Abiraterone

Identification

Summary

Abiraterone is an antiandrogen used in the treatment of metastatic castration-resistant prostate cancer and metastatic high-risk castration-sensitive prostate cancer.

Brand Names
Yonsa, Zytiga
Generic Name
Abiraterone
DrugBank Accession Number
DB05812
Background

Abiraterone is a potent, irreversible, and selective inhibitor of 17 αhydroxylase/C17,20-lyase (CYP17), an enzyme expressed in testicular, adrenal, and prostatic tumour tissues, to regulate androgen biosynthesis.2,7,9 Abiraterone was first approved by the FDA and EMA on April,7 July,14 and September 2011,7 respectively. It is used to treat metastatic castration-resistant prostate cancer and hormone-sensitive high-risk metastatic prostate cancer.9,10,13,14

As abiraterone has poor oral bioavailability and is susceptible to hydrolysis by esterases, abiraterone acetate was developed as an orally bioavailable prodrug with enhanced stability and absorption.2,4

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 349.509
Monoisotopic: 349.240564619
Chemical Formula
C24H31NO
Synonyms
  • (3β)-17-(pyridin-3-yl)androsta-5,16-dien-3-ol
  • 17-(3-Pyridyl)androsta-5,16-dien-3beta-ol
  • Abiraterona
  • Abiraterone
External IDs
  • CB 7598
  • CB-7598
  • CB7598

Pharmacology

Indication

Abiraterone is indicated for the treatment of metastatic castration-resistant prostate cancer (mCRPC) in combination with methylprednisolone 9 or prednisone.10,13,14

In Europe and Canada, it is also used in patients with mCRPC who are asymptomatic or mildly symptomatic after the failure of androgen deprivation therapy for whom chemotherapy is not yet clinically indicated.13,14 In Europe, it is used in patients whose disease has progressed on or after a docetaxel-based chemotherapy regimen.13 In Canada, it is used in patients who have received prior chemotherapy containing docetaxel after the failure of androgen deprivation therapy.14

Abiraterone is indicated in combination with prednisone for the treatment of metastatic high-risk castration-sensitive prostate cancer (CSPC).10 In Europe and Canada, it may also be used in combination with prednisolone and androgen deprivation therapy in newly diagnosed patients.13,14

In Canada and the US, abiraterone is also available in a combination product with niraparib, which is indicated with prednisone for the treatment of adults with deleterious or suspected deleterious BRCA-mutated (BRCAm) mCRPC.11,15 In Canada, this combination product is also used with prednisolone and is reserved for patients who are asymptomatic or mildly symptomatic, and in whom chemotherapy is not clinically indicated.11

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatMetastatic castration sensitive prostate cancerRegimen in combination with: Prednisone (DB00635)•••••••••••••••• •••• •••••••• ••••••
Used in combination to treatMetastatic castration-resistant prostate cancerRegimen in combination with: Prednisone (DB00635)•••••••••••••••••••• ••••••••• •••••••••• •••••••• ••••••••••• ••••••• •••••••
Used in combination to treatMetastatic castration-resistant prostate cancerRegimen in combination with: Prednisone (DB00635)••••••••••••••••••• ••••••••••• ••••• •••••••• •••••••••• •••••••• ••••••••• •••••••••
Used in combination to treatMetastatic castration-resistant prostate cancerRegimen in combination with: Prednisone (DB00635), Prednisolone (DB00860)••••••••••••••••••• ••••••••••• ••••• •••••••• •••••••••• •••••••• ••••••••• •••••••••
Used in combination to treatMetastatic castration-resistant prostate cancerRegimen in combination with: Prednisone (DB00635)••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

In vivo, abiraterone acetate is rapidly hydrolyzed to abiraterone, which mediates its pharmacological actions.1 Abiraterone decreases serum testosterone and other androgens. A change in serum prostate-specific antigen (PSA) levels may be observed.9

Mechanism of action

17α-hydroxylase/C17,20-lyase (CYP17) is a key enzyme in androgen biosynthesis. It is primarily expressed in testicular, adrenal, and prostatic tumours. CYP17 catalyzes the 17α-hydroxylation of pregnenolone and progesterone to their 17α-hydroxy derivative, followed by subsequent cleavage of the C 20,21-acetyl group to yield dehydroepiandrosterone (DHEA) and androstenedione. DHEA and androstenedione are precursors of testosterone.5,9 Aberrant androgen levels and unregulated androgen receptor signalling have been implicated in the development and progression of various prostate cancers.6 Androgen-sensitive prostatic carcinoma responds to treatment that decreases androgen levels. Androgen deprivation therapies, such as treatment with GnRH agonists or orchiectomy, decrease androgen production in the testes but do not affect androgen production by the adrenals or in the tumour.1,9

Abiraterone inhibits CYP17 to block androgen production. Inhibition of CYP17 can also result in increased mineralocorticoid production by the adrenals.9

TargetActionsOrganism
ASteroid 17-alpha-hydroxylase/17,20 lyase
inhibitor
Humans
Absorption

Geometric mean (± SD) Cmax was 73 (± 44) ng/mL and AUC0-∞ was 373 (± 249) ng x hr/mL following a single dose of 500 mg abiraterone acetate in overnight-fasted healthy subjects. Dose proportionality was observed in single doses of abiraterone acetate ranging from 125 mg to 625 mg.9 A group of patients with mCRPC received a daily dose of 1,000 mg: at steady-state, the mean (± SD) Cmax was 226 (± 178) ng/mL and AUC was 993 (± 639) ng x hr/mL.10

Following oral administration of abiraterone acetate to patients with metastatic castration-resistant prostate cancer, the median Tmax was two hours. In vivo, abiraterone acetate is converted to abiraterone. In clinical studies of other abiraterone acetate formulations, abiraterone acetate plasma concentrations were below detectable levels (< 0.2 ng/mL) in > 99% of the analyzed samples.9

Systemic exposure to abiraterone is increased when abiraterone acetate is administered with food. Abiraterone Cmax was approximately 6.5-fold higher, and AUC0-∞ was 4.4-fold higher when a single dose of abiraterone acetate 500 mg was administered with a high-fat meal (56-60% fat, 900-1,000 calories) compared to overnight fasting in healthy subjects.9 Given the normal variation in the content and composition of meals, taking abiraterone with meals has the potential to result in increased and highly variable exposures.10

Volume of distribution

The mean (± SD) apparent steady-state volume of distribution is 19,669 (± 13,358) L.9,10

Protein binding

Abiraterone is highly bound (>99%) to the human plasma proteins, albumin and alpha-1 acid glycoprotein.9,10

Metabolism

The conversion of abiraterone acetate to abiraterone, the active metabolite, is likely to be mediated by esterases, although specific esterases have not been identified. In human plasma, the two main circulating metabolites are abiraterone sulfate, which is formed by CYP3A4 and SULT2A1, and N-oxide abiraterone sulfate, which is formed by SULT2A1. These metabolites each account for about 43% of abiraterone exposure and are pharmacologically inactive.8,9,10

Hover over products below to view reaction partners

Route of elimination

Following oral administration of 14C-abiraterone acetate, approximately 88% of the radioactive dose is recovered in feces: the major compounds present in feces are unchanged abiraterone acetate and abiraterone, accounting for approximately 55% and 22% of the administered dose, respectively. Approximately 5% of the dose is recovered in urine.9,10

Half-life

In patients with mCRPC, the mean (± SD) terminal half-life of abiraterone in plasma is 12 (± 5) hours.9,10

Clearance

Not Available

Adverse Effects
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Toxicity

The oral LD50 is > 400 mg/kg in rats and 800 mg/kg in mice.12

The human experience of overdose with abiraterone is limited. Toxicity is related to the blockade of CYP17 activity. Blockade results in the accumulation of upstream mineralocorticoids like 11-deoxycorticosterone, leading to secondary hyperaldosteronism. Signs of hyperaldosteronism include fluid retention and hypokalemia.3 As there is no specific antidote for abiraterone overdose, overdosage should be managed with general supportive measures, including monitoring and assessment of cardiac and liver function.9,10

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 Abiraterone can be increased when it is combined with Abametapir.
AcebutololThe metabolism of Acebutolol can be decreased when combined with Abiraterone.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Abiraterone.
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Abiraterone.
AcyclovirThe serum concentration of Acyclovir can be increased when it is combined with Abiraterone.
Food Interactions
  • Exercise caution with St. John's Wort. This herb induces CYP3A4 and may increase the serum levels of abiraterone.
  • Take on an empty stomach. Food increases Cmax and AUC. Take ZYTIGA , a product of abiraterone, at least 1 hour before or 2 hours after eating as food may increase exposure to abiraterone by 4-fold.
  • Take with or without food. Food increases Cmax and AUC. YONSA, a product of abiraterone, can be taken with or without food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Abiraterone acetateEM5OCB9YJ6154229-18-2UVIQSJCZCSLXRZ-UBUQANBQSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AbirateroneTablet500 mgOralJamp Pharma Corporation2022-07-12Not applicableCanada flag
AbirateroneTablet250 mgOralJamp Pharma CorporationNot applicableNot applicableCanada flag
Abiraterone AccordTablet, film coated500 mgOralAccord Healthcare S.L.U.2022-06-06Not applicableEU flag
Abiraterone AccordTablet250 mgOralAccord Healthcare S.L.U.2022-06-06Not applicableEU flag
Abiraterone AccordTablet, film coated500 mgOralAccord Healthcare S.L.U.2022-06-06Not applicableEU flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AbirateroneTablet250 mg/1OralCivicaScript, LLC2018-11-23Not applicableUS flag
AbirateroneTablet250 mg/1OralBluePoint Laboratories2019-07-10Not applicableUS flag
AbirateroneTablet250 mg/1OralHikma Pharmaceuticals USA Inc.2018-11-23Not applicableUS flag
AbirateroneTablet250 mg/1OralNovadoz Pharmaceuticals Llc2019-07-10Not applicableUS flag
AbirateroneTablet250 mg/1OralPD-Rx Pharmaceuticals, Inc.2018-11-23Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AkeegaAbiraterone acetate (500 mg) + Niraparib tosylate (50 mg)TabletOralJanssen Pharmaceuticals2023-08-14Not applicableCanada flag
AkeegaAbiraterone acetate (500 mg) + Niraparib (100 mg)Tablet, film coatedOralJanssen Cilag International Nv2023-06-09Not applicableEU flag
AkeegaAbiraterone acetate (500 mg/1) + Niraparib tosylate monohydrate (100 mg/1)Tablet, film coatedOralJanssen Biotech, Inc.2023-08-11Not applicableUS flag
AkeegaAbiraterone acetate (500 mg) + Niraparib (50 mg)Tablet, film coatedOralJanssen Cilag International Nv2023-06-09Not applicableEU flag
AkeegaAbiraterone acetate (500 mg) + Niraparib tosylate (100 mg)TabletOralJanssen Pharmaceuticals2023-08-14Not applicableCanada flag

Categories

ATC Codes
L02BX03 — Abiraterone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Androstane steroids
Direct Parent
Androgens and derivatives
Alternative Parents
3-beta-hydroxysteroids / 3-beta-hydroxy delta-5-steroids / Delta-5-steroids / Pyridines and derivatives / Heteroaromatic compounds / Secondary alcohols / Cyclic alcohols and derivatives / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 1 more
Substituents
3-beta-hydroxy-delta-5-steroid / 3-beta-hydroxysteroid / 3-hydroxy-delta-5-steroid / 3-hydroxysteroid / Alcohol / Androgen-skeleton / Aromatic heteropolycyclic compound / Azacycle / Cyclic alcohol / Delta-5-steroid
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyridines, 3beta-sterol (CHEBI:68642)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
G819A456D0
CAS number
154229-19-3
InChI Key
GZOSMCIZMLWJML-VJLLXTKPSA-N
InChI
InChI=1S/C24H31NO/c1-23-11-9-18(26)14-17(23)5-6-19-21-8-7-20(16-4-3-13-25-15-16)24(21,2)12-10-22(19)23/h3-5,7,13,15,18-19,21-22,26H,6,8-12,14H2,1-2H3/t18-,19-,21-,22-,23-,24+/m0/s1
IUPAC Name
(3aS,3bR,7S,9aR,9bS,11aS)-9a,11a-dimethyl-1-(pyridin-3-yl)-3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol
SMILES
[H][C@@]12CC=C(C3=CC=CN=C3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

References

General References
  1. O'Donnell A, Judson I, Dowsett M, Raynaud F, Dearnaley D, Mason M, Harland S, Robbins A, Halbert G, Nutley B, Jarman M: Hormonal impact of the 17alpha-hydroxylase/C(17,20)-lyase inhibitor abiraterone acetate (CB7630) in patients with prostate cancer. Br J Cancer. 2004 Jun 14;90(12):2317-25. [Article]
  2. Ryan CJ, Cheng ML: Abiraterone acetate for the treatment of prostate cancer. Expert Opin Pharmacother. 2013 Jan;14(1):91-6. doi: 10.1517/14656566.2013.745852. Epub 2012 Nov 30. [Article]
  3. Gill D, Gaston D, Bailey E, Hahn A, Gupta S, Batten J, Alex A, Boucher K, Stenehjem D, Agarwal N: Efficacy of Eplerenone in the Management of Mineralocorticoid Excess in Men With Metastatic Castration-resistant Prostate Cancer Treated With Abiraterone Without Prednisone. Clin Genitourin Cancer. 2017 Aug;15(4):e599-e602. doi: 10.1016/j.clgc.2016.12.008. Epub 2017 Jan 5. [Article]
  4. Stappaerts J, Geboers S, Snoeys J, Brouwers J, Tack J, Annaert P, Augustijns P: Rapid conversion of the ester prodrug abiraterone acetate results in intestinal supersaturation and enhanced absorption of abiraterone: in vitro, rat in situ and human in vivo studies. Eur J Pharm Biopharm. 2015 Feb;90:1-7. doi: 10.1016/j.ejpb.2015.01.001. Epub 2015 Jan 12. [Article]
  5. Haidar S, Ehmer PB, Barassin S, Batzl-Hartmann C, Hartmann RW: Effects of novel 17alpha-hydroxylase/C17, 20-lyase (P450 17, CYP 17) inhibitors on androgen biosynthesis in vitro and in vivo. J Steroid Biochem Mol Biol. 2003 Apr;84(5):555-62. doi: 10.1016/s0960-0760(03)00070-0. [Article]
  6. Basu S, Tindall DJ: Androgen action in prostate cancer. Horm Cancer. 2010 Oct;1(5):223-8. doi: 10.1007/s12672-010-0044-4. [Article]
  7. James A, Vincent B, Sivadas A, Pavithran K: A Study on the Clinical Outcome of Abiraterone Acetate in Castration Resistant Prostate Cancer Patients. Int J Hematol Oncol Stem Cell Res. 2018 Jan 1;12(1):4-7. [Article]
  8. Acharya M, Gonzalez M, Mannens G, De Vries R, Lopez C, Griffin T, Tran N: A phase I, open-label, single-dose, mass balance study of 14C-labeled abiraterone acetate in healthy male subjects. Xenobiotica. 2013 Apr;43(4):379-89. doi: 10.3109/00498254.2012.721022. Epub 2012 Sep 28. [Article]
  9. FDA Approved Drug Products: YONSA (abiraterone acetate) tablets for oral use (March 2022) [Link]
  10. FDA Approved Drug Products: ZYTIGA (abiraterone acetate) tablets for oral use (August 2021) [Link]
  11. Health Canada Approved Drug Proucts: AKEEGA (Niraparib and abiraterone acetate) tablets for oral use [Link]
  12. Janssen: Abiraterone acetate MSDS [Link]
  13. EMA Approved Drug Products: ZYTIGA (abiraterone acetate) Oral Tablets [Link]
  14. Health Canada Approved Drug Products: ZYTIGA (Abiraterone) Oral Tablets [Link]
  15. FDA Approved Drug Products: AKEEGA (niraparib and abiraterone acetate) tablets, for oral use [Link]
KEGG Drug
D09701
PubChem Compound
132971
PubChem Substance
175427038
ChemSpider
117349
BindingDB
25458
RxNav
1100072
ChEBI
68642
ChEMBL
CHEMBL254328
ZINC
ZINC000003797541
PharmGKB
PA166123407
PDBe Ligand
AER
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Abiraterone_acetate
PDB Entries
3ruk / 4nkv / 4r1z / 4r20 / 6b82 / 6wr1

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral1000 mg
TabletOral250 mg/1
TabletOral500 mg/1
Tablet, film coatedOral500 mg/1
Tablet, coatedOral250 mg
TabletOral250.000 mg
TabletOral
Tablet, film coatedOral
TabletOral250 mg
TabletOral500.000 mg
Tablet, film coatedOral250 MG
TabletOral250.00 mg
TabletOral1000 mg
Tablet, film coatedOral1000.00 mg
Tablet, film coatedOral250.00 mg
Tablet, film coatedOral500.00 mg
TabletOral125 mg/1
TabletOral
Tablet, film coatedOral
Tablet, film coatedOral250 mg/1
Tablet, coatedOral500 mg
TabletOral500 mg
Tablet, film coatedOral500 mg
Tablet, film coatedOral50000000 mg
TabletOral25000000 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5604213No1997-02-182016-12-13US flag
US8822438No2014-09-022027-08-24US flag
US8859562No2014-10-142031-08-04US flag
US8143241No2012-03-272027-08-12US flag
US8071579No2011-12-062027-08-12US flag
US8071623No2011-12-062030-03-22US flag
US8436185No2013-05-072029-04-24US flag
US9889144No2018-02-132034-03-17US flag
US10292990No2019-05-212034-05-20US flag
US11091459No2021-08-172038-03-27US flag
US11673877No2018-03-272038-03-27US flag
US11207311No2021-12-282037-07-28US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)147https://www.fishersci.com/store/msds?partNumber=AC466730010&productDescription=ABIRATERONE+ACETATE+1GR&vendorId=VN00032119&countryCode=US&language=en
Predicted Properties
PropertyValueSource
Water Solubility0.00305 mg/mLALOGPS
logP5.1ALOGPS
logP3.97Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)18.2Chemaxon
pKa (Strongest Basic)4.81Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area33.12 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity107.3 m3·mol-1Chemaxon
Polarizability42.03 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.98
Caco-2 permeable+0.7245
P-glycoprotein substrateSubstrate0.6583
P-glycoprotein inhibitor IInhibitor0.5
P-glycoprotein inhibitor IINon-inhibitor0.8831
Renal organic cation transporterNon-inhibitor0.7453
CYP450 2C9 substrateNon-substrate0.854
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6478
CYP450 1A2 substrateInhibitor0.5124
CYP450 2C9 inhibitorNon-inhibitor0.8046
CYP450 2D6 inhibitorNon-inhibitor0.8693
CYP450 2C19 inhibitorNon-inhibitor0.5349
CYP450 3A4 inhibitorInhibitor0.7176
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5363
Ames testNon AMES toxic0.8499
CarcinogenicityNon-carcinogens0.9616
BiodegradationNot ready biodegradable0.9565
Rat acute toxicity2.4407 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8318
hERG inhibition (predictor II)Non-inhibitor0.7059
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-41f0d385bfb1221a6276
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-289ff6affd53b0c6ce36
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-cd65e5687ca13b4a2436
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0859000000-06f876c46994aa106256
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-3371f52b63298993a431
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uxr-1943000000-6fa5dcb1dd0bb3576acf
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]-186.24211
predicted
DeepCCS 1.0 (2019)
[M+H]+188.16176
predicted
DeepCCS 1.0 (2019)
[M+Na]+195.00862
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Steroid 17-alpha-monooxygenase activity
Specific Function
Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation ...
Gene Name
CYP17A1
Uniprot ID
P05093
Uniprot Name
Steroid 17-alpha-hydroxylase/17,20 lyase
Molecular Weight
57369.995 Da
References
  1. Vogiatzi P, Claudio PP: Efficacy of abiraterone acetate in post-docetaxel castration-resistant prostate cancer. Expert Rev Anticancer Ther. 2010 Jul;10(7):1027-30. doi: 10.1586/era.10.84. [Article]
  2. O'Donnell A, Judson I, Dowsett M, Raynaud F, Dearnaley D, Mason M, Harland S, Robbins A, Halbert G, Nutley B, Jarman M: Hormonal impact of the 17alpha-hydroxylase/C(17,20)-lyase inhibitor abiraterone acetate (CB7630) in patients with prostate cancer. Br J Cancer. 2004 Jun 14;90(12):2317-25. [Article]
  3. FDA Approved Drug Products: ZYTIGA (abiraterone acetate) tablets for oral use (August 2021) [Link]
  4. FDA Approved Drug Products: YONSA (abiraterone acetate) tablets for oral use (March 2022) [Link]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Beckett RD, Rodeffer KM, Snodgrass R: Abiraterone for the treatment of metastatic castrate-resistant prostate cancer. Ann Pharmacother. 2012 Jul-Aug;46(7-8):1016-24. doi: 10.1345/aph.1Q758. Epub 2012 Jun 19. [Article]
  2. Flockhart Table of Drug Interactions [Link]
  3. FDA Approved Drug Products: YONSA (abiraterone acetate) tablets for oral use (March 2022) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Malikova J, Brixius-Anderko S, Udhane SS, Parween S, Dick B, Bernhardt R, Pandey AV: CYP17A1 inhibitor abiraterone, an anti-prostate cancer drug, also inhibits the 21-hydroxylase activity of CYP21A2. J Steroid Biochem Mol Biol. 2017 Nov;174:192-200. doi: 10.1016/j.jsbmb.2017.09.007. Epub 2017 Sep 8. [Article]
  2. Benoist GE, Hendriks RJ, Mulders PF, Gerritsen WR, Somford DM, Schalken JA, van Oort IM, Burger DM, van Erp NP: Pharmacokinetic Aspects of the Two Novel Oral Drugs Used for Metastatic Castration-Resistant Prostate Cancer: Abiraterone Acetate and Enzalutamide. Clin Pharmacokinet. 2016 Nov;55(11):1369-1380. doi: 10.1007/s40262-016-0403-6. [Article]
  3. Beckett RD, Rodeffer KM, Snodgrass R: Abiraterone for the treatment of metastatic castrate-resistant prostate cancer. Ann Pharmacother. 2012 Jul-Aug;46(7-8):1016-24. doi: 10.1345/aph.1Q758. Epub 2012 Jun 19. [Article]
  4. FDA Approved Drug Products: ZYTIGA (abiraterone acetate) tablets for oral use (August 2021) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Chi KN, Tolcher A, Lee P, Rosen PJ, Kollmannsberger CK, Papadopoulos KP, Patnaik A, Molina A, Jiao J, Pankras C, Kaiser B, Bernard A, Tran N, Acharya M: Effect of abiraterone acetate plus prednisone on the pharmacokinetics of dextromethorphan and theophylline in patients with metastatic castration-resistant prostate cancer. Cancer Chemother Pharmacol. 2013 Jan;71(1):237-44. doi: 10.1007/s00280-012-2001-0. Epub 2012 Oct 12. [Article]
  2. Flockhart Table of Drug Interactions [Link]
  3. FDA Approved Drug Products: YONSA (abiraterone acetate) tablets for oral use (March 2022) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [Article]
  2. Monbaliu J, Gonzalez M, Bernard A, Jiao J, Sensenhauser C, Snoeys J, Stieltjes H, Wynant I, Smit JW, Chien C: In Vitro and In Vivo Drug-Drug Interaction Studies to Assess the Effect of Abiraterone Acetate, Abiraterone, and Metabolites of Abiraterone on CYP2C8 Activity. Drug Metab Dispos. 2016 Oct;44(10):1682-91. doi: 10.1124/dmd.116.070672. Epub 2016 Aug 8. [Article]
  3. Flockhart Table of Drug Interactions [Link]
  4. FDA Approved Drug Products: YONSA (abiraterone acetate) tablets for oral use (March 2022) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Beckett RD, Rodeffer KM, Snodgrass R: Abiraterone for the treatment of metastatic castrate-resistant prostate cancer. Ann Pharmacother. 2012 Jul-Aug;46(7-8):1016-24. doi: 10.1345/aph.1Q758. Epub 2012 Jun 19. [Article]
  2. FDA Approved Drug Products: ZYTIGA (abiraterone acetate) tablets for oral use (August 2021) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Goldberg T, Berrios-Colon E: Abiraterone (zytiga), a novel agent for the management of castration-resistant prostate cancer. P T. 2013 Jan;38(1):23-6. [Article]
  2. Beckett RD, Rodeffer KM, Snodgrass R: Abiraterone for the treatment of metastatic castrate-resistant prostate cancer. Ann Pharmacother. 2012 Jul-Aug;46(7-8):1016-24. doi: 10.1345/aph.1Q758. Epub 2012 Jun 19. [Article]
  3. FDA Approved Drug Products: ZYTIGA (abiraterone acetate) tablets for oral use (August 2021) [Link]
  4. Zytiga product monograph [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. FDA Approved Drug Products: ZYTIGA (abiraterone acetate) tablets for oral use (August 2021) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sulfotransferase activity
Specific Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
Gene Name
SULT2A1
Uniprot ID
Q06520
Uniprot Name
Bile salt sulfotransferase
Molecular Weight
33779.57 Da
References
  1. Beckett RD, Rodeffer KM, Snodgrass R: Abiraterone for the treatment of metastatic castrate-resistant prostate cancer. Ann Pharmacother. 2012 Jul-Aug;46(7-8):1016-24. doi: 10.1345/aph.1Q758. Epub 2012 Jun 19. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Ryan CJ, Cheng ML: Abiraterone acetate for the treatment of prostate cancer. Expert Opin Pharmacother. 2013 Jan;14(1):91-6. doi: 10.1517/14656566.2013.745852. Epub 2012 Nov 30. [Article]
  2. FDA Approved Drug Products: YONSA (abiraterone acetate) tablets for oral use (March 2022) [Link]
  3. FDA Approved Drug Products: ZYTIGA (abiraterone acetate) tablets for oral use (August 2021) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. Ryan CJ, Cheng ML: Abiraterone acetate for the treatment of prostate cancer. Expert Opin Pharmacother. 2013 Jan;14(1):91-6. doi: 10.1517/14656566.2013.745852. Epub 2012 Nov 30. [Article]
  2. FDA Approved Drug Products: YONSA (abiraterone acetate) tablets for oral use (March 2022) [Link]
  3. FDA Approved Drug Products: ZYTIGA (abiraterone acetate) tablets for oral use (August 2021) [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
In vitro, abiraterone acetate is an inhibitor of P-gp.
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Beckett RD, Rodeffer KM, Snodgrass R: Abiraterone for the treatment of metastatic castrate-resistant prostate cancer. Ann Pharmacother. 2012 Jul-Aug;46(7-8):1016-24. doi: 10.1345/aph.1Q758. Epub 2012 Jun 19. [Article]
  2. Benoist GE, Hendriks RJ, Mulders PF, Gerritsen WR, Somford DM, Schalken JA, van Oort IM, Burger DM, van Erp NP: Pharmacokinetic Aspects of the Two Novel Oral Drugs Used for Metastatic Castration-Resistant Prostate Cancer: Abiraterone Acetate and Enzalutamide. Clin Pharmacokinet. 2016 Nov;55(11):1369-1380. doi: 10.1007/s40262-016-0403-6. [Article]
  3. FDA Approved Drug Products: ZYTIGA (abiraterone acetate) tablets for oral use (August 2021) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
In vitro, abiraterone and its major metabolites were shown to inhibit the hepatic uptake transporter OATP1B1.
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. FDA Approved Drug Products: ZYTIGA (abiraterone acetate) tablets for oral use (August 2021) [Link]

Drug created at November 18, 2007 18:28 / Updated at February 25, 2024 21:03