Prednisolone acetate
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Identification
- Summary
Prednisolone acetate is a glucocorticoid used to treat a wide variety of endocrine, inflammatory, and immune conditions as well as for palliation of neoplastic conditions.
- Brand Names
- Blephamide, Econopred Plus, Flo-pred, Pred Forte, Pred Mild, Pred-G
- Generic Name
- Prednisolone acetate
- DrugBank Accession Number
- DB15566
- Background
Prednisolone acetate is a prednisolone molecule bound to an acetate functional group by an ester bond.5
Prednisolone acetate was granted FDA approval in 1955.5
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
- Weight
- Average: 402.4807
Monoisotopic: 402.204238692 - Chemical Formula
- C23H30O6
- Synonyms
- Prednisolone acetate
Pharmacology
- Indication
Prednisolone acetate is indicated as an anti-inflammatory or immunosuppressive agent for allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, or infectious conditions.5 Prednisolone acetate is also indicated in organ transplant patients, as well as endocrine or neoplastic conditions.5
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Eye inflammation Combination Product in combination with: Sulfacetamide (DB00634) •••••••••••• •••• •• ••••••••• •••••• ••••••••• •••••••••• • ••••• Used in combination to treat Eye inflammation Combination Product in combination with: Sulfacetamide (DB00634) •••••••••••• ••••••••••• •••••• •••••••••• •••••••••• • ••••• Treatment of Inflammation •••••••••••• Management of Inflammatory conditions •••••••••••• Used in combination to treat Ocular infections, irritations and inflammations Combination Product in combination with: Gatifloxacin (DB01044) •••••••••••• •••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals.4 Prednisolone acetate has a short duration of action as the half life is 2-3 hours.5 Corticosteroids have a wide therapeutic window as patients make require doses that are multiples of what the body naturally produces.4 Patients taking corticosteroids should be counselled regarding the risk of hypothalamic-pituitary-adrenal axis suppression and increased susceptibility to infections.4
- Mechanism of action
The short term effects of corticosteroids are decreased vasodilation and permeability of capillaries, as well as decreased leukocyte migration to sites of inflammation.4 Corticosteroids binding to the glucocorticoid receptor mediates changes in gene expression that lead to multiple downstream effects over hours to days.4
Glucocorticoids inhibit neutrophil apoptosis and demargination; they inhibit phospholipase A2, which decreases the formation of arachidonic acid derivatives; they inhibit NF-Kappa B and other inflammatory transcription factors; they promote anti-inflammatory genes like interleukin-10.4
Lower doses of corticosteroids provide an anti-inflammatory effect, while higher doses are immunosuppressive.4 High doses of glucocorticoids for an extended period bind to the mineralocorticoid receptor, raising sodium levels and decreasing potassium levels.4
Target Actions Organism AGlucocorticoid receptor agonistHumans - Absorption
Prednisolone acetate oral suspension given at a dose equivalent to 15mg prednisolone has a Cmax of 321.1ng/hr, a Tmaxof 1-2 hours, and an AUC of 1999.4ng*hr/mL.5 The absorption pharmacokinetics of prednisolone acetate are not significantly different from a comparable dose of prednisolone.5
- Volume of distribution
The volume of distribution of the active metabolite, prednisolone, is 0.22/0.7L/kg.5
- Protein binding
The active metabolite, prednisolone, is 70-90% protein bound in plasma.5
- Metabolism
Prednisolone acetate undergoes ester hydrolysis to prednisolone.1 After this step, the drug undergoes the normal metabolism of prednisolone.
Prednisolone can be reversibly metabolized to prednisone which is then metabolized to 17α,21-dihydroxy-pregnan-1,4,6-trien-3,11,30-trione (M-XVII), 20α-dihydro-prednisone (M-V), 6βhydroxy-prednisone (M-XII), 6α-hydroxy-prednisone (M-XIII), or 20β-dihydro-prednisone (M-IV).2 20β-dihydro-prednisone is metabolized to 17α,20ξ,21-trihydroxy-5ξ-pregn-1-en-3,11-dione(M-XVIII).2 Prednisolone is metabolized to Δ6-prednisolone (M-XI), 20α-dihydro-prednisolone (M-III), 20β-dihydro-prednisolone (M-II), 6αhydroxy-prednisolone (M-VII), or 6βhydroxy-prednisolone(M-VI).2 6αhydroxy-prednisolone is metabolized to 6α,11β,17α,20β,21-pentahydroxypregnan-1,4-diene-3-one (M-X).2 6βhydroxy-prednisolone is metabolized to 6β,11β,17α,20β,21-pentahydroxypregnan-1,4-diene-3-one (M-VIII), 6β,11β,17α,20α,21-pentahydroxypregnan-1,4-diene-3-one (M-IX), and 6β,11β,17α,21-tetrahydroxy-5ξ-pregn-1-en-3,20-dione (M-XIV).2 MVIII is metabolized to 6β,11β,17α,20β,21-pentahydroxy-5ξ-pregn-1-en-3-one (M-XV) and then to MXIV, while MIX is metabolized to 6β,11β,17α,20α,21-pentahydroxy-5ξ-pregn-1-en-3-one (M-XVI) and then to MXIV.2 These metabolites and their glucuronide conjugates are excreted predominantly in the urine.2,5
Hover over products below to view reaction partners
- Route of elimination
Prednisolone acetate is predominantly excreted in the urine.5
- Half-life
Oral prednisolone acetate has a plasma half life of 2-3 hours.5
- Clearance
Data regarding the clearance of prednisolone acetate is not readily available.6,7,8
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
The oral LD50 of prednisolone acetate in mice is 1680 mg/kg.8 Patients experiencing an overdose of oral prednisolone acetate may experience an increased severity in the adverse effects of corticosteroids.5 Overdose of oral prednisolone acetate may be treated by gastric lavage or inducing vomiting if the overdose was recent, as well as supportive and symptomatic therapy.5 Chronic overdosage may be treated by dose reduction or treating patients on alternate days.5 An overdose by the ophthalmic route is not expected to cause problems.5
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Prednisolone acetate can be increased when it is combined with Abametapir. Abemaciclib The metabolism of Abemaciclib can be increased when combined with Prednisolone acetate. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Prednisolone acetate. Acarbose The risk or severity of hyperglycemia can be increased when Prednisolone acetate is combined with Acarbose. Aceclofenac The risk or severity of gastrointestinal irritation can be increased when Prednisolone acetate is combined with Aceclofenac. - Food Interactions
- Avoid excessive or chronic alcohol consumption. Alcohol may cause gastric irritation.
- Take with food. Food reduces gastrointestinal irritation.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ak Tate Oph Sus 1% Suspension 1 % Ophthalmic Sandoz S.P.A. 1985-12-31 2008-08-07 Canada Diopred Suspension 1% Suspension 1 % Ophthalmic Sandoz S.P.A. 1994-12-31 2024-07-31 Canada Econopred Suspension 1.25 mg/1 Ophthalmic ALCON LABORATORIES, INC. 2006-09-13 Not applicable US Econopred Suspension 10 mg/10mL Ophthalmic Physicians Total Care, Inc. 1994-05-05 2011-05-31 US Econopred Suspension 10 mg/1mg Ophthalmic ALCON LABORATORIES, INC. 1973-07-10 2007-12-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Prednisolone Acetate Suspension / drops 10 mg/1mL Ophthalmic A-S Medication Solutions 1997-08-19 Not applicable US Prednisolone Acetate Suspension 10 mg/1mL Ophthalmic Physicians Total Care, Inc. 2002-11-04 Not applicable US Prednisolone Acetate Suspension / drops 10 mg/1mL Ophthalmic RedPharm Drug, Inc. 1997-08-19 Not applicable US Prednisolone Acetate Suspension / drops 10 mg/1mL Ophthalmic A-S Medication Solutions 1997-08-19 Not applicable US Prednisolone Acetate Suspension / drops 10 mg/1mL Ophthalmic Lupin Pharmaceuticals, Inc. 2024-10-01 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Blephamide Prednisolone acetate (2 mg/1g) + Sulfacetamide sodium (100 mg/1g) Ointment Ophthalmic Allergan, Inc. 1987-01-01 Not applicable US Blephamide Prednisolone acetate (2 mg/1g) + Sulfacetamide sodium (100 mg/1g) Ointment Ophthalmic A-S Medication Solutions 1987-01-01 Not applicable US Blephamide Prednisolone acetate (2 mg/1g) + Sulfacetamide sodium (100 mg/1g) Ointment Ophthalmic Physicians Total Care, Inc. 2012-03-04 Not applicable US Blephamide Prednisolone acetate (2 mg/1mL) + Sulfacetamide sodium (100 mg/1mL) Suspension / drops Ophthalmic Allergan, Inc. 1961-10-01 Not applicable US Blephamide Prednisolone acetate (2 mg/1mL) + Sulfacetamide sodium (100 mg/1mL) Suspension / drops Ophthalmic Physicians Total Care, Inc. 1961-10-01 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Ixoba M Prednisolone acetate (10 mg/1mL) + Ketorolac tromethamine (5 mg/1mL) + Moxifloxacin hydrochloride monohydrate (5 mg/1mL) Kit Ophthalmic Brisk Pharmaceuticals, Inc. 2021-08-26 Not applicable US Pred-Brom Prednisolone acetate (10 mg/1mL) + Bromfenac (0.75 mg/1mL) Suspension / drops Ophthalmic ImprimisRx NJ 2018-02-01 Not applicable US Pred-Brom Prednisolone acetate (10 mg/1mL) + Bromfenac sodium (0.75 mg/1mL) Suspension / drops Ophthalmic Imprimis Njof, Llc 2018-01-05 Not applicable US Pred-Gati Prednisolone acetate (10 mg/1mL) + Gatifloxacin sesquihydrate (5 mg/1mL) Suspension / drops Ophthalmic Imprimis Njof, Llc 2018-01-05 2019-07-01 US Pred-Gati Prednisolone acetate (10 mg/1mL) + Gatifloxacin hemihydrate (5 mg/1mL) Suspension Ophthalmic ImprimisRx NJ 2018-03-01 Not applicable US
Categories
- Drug Categories
- Adrenal Cortex Hormones
- Anti-Inflammatory Agents
- Corticosteroids
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Substrates
- Fused-Ring Compounds
- P-glycoprotein substrates
- Pregnadienes
- Pregnadienetriols
- Pregnanes
- Prodrugs
- Steroids
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Pregnane steroids
- Direct Parent
- Gluco/mineralocorticoids, progestogins and derivatives
- Alternative Parents
- 20-oxosteroids / 3-oxo delta-1,4-steroids / 17-hydroxysteroids / 11-beta-hydroxysteroids / Delta-1,4-steroids / Alpha-acyloxy ketones / Tertiary alcohols / Alpha-hydroxy ketones / Secondary alcohols / Cyclic ketones show 5 more
- Substituents
- 11-beta-hydroxysteroid / 11-hydroxysteroid / 17-hydroxysteroid / 20-oxosteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Alpha-acyloxy ketone / Alpha-hydroxy ketone show 17 more
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- corticosteroid hormone (CHEBI:8380)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 8B2807733D
- CAS number
- 52-21-1
- InChI Key
- LRJOMUJRLNCICJ-JZYPGELDSA-N
- 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
- IUPAC Name
- 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
- SMILES
- [H][C@@]12CC[C@](O)(C(=O)COC(C)=O)[C@@]1(C)C[C@]([H])(O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
References
- General References
- Musson DG, Bidgood AM, Olejnik O: Assay methodology for prednisolone, prednisolone acetate and prednisolone sodium phosphate in rabbit aqueous humor and ocular physiological solutions. J Chromatogr. 1991 Apr 19;565(1-2):89-102. doi: 10.1016/0378-4347(91)80373-k. [Article]
- Matabosch X, Pozo OJ, Perez-Mana C, Papaseit E, Segura J, Ventura R: Detection and characterization of prednisolone metabolites in human urine by LC-MS/MS. J Mass Spectrom. 2015 Mar;50(3):633-42. doi: 10.1002/jms.3571. [Article]
- Doppenschmitt SA, Scheidel B, Harrison F, Surmann JP: Simultaneous determination of prednisolone, prednisolone acetate and hydrocortisone in human serum by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1995 Dec 15;674(2):237-46. doi: 10.1016/0378-4347(95)00317-7. [Article]
- Yasir M, Sonthalia S: Corticosteroid Adverse Effects . [Article]
- FDA Approved Drug Products: Prednisolone Acetate Oral Suspension [Link]
- FDA Approved Drug Products: Prednisolone Acetate Ophthalmic Suspension [Link]
- FDA Approved Drug Products: Prednisolone Acetate Ophthalmic Suspension 1% [Link]
- Greenstone LLC: Prednisolone Acetate Ophthalmic Suspension MSDS [Link]
- External Links
- KEGG Compound
- C08180
- PubChem Compound
- 5834
- ChemSpider
- 5629
- ChEBI
- 8380
- ChEMBL
- CHEMBL1152
- ZINC
- ZINC000003875348
- Wikipedia
- Prednisolone_acetate
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Treatment Lumbar Discogenic Pain (Disorder) 1 somestatus stop reason just information to hide Not Available Completed Prevention Epiretinal Membranes 1 somestatus stop reason just information to hide Not Available Completed Treatment Glaucoma 1 somestatus stop reason just information to hide Not Available Terminated Treatment Open Angle Glaucoma (OAG) 1 somestatus stop reason just information to hide Not Available Unknown Status Treatment Cataracts / Ocular Hypertension / Ocular Inflammation / Post-Op Complications 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Ointment Ophthalmic Solution / drops Ophthalmic Ointment Ophthalmic; Topical Suspension Ophthalmic 1.25 mg/1 Suspension Ophthalmic 10 mg/1mg Suspension Ophthalmic 10 mg/10mL Suspension Ophthalmic 1 % Suspension Oral 16.7 mg/5mL Suspension Oral 5 mg/5mL Kit Ophthalmic Solution Ophthalmic Suspension / drops Ophthalmic Suspension / drops Ophthalmic 1 % Solution Ophthalmic 10 mg/ml Suspension Ophthalmic 1 % w/v Solution / drops Ophthalmic 0.12 % Suspension / drops Ophthalmic 1.2 mg/1mL Suspension Ophthalmic 10.000 mg Suspension Ophthalmic Suspension Conjunctival; Ophthalmic 1000000 mg Suspension Ophthalmic 1.2 mg Suspension / drops Ophthalmic 10 mg/ml Suspension Ophthalmic 10 mg/1mL Suspension / drops Ophthalmic 10 mg/1 Suspension / drops Ophthalmic 10 mg/1mL Injection Intra-articular; Intramuscular 25 mg/ml Injection, suspension Intramuscular Suspension Conjunctival; Ophthalmic 10 mg Suspension Ophthalmic 0.12 % Suspension Ophthalmic 10 mg Suspension Ophthalmic 10.0000 mg Suspension Ophthalmic 1000000 mg Suspension Ophthalmic 1.2 mg Solution / drops Ophthalmic 0.5 % Solution, gel forming / drops Intraocular 0.5 g Suspension Conjunctival; Ophthalmic Suspension Conjunctival; Ophthalmic 5 mg Suspension Intraocular; Ophthalmic Liquid Ophthalmic 10 mg/1ml - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7799331 No 2010-09-21 2028-10-11 US US6071523 No 2000-06-06 2018-06-03 US US6399079 No 2002-06-04 2018-06-03 US US5881926 No 1999-03-16 2016-03-16 US US6656482 No 2003-12-02 2018-06-03 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 238 ChemSpider logP 1.332 ChemSpider - Predicted Properties
Property Value Source Water Solubility 0.0417 mg/mL ALOGPS logP 2.17 ALOGPS logP 1.71 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 12.61 Chemaxon pKa (Strongest Basic) -2.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 100.9 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 107.64 m3·mol-1 Chemaxon Polarizability 42.93 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 205.3036396 predictedDarkChem Lite v0.1.0 [M-H]- 197.31555 predictedDeepCCS 1.0 (2019) [M+H]+ 205.0126396 predictedDarkChem Lite v0.1.0 [M+H]+ 199.21097 predictedDeepCCS 1.0 (2019) [M+Na]+ 204.6210396 predictedDarkChem Lite v0.1.0 [M+Na]+ 205.86543 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor for glucocorticoids (GC) (PubMed:27120390, PubMed:37478846). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modulator of other transcription factors (PubMed:28139699). Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Involved in chromatin remodeling (PubMed:9590696). Plays a role in rapid mRNA degradation by binding to the 5' UTR of target mRNAs and interacting with PNRC2 in a ligand-dependent manner which recruits the RNA helicase UPF1 and the mRNA-decapping enzyme DCP1A, leading to RNA decay (PubMed:25775514). Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth (By similarity)
- Specific Function
- core promoter sequence-specific DNA binding
- Gene Name
- NR3C1
- Uniprot ID
- P04150
- Uniprot Name
- Glucocorticoid receptor
- Molecular Weight
- 85658.57 Da
References
- Ikonomidis I, Tzortzis S, Lekakis J, Paraskevaidis I, Andreadou I, Nikolaou M, Kaplanoglou T, Katsimbri P, Skarantavos G, Soucacos P, Kremastinos DT: Lowering interleukin-1 activity with anakinra improves myocardial deformation in rheumatoid arthritis. Heart. 2009 Sep;95(18):1502-7. doi: 10.1136/hrt.2009.168971. Epub 2009 May 28. [Article]
- Boudinot FD, D'Ambrosio R, Jusko WJ: Receptor-mediated pharmacodynamics of prednisolone in the rat. J Pharmacokinet Biopharm. 1986 Oct;14(5):469-93. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Usui T, Saitoh Y, Komada F: Induction of CYP3As in HepG2 cells by several drugs. Association between induction of CYP3A4 and expression of glucocorticoid receptor. Biol Pharm Bull. 2003 Apr;26(4):510-7. doi: 10.1248/bpb.26.510. [Article]
- Pichard L, Fabre I, Daujat M, Domergue J, Joyeux H, Maurel P: Effect of corticosteroids on the expression of cytochromes P450 and on cyclosporin A oxidase activity in primary cultures of human hepatocytes. Mol Pharmacol. 1992 Jun;41(6):1047-55. [Article]
- Litt J. (2016). Litt's Drug eruption & reaction manual (22nd ed.). CRC Press LLc.
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species
- Specific Function
- serine-type endopeptidase inhibitor activity
- Gene Name
- SERPINA6
- Uniprot ID
- P08185
- Uniprot Name
- Corticosteroid-binding globulin
- Molecular Weight
- 45140.49 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Frey BM, Frey FJ: Estimation of transcortin concentration by measurements of plasma protein-binding of prednisolone and by electroimmunodiffusion. Br J Clin Pharmacol. 1982 Feb;13(2):245-9. [Article]
- Ko HC, Almon RR, Jusko WJ: Effect of corticosteroid binding globulin on the pharmacokinetics of prednisolone in rats. Pharm Res. 1995 Jun;12(6):902-4. [Article]
- Angeli A, Frajria R, De Paoli R, Fonzo D, Ceresa F: Diurnal variation of prednisolone binding to serum corticosteroid-binding globulin in man. Clin Pharmacol Ther. 1978 Jan;23(1):47-53. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- Czock D, Keller F, Rasche FM, Haussler U: Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids. Clin Pharmacokinet. 2005;44(1):61-98. doi: 10.2165/00003088-200544010-00003. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Na(+)-independent transporter that mediates the cellular uptake of a broad range of organic anions such as the endogenous bile salts cholate and deoxycholate, either in their unconjugated or conjugated forms (taurocholate and glycocholate), at the plasmam membrane (PubMed:19129463, PubMed:7557095). Responsible for intestinal absorption of bile acids (By similarity). Transports dehydroepiandrosterone 3-sulfate (DHEAS), a major circulating steroid secreted by the adrenal cortex, as well as estrone 3-sulfate and 17beta-estradiol 17-O-(beta-D-glucuronate) (PubMed:11159893, PubMed:12568656, PubMed:19129463, PubMed:23918469, PubMed:25560245, PubMed:9539145). Mediates apical uptake of all-trans-retinol (atROL) across human retinal pigment epithelium, which is essential to maintaining the integrity of the visual cycle and thus vision (PubMed:25560245). Involved in the uptake of clinically used drugs (PubMed:17301733, PubMed:20686826, PubMed:27777271). Capable of thyroid hormone transport (both T3 or 3,3',5'-triiodo-L-thyronine, and T4 or L-tyroxine) (PubMed:19129463, PubMed:20358049). Also transports prostaglandin E2 (PubMed:19129463). Plays roles in blood-brain and -cerebrospinal fluid barrier transport of organic anions and signal mediators, and in hormone uptake by neural cells (By similarity). May also play a role in the reuptake of neuropeptides such as substance P/TAC1 and vasoactive intestinal peptide/VIP released from retinal neurons (PubMed:25132355). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drugs methotrexate and paclitaxel (PubMed:23243220). Shows a pH-sensitive substrate specificity which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
- Specific Function
- bile acid transmembrane transporter activity
- Gene Name
- SLCO1A2
- Uniprot ID
- P46721
- Uniprot Name
- Solute carrier organic anion transporter family member 1A2
- Molecular Weight
- 74144.105 Da
References
- Bossuyt X, Muller M, Hagenbuch B, Meier PJ: Polyspecific drug and steroid clearance by an organic anion transporter of mammalian liver. J Pharmacol Exp Ther. 1996 Mar;276(3):891-6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [Article]
- Yates CR, Chang C, Kearbey JD, Yasuda K, Schuetz EG, Miller DD, Dalton JT, Swaan PW: Structural determinants of P-glycoprotein-mediated transport of glucocorticoids. Pharm Res. 2003 Nov;20(11):1794-803. [Article]
Drug created at October 23, 2019 21:18 / Updated at October 10, 2024 12:49