Prednisolone Acetate

Details

• Internal ID: b0cc0389-0807-4508-94b4-28d3f6793f3b
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Pregnane steroids > Gluco/mineralocorticoids, progestogins and derivatives
• IUPAC Name: [2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
• SMILES (Canonical): CC(=O)OCC(=O)C1(CCC2C1(CC(C3C2CCC4=CC(=O)C=CC34C)O)C)O
• SMILES (Isomeric): CC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)C=C[C@]34C)O)C)O
• InChI: 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
• InChI Key: LRJOMUJRLNCICJ-JZYPGELDSA-N
• Popularity: 4,507 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₀O₆
• Molecular Weight: 402.50 g/mol
• Exact Mass: 402.20423867 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.13
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 52-21-1
• Omnipred
• Prednisolone 21-acetate
• Pred Forte
• Econopred
• Pricortin
• Prediacortine
• Cormalone
• Cortipred
• Deltilen
• Durapred
• Nisolone
• Predicort
• Prednidoren
• Supercortyl
• Prenema
• Meticortelone acetate
• Prednelan-N
• Delcort-E
• Pred Mild
• Econopred Plus
• Flo-Pred
• Predalone 50
• Predonine injection
• Prednisolone (21-acetate)
• ster
• Pred-Forte
• Cetapred Ointment
• Pred-G Liquifilm
• Vasocidin Ointment
• Blephamide Liquifilm
• PREDNISOLONE-21-ACETATE
• EINECS 200-134-1
• NSC 10966
• NSC-10966
• BRN 3111798
• MLS000028512
• MLS001148097
• CHEBI:8380
• [2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
• DTXSID3023502
• Prednisolone acetate [BAN:JAN]
• Prednisolone acetate [USP:JAN]
• 11beta,17,21-Trihydroxypregna-1,4-diene-3,20-dione 21-acetate
• UNII-8B2807733D
• SMR000058326
• 8B2807733D
• 4-08-00-03468 (Beilstein Handbook Reference)
• DTXCID103502
• PrednisoloneAcetate
• 21-Acetoxy-1,4-pregnadiene-11beta,17alpha-diol-3,20-dione
• Meticotelone acetate
• Pregna-1,4-diene-3,20-dione, 11beta,17,21-trihydroxy-, 21-acetate
• Pregna-1,4-diene-3,20-dione, 11-beta,17,21-trihydroxy-, 21-acetate
• Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-11,17-dihydroxy-, (11beta)-
• hydroprednisone acetate
• CAS-52-21-1
• Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-11,17-dihydroxy-, (11.beta.)-
• Prednisolone acetate (Omnipred)
• Econopred (TN)
• Prednisoloni acetas
• NCGC00094765-01
• prednisolone-acetate
• Pred forte (TN)
• component of Metimyd
• MFCD00037710
• Sterane IM and IA
• Blephamide S.O.P.
• component of Composone
• Pred Forte TM 1%
• Pred-G S.O.P
• Opera_ID_332
• Pred-G S.O.P.
• SCHEMBL7999
• CHEMBL1152
• component of Isopto Cetapred
• MLS002207146
• MLS002548870
• component of Neo-Delta-Cortef
• LRJOMUJRLNCICJ-JZYPGELDSA-N
• HMS2234F18
• HMS3259O07
• PREDNISOLONE ACETATE [JAN]
• Prednisolone 21-acetate, >=97%
• PREDNISONE IMPURITY L [EP]
• 2-((8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
• BCP18958
• HY-B1214
• NSC10966
• PREDNISOLONE ACETATE [VANDF]
• Tox21_111328
• PREDNISOLONE ACETATE [MART.]
• s2570
• PREDNISOLONE ACETATE [USP-RS]
• PREDNISOLONE ACETATE [WHO-DD]
• PREDNISOLONE ACETATE [WHO-IP]
• AKOS007930677
• AKOS015960469
• PREDNISOLONE 21-ACETATE [MI]
• Tox21_111328_1
• AC-2176
• CCG-268673
• CS-4642
• CS-O-11052
• DB15566
• NC00470
• Prednisolone acetate (JP17/USP/INN)
• NCGC00021925-03
• NCGC00021925-05
• PREDNISOLONE ACETATE [GREEN BOOK]
• 2-((1S,10S,11S,15S,17S,2R,14R)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8 .7.0.0<2,7>.0<11,15>]heptadeca-3,6-dien-14-yl)-2-oxoethyl acetate
• AS-11673
• PREDNISOLONE ACETATE [ORANGE BOOK]
• PREDNISOLONE ACETATE [EP MONOGRAPH]
• PREDNISOLONE ACETATE [USP IMPURITY]
• PREDNISOLONI ACETAS [WHO-IP LATIN]
• LS-118501
• PREDNISOLONE ACETATE [USP MONOGRAPH]
• Prednisolone acetate for peak identification
• METIMYD COMPONENT PREDNISOLONE ACETATE
• P1283
• PRED-G COMPONENT PREDNISOLONE ACETATE
• PREDNISOLONE IMPURITY C [EP IMPURITY]
• CETAPRED COMPONENT PREDNISOLONE ACETATE
• SULPHRIN COMPONENT PREDNISOLONE ACETATE
• BLEPHAMIDE COMPONENT PREDNISOLONE ACETATE
• C08180
• D00980
• PREDAMIDE COMPONENT PREDNISOLONE ACETATE
• PREDNISOLONE ACETATE COMPONENT OF PRED-G
• AB00443788-11
• AB00443788_13
• PREDNISOLONE ACETATE COMPONENT OF CETAPRED
• PREDNISOLONE ACETATE COMPONENT OF METIMYD
• PREDNISOLONE ACETATE COMPONENT OF SULPHRIN
• PREDSULFAIR COMPONENT PREDNISOLONE ACETATE
• A828982
• EN300-19628782
• PREDNISOLONE ACETATE COMPONENT OF BLEPHAMIDE
• PREDNISOLONE ACETATE COMPONENT OF PREDAMIDE
• PREDNISOLONE ACETATE COMPONENT OF PREDSULFAIR
• Q-201614
• HYDROCORTISONE ACETATE IMPURITY C [EP IMPURITY]
• ISOPTO CETAPRED COMPONENT PREDNISOLONE ACETATE
• NEO-DELTA-CORTEF COMPONENT PREDNISOLONE ACETATE
• Q27108063
• BLEPHAMIDE S.O.P. COMPONENT PREDNISOLONE ACETATE
• PREDNISOLONE ACETATE COMPONENT OF ISOPTO CETAPRED
• PREDNISOLONE ACETATE COMPONENT OF NEO-DELTA-CORTEF
• METHYLPREDNISOLONE ACETATE IMPURITY E [EP IMPURITY]
• Prednisolone 21-acetate, VETRANAL(TM), analytical standard
• PREDNISOLONE ACETATE COMPONENT OF BLEPHAMIDE S.O.P.
• 11b,17,21-Trihydroxypregna-1,4-diene-3,20-dione 21-acetate
• Pregna-1,20-dione, 11.beta.,17,21-trihydroxy-, 21-acetate
• Prednisolone acetate, British Pharmacopoeia (BP) Reference Standard
• Prednisolone acetate, European Pharmacopoeia (EP) Reference Standard
• (11beta)-11,17-dihydroxy-3,20-dioxopregna-1,4-dien-21-yl acetate
• 11.BETA.,17-DIHYDROXY-3,20-DIOXOPREGNA-1,4-DIEN-21-YL ACETATE
• Prednisolone acetate, United States Pharmacopeia (USP) Reference Standard
• Pregna-1,20-dione, 21-(acetyloxy)-11,17-dihydroxy-, (11.beta.)-
• Prednisolone acetate for peak identification, European Pharmacopoeia (EP) Reference Standard
• Prednisolone Acetate, Pharmaceutical Secondary Standard; Certified Reference Material
• [2-[(8S,9S,10R,11S,13S,14S,17R)-10,13-dimethyl-11,17-bis(oxidanyl)-3-oxidanylidene-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxidanylidene-ethyl] ethanoate
• 2-[(1R,3aS,3bS,9aR,9bS,10S,11aS)-1,10-dihydroxy-9a,11a-dimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]-2-oxoethyl acetate
• acetic acid [2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9900	99.00%
Caco-2	-	0.7333	73.33%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	+	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8935	89.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6329	63.29%
BSEP inhibitior	+	0.9926	99.26%
P-glycoprotein inhibitior	-	0.6232	62.32%
P-glycoprotein substrate	-	0.7495	74.95%
CYP3A4 substrate	+	0.7827	78.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9170	91.70%
CYP3A4 inhibition	-	0.8459	84.59%
CYP2C9 inhibition	-	0.9104	91.04%
CYP2C19 inhibition	-	0.9384	93.84%
CYP2D6 inhibition	-	0.9564	95.64%
CYP1A2 inhibition	-	0.9032	90.32%
CYP2C8 inhibition	+	0.7118	71.18%
CYP inhibitory promiscuity	-	0.9196	91.96%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6534	65.34%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.9708	97.08%
Skin irritation	+	0.7632	76.32%
Skin corrosion	-	0.9590	95.90%
Ames mutagenesis	-	0.9079	90.79%
Human Ether-a-go-go-Related Gene inhibition	+	0.7382	73.82%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7342	73.42%
skin sensitisation	-	0.9448	94.48%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8936	89.36%
Acute Oral Toxicity (c)	IV	0.6181	61.81%
Estrogen receptor binding	+	0.9102	91.02%
Androgen receptor binding	+	0.8961	89.61%
Thyroid receptor binding	-	0.7155	71.55%
Glucocorticoid receptor binding	+	0.9208	92.08%
Aromatase binding	+	0.8688	86.88%
PPAR gamma	-	0.7544	75.44%
Honey bee toxicity	-	0.7631	76.31%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9950	99.50%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	25.1 nM; 25.1 nM; 25.1 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.74%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	97.48%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.56%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.36%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	90.86%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.06%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.36%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.77%	98.95%
CHEMBL1871	P10275	Androgen Receptor	88.63%	96.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.28%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.28%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.22%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.12%	95.56%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	87.04%	89.05%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.85%	96.38%
CHEMBL1937	Q92769	Histone deacetylase 2	82.48%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.87%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.50%	94.00%

Plants that contains it

• Rehmannia glutinosa

Cross-Links

• PubChem: 5834
• NPASS: NPC44063
• ChEMBL: CHEMBL1152
• LOTUS: LTS0134274
• wikiData: Q27108063