21-Desacetyldeflazacort

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H29NO5
Molecular Weight	399.4801
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC1=N[C@@]2([C@@H](C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O)C[C@]23C)O1)C(=O)CO

InChI

InChIKey=KENSGCYKTRNIST-RVUAFKSESA-N

InChI=1S/C23H29NO5/c1-12-24-23(18(28)11-25)19(29-12)9-16-15-5-4-13-8-14(26)6-7-21(13,2)20(15)17(27)10-22(16,23)3/h6-8,15-17,19-20,25,27H,4-5,9-11H2,1-3H3/t15-,16-,17-,19+,20+,21-,22-,23+/m0/s1

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Description

Deflazacort is a glucocorticoid developed for the treatment of different inflammatory and immune conditions. The drug is rapidly metabolized to an active metabolite, 21-hydroxy-deflazaxort that may cross the blood brain barrier. Deflazacort acts by suppressing inflammatory response.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
inflammatory response 47	Inhibitor 8,504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Immune system diseases 2	Primary		Approved 8,583	CALCORT

C_max

Value	Dose	Co-administered	Analyte	Population
206 ng/mL	0.9 mg/kg single, oral		21-DESACETYLDEFLAZACORT plasma	Homo sapiens
381 ng/mL	0.9 mg/kg single, oral		21-DESACETYLDEFLAZACORT plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
400 ng × h/mL	0.9 mg/kg single, oral		21-DESACETYLDEFLAZACORT plasma	Homo sapiens
655 ng × h/mL	0.9 mg/kg single, oral		21-DESACETYLDEFLAZACORT plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
2 h	36 mg single, oral		21-DESACETYLDEFLAZACORT plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
60%	0.9 mg/kg single, oral		21-DESACETYLDEFLAZACORT plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
1.2 mg/kg 1 times / day multiple, oral Higher than recommended	unhealthy, 5 - 15 years	Other AEs: Cushingoid, Erythema...
0.9 mg/kg 1 times / day multiple, oral Recommended	unhealthy, 5 - 15 years	Other AEs: Cushingoid, Weight increased...
0.9 mg/kg 1 times / day multiple, oral Recommended	unhealthy, 5 - 15 years	Other AEs: Cushingoid, Hirsutism...

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AEs

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AE	Significance	Dose	Population
Acne	11%	1.2 mg/kg 1 times / day multiple, oral Higher than recommended	unhealthy, 5 - 15 years
Skin striae	11%	1.2 mg/kg 1 times / day multiple, oral Higher than recommended	unhealthy, 5 - 15 years
Abdominal pain upper	14%	1.2 mg/kg 1 times / day multiple, oral Higher than recommended	unhealthy, 5 - 15 years
Constipation	15%	1.2 mg/kg 1 times / day multiple, oral Higher than recommended	unhealthy, 5 - 15 years
Weight increased	32%	1.2 mg/kg 1 times / day multiple, oral Higher than recommended	unhealthy, 5 - 15 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946 inhibitor 2,252 inducer 1,087	inhibitor 2,438	inhibitor 2,507	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2,153 CYP2C19 2,057 UGT1A1 246 UGT1A4 98 UGT1A6 136 UGT1A9 148 UGT2B7 197 CYP2B6 926 CYP2C8 1,057 UGT1A3 89 UGT2B15 84 P-gp 1,741 BCRP 910 OATP1B1 1,079 OATP1B3 961 OAT1 725 OAT3 747 OCT2 779	esterase 74 P-gp 2,052 BCRP 697 OATP1B1 503 OATP1B3 435	CYP1A2 832 CYP2B6 669

Drug as perpetrator

Show entries

Target	Modality	Activity	Metabolite
BCRP 985	inhibitor 4,027	no	21-DESACETYLDEFLAZACORT 2
CYP1A2 2,333	inducer 1,966	no	21-DESACETYLDEFLAZACORT 2
CYP1A2 2,333	inhibitor 4,027	no	21-DESACETYLDEFLAZACORT 2
CYP2B6 1,160	inducer 1,966	no	21-DESACETYLDEFLAZACORT 2
CYP2C19 2,141	inhibitor 4,027	no	21-DESACETYLDEFLAZACORT 2

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Drug as victim

Show entries

Target	Modality	Activity	Metabolite
BCRP 697	substrate 4,014	no	21-DESACETYLDEFLAZACORT 2
OATP1B1 503	substrate 4,014	no	21-DESACETYLDEFLAZACORT 2
OATP1B3 435	substrate 4,014	no	21-DESACETYLDEFLAZACORT 2
P-gp 2,052	substrate 4,014	yes	21-DESACETYLDEFLAZACORT 2
esterase 74	substrate 4,014	yes

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237		21-DESACETYLDEFLAZACORT 2

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PubMed

Title	Date	PubMed
No data available in table

Patents

Sample Use Guides

In Vivo Use Guide

The usual dose for most conditions, including rheumatoid arthritis is half to three tablets each day, the dose for severe asthma may be up to 8 or 12 tablets each day.

Route of Administration: Oral

In Vitro Use Guide

Phytohaemagglutinin stimulated peripheral blood lymphocytes, NK and K cells were incubated with different concentrations of the drug (0, 1.2, 6.0, 24, 60, 240, and 600 x 10(-7) M) and the immunosuppressive effect was measured. Deflazacort suppressed the cells in a dose dependent way.

Show entries

Name

Type

Language

L 6485

Preferred Name

English

21-Desacetyldeflazacort

Common Name

English

21-DESDFZ

Common Name

English

5'.BETA.H-PREGNA-1,4-DIENO(17,16-D)OXAZOLE-3,20-DIONE, 11.BETA.,21-DIHYDROXY-2'-METHYL-

Systematic Name

English

5'H-PREGNA-1,4-DIENO(17,16-D)OXAZOLE-3,20-DIONE, 11,21-DIHYDROXY-2'-METHYL-, (11.BETA.,16.BETA.)-

Systematic Name

English

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Code System

Code

Type

Description

PUBCHEM

3081431

PRIMARY

SMS_ID

300000052919

PRIMARY

FDA UNII

T1LWN33J2P

PRIMARY

CAS

13649-57-5

PRIMARY

EPA CompTox

DTXSID201043063

PRIMARY

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ACTIVE MOIETY


					T1LWN33J2P

21-Desacetyldeflazacort

METABOLITE (PARENT)


					L93L6AWV7W

6BETA-HYDROXY-21-DESACETYL DEFLAZACORT

PRODRUG (METABOLITE ACTIVE)


					KR5YZ6AE4B

Deflazacort

SMILES

InChI

CNS Activity

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator