Bexarotene

Các tên gọi khác (11 ) :

4-[1-(3,5,5,8,8-pentamethyltetralin-2-yl)ethenyl]benzoic acid
4-[1-(5,6,7,8,-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphtalenyl)ethenyl]benzoic acid
Bexaroten
Bexarotène
Bexarotene
Bexaroteno
Bexarotenum
P-(1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)vinyl)benzoic acid
p-[1-(5,6,7,8,-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)vinyl]benzoic acid
Targretyn
Targrexin

Thuốc Gốc

Small Molecule

CAS: 153559-49-0

ATC: L01XX25

ĐG : Catalent Pharma Solutions , http://www.catalent.com

CTHH: C₂₄H₂₈O₂

PTK: 348.4779

Bexarotene (Targretin) is an antineoplastic agent indicated by the FDA for Cutaneous T cell lymphoma. It has been used off-label for lung cancer, breast cancer, and Kaposi's sarcoma. [Wikipedia]

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₂₄H₂₈O₂

Phân tử khối

348.4779

Monoisotopic mass

348.20893014

InChI

InChI=1S/C24H28O2/c1-15-13-20-21(24(5,6)12-11-23(20,3)4)14-19(15)16(2)17-7-9-18(10-8-17)22(25)26/h7-10,13-14H,2,11-12H2,1,3-6H3,(H,25,26)

InChI Key

InChIKey=NAVMQTYZDKMPEU-UHFFFAOYSA-N

IUPAC Name

4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoic acid

Traditional IUPAC Name

bexarotene

SMILES

CC1=CC2=C(C=C1C(=C)C1=CC=C(C=C1)C(O)=O)C(C)(C)CCC2(C)C

Độ hòa tan

1.49e-04 g/l

logP

6.9

logS

-6.4

pKa (strongest acidic)

4.07

PSA

37.3 Å²

Refractivity

117.12 m³·mol^-1

Polarizability

40.89 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

-1

Number of Rings

Bioavailability

Dược Lực Học : Bexarotene is a member of a subclass of retinoids that selectively activate retinoid X receptors (RXRs). These retinoid receptors have biologic activity distinct from that of retinoic acid receptors (RARs). Bexarotene is indicated for the treatment of cutaneous manifestations of cutaneous T-cell lymphoma in patients who are refractory to at least one prior systemic therapy. Bexarotene selectively binds and activates retinoid X receptor subtypes (RXR_α, RXR_β, RXR_γ). RXRs can form heterodimers with various receptor partners such as retinoic acid receptors (RARs), vitamin D receptor, thyroid receptor, and peroxisome proliferator activator receptors (PPARs). Once activated, these receptors function as transcription factors that regulate the expression of genes that control cellular differentiation and proliferation. Bexarotene inhibits the growth in vitro of some tumor cell lines of hematopoietic and squamous cell origin. It also induces tumor regression in vivo in some animal models.

Cơ Chế Tác Dụng : Bexarotene (Targretin) is an antineoplastic agent indicated by the FDA for Cutaneous T cell lymphoma. It has been used off-label for lung cancer, breast cancer, and Kaposi's sarcoma. [Wikipedia] Bexarotene selectively binds with and activates retinoid X receptor subtypes. There are three subtypes in total: RXR_α, RXR_β, RXR_γ. The exact mechanism of action of bexarotene in the treatment of CTCL is unknown but the drug has activity in all clinical stages of CTCL.

Dược Động Học :

▧ Protein binding :
>99%
▧ Route of Elimination :
Urinary elimination of bexarotene and its known metabolites is a minor excretory pathway (<1% of administered dose).
▧ Half Life :
7 hours

Chỉ Định : Used orally for the treatment of skin manifestations of cutaneous T-cell lymphoma (CTCL) in patients who are refractory to at least one prior systemic therapy. Also used topically for the treatment of skin lesions in early (stage IA and IB) CTCL in patients who experience refractory or persistent disease with the use of other therapies or are intolerant of other therapies.

Tương Tác Thuốc :

Conivaptan Conivaptan may increase the serum concentration of CYP3A4 substrates such as bexarotene. Upon completion/discontinuation of conivaptan, allow at least 7 days before initiating therapy with drugs that are CYP3A4 substrates. Consider therapy modification.
Demeclocycline Tetracycline derivatives like demeclocycline may enhance the adverse/toxic effect of Retinoic Acid Derivatives. Due to the risk of developing pseudotumor cerebri (also known as intracranial hypertension), avoid this combination of drugs if possible. If used concomitantly, monitor for evidence of this interaction (eg, dizziness, diplopia, headache).
Desogestrel Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of desogestrel, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Doxycycline Tetracycline derivatives like doxycycline may enhance the adverse/toxic effect of Retinoic Acid Derivatives. Due to the risk of developing pseudotumor cerebri (also known as intracranial hypertension), avoid this combination of drugs if possible. If used concomitantly, monitor for evidence of this interaction (eg, dizziness, diplopia, headache).
Drospirenone Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of drospirenone, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Ethynodiol Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of ethynodiol diacetate it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Etonogestrel Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of etonogestrel, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Gemfibrozil Gemfibrozil may increase the serum concentration of bexarotene. This combination should be avoided.
Levonorgestrel Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of levonorgestrel, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Medroxyprogesterone Acetate Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of medroxyprogesterone, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Minocycline Tetracycline derivatives like minocycline may enhance the adverse/toxic effect of Retinoic Acid Derivatives. Due to the risk of developing pseudotumor cerebri (also known as intracranial hypertension), avoid this combination of drugs if possible. If used concomitantly, monitor for evidence of this interaction (eg, dizziness, diplopia, headache).
Norelgestromin Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of norelgestromin, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Norethindrone Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of norethindrone, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Norgestimate Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of norgestimate, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Tetracycline Tetracycline may enhance the adverse/toxic effect of Retinoic Acid Derivatives. Due to the risk of developing pseudotumor cerebri (also known as intracranial hypertension), avoid this combination of drugs if possible. If used concomitantly, monitor for evidence of this interaction (eg, dizziness, diplopia, headache).
Tigecycline Tigecycline may enhance the adverse/toxic effect of Retinoic Acid Derivatives. The development of pseudotumor cerebri (intracranial hypertension) is of particular concern. Avoid this combination.
Vitamin A Bexarotene increases the risk of vitamin A toxicity. Avoid vitamin A supplementation while taking bexarotene.

Liều Lượng & Cách Dùng : Capsule - Oral
Gel - Topical

Dữ Kiện Thương Mại

Giá thị trường

Biệt dược thương mại : Targretin 1% gel

Giá bán buôn : USD >30.08

Đơn vị tính : g
Biệt dược thương mại : Targretin 75 mg softgel

Giá bán buôn : USD >36.54

Đơn vị tính : softget capsule
Biệt dược thương mại : Targretin 75 mg capsule

Giá bán buôn : USD >38.0

Đơn vị tính : capsule

Nhà Sản Xuất

Công ty : Eisai

Sản phẩm biệt dược : Targretin

Đóng gói

Công ty : Catalent Pharma Solutions

Website : http://www.catalent.com
Công ty : Contract Pharm

Website : http://www.contractpharma.com
Công ty : Eisai Inc.

Website : http://www.eisai.com

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB00307

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=82146

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46509119

ChemSpider

http://www.chemspider.com/Chemical-Structure.74139.html

National Drug Code Directory

http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/64365-502-01

PharmGKB

http://www.pharmgkb.org/drug/PA164752250

Wikipedia

http://en.wikipedia.org/wiki/Bexarotene

RxList

http://www.rxlist.com/cgi/generic3/bexarotene.htm

Drugs.com

http://www.drugs.com/cdi/bexarotene.html

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