968
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
RXCUI
34369
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY RxNorm
CAS
73771-04-7
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
DAILYMED
V901LV1K7D
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
MESH
C035287
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200386
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
USAN
T-122
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
SMS_ID
100000081404
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
NCI_THESAURUS
C47684
Created by admin on Fri Dec 15 14:59:12 UTC 2023 , Edited by admin on Fri Dec 15 14:59:12 UTC 2023
PRIMARY
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