Identification

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Name
Abiraterone
Accession Number
DB05812
Type
Small Molecule
Groups
Approved
Description

Abiraterone is a derivative of steroidal progesterone and is an innovative drug that offers clinical benefit to patients with hormone refractory prostate cancer. Abiraterone is administered as an acetate salt prodrug because it has a higher bioavailability and less susceptible to hydrolysis than abiraterone itself. FDA approved on April 28, 2011.

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Abiraterone acetateEM5OCB9YJ6154229-18-2UVIQSJCZCSLXRZ-UBUQANBQSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Abiraterone acetateTablet, film coated500 mg/1OralJanssen Biotech, Inc.2018-03-05Not applicableUs
YonsaTablet125 mg/1OralSun Pharmaceutical Industries, Inc.2018-05-22Not applicableUs
ZytigaTablet, film coated500 mg/1OralJanssen Biotech, Inc.2017-04-17Not applicableUs
ZytigaTablet, film coated250 mg/1OralJanssen Biotech, Inc.2017-04-172017-04-18Us
ZytigaTablet500 mgOralJanssen Pharmaceuticals2016-09-22Not applicableCanada
ZytigaTablet250 mg/1OralJanssen Biotech, Inc.2011-04-28Not applicableUs
ZytigaTablet250 mgOralJanssen Pharmaceuticals2011-07-28Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AbirateroneTablet250 mg/1OralNovadoz Pharmaceuticals Llc2019-07-10Not applicableUs
AbirateroneTablet250 mg/1OralMsn Laboratories Private Limited2019-07-10Not applicableUs
AbirateroneTablet250 mg/1OralHikma Pharmaceuticals USA Inc.2018-11-23Not applicableUs
Abiraterone AcetateTablet250 mg/1OralAmerican Health Packaging2019-10-01Not applicableUs
Abiraterone AcetateTablet250 mg/1OralApotex Corp.2018-11-23Not applicableUs
Abiraterone acetateTablet250 mg/1OralWockhardt USA LLC.2019-02-27Not applicableUs
Abiraterone AcetateTablet, film coated250 mg/1OralTeva Pharmaceuticals USA, Inc.2018-11-21Not applicableUs
Abiraterone AcetateTablet250 mg/1OralMylan Pharmaceuticals Inc.2018-11-21Not applicableUs
Abiraterone acetateTablet250 mg/1OralRising Pharmaceuticals, Inc.2019-02-25Not applicableUs
Abiraterone AcetateTablet250 mg/1OralAmneal Pharmaceuticals NY LLC2019-01-07Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories
UNII
G819A456D0
CAS number
154229-19-3
Weight
Average: 349.509
Monoisotopic: 349.240564619
Chemical Formula
C24H31NO
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
(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-(pyridin-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,13-dien-5-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

Pharmacology

Indication

Used in combination with prednisone for the treatment of metastatic, castration-resistant prostate cancer.

Associated Conditions
Pharmacodynamics

Abiraterone is associated with decreases in PSA levels, tumor shrinkage (as evaluated by RECIST criteria), radiographic regression of bone metastases and improvement in pain. Levels of adrenocorticotropic hormones increased up to 6-fold but this can be suppressed by dexamethasone.

Mechanism of action

Abiraterone is an orally active inhibitor of the steroidal enzyme CYP17A1 (17 alpha-hydroxylase/C17,20 lyase). It inhibits CYP17A1 in a selective and irreversible manner via covalent binding mechanism. CYP17A1 is an enzyme that catalyzes the biosynthesis of androgen and is highly expressed in testicular, adrenal, and prostatic tumor tissue. More specifically, abiraterone inhibits the conversion of 17-hydroxyprognenolone to dehydroepiandrosterone (DHEA) by the enzyme CYP17A1 to decrease serum levels of testosterone and other androgens.

TargetActionsOrganism
ASteroid 17-alpha-hydroxylase/17,20 lyase
inhibitor
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Abiraterone itself is poorly absorbed and is susceptible to hydrolysis by esterases. The salt form, abiraterone acetate, is a prodrug which has a much higher oral bioavailability and is also esterase resistant. Peak drug concentrations of abiraterone were reached in 1.5 - 4 hours. Abiraterone acetate was rapidly and completely deacetylated into abiraterone-the parent salt form was not detectable in early pharmacokinetic studies. Food and high fat meals increases absorption 4.4-fold.

Volume of distribution

Vdss= 19,669 ± 13,358 L

Protein binding

>99% protein bound to alpha-1-acid glycoprotein and albumin.

Metabolism

Abiraterone acetate is hydrolyzed into active metabolite abiraterone via esterases. CYP3A4 and SULT2A1 further metabolizes abiraterone into two inactive metabolites called abiraterone sulfate and N-oxide abiraterone sulfate.

Route of elimination

Excreted via feces (~88%) and urine (~5%)

Half life

Terminal elimination half-life = 5-14 hours

Clearance
Not Available
Toxicity

Toxicity is related to the blockade of 17α-hydroxylase activity. Blockade results in the accumulation of upstream mineralocorticoids like 11-deoxycorticosterone leading to secondary hyperaldosteronism. Signs of hydroaldosteronism include fluid retention and hypokalemia. Mineralocorticoid receptor antagonists may be used to treat signs and symptoms.

Affected organisms
  • Humans and other mammals
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
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Abiraterone.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Abiraterone.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Abiraterone.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Abiraterone.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Abiraterone.
6-O-benzylguanineThe serum concentration of 6-O-benzylguanine can be increased when it is combined with Abiraterone.
7-DeazaguanineThe serum concentration of 7-Deazaguanine can be increased when it is combined with Abiraterone.
7,9-DimethylguanineThe serum concentration of 7,9-Dimethylguanine can be increased when it is combined with Abiraterone.
8-azaguanineThe serum concentration of 8-azaguanine can be increased when it is combined with Abiraterone.
8-chlorotheophyllineThe serum concentration of 8-chlorotheophylline can be increased when it is combined with Abiraterone.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
  • Food and high fat meals increases the drug exposure 4.4-fold. It is suggested that abiraterone is taken on an empty stomach.

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. [PubMed:15150570]
  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. [PubMed:23199349]
External Links
KEGG Drug
D09701
PubChem Compound
132971
PubChem Substance
175427038
ChemSpider
117349
BindingDB
25458
ChEBI
68642
ChEMBL
CHEMBL254328
PharmGKB
PA166123407
HET
AER
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Abiraterone
ATC Codes
L02BX03 — Abiraterone
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
PDB Entries
3ruk / 4nkv / 4r1z / 4r20 / 6b82
FDA label
Download (418 KB)
MSDS
Download (480 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentAdenocarcinoma of the Prostate / Advanced Prostate Cancer / Prostate Cancer / Stage IV Prostate Cancer1
1Active Not RecruitingTreatmentAdvanced Castrate-resistant Prostate Cancer (CRPC) / Advanced Castrate-resistant Prostate Cancer CRPC / Squamous Non-Small Cell Lung Cancer (sqNSCLC) / Squamous Non-Small Cell Lung Cancer sqNSCLC / Triple Negative Breast Cancer (TNBC) / Triple Negative Breast Cancer TNBC1
1Active Not RecruitingTreatmentMetastatic Castration Resistant Prostate Cancer / Metastatic Castration-Resistant Prostate Cancer (mCRPC) / Prostatic Neoplasms1
1Active Not RecruitingTreatmentProstate Cancer2
1CompletedNot AvailableHealthy Volunteers1
1CompletedTreatment21-Hydroxylase Deficiency1
1CompletedTreatmentCastration-Resistant Prostate Cancer (CRPC)1
1CompletedTreatmentHealthy Volunteers7
1CompletedTreatmentImpaired Renal Function1
1CompletedTreatmentPharmacology1
1CompletedTreatmentProstate Cancer1
1CompletedTreatmentProstate Neoplasms4
1CompletedTreatmentProstatic Neoplasms2
1Not Yet RecruitingTreatmentCancer, Advanced1
1RecruitingTreatmentAcute Myelogenous Leukaemia (AML) / Cancer, Breast / Malignant Neoplasm of Pancreas / Prostate Cancer1
1RecruitingTreatmentAdvanced Solid Malignancies / Colorectal Carcinoma (CRC) / Lung Cancer Non-Small Cell Cancer (NSCLC) / Metastatic Castrate-Resistant Prostate Carcinoma (mCRPC)1
1RecruitingTreatmentCongenital Adrenal Hyperplasia (CAH)1
1RecruitingTreatmentMetastatic Castration Resistant Prostate Cancer / Prostatic Neoplasms1
1RecruitingTreatmentMetastatic Hormone Refractory Prostate Cancer1
1RecruitingTreatmentProstate Cancer3
1RecruitingTreatmentProstate Cancer Castration-resistant Prostate Cancer1
1RecruitingTreatmentTumors, Solid1
1TerminatedTreatmentAdenocarcinoma of the Prostate / Hormone-Resistant Prostate Cancer / Recurrent Prostate Cancer / Stage IV Prostate Cancer1
1TerminatedTreatmentProstate Cancer1
1WithdrawnTreatmentMalignancies1
1, 2Active Not RecruitingTreatmentBiochemically-relapsing Prostate Adenocarcinoma Following Radical Prostatectomy1
1, 2Active Not RecruitingTreatmentProstate Cancer1
1, 2Active Not RecruitingTreatmentProstatic Neoplasms1
1, 2CompletedTreatmentAdenocarcinoma of the Prostate / Hormone-Resistant Prostate Cancer / Recurrent Prostate Cancer / Stage IV Prostate Cancer1
1, 2CompletedTreatmentCancer, Breast1
1, 2CompletedTreatmentProstate Cancer2
1, 2CompletedTreatmentProstate Neoplasms1
1, 2CompletedTreatmentProstatic Neoplasms1
1, 2RecruitingTreatmentAdvanced Solid Tumors / Metastatic Castration Resistant Prostate Cancer1
1, 2RecruitingTreatmentAndrogen-independent Prostate Cancer / Metastatic Hormone Refractory Prostate Cancer / Prostate Cancer / Recurrent Prostate Cancer1
1, 2RecruitingTreatmentMetastatic Castration Resistant Prostate Cancer (mCRPC)1
1, 2RecruitingTreatmentProstatic Neoplasms, Castration-Resistant1
1, 2TerminatedTreatmentCancer, Advanced / Solid Tumors and Hematologic Malignancy / Tumors, Solid1
1, 2TerminatedTreatmentCastrate-resistant Prostate Cancer (CRPC) / Castrate-resistant Prostate Cancer Patients1
2Active Not RecruitingOtherMetastatic Castration Resistant Prostate Cancer1
2Active Not RecruitingTreatmentAdenocarcinoma, Prostate / Diseases of Male Genital Organs / Prostate Cancer / PSA Level Greater Than Ten / Stage IIB Prostate Cancer AJCC v8 / Stage IIC Prostate Cancer AJCC v8 / Stage IIIA Prostate Cancer AJCC v8 / Stage IIIC Prostate Cancer AJCC v8 / Testosterone Greater Than 150 ng/dL1
2Active Not RecruitingTreatmentAdenocarcinoma, Prostate / High Risk Prostate Cancer / Prostate Cancer1
2Active Not RecruitingTreatmentAdenocarcinoma, Prostate / Prostate Cancer / PSA Level Greater Than or Equal to 0.2 / PSA Progression / Recurrent Prostate Carcinoma1
2Active Not RecruitingTreatmentAdrenocortical Carcinoma / Cushing's Syndrome1
2Active Not RecruitingTreatmentCancer, Breast1
2Active Not RecruitingTreatmentCastration Levels of Testosterone / Castration-Resistant Prostate Carcinoma / Hormone-Resistant Prostate Cancer / PSA Progression / Recurrent Prostate Carcinoma / Stage IV Prostate Cancer / Stage IV Prostate Cancer AJCC v71
2Active Not RecruitingTreatmentCastration Levels of Testosterone / Castration-Resistant Prostate Carcinoma / Metastatic Hormone Refractory Prostate Cancer / Prostate Cancer / PSA Progression / Stage IV Prostate Adenocarcinoma AJCC v71
2Active Not RecruitingTreatmentCastration Resistant Prostate Cancer (CRPC)1
2Active Not RecruitingTreatmentCastration-Resistant Prostate Cancer (CRPC)2
2Active Not RecruitingTreatmentHormone-Resistant Prostate Cancer / Metastatic Hormone Refractory Prostate Cancer / Recurrent Prostate Carcinoma / Stage IV Prostate Adenocarcinoma1
2Active Not RecruitingTreatmentHormone-Resistant Prostate Cancer / Recurrent Prostate Cancer / Stage IV Prostate Cancer1
2Active Not RecruitingTreatmentMetastatic Castration Resistant Prostate Cancer1
2Active Not RecruitingTreatmentMetastatic Castration-Resistant Prostatic Cancer1
2Active Not RecruitingTreatmentMetastatic Hormone Refractory Prostate Cancer1
2Active Not RecruitingTreatmentProstate Cancer9
2Active Not RecruitingTreatmentProstate Cancer / Prostatic Neoplasms1
2Active Not RecruitingTreatmentReccurent/Metastatic Solid Tumor Disease1
2Active Not RecruitingTreatmentStage III Prostate Adenocarcinoma / Stage III Prostate Adenocarcinoma AJCC v7 / Stage III Prostate Cancer / Stage III Prostate Cancer AJCC v7 / Stage IV Prostate Adenocarcinoma / Stage IV Prostate Adenocarcinoma AJCC v7 / Stage IV Prostate Cancer / Stage IV Prostate Cancer AJCC v71
2CompletedBasic ScienceCastration-Resistant Prostate Cancer (CRPC) / Hormone Refractory Prostate Cancer / Metastatic Hormone Refractory Prostate Cancer1
2CompletedTreatmentAdenocarcinoma of the Prostate / Stage IIA Prostate Cancer / Stage IIB Prostate Cancer / Stage III Prostate Cancer / Stage IV Prostate Cancer1
2CompletedTreatmentCastration-Resistant Prostate Cancer (CRPC) / Stage IV Prostate Cancer1
2CompletedTreatmentMetastatic Castration Resistant Prostate Cancer1
2CompletedTreatmentMetastatic ER+ Her2- Breast Cancer / One to five years postmenopausal1
2CompletedTreatmentMetastatic Hormone Refractory Prostate Cancer2
2CompletedTreatmentProstate Cancer11
2CompletedTreatmentProstate Cancer / Prostate Neoplasms1
2CompletedTreatmentProstate Cancer / Prostate Neoplasms / Prostatic Neoplams / Prostatic Neoplasms1
2CompletedTreatmentProstate Cancer / Prostatic Neoplasms1
2CompletedTreatmentProstate Neoplasms2
2CompletedTreatmentProstatic Neoplasms2
2Not Yet RecruitingTreatmentAdenocarcinoma, Prostate / Castration Levels of Testosterone / Castration-Resistant Prostate Carcinoma / Double-Negative Prostate Carcinoma / Metastatic Hormone Refractory Prostate Cancer / PSA Progression / Stage IV Prostate Cancer AJCC v8 / Stage IVA Prostate Cancer AJCC v8 / Stage IVB Prostate Cancer AJCC v81
2Not Yet RecruitingTreatmentAdenocarcinoma, Prostate / Castration-Resistant Prostate Cancer (CRPC) / Metastatic Hormone Refractory Prostate Cancer / Prostate Carcinoma Metastatic in the Bone / Prostate Small Cell Carcinoma1
2Not Yet RecruitingTreatmentCastration-Resistant Prostate Cancer (CRPC) / Drugs / Prostate Cancer1
2Not Yet RecruitingTreatmentCongenital Adrenal Hyperplasia (CAH)1
2Not Yet RecruitingTreatmentMetastatic Prostate Adenocarcinoma / Prostate Adenocarcinoma With Focal Neuroendocrine Differentiation / Recurrent Prostate Carcinoma / Stage IVB Prostate Cancer AJCC v81
2Not Yet RecruitingTreatmentProstate Cancer1
2Not Yet RecruitingTreatmentProstatic Neoplasms1
2Not Yet RecruitingTreatmentProstatic Neoplasms, Castration-Resistant1
2RecruitingScreeningCastrate Sensitive Prostate Cancer1
2RecruitingTreatmentAbnormal DNA Repair / Hormone-Resistant Prostate Cancer / Metastatic Hormone Refractory Prostate Cancer / Prostate Cancer Metastatic Castration-Resistant / Stage IV Prostate Cancer1
2RecruitingTreatmentAdenocarcinoma, Prostate / Metastatic Hormone Refractory Prostate Cancer / Prostate Carcinoma Metastatic in the Bone / Stage IV Prostate Cancer AJCC v8 / Stage IVA Prostate Cancer AJCC v8 / Stage IVB Prostate Cancer AJCC v81
2RecruitingTreatmentCastration Levels of Testosterone / Castration-Resistant Prostate Carcinoma / Metastatic Prostate Carcinoma in the Soft Tissue / Prostate Carcinoma Metastatic in the Bone / PSA Progression / Stage IV Prostate Adenocarcinoma AJCC v7 / Stage IV Prostate Cancer AJCC v71
2RecruitingTreatmentCastration-Resistant Prostate Cancer (CRPC) / Metastatic Castration Resistant Prostate Cancer1
2RecruitingTreatmentCastration-Resistant Prostate Cancer (CRPC) / Prostate Cancer1
2RecruitingTreatmentCastration-Sensitive Prostate Carcinoma / Metastatic Prostatic Adenocarcinoma / Stage IV Prostate Cancer / Stage IVA Prostate Cancer / Stage IVB Prostate Cancer1
2RecruitingTreatmentHigh Risk Localised Prostate Carcinoma1
2RecruitingTreatmentMetastatic Castration Resistant Prostate Cancer2
2RecruitingTreatmentMetastatic Hormone Refractory Prostate Cancer / Prostate Cancer1
2RecruitingTreatmentMetastatic Hormone Refractory Prostate Cancer / Recurrent Prostate Carcinoma / Stage IV Prostate Cancer1
2RecruitingTreatmentNewly Diagnosed Oligometastatic Prostate Cancer1
2RecruitingTreatmentProstate Cancer14
2RecruitingTreatmentProstatic Neoplasms1
2RecruitingTreatmentSalivary Glands Tumors1
2RecruitingTreatmentStage II Prostate Adenocarcinoma / Stage III Prostate Adenocarcinoma1
2TerminatedTreatmentCastration Resistant Prostate Cancer (CRPC) / Prostate Cancer / Prostatic Neoplasms1
2TerminatedTreatmentMetastatic Castrate-Resistant Prostate Cancer / Prostate Cancer / PsA1
2TerminatedTreatmentMetastatic Hormone Refractory Prostate Cancer1
2TerminatedTreatmentProstate Cancer5
2WithdrawnBasic SciencePost-menopausal ER+ Stage I-IIIA Primary Operable Breast Cancer1
2WithdrawnTreatmentLocalized Prostate Cancer / Prostate Cancer1
2, 3RecruitingTreatmentMetastasis / Metastatic Hormone Refractory Prostate Cancer1
2, 3RecruitingTreatmentProstate Cancer1
3Active Not RecruitingTreatmentAdenocarcinoma of the Prostate / Hormone-Resistant Prostate Cancer / Recurrent Prostate Cancer / Stage IV Prostate Cancer1
3Active Not RecruitingTreatmentGeneral Surgery / Stage, Prostate Cancer1
3Active Not RecruitingTreatmentMetastatic Breast Cancer (MBC) / Metastatic Castration Resistant Prostate Cancer1
3Active Not RecruitingTreatmentMetastatic Castration Resistant Prostate Cancer1
3Active Not RecruitingTreatmentMetastatic Hormone Refractory Prostate Cancer1
3Active Not RecruitingTreatmentMetastatic Hormone Refractory Prostate Cancer / Prostate Cancer Adenocarcinoma Metastatic1
3Active Not RecruitingTreatmentProstate Neoplasms1
3Active Not RecruitingTreatmentProstatic Neoplasms2
3CompletedTreatmentMetastatic Castration Resistant Prostate Cancer1
3CompletedTreatmentProstate Cancer2
3CompletedTreatmentProstate Neoplasms2
3CompletedTreatmentProstatic Neoplasms1
3Not Yet RecruitingTreatmentAdenocarcinoma, Prostate / Positive Lymph Node / PSA Level Greater Than Zero / Stage I Prostate Cancer AJCC v8 / Stage II Prostate Cancer AJCC v8 / Stage IIA Prostate Cancer AJCC v8 / Stage IIB Prostate Cancer AJCC v8 / Stage IIC Prostate Cancer AJCC v8 / Stage III Prostate Cancer AJCC v8 / Stage IIIA Prostate Cancer AJCC v8 / Stage IIIB Prostate Cancer AJCC v8 / Stage IIIC Prostate Cancer AJCC v8 / Stage IVA Prostate Cancer AJCC v81
3Not Yet RecruitingTreatmentProstate Cancer1
3RecruitingTreatmentCastration Levels of Testosterone / Metastatic Prostatic Adenocarcinoma / Stage IV Prostate Cancer AJCC v8 / Stage IVA Prostate Cancer AJCC v8 / Stage IVB Prostate Cancer AJCC v81
3RecruitingTreatmentMetastatic Castration Resistant Prostate Cancer2
3RecruitingTreatmentMetastatic Castration-Resistant Prostatic Cancer1
3RecruitingTreatmentMetastatic Castration-resistent Prostate Cancer1
3RecruitingTreatmentMetastatic Hormone Refractory Prostate Cancer1
3RecruitingTreatmentProstate Cancer2
3RecruitingTreatmentProstatic Neoplasms1
4Active Not RecruitingTreatmentMetastatic Hormone Refractory Prostate Cancer1
4Active Not RecruitingTreatmentProstate Cancer1
4CompletedTreatmentMetastatic Castration Resistant Prostate Cancer1
4RecruitingSupportive CareCastration-Resistant Prostatic Cancer / Hormone-Refractory Prostate Cancer / Metastatic Hormone Refractory Prostate Cancer / Recurrent Prostate Carcinoma / Stage IV Prostate Cancer1
4WithdrawnNot AvailableProstate Neoplasms1
Not AvailableActive Not RecruitingNot AvailableMetastatic Castration-Resistant Prostate Cancer (mCRPC)1
Not AvailableActive Not RecruitingOtherPharmacogenetic Study1
Not AvailableActive Not RecruitingTreatmentProstate Cancer1
Not AvailableApproved for MarketingNot AvailableGenital Diseases, Male / Genital Neoplasms, Male / Genitourinary tract neoplasm / Prostate Neoplasms1
Not AvailableCompletedNot AvailableProstate Cancer1
Not AvailableNot Yet RecruitingTreatmentRate of PSA Response in Oligometastatic,CRPC Undergoing SBRT in Combination With Abiraterone Acetate (AA), Compared to Patients Treated With AA Alone1
Not AvailableRecruitingNot AvailableProstate Cancer1
Not AvailableRecruitingNot AvailableProstatic Neoplasms1
Not AvailableRecruitingTreatmentProstate Cancer1
Not AvailableTerminatedNot AvailableProstatic Neoplasms1
Not AvailableWithdrawnNot AvailableProstatic Neoplasms, Castration-Resistant1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral250 mg/1
TabletOral125 mg/1
TabletOral250 mg
TabletOral500 mg
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5604213No1997-02-182016-12-13Us
US8822438No2014-09-022027-08-24Us
US9889144No2018-02-132034-03-17Us
US10292990No2014-05-202034-05-20Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
Not Available
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
Polarizability42.04 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, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Androgen-skeleton / 3-hydroxy-delta-5-steroid / 3-hydroxysteroid / Hydroxysteroid / 3-beta-hydroxy-delta-5-steroid / 3-beta-hydroxysteroid / Delta-5-steroid / Pyridine / Cyclic alcohol / Heteroaromatic compound
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyridines, 3beta-sterol (CHEBI:68642)

Targets

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. [PubMed:20645691]

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. [PubMed:22714819]
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. [PubMed:22714819]
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. [PubMed:23064959]
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. [PubMed:26721703]
  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. [PubMed:27504016]
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. [PubMed:28893623]
  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. [PubMed:27106175]
  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. [PubMed:22714819]
  4. Abiraterone FDA label [File]
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. [PubMed:23599666]
  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. [PubMed:22714819]
  3. Zytiga product monograph [File]
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. [PubMed:22714819]

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. [PubMed:23199349]
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. [PubMed:23199349]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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. [PubMed:22714819]
  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. [PubMed:27106175]

Drug created on November 18, 2007 11:28 / Updated on November 11, 2019 06:55