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Abiraterone acetate

Product Name
Abiraterone acetate
CAS No.
154229-18-2
Chemical Name
Abiraterone acetate
Synonyms
ZYTIGA;17-(3-pyridyl)-5,16-androstadien-3beta-acetate;Abiraterone Acotate;(3)-17-(3-Pyridinyl)androsta-5,16-dien-3-ol Acetate (Ester);(3beta)-17-(3-pyridinyl)-Androsta-5,16-dien-3-ol acetate (ester);[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate;(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-(pyridin-3-yl)-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate;CS-212;CB 7630;Abiraterone WS
CBNumber
CB81396153
Molecular Formula
C26H33NO2
Formula Weight
391.55
MOL File
154229-18-2.mol
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Abiraterone acetate Property

Melting point:
127-130°C
Boiling point:
506.7±50.0 °C(Predicted)
Density 
1.14±0.1 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
Chloroform (Slightly), DMSO (Sparingly), Methanol (Sparingly)
pka
5.31±0.12(Predicted)
form 
powder
color 
white to beige
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Safety

WGK Germany 
3
RTECS 
BV7992100
HS Code 
2937290000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H360May damage fertility or the unborn child

H372Causes damage to organs through prolonged or repeated exposure

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML1527
Product name
Abiraterone acetate
Purity
≥98% (HPLC)
Packaging
25mg
Price
$543
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR2410
Product name
Abiraterone Acetate
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
500MG
Price
$534
Updated
2024/03/01
Sigma-Aldrich
Product number
1000818
Product name
Abiraterone acetate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$1730
Updated
2024/03/01
TCI Chemical
Product number
A2891
Product name
Abiraterone Acetate
Purity
>98.0%(HPLC)(T)
Packaging
200mg
Price
$291
Updated
2024/03/01
TCI Chemical
Product number
A2891
Product name
Abiraterone Acetate
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$866
Updated
2024/03/01
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Abiraterone acetate Chemical Properties,Usage,Production

Description

In April 2011, the United States FDA approved abiraterone acetate (CB7630) in combination with the steroid prednisone for the treatment of metastatic castration-resistant prostate cancer (mCRPC) for patients who were previously treated with a docetaxel containing regimen for late-stage disease. Abiraterone acetate affects prostate, testicular, and adrenal androgens by irreversibly inhibiting both the lyase and hydroxylase activity of cytochrome P450 17A (CYP17) signaling pathways (IC50's of 2.9 and 4 nM, respectively) thereby decreasing testosterone levels.Most common serious adverse events for abiraterone acetate versus placebo included fluid retention (30.5% vs. 22.3%), hypokalemia (17.1% vs. 8.4%), hypertension (9.7% vs. 7.9%), hepatic transaminase abnormalities (10.4% vs. 8.1%), and cardiac abnormalities (13.3% vs. 10.4%).

Chemical Properties

Off-White Solid

Originator

Institute of Cancer Research, London (United Kingdom)

Uses

Abiraterone acetate was approved by the U.S. Food and Drug Administration (FDA) in April 2011 for the treatment of castrationresistant prostate cancer. The drug, marketed under the trade name Zytiga, was originally discovered by researchers at the Cancer Research UK Centre for Cancer Therapeutics in 1990, developed by Cougar Biotechnology, and ultimately commercialized by Johnson & Johnson after its acquisition of Cougar in 2009. Abiraterone acetate inhibits CYP17A1—an enzyme expressed in testicular, adrenal, and prostatic tumor tissues—which has been implied in the production of testosterone and the proliferation of such tumor cell lines.

Uses

A novel steroidal inhibitor of human Cytochrome P450(17a-Hydroxylase-C17,20-lyase): potential agent for the treatment of prostatic cancer.

Uses

Abiraterone acetate is a novel steroidal inhibitor of human Cytochrome P450 (17α-Hydroxylase-C17,20-lyase): potential agent for the treatment of prostatic cancer.

Definition

ChEBI: A sterol ester obtained by formal condensation of the 3-hydroxy group of abiraterone with the carboxy group of acetic acid. A prodrug that is converted in vivo to abiraterone. Used for treatment of metastatic castrate-resistant prostate cance .

brand name

Zytiga

Biochem/physiol Actions

Abiraterone acetate is a prodrug of abiraterone, which is a potent, selective, and orally bioavailable inhibitor of CYP17A1 (CYP450c17), an enzyme that catalyzes two key serial reactions (17α hydroxylase and 17,20 lyase) in androgen and estrogen biosynthesis resulting in the formation of DHEA and androstenedione, which may ultimately be metabolized into testosterone. CYP17 is the key enzyme for androgen biosynthesis in both the testes and adrenals, so its inhibition should stop the production of androgens in both places. Abiraterone acetate is used for the treatment of metastatic castration-resistant prostate cancer. Abiraterone acetate possesses significant antitumor activity in post-docetaxel patients with CRPC (castration-resistant prostate cancer). It is highly essential for androgen biosynthesis in the testes, adrenal glands, and prostate tissue.

Clinical Use

Hormone antagonist:
Treatment of metastatic prostate cancer

Synthesis

The most convenient synthesis for scale-up will be highlighted from two published syntheses. Commercially available androstenolone 1 was acylated with acetic anhydride in the presence of boron trifluoride-diethyl etherate to give a near quantitative yield of acetate 2. The conversion of ketone 2 to vinyl triflate 3 involved careful selection of base to prevent elimination of the acetate group. To this extent, subjection of 2 to triflic anhydride in dichloromethane at ambient temperature followed by slow addition of triethylamine minimized undesired side products and delivered triflate 3 in 60% isolated yield. Subsequent Suzuki coupling with diethylborane 4 under standard conditions ultimately furnished abiraterone acetate (I) in 75% yield.

target

P450 (e.g. CYP17)

Drug interactions

Potentially hazardous interactions with other drugs
Antibacterials: concentration possibly reduced by rifabutin and rifampicin - avoid.
Antidepressants: concentration possibly reduced by St John’s wort - avoid.
Antiepileptics: concentration possibly reduced by carbamazepine, fosphenytoin, phenobarbital, phenytoin and primidone - avoid.

Metabolism

Abiraterone acetate is hydrolysed to abiraterone, which then undergoes metabolism including sulphation, hydroxylation and oxidation mainly in the liver to form inactive metabolites. About 88% of a dose is excreted in the faeces, of which about 55% is unchanged abiraterone acetate and about 22% is abiraterone; about 5% of a dose is excreted in the urine.

storage

Store at -20°C

Abiraterone acetate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Abiraterone acetate manufacturers

hebei hongtan Biotechnology Co., Ltd
Product
Abiraterone Acetate 154229-18-2
Price
US $30.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
2000kg
Release date
2024-05-14
hebei hongtan Biotechnology Co., Ltd
Product
Stanozolol 10418-03-8
Price
US $30.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
2000kg
Release date
2024-05-16
Jinan Million Pharmaceutical Co., Ltd
Product
Abiraterone acetate 154229-18-2
Price
US $1.00-0.50/kg
Min. Order
1kg
Purity
99%
Supply Ability
200
Release date
2024-03-22

154229-18-2, Abiraterone acetateRelated Search:

ETOFIBRATE ABiraterone impurity 15 Abiraterone Acetate Dimer Impurity (3β)-Androsta-5,16-diene-3,17-diol 3-Acetate 17-(Trifluoromethanesulfonate) DIETHYL(3-PYRIDYL)BORANE Abiraterone Sulfate Sodium Salt Abiraterone Impurity 4 Abiraterone Ethyl Ether Dehydroepiandrosterone acetate Abiraterone 10,13-dimethyl-17-oxo-3-sulfooxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene Abiraterone Related Compound 8 Dehydroepiandrosterone Abiraterone Sulfate Abiraterone Related CoMpound 2 (Prasterone Triflate) Abiraterone N-Oxide Abiraterone DiMer IMpurity (Prasteronyl Abiraterone) 17-Iodoandrosta-5,16-dien-3beta-ol

  • Abiraterone Acotate
  • Abiraterone Acetate impurity
  • (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-(pyridin-3-yl)-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
  • [(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
  • (3β)-17-(3-pyridinyl) androsta-5,16-dien-3-yl acetate
  • Abiraterone acetate, >=99%
  • Abirteroneacetate
  • ZYTIGA
  • ABITATERONE ACETATE
  • 2-((3S,8R,9S,10R,13S,14S)-10,13-Dimethyl-17-(pyridin-3-yl)-2,3,4,7,8,9,10,11,12,13,14,15-dodec
  • 17-(3-pyridyl)-5,16-androstadien-3beta-acetate
  • (3)-17-(3-Pyridinyl)androsta-5,16-dien-3-ol Acetate (Ester)
  • Abiraterone Acetate
  • CB 7630
  • Abiraterone acetate 99.5%
  • Abiraterone acetate(CB7630)
  • 3β-acetoxy-17-(3-pyridyl)androsta-5,16-diene
  • (3beta)-17-(3-pyridinyl)-Androsta-5,16-dien-3-ol acetate (ester)
  • 2-((3S,8R,9S,10R,13S,14S)-10,13-diMethyl-17-(pyridin-3-yl)-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl)acetate
  • Abiraterone acetate ester
  • Androsta-5,16-dien-3-ol,17-(3-pyridinyl)-, acetate (ester), (3b)-
  • Abiraterone acetate - CB 7630 | JNJ 212082
  • CS-212
  • Androsta-5,16-dien-3-ol,17-(3-pyridinyl)
  • 3-Epi-abiraterone Acetate stereoisomer
  • Abiraterone Acetate &gt
  • 17-(3-pyridyl)-5,16-androstadien-3beta-acetatee
  • 17-(Pyridin-3-yl)androsta-5,16-dien-3β-yl acetate
  • Androsta-5,16-dien-3-ol, 17-(3-pyridinyl)-, acetate (ester), (3β)-
  • Abiraterone Impurity 81
  • 3beta-17-(3-Pyridyl)androsta-5,16-dien-3-ol Acetate
  • Abiraterone acetate ISO 9001：2015 REACH
  • (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-yl acetate
  • Abiraterone acetate (USFDA)
  • Abiraterone acetate- USP
  • Abiraterone Acetate CAS 154229-18-2
  • (3β)-17-(3-pyridyl)- androsta-5,16-dien-3-ol-acetate
  • Abiraterone Acetate (Zytiga
  • formerly CB-7598
  • Abiraterone Acetate D4Q: What is Abiraterone Acetate D4 Q: What is the CAS Number of Abiraterone Acetate D4 Q: What is the storage condition of Abiraterone Acetate D4 Q: What are the applications of Abiraterone Acetate D4
  • Abiraterone Acetate (1000818)
  • 8-Dihydroxyquinaldic acid
  • Androsta-5,16-dien-3-ol, 17-(3-pyridinyl)-, acetate (ester), (3β)-
  • Abiteron Acetate
  • Abiraterone WS
  • (3S,8R,9S,10R,13S,14S)-10,13-Dimethyl-17-(3-pyridyl)-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl Acetate
  • ABIRATERONE ACTATE
  • 154229-18-2
  • 54229-18-2
  • C26H32NO2
  • Inhibitors
  • Inhibitor
  • Final material
  • Anti-cancer & immunity
  • DQM
  • API
  • Intermediates & Fine Chemicals
  • Pharmaceuticals