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

Structure Search

SMILES

[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(N=C(C)O2)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

HIDE SMILES / InChI

Description
Sources: http://e-lactancia.org/media/papers/Deflazacort-DS-eMC2015.pdf
Curator's Comment: description was created based on several sources, including, http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2763756/

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 Target ID: GO:0006954 Sources: http://www.dmpharma.co.in/deflazacort.html	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Immune system diseases 2 Sources: http://e-lactancia.org/media/papers/Deflazacort-DS-eMC2015.pdf	Primary		Approved 8429	CALCORT Approved Use Treat inflammation including asthma, arthritis and allergies; treat problems with skin, kidney, heart, digestive system, eyes or blood, treat problems where body has growths (tumours), suppress the immune system in transplant operations.

C_max

Value	Dose	Co-administered	Analyte	Population
381 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208684s000,208685s000lbl.pdf	0.9 mg/kg single, oral dose: 0.9 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		21-DESACETYLDEFLAZACORT plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: UNKNOWN food status: UNKNOWN
206 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208684s000,208685s000lbl.pdf	0.9 mg/kg single, oral dose: 0.9 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		21-DESACETYLDEFLAZACORT plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
655 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208684s000,208685s000lbl.pdf	0.9 mg/kg single, oral dose: 0.9 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		21-DESACETYLDEFLAZACORT plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: UNKNOWN food status: UNKNOWN
400 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208684s000,208685s000lbl.pdf	0.9 mg/kg single, oral dose: 0.9 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		21-DESACETYLDEFLAZACORT plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
60% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208684s000,208685s000lbl.pdf	0.9 mg/kg single, oral dose: 0.9 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		21-DESACETYLDEFLAZACORT plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
1.2 mg/kg 1 times / day multiple, oral Higher than recommended Dose: 1.2 mg/kg, 1 times / day Route: oral Route: multiple Dose: 1.2 mg/kg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208684s000,208685s000lbl.pdf Page: 6.1	unhealthy, 5 - 15 years Health Status: unhealthy Condition: Duchenne muscular dystrophy Age Group: 5 - 15 years Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208684s000,208685s000lbl.pdf Page: 6.1	Other AEs: Cushingoid, Erythema... Other AEs: Cushingoid (69%) Erythema (49%) Hirsutism (37%) Headache (34%) Weight increased (32%) Constipation (15%) Abdominal pain upper (14%) Skin striae (11%) Acne (11%) Abdominal discomfort (8%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208684s000,208685s000lbl.pdf Page: 6.1
0.9 mg/kg 1 times / day multiple, oral Recommended Dose: 0.9 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.9 mg/kg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208684s000,208685s000lbl.pdf Page: Table 1	unhealthy, 5 - 15 years n = 51 Health Status: unhealthy Condition: Duchenne muscular dystrophy Age Group: 5 - 15 years Sex: unknown Population Size: 51 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208684s000,208685s000lbl.pdf Page: Table 1	Other AEs: Cushingoid, Weight increased... Other AEs: Cushingoid (33%) Weight increased (20%) Increased appetite (14%) Upper respiratory tract infection (12%) Cough (12%) Pollakiuria (12%) Nasopharyngitis (10%) Hirsutism (10%) Central obesity (10%) Erythema (8%) Irritability (8%) Rhinorrhea (8%) Abdominal discomfort (6%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208684s000,208685s000lbl.pdf Page: Table 1
0.9 mg/kg 1 times / day multiple, oral Recommended Dose: 0.9 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.9 mg/kg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208684s000,208685s000lbl.pdf Page: Table 1	unhealthy, 5 - 15 years n = 51 Health Status: unhealthy Condition: Duchenne muscular dystrophy Age Group: 5 - 15 years Sex: unknown Population Size: 51 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208684s000,208685s000lbl.pdf Page: Table 1	Other AEs: Cushingoid, Hirsutism... Other AEs: Cushingoid (60%) Hirsutism (35%) Weight increased (28%) Erythema (28%) Central obesity (25%) Abdominal pain (18%) Pollakiuria (15%) Constipation (10%) Irritability (10%) Abnormal behavior (9%) Pyrexia (9%) Back pain (7%) Rash (7%) Contusion (6%) Nausea (6%) Psychomotor hyperactivity (6%) Epistaxis (6%) Skin striae (6%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208684s000,208685s000lbl.pdf Page: Table 1

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587 inducer 781	inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478 UGT1A1 204 UGT1A4 77 UGT1A6 108 UGT1A9 116 UGT2B7 146 CYP2B6 810 CYP2C8 911 UGT1A3 84 UGT2B15 64 P-gp 1461 BCRP 699 OATP1B1 788 OATP1B3 706 OAT1 599 OAT3 642 OCT2 647	esterase 72 P-gp 1537 BCRP 561 OATP1B1 406 OATP1B3 350	CYP1A2 701 CYP2B6 547

Drug as perpetrator

Target	Modality	Activity	Metabolite
BCRP 773	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
CYP2B6 1001	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
CYP3A4 1925	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
OAT1 603	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
OAT3 644	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
OATP1B1 803	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
OATP1B3 715	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
OCT2 648	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
P-gp 1650	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
UGT1A1 254	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
UGT1A4 80	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
UGT1A6 141	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
UGT1A9 121	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
UGT2B7 157	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	weak	21-DESACETYLDEFLAZACORT 2
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	weak	21-DESACETYLDEFLAZACORT 2
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	weak	21-DESACETYLDEFLAZACORT 2
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	weak	21-DESACETYLDEFLAZACORT 2
UGT1A3 93	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	weak	21-DESACETYLDEFLAZACORT 2
UGT2B15 64	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	weak	21-DESACETYLDEFLAZACORT 2

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
BCRP 561	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
OATP1B1 406	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
OATP1B3 350	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	no	21-DESACETYLDEFLAZACORT 2
P-gp 1537	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/208684s004,208685s004lbl.pdf#page=17 Page: 17.0	yes	21-DESACETYLDEFLAZACORT 2
esterase 72	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208684,208685Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	yes
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208684,208685Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	yes	21-DESACETYLDEFLAZACORT 2	yes (co-administration study) Comment: In a dedicated drug-drug interaction (DDI) study with multiple doses of clarithromycin, a strong CYP3A4 inhibitor, a 2 to 3 fold increase in Cmax, and AUCinf values of 21-des-DFZ was observed. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208684,208685Orig1s000ClinPharmR.pdf#page=3 Page: 3.0

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208684,208685Orig1s000PharmR.pdf#page=6 Page: 6.0		21-DESACETYLDEFLAZACORT 2

PubMed

Title	Date	PubMed
Prednisone versus deflazacort in the treatment of autoimmune thrombocytopenic purpura: evaluation of clinical response and immunological modifications.	1991 Jul-Aug	1794742
Effectiveness of nifedipine and deflazacort in the management of distal ureter stones.	2000 Oct 1	11018608
Transactivation via the human glucocorticoid and mineralocorticoid receptor by therapeutically used steroids in CV-1 cells: a comparison of their glucocorticoid and mineralocorticoid properties.	2004 Sep	15362971

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.

Name

Type

Language

21-DESACETYLDEFLAZACORT

Common Name

English

L 6485

Code

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

L-6485

Code

English

DEFLAZACORT METABOLITE II

Common Name

English

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

Systematic Name

English

DEACETYLDEFLAZACORT

Common Name

English

Code System Code Type Description

PUBCHEM

3081431

Created by admin on Sat Dec 16 14:00:37 GMT 2023 , Edited by admin on Sat Dec 16 14:00:37 GMT 2023

PRIMARY

FDA UNII

T1LWN33J2P

Created by admin on Sat Dec 16 14:00:37 GMT 2023 , Edited by admin on Sat Dec 16 14:00:37 GMT 2023

PRIMARY

CAS

13649-57-5

Created by admin on Sat Dec 16 14:00:37 GMT 2023 , Edited by admin on Sat Dec 16 14:00:37 GMT 2023

PRIMARY

EPA CompTox

DTXSID201043063

Created by admin on Sat Dec 16 14:00:37 GMT 2023 , Edited by admin on Sat Dec 16 14:00:37 GMT 2023

PRIMARY

ACTIVE MOIETY


					T1LWN33J2P

21-DESACETYLDEFLAZACORT

METABOLITE (PARENT)


					L93L6AWV7W

6BETA-HYDROXY-21-DESACETYL DEFLAZACORT

PRODRUG (METABOLITE ACTIVE)


					KR5YZ6AE4B

DEFLAZACORT

Details

SMILES

InChI

DescriptionSources: http://e-lactancia.org/media/papers/Deflazacort-DS-eMC2015.pdfCurator's Comment: description was created based on several sources, including, http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2763756/

CNS Activity

Approval Year

Targets

Conditions

Approved Use

Cmax

AUC

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Patents

Sample Use Guides

Description
Sources: http://e-lactancia.org/media/papers/Deflazacort-DS-eMC2015.pdf
Curator's Comment: description was created based on several sources, including, http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2763756/

C_max

F_unbound

Drug as perpetrator