Prednisolone acetate

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatEye inflammationCombination Product in combination with: Sulfacetamide (DB00634)•••••••••••••••• •• ••••••••• •••••• ••••••••••••••••••• • •••••
Used in combination to treatEye inflammationCombination Product in combination with: Sulfacetamide (DB00634)••••••••••••••••••••••• •••••• •••••••••••••••••••• • •••••
Treatment ofInflammation••••••••••••
Management ofInflammatory conditions••••••••••••
Used in combination to treatOcular infections, irritations and inflammationsCombination Product in combination with: Gatifloxacin (DB01044)••••••••••••••••••
Contraindications & Blackbox Warnings
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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

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Humans
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

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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
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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.
DrugInteraction
AbametapirThe serum concentration of Prednisolone acetate can be increased when it is combined with Abametapir.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Prednisolone acetate.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Prednisolone acetate.
AcarboseThe risk or severity of hyperglycemia can be increased when Prednisolone acetate is combined with Acarbose.
AceclofenacThe 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

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ak Tate Oph Sus 1%Suspension1 %OphthalmicSandoz S.P.A.1985-12-312008-08-07Canada flag
Diopred Suspension 1%Suspension1 %OphthalmicSandoz S.P.A.1994-12-312024-07-31Canada flag
EconopredSuspension1.25 mg/1OphthalmicALCON LABORATORIES, INC.2006-09-13Not applicableUS flag
EconopredSuspension10 mg/10mLOphthalmicPhysicians Total Care, Inc.1994-05-052011-05-31US flag
EconopredSuspension10 mg/1mgOphthalmicALCON LABORATORIES, INC.1973-07-102007-12-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Prednisolone AcetateSuspension / drops10 mg/1mLOphthalmicA-S Medication Solutions1997-08-19Not applicableUS flag
Prednisolone AcetateSuspension10 mg/1mLOphthalmicPhysicians Total Care, Inc.2002-11-04Not applicableUS flag
Prednisolone AcetateSuspension / drops10 mg/1mLOphthalmicRedPharm Drug, Inc.1997-08-19Not applicableUS flag
Prednisolone AcetateSuspension / drops10 mg/1mLOphthalmicA-S Medication Solutions1997-08-19Not applicableUS flag
Prednisolone AcetateSuspension / drops10 mg/1mLOphthalmicLupin Pharmaceuticals, Inc.2024-10-01Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BlephamidePrednisolone acetate (2 mg/1g) + Sulfacetamide sodium (100 mg/1g)OintmentOphthalmicAllergan, Inc.1987-01-01Not applicableUS flag
BlephamidePrednisolone acetate (2 mg/1g) + Sulfacetamide sodium (100 mg/1g)OintmentOphthalmicA-S Medication Solutions1987-01-01Not applicableUS flag
BlephamidePrednisolone acetate (2 mg/1g) + Sulfacetamide sodium (100 mg/1g)OintmentOphthalmicPhysicians Total Care, Inc.2012-03-04Not applicableUS flag
BlephamidePrednisolone acetate (2 mg/1mL) + Sulfacetamide sodium (100 mg/1mL)Suspension / dropsOphthalmicAllergan, Inc.1961-10-01Not applicableUS flag
BlephamidePrednisolone acetate (2 mg/1mL) + Sulfacetamide sodium (100 mg/1mL)Suspension / dropsOphthalmicPhysicians Total Care, Inc.1961-10-01Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Ixoba MPrednisolone acetate (10 mg/1mL) + Ketorolac tromethamine (5 mg/1mL) + Moxifloxacin hydrochloride monohydrate (5 mg/1mL)KitOphthalmicBrisk Pharmaceuticals, Inc.2021-08-26Not applicableUS flag
Pred-BromPrednisolone acetate (10 mg/1mL) + Bromfenac (0.75 mg/1mL)Suspension / dropsOphthalmicImprimisRx NJ2018-02-01Not applicableUS flag
Pred-BromPrednisolone acetate (10 mg/1mL) + Bromfenac sodium (0.75 mg/1mL)Suspension / dropsOphthalmicImprimis Njof, Llc2018-01-05Not applicableUS flag
Pred-GatiPrednisolone acetate (10 mg/1mL) + Gatifloxacin sesquihydrate (5 mg/1mL)Suspension / dropsOphthalmicImprimis Njof, Llc2018-01-052019-07-01US flag
Pred-GatiPrednisolone acetate (10 mg/1mL) + Gatifloxacin hemihydrate (5 mg/1mL)SuspensionOphthalmicImprimisRx NJ2018-03-01Not applicableUS flag

Categories

Drug Categories
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
  1. 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]
  2. 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]
  3. 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]
  4. Yasir M, Sonthalia S: Corticosteroid Adverse Effects . [Article]
  5. FDA Approved Drug Products: Prednisolone Acetate Oral Suspension [Link]
  6. FDA Approved Drug Products: Prednisolone Acetate Ophthalmic Suspension [Link]
  7. FDA Approved Drug Products: Prednisolone Acetate Ophthalmic Suspension 1% [Link]
  8. Greenstone LLC: Prednisolone Acetate Ophthalmic Suspension MSDS [Link]
KEGG Compound
C08180
PubChem Compound
5834
ChemSpider
5629
ChEBI
8380
ChEMBL
CHEMBL1152
ZINC
ZINC000003875348
Wikipedia
Prednisolone_acetate

Clinical Trials

Clinical Trials
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Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableActive Not RecruitingTreatmentLumbar Discogenic Pain (Disorder)1somestatusstop reasonjust information to hide
Not AvailableCompletedPreventionEpiretinal Membranes1somestatusstop reasonjust information to hide
Not AvailableCompletedTreatmentGlaucoma1somestatusstop reasonjust information to hide
Not AvailableTerminatedTreatmentOpen Angle Glaucoma (OAG)1somestatusstop reasonjust information to hide
Not AvailableUnknown StatusTreatmentCataracts / Ocular Hypertension / Ocular Inflammation / Post-Op Complications1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
OintmentOphthalmic
Solution / dropsOphthalmic
OintmentOphthalmic; Topical
SuspensionOphthalmic1.25 mg/1
SuspensionOphthalmic10 mg/1mg
SuspensionOphthalmic10 mg/10mL
SuspensionOphthalmic1 %
SuspensionOral16.7 mg/5mL
SuspensionOral5 mg/5mL
KitOphthalmic
SolutionOphthalmic
Suspension / dropsOphthalmic
Suspension / dropsOphthalmic1 %
SolutionOphthalmic10 mg/ml
SuspensionOphthalmic1 % w/v
Solution / dropsOphthalmic0.12 %
Suspension / dropsOphthalmic1.2 mg/1mL
SuspensionOphthalmic10.000 mg
SuspensionOphthalmic
SuspensionConjunctival; Ophthalmic1000000 mg
SuspensionOphthalmic1.2 mg
Suspension / dropsOphthalmic10 mg/ml
SuspensionOphthalmic10 mg/1mL
Suspension / dropsOphthalmic10 mg/1
Suspension / dropsOphthalmic10 mg/1mL
InjectionIntra-articular; Intramuscular25 mg/ml
Injection, suspensionIntramuscular
SuspensionConjunctival; Ophthalmic10 mg
SuspensionOphthalmic0.12 %
SuspensionOphthalmic10 mg
SuspensionOphthalmic10.0000 mg
SuspensionOphthalmic1000000 mg
SuspensionOphthalmic1.2 mg
Solution / dropsOphthalmic0.5 %
Solution, gel forming / dropsIntraocular0.5 g
SuspensionConjunctival; Ophthalmic
SuspensionConjunctival; Ophthalmic5 mg
SuspensionIntraocular; Ophthalmic
LiquidOphthalmic10 mg/1ml
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7799331No2010-09-212028-10-11US flag
US6071523No2000-06-062018-06-03US flag
US6399079No2002-06-042018-06-03US flag
US5881926No1999-03-162016-03-16US flag
US6656482No2003-12-022018-06-03US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)238ChemSpider
logP1.332ChemSpider
Predicted Properties
PropertyValueSource
Water Solubility0.0417 mg/mLALOGPS
logP2.17ALOGPS
logP1.71Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)12.61Chemaxon
pKa (Strongest Basic)-2.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area100.9 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity107.64 m3·mol-1Chemaxon
Polarizability42.93 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-000i-0797000000-836ba07555e28d36300f
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-00dj-2950000000-e2793b767fd6fd52b223
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0797000000-836ba07555e28d36300f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00dj-2950000000-e2793b767fd6fd52b223
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f9i-0019200000-95c380920a55764fab5d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0k96-9104400000-f69d937affa03380d2cf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gw3-0879200000-7afd20339a4cada1cb23
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9007100000-10862352a1c548ab8a61
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pba-9063000000-e3c9dc37563eb39ef5f0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0229-0922000000-1073d2960d78897860ec
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-205.3036396
predicted
DarkChem Lite v0.1.0
[M-H]-197.31555
predicted
DeepCCS 1.0 (2019)
[M+H]+205.0126396
predicted
DarkChem Lite v0.1.0
[M+H]+199.21097
predicted
DeepCCS 1.0 (2019)
[M+Na]+204.6210396
predicted
DarkChem Lite v0.1.0
[M+Na]+205.86543
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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
  1. 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]
  2. 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
Substrate
Inducer
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
  1. 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]
  2. 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]
  3. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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
  1. 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
  1. 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
  1. 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]
  2. 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