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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
Structure for Abiraterone (DB05812)
- 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
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 Metastatic castration sensitive prostate cancer Regimen in combination with: Prednisone (DB00635) •••••••••••• •••• •••• •••••••• •••••• Used in combination to treat Metastatic castration-resistant prostate cancer Regimen in combination with: Prednisone (DB00635) •••••••••••• •••••••• ••••••••• •••••••••• •••••••• ••••••••••• ••••••• ••••••• Used in combination to treat Metastatic castration-resistant prostate cancer Regimen in combination with: Prednisone (DB00635) •••••••••••• ••••••• ••••••••••• ••••• •••••••• •••••••••• •••••••• ••••••••• ••••••••• Used in combination to treat Metastatic castration-resistant prostate cancer Regimen in combination with: Prednisone (DB00635), Prednisolone (DB00860) •••••••••••• ••••••• ••••••••••• ••••• •••••••• •••••••••• •••••••• ••••••••• ••••••••• Used in combination to treat Metastatic castration-resistant prostate cancer Regimen in combination with: Prednisone (DB00635) •••••••••••• - 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
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
Target Actions Organism ASteroid 17-alpha-hydroxylase/17,20 lyase inhibitorHumans - 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
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 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Abiraterone can be increased when it is combined with Abametapir. Acebutolol The metabolism of Acebutolol can be decreased when combined with Abiraterone. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Abiraterone. Acetaminophen The serum concentration of Acetaminophen can be increased when it is combined with Abiraterone. Acyclovir The 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
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.- Product Ingredients
Ingredient UNII CAS InChI Key Abiraterone acetate EM5OCB9YJ6 154229-18-2 UVIQSJCZCSLXRZ-UBUQANBQSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Abiraterone Tablet 500 mg Oral Jamp Pharma Corporation 2022-07-12 Not applicable Canada 
Abiraterone Tablet 250 mg Oral Jamp Pharma Corporation Not applicable Not applicable Canada Abiraterone Accord Tablet, film coated 500 mg Oral Accord Healthcare S.L.U. 2022-06-06 Not applicable EU 
Abiraterone Accord Tablet, film coated 500 mg Oral Accord Healthcare S.L.U. 2024-07-10 Not applicable EU Abiraterone Accord Tablet, film coated 500 mg Oral Accord Healthcare S.L.U. 2022-06-06 Not applicable EU - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Abiraterone Tablet, film coated 250 mg/1 Oral Msn Laboratories Private Limited 2024-04-26 Not applicable US 
Abiraterone Tablet 250 mg/1 Oral Msn Laboratories Private Limited 2019-07-10 Not applicable US Abiraterone Tablet 250 mg/1 Oral Quallent Pharmaceuticals Health LLC 2019-10-07 Not applicable US Abiraterone Tablet, film coated 500 mg/1 Oral Novadoz Pharmaceuticals Llc 2024-04-24 Not applicable US Abiraterone Tablet 250 mg/1 Oral CivicaScript, LLC 2018-11-23 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Akeega Abiraterone acetate (500 mg) + Niraparib (50 mg) Tablet, film coated Oral Janssen Cilag International Nv 2023-06-09 Not applicable EU Akeega Abiraterone acetate (500 mg) + Niraparib tosylate (100 mg) Tablet Oral Janssen Pharmaceuticals 2023-08-14 Not applicable Canada Akeega Abiraterone acetate (500 mg/1) + Niraparib tosylate monohydrate (50 mg/1) Tablet, film coated Oral Janssen Biotech, Inc. 2023-08-11 Not applicable US Akeega Abiraterone acetate (500 mg) + Niraparib tosylate (50 mg) Tablet Oral Janssen Pharmaceuticals 2023-08-14 Not applicable Canada Akeega Abiraterone acetate (500 mg) + Niraparib (100 mg) Tablet, film coated Oral Janssen Cilag International Nv 2023-06-09 Not applicable EU
Categories
- ATC Codes
- L01XK52 — Niraparib and abiraterone
- L01XK — Poly (ADP-ribose) polymerase (PARP) inhibitors
- L01X — OTHER ANTINEOPLASTIC AGENTS
- L01 — ANTINEOPLASTIC AGENTS
- L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
- L02BX — Other hormone antagonists and related agents
- L02B — HORMONE ANTAGONISTS AND RELATED AGENTS
- L02 — ENDOCRINE THERAPY
- L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
- Drug Categories
- Androstanes
- Androstenes
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (moderate)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (moderate)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Inhibitors
- Cytochrome P-450 CYP3A5 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Cytochrome P450 17A1 Inhibitors
- Endocrine Therapy
- Enzyme Inhibitors
- Fused-Ring Compounds
- Hormone Antagonists
- Hormone Antagonists and Related Agents
- Hormones, Hormone Substitutes, and Hormone Antagonists
- OATP1B1/SLCO1B1 Inhibitors
- P-glycoprotein inhibitors
- Poly (ADP-ribose) polymerase (PARP) inhibitors
- Steroid Synthesis Inhibitors
- Steroids
- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- FDA Approved Drug Products: YONSA (abiraterone acetate) tablets for oral use (March 2022) [Link]
- FDA Approved Drug Products: ZYTIGA (abiraterone acetate) tablets for oral use (August 2021) [Link]
- Health Canada Approved Drug Proucts: AKEEGA (Niraparib and abiraterone acetate) tablets for oral use [Link]
- Janssen: Abiraterone acetate MSDS [Link]
- EMA Approved Drug Products: ZYTIGA (abiraterone acetate) Oral Tablets [Link]
- Health Canada Approved Drug Products: ZYTIGA (Abiraterone) Oral Tablets [Link]
- FDA Approved Drug Products: AKEEGA (niraparib and abiraterone acetate) tablets, for oral use [Link]
- External Links
- KEGG Drug
- D09701
- PubChem Compound
- 132971
- PubChem Substance
- 175427038
- ChemSpider
- 117349
- BindingDB
- 25458
- 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
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 Not Available Advanced carcinoma of the prostate 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Not Available Castration Resistant Prostatic Neoplasms 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Not Available Neoplasms of the Prostate 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Not Available Prostate Cancer 1 somestatus stop reason just information to hide Not Available Approved for Marketing Not Available Genital Diseases, Male / Genital Neoplasms, Male / Genitourinary tract neoplasm / Neoplasms of the Prostate 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, film coated Oral 1000 mg Tablet, film coated Oral Tablet Oral 250 mg/1 Tablet Oral 500 mg/1 Tablet, film coated Oral 500 mg/1 Tablet, coated Oral 250 mg Tablet Oral Tablet Oral 250.000 mg Tablet Oral Tablet, film coated Oral Tablet Oral 500.000 mg Tablet, film coated Oral 250 MG Tablet Oral 250.00 mg Tablet Oral 1000 mg Tablet, film coated Oral 1000.00 mg Tablet, film coated Oral 250.00 mg Tablet, film coated Oral 500.00 mg Tablet Oral 125 mg/1 Tablet Oral 500 mg Tablet, film coated Oral 250 mg/1 Tablet Oral 250 mg Tablet, coated Oral 500 mg Tablet, film coated Oral 500 mg Tablet, film coated Oral 50000000 mg Tablet Oral 25000000 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5604213 No 1997-02-18 2016-12-13 US US8822438 No 2014-09-02 2027-08-24 US US8859562 No 2014-10-14 2031-08-04 US US8143241 No 2012-03-27 2027-08-12 US US8071579 No 2011-12-06 2027-08-12 US US8071623 No 2011-12-06 2030-03-22 US US8436185 No 2013-05-07 2029-04-24 US US9889144 No 2018-02-13 2034-03-17 US US10292990 No 2019-05-21 2034-05-20 US US11091459 No 2021-08-17 2038-03-27 US US11673877 No 2018-03-27 2038-03-27 US US11207311 No 2021-12-28 2037-07-28 US US11992486 No 2017-07-28 2037-07-28 US US11986469 No 2017-07-28 2037-07-28 US US11986468 No 2017-07-28 2037-07-28 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 147 https://www.fishersci.com/store/msds?partNumber=AC466730010&productDescription=ABIRATERONE+ACETATE+1GR&vendorId=VN00032119&countryCode=US&language=en - Predicted Properties
Property Value Source Water Solubility 0.00305 mg/mL ALOGPS logP 5.1 ALOGPS logP 3.97 Chemaxon logS -5.1 ALOGPS pKa (Strongest Acidic) 18.2 Chemaxon pKa (Strongest Basic) 4.81 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 33.12 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 107.3 m3·mol-1 Chemaxon Polarizability 42.03 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.98 Caco-2 permeable + 0.7245 P-glycoprotein substrate Substrate 0.6583 P-glycoprotein inhibitor I Inhibitor 0.5 P-glycoprotein inhibitor II Non-inhibitor 0.8831 Renal organic cation transporter Non-inhibitor 0.7453 CYP450 2C9 substrate Non-substrate 0.854 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.6478 CYP450 1A2 substrate Inhibitor 0.5124 CYP450 2C9 inhibitor Non-inhibitor 0.8046 CYP450 2D6 inhibitor Non-inhibitor 0.8693 CYP450 2C19 inhibitor Non-inhibitor 0.5349 CYP450 3A4 inhibitor Inhibitor 0.7176 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5363 Ames test Non AMES toxic 0.8499 Carcinogenicity Non-carcinogens 0.9616 Biodegradation Not ready biodegradable 0.9565 Rat acute toxicity 2.4407 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8318 hERG inhibition (predictor II) Non-inhibitor 0.7059
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0009000000-41f0d385bfb1221a6276 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0009000000-289ff6affd53b0c6ce36 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0009000000-cd65e5687ca13b4a2436 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0859000000-06f876c46994aa106256 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0009000000-3371f52b63298993a431 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0uxr-1943000000-6fa5dcb1dd0bb3576acf Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 186.24211 predictedDeepCCS 1.0 (2019) [M+H]+ 188.16176 predictedDeepCCS 1.0 (2019) [M+Na]+ 195.00862 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in corticoid and androgen biosynthesis (PubMed:22266943, PubMed:25301938, PubMed:27339894, PubMed:9452426). Catalyzes 17-alpha hydroxylation of C21 steroids, which is common for both pathways. A second oxidative step, required only for androgen synthesis, involves an acyl-carbon cleavage. The 17-alpha hydroxy intermediates, as part of adrenal glucocorticoids biosynthesis pathway, are precursors of cortisol (Probable) (PubMed:25301938, PubMed:9452426). Hydroxylates steroid hormones, pregnenolone and progesterone to form 17-alpha hydroxy metabolites, followed by the cleavage of the C17-C20 bond to form C19 steroids, dehydroepiandrosterone (DHEA) and androstenedione (PubMed:22266943, PubMed:25301938, PubMed:27339894, PubMed:36640554, PubMed:9452426). Has 16-alpha hydroxylase activity. Catalyzes 16-alpha hydroxylation of 17-alpha hydroxy pregnenolone, followed by the cleavage of the C17-C20 bond to form 16-alpha-hydroxy DHEA (PubMed:36640554). Also 16-alpha hydroxylates androgens, relevant for estriol synthesis (PubMed:25301938, PubMed:27339894). 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 (CPR; NADPH-ferrihemoprotein reductase) (PubMed:22266943, PubMed:25301938, PubMed:27339894, PubMed:9452426)
- Specific Function
- 17-alpha-hydroxyprogesterone aldolase activity
- Gene Name
- CYP17A1
- Uniprot ID
- P05093
- Uniprot Name
- Steroid 17-alpha-hydroxylase/17,20 lyase
- Molecular Weight
- 57369.995 Da
References
- 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]
- 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]
- FDA Approved Drug Products: ZYTIGA (abiraterone acetate) tablets for oral use (August 2021) [Link]
- FDA Approved Drug Products: YONSA (abiraterone acetate) tablets for oral use (March 2022) [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- 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]
- Flockhart Table of Drug Interactions [Link]
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). 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) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)
- Specific Function
- Aromatase activity
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58406.915 Da
References
- 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]
- 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]
- 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]
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, 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) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- Anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- 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]
- Flockhart Table of Drug Interactions [Link]
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). 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) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
- Specific Function
- Arachidonic acid epoxygenase activity
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- 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]
- 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]
- Flockhart Table of Drug Interactions [Link]
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). 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) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (r)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- 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]
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). 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) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). 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 imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
- Specific Function
- (r)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55944.565 Da
References
- 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]
- 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]
- FDA Approved Drug Products: ZYTIGA (abiraterone acetate) tablets for oral use (August 2021) [Link]
- Zytiga product monograph [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). 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:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion 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 all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
- Specific Function
- Aromatase activity
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- 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 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. Mediates the sulfation of a wide range of steroids and sterols, including pregnenolone, androsterone, DHEA, bile acids, cholesterol and as well many xenobiotics that contain alcohol and phenol functional groups (PubMed:14573603, PubMed:18042734, PubMed:19589875, PubMed:21187059, PubMed:2268288, PubMed:29671343, PubMed:7678732, PubMed:7854148). Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Plays an important role in maintening steroid and lipid homeostasis (PubMed:14573603, PubMed:19589875, PubMed:21187059). Plays a key role in bile acid metabolism (PubMed:2268288). In addition, catalyzes the metabolic activation of potent carcinogenic polycyclic arylmethanols (By similarity)
- Specific Function
- 3'-phosphoadenosine 5'-phosphosulfate binding
- Gene Name
- SULT2A1
- Uniprot ID
- Q06520
- Uniprot Name
- Sulfotransferase 2A1
- Molecular Weight
- 33779.57 Da
References
- 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
- 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
- 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]
- FDA Approved Drug Products: YONSA (abiraterone acetate) tablets for oral use (March 2022) [Link]
- 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
- Functions as a 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 the body. Appears to function in modulating the activity of the immune system during the acute-phase reaction
- Specific Function
- Not Available
- Gene Name
- ORM1
- Uniprot ID
- P02763
- Uniprot Name
- Alpha-1-acid glycoprotein 1
- Molecular Weight
- 23539.43 Da
References
- 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]
- FDA Approved Drug Products: YONSA (abiraterone acetate) tablets for oral use (March 2022) [Link]
- 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
- Mediates export of organic anions and drugs from the cytoplasm (PubMed:10064732, PubMed:11114332, PubMed:16230346, PubMed:7961706, PubMed:9281595). Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotrexate, antiviral drugs and other xenobiotics (PubMed:10064732, PubMed:11114332, PubMed:16230346, PubMed:7961706, PubMed:9281595). Confers resistance to anticancer drugs by decreasing accumulation of drug in cells, and by mediating ATP- and GSH-dependent drug export (PubMed:9281595). Hydrolyzes ATP with low efficiency (PubMed:16230346). Catalyzes the export of sphingosine 1-phosphate from mast cells independently of their degranulation (PubMed:17050692). Participates in inflammatory response by allowing export of leukotriene C4 from leukotriene C4-synthezing cells (By similarity). Mediates ATP-dependent, GSH-independent cyclic GMP-AMP (cGAMP) export (PubMed:36070769). Thus, by limiting intracellular cGAMP concentrations negatively regulates the cGAS-STING pathway (PubMed:36070769)
- Specific Function
- Abc-type glutathione s-conjugate transporter activity
- Gene Name
- ABCC1
- Uniprot ID
- P33527
- Uniprot Name
- Multidrug resistance-associated protein 1
- Molecular Weight
- 171589.5 Da
References
- 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]
- 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]
- 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
- Mediates the Na(+)-independent uptake of organic anions (PubMed:10358072, PubMed:15159445, PubMed:17412826). Shows broad substrate specificity, can transport both organic anions such as bile acid taurocholate (cholyltaurine) and conjugated steroids (dehydroepiandrosterone 3-sulfate, 17-beta-glucuronosyl estradiol, and estrone 3-sulfate), as well as eicosanoids (prostaglandin E2, thromboxane B2, leukotriene C4, and leukotriene E4), and thyroid hormones (T4/L-thyroxine, and T3/3,3',5'-triiodo-L-thyronine) (PubMed:10358072, PubMed:10601278, PubMed:10873595, PubMed:11159893, PubMed:12196548, PubMed:12568656, PubMed:15159445, PubMed:15970799, PubMed:16627748, PubMed:17412826, PubMed:19129463, PubMed:26979622). Can take up bilirubin glucuronides from plasma into the liver, contributing to the detoxification-enhancing liver-blood shuttling loop (PubMed:22232210). Involved in the clearance of endogenous and exogenous substrates from the liver (PubMed:10358072, PubMed:10601278). Transports coproporphyrin I and III, by-products of heme synthesis, and may be involved in their hepatic disposition (PubMed:26383540). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can transport HMG-CoA reductase inhibitors (also known as statins), such as pravastatin and pitavastatin, a clinically important class of hypolipidemic drugs (PubMed:10601278, PubMed:15159445, PubMed:15970799). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drug methotrexate (PubMed:23243220). May also transport antihypertension agents, such as the angiotensin-converting enzyme (ACE) inhibitor prodrug enalapril, and the highly selective angiotensin II AT1-receptor antagonist valsartan, in the liver (PubMed:16624871, PubMed:16627748). Shows a pH-sensitive substrate specificity towards prostaglandin E2 and T4 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)
- Specific Function
- Bile acid transmembrane transporter activity
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- FDA Approved Drug Products: ZYTIGA (abiraterone acetate) tablets for oral use (August 2021) [Link]
Drug created at November 18, 2007 18:28 / Updated at September 18, 2024 17:45