PREDNISOLONE ACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H30O6
Molecular Weight	402.4807
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC(=O)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@]12C

InChI

InChIKey=LRJOMUJRLNCICJ-JZYPGELDSA-N

InChI=1S/C23H30O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h6,8,10,16-18,20,26,28H,4-5,7,9,11-12H2,1-3H3/t16-,17-,18-,20+,21-,22-,23-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C23H30O6
Molecular Weight	402.4807
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Prednisolone hemisuccinate is a prodrug of a glucocorticoid agonist prednisolone, which is marketed under trade name Prednisolut in Germany and Austria. Prednisolone hemisuccinate is used in emergency medicine to treate shock due to allergic reaction, insect and snake bites, in neurology to treat brain edema and meningitis, in transplantation medicine to reduce risk of organ refection after kidney transplane, in pneumology to treat acute asthma attack, pulmonary edema, in severe or life-threatening situation in rheumatic diseases.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Glucocorticoid receptor 173	Agonist 2,752	5.7 nM [EC50]
Glucocorticoid receptor 173	Agonist 2,752
Glucocorticoid receptor 173	Agonist 2,752
Glucocorticoid receptor 173	Agonist 2,752
Glucocorticoid receptor 173	Agonist 2,752	2.4 nM [Ki]
Glucocorticoid and meneralocorticoid receptor agonists/antagonists 23	Agonist 2,752

Conditions

Condition	Modality	Highest Phase	Product
Allergic states 22	Primary	Approved 8,583	Prednisolone
Mycosis fungoides 31	Primary	Approved 8,583	Prednisolone
Primary or secondary adrenocortical insufficiency 22	Primary	Approved 8,583	Prednisolone
Hematologic disorders 22	Primary	Approved 8,583	Prednisolone
Acute leukemia 32	Primary	Approved 8,583	Prednisolone
Multiple sclerosis 107	Primary	Approved 8,583	Prednisolone
Uveitis 28	Primary	Approved 8,583	Prednisolone
Symptomatic sarcoidosis 22	Primary	Approved 8,583	Prednisolone
Rheumatic diseases 31	Primary	Approved 8,583	Prednisolone
Inflammation and pain 22	Palliative	Approved 8,583	Sixtysix-20
Atopic dermatitis 64	Palliative	Approved 8,583	RAYOS
Severe erythema multiforme (Stevens-Johnson syndrome) 22	Palliative	Approved 8,583	RAYOS
Congenital adrenal hyperplasia 62	Palliative	Approved 8,583	RAYOS
Crohn's disease 64	Palliative	Approved 8,583	RAYOS
Diamond-Blackfan anemia 24	Palliative	Approved 8,583	RAYOS
Aggressive lymphoma 24	Palliative	Approved 8,583	RAYOS
Allergic conjunctivitis 101	Primary	Approved 8,583	OMNIPRED
Acne rosacea 44	Primary	Approved 8,583	OMNIPRED
Superficial punctate keratitis 43	Primary	Approved 8,583	OMNIPRED
Herpes zoster keratitis 44	Primary	Approved 8,583	OMNIPRED
Iritis 43	Primary	Approved 8,583	OMNIPRED
Anaphylaxis 47	Curative	Approved 8,583	Prednisolut
Brain edema 22	Primary	Approved 8,583	Prednisolut
Acute asthma attack 22	Primary	Approved 8,583	Prednisolut
Pulmonary edema 25	Primary	Approved 8,583	Prednisolut
Rheumatoid arthritis 320	Primary	Approved 8,583	Prednisolut

C_max

Value	Dose	Analyte	Population
0.054 mg/L	60 mg single, enteral	PREDNISONE plasma	Homo sapiens
33.2 ng/mL	30 mg single, oral	PREDNISONE plasma	Homo sapiens
41.8 ng/mL	40 mg single, oral	PREDNISONE plasma	Homo sapiens
43.9 ng/mL	40 mg single, oral	PREDNISONE plasma	Homo sapiens
15.4 μg/L	20 mg single, oral	PREDNISONE plasma	Homo sapiens
420.91 ng/mL	30 mg single, oral	PREDNISOLONE plasma	Homo sapiens
14.43 ng/mL	40 mg single, intramuscular	PREDNISOLONE blood	Homo sapiens
86 μg/dL	20 mg single, intramuscular	PREDNISOLONE HEMISUCCINATE serum	Homo sapiens
36 μg/dL	20 mg single, intramuscular	PREDNISOLONE serum	Homo sapiens

AUC

Value	Dose	Analyte	Population
0.484 mg × h/L	60 mg single, enteral	PREDNISONE plasma	Homo sapiens
298 ng × h/mL	30 mg single, oral	PREDNISONE plasma	Homo sapiens
358 ng × h/mL	40 mg single, oral	PREDNISONE plasma	Homo sapiens
387 ng × h/mL	40 mg single, oral	PREDNISONE plasma	Homo sapiens
97 μg × h/L	20 mg single, oral	PREDNISONE plasma	Homo sapiens
2408.1 ng × h/mL	30 mg single, oral	PREDNISOLONE plasma	Homo sapiens
0.025 μg × h/mL	1200 mg single, intravenous	PREDNISOLONE HEMISUCCINATE plasma	Homo sapiens
0.0173 μg × h/mL	75 mg single, intravenous	PREDNISOLONE HEMISUCCINATE plasma	Homo sapiens
0.085 μg × h/mL	1200 mg single, intravenous	PREDNISOLONE plasma	Homo sapiens
0.0601 μg × h/mL	75 mg single, intravenous	PREDNISOLONE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
5.11 h	60 mg single, enteral	PREDNISONE plasma	Homo sapiens
3.3 h	40 mg single, oral	PREDNISONE plasma	Homo sapiens
3.6 h	40 mg single, oral	PREDNISONE plasma	Homo sapiens
3.85 h	20 mg single, oral	PREDNISONE plasma	Homo sapiens
2.6 h	30 mg single, oral	PREDNISOLONE plasma	Homo sapiens
4 h		PREDNISOLONE plasma	Homo sapiens
30 min	20 mg single, intramuscular	PREDNISOLONE HEMISUCCINATE serum	Homo sapiens
25 min	1200 mg single, intravenous	PREDNISOLONE HEMISUCCINATE plasma	Homo sapiens
18 min	75 mg single, intravenous	PREDNISOLONE HEMISUCCINATE plasma	Homo sapiens
3.7 h	1200 mg single, intravenous	PREDNISOLONE plasma	Homo sapiens
3.5 h	75 mg single, intravenous	PREDNISOLONE plasma	Homo sapiens

F_unbound

Value	Dose	Analyte	Population
50%		PREDNISONE plasma	Homo sapiens
20%	30 mg single, oral	PREDNISOLONE plasma	Homo sapiens
10%		PREDNISOLONE plasma	Homo sapiens
23%	75 mg single, intravenous	PREDNISOLONE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
100 mg 1 times / day multiple, oral Highest studied dose	unhealthy, adult
5 mg 1 times / day steady, oral Recommended	unhealthy, adult	Disc. AE: Vertigo, Abdominal pain upper...
1 % 4 times / day multiple, ophthalmic Recommended	unhealthy, ADULT

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AEs

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AE	Significance	Dose	Population
Abdominal pain upper	1% Disc. AE	5 mg 1 times / day steady, oral Recommended	unhealthy, adult
Aphasia	1% Disc. AE	5 mg 1 times / day steady, oral Recommended	unhealthy, adult
Dizziness	1% Disc. AE	5 mg 1 times / day steady, oral Recommended	unhealthy, adult
Gastroesophageal reflux disease	1% Disc. AE	5 mg 1 times / day steady, oral Recommended	unhealthy, adult
Headache	1% Disc. AE	5 mg 1 times / day steady, oral Recommended	unhealthy, adult

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	11-beta-HSD2 48 11-beta-HSD1 33 P-gp 2,052	P-gp 301 BCRP 101 MRP1 74 MRP4 53 MRP5 45 ABCC12 43 MRP2 146 MRP3 83

Drug as perpetrator

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Target	Modality	Activity
ABCC12 43	inducer 1,966	no
BCRP 985	inducer 1,966	no
MRP1 232	inducer 1,966	no
MRP3 326	inducer 1,966	no
MRP4 345	inducer 1,966	no

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Drug as victim

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Target	Modality	Activity
11-beta-HSD2 48	substrate 4,014	major
11-beta-HSD1 33	substrate 4,014	minor
P-gp 2,052	substrate 4,014	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8382	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8382
ChemicalBook	CB44844383	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB44844383
ChemicalBook	CB6716222	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6716222
eMolecules	29549912	https://www.emolecules.com/cgi-bin/more?vid=29549912
eMolecules	29703823	https://www.emolecules.com/cgi-bin/more?vid=29703823

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PubMed

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Title	Date	PubMed
In vivo effects of orally administered prednisolone on prostaglandin and leucotriene production in ulcerative colitis.	1987 Sep	2824300
Role of platelet-activating factor in ulcerative colitis. Enhanced production during active disease and inhibition by sulfasalazine and prednisolone.	1988 Nov	2901995
Relation between long-term steroid treatment after heart transplantation, hypofibrinolysis and myocardial microthrombi generation.	1999 Jul	10452346
Pseudotumor cerebri secondary to intermediate-dose cytarabine HCl.	1999 May	10369621
Low-dose oral pulse methotrexate as monotherapy in elderly patients with bullous pemphigoid.	1999 May	10321603

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Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical
Record UNII	8B2807733D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PREDNISOLONE ACETATE

Common Name

English

PREDNISOLONE 21-ACETATE

Preferred Name

English

METHYLPREDNISOLONE ACETATE IMPURITY E [EP IMPURITY]

Common Name

English

PRED-G COMPONENT PREDNISOLONE ACETATE

Common Name

English

PREGNA-1,4-DIENE-3,20-DIONE, 21-(ACETYLOXY)-11,17-DIHYDROXY-, (11.BETA.)-

Systematic Name

English

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Classification Tree

Code System

Code

Therapeutic Corticosteroid

NCI_THESAURUS

C521

PART 522 IMPLANTATION OR INJECTABLE DOSAGE FORM NEW ANIMAL DRUGS

CFR

21 CFR 522.1881

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Code System

Code

Type

Description

FDA UNII

8B2807733D

PRIMARY

EPA CompTox

DTXSID3023502

PRIMARY

MERCK INDEX

m9111

PRIMARY

Merck Index

EVMPD

SUB04014MIG

PRIMARY

DRUG BANK

DB15566

PRIMARY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator