Tìm theo
Ingenol Mebutate
Các tên gọi khác (5 ) :
  • 3-Ingenyl Angelate
  • Ingenol 3-angelate
  • ingenol mebutate
  • PEP005
  • Picato
Thuốc điều trị ung thư
Thuốc Gốc
Small Molecule
CAS: 75567-37-2
ATC: D06BX02
CTHH: C25H34O6
PTK: 430.5339
Ingenol mebutate was approved by the FDA in January 2012, and it is marketed under the name Picato®. Picato gel is indicated for the topical treatment of actinic keratosis. Before approval, ingenol mebutate was called PEP005 as an investigational drug. PEP005 is a selective small molecule activator of protein kinase C (PKC) extracted from the plant Euphorbia peplus, whose sap has been used as a traditional medicine for the treatment of skin conditions including warts and cancer. PEP005 also has potent anti-leukemic effects, inducing apoptosis in myeloid leukemia cell lines and primary AML cells at nanomolar concentrations.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C25H34O6
Phân tử khối
430.5339
Monoisotopic mass
430.23553882
InChI
InChI=1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3/b12-7-/t14-,16+,17-,18+,19-,21+,24+,25+/m1/s1
InChI Key
InChIKey=VDJHFHXMUKFKET-WDUFCVPESA-N
IUPAC Name
(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-4-yl (2Z)-2-methylbut-2-enoate
Traditional IUPAC Name
(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-4-yl (2Z)-2-methylbut-2-enoate
SMILES
OCC1=C[C@]2([H])C(=O)[C@]3(C=C(C)[C@H](OC(=O)C(\C)=C/C)[C@@]3(O)[C@@H]1O)[C@H](C)C[C@@]1([H])C(C)(C)[C@@]21[H]
Độ hòa tan
2.79e-01 g/l
logP
2.51
logS
-3.2
pKa (strongest acidic)
12.09
pKa (Strongest Basic)
-2.8
PSA
104.06 Å2
Refractivity
117.86 m3·mol-1
Rotatable Bond Count
4
H Bond Acceptor Count
5
H Bond Donor Count
3
Physiological Charge
0
Number of Rings
4
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : The pharmacodynamics of ingenol mebutate in producing cell death in actinic keratosis is unknown.
Cơ Chế Tác Dụng : Ingenol mebutate was approved by the FDA in January 2012, and it is marketed under the name Picato®. Picato gel is indicated for the topical treatment of actinic keratosis. Before approval, ingenol mebutate was called PEP005 as an investigational drug. PEP005 is a selective small molecule activator of protein kinase C (PKC) extracted from the plant Euphorbia peplus, whose sap has been used as a traditional medicine for the treatment of skin conditions including warts and cancer. PEP005 also has potent anti-leukemic effects, inducing apoptosis in myeloid leukemia cell lines and primary AML cells at nanomolar concentrations. The exact mechanism of action of ingenol mebutate in actinic keratosis is unknown. It is presumed to involve primary necrosis then neutrophil-mediated inflammation and antibody-dependent cell death of residual disease cells. Additionally in early studies, PEP005 was shown to be an effective activator of PKC-delta and PKC-delta translocation into nucleus and membranes. PEP005 also downregulates the expression and activity of PKC-alpha. PEP005 induced modulation of PKCs leads to Ras/Raf/MAPK and p38 activation and AKT/PKB inhibition.
Dược Động Học :
▧ Absorption :
Since ingenol mebutate is a topical treatment, the systemic absorption is less than 0.1 ng/mL.
▧ Volume of Distribution :
There is no volume of distribution quantity since ingenol mebutate is a topical treatment.
▧ Protein binding :
There is no plasma protein binding quantity since ingenol mebutate is a topical treatment
▧ Metabolism :
There is no metabolism of Picato since ingenol mebutate is a topical treatment, and ingenol mebutate does not inhibit or induce a majority of the cytochrome P450 (CYP) enzymes.
▧ Route of Elimination :
There is no route of elimination since ingenol mebutate is a topical treatment.
▧ Half Life :
There is no half-life quantity since ingenol mebutate is a topical treatment.
▧ Clearance :
There is no clearance quantity since ingenol mebutate is a topical treatment.
Độc Tính : The most common adverse reactions are local skin reactions at the application site, headache, periorbital edema,and nasopharyngitis.
Chỉ Định : For the topical treatment of actinic keratosis.
Liều Lượng & Cách Dùng : Gel - Topical - 0.015%
Gel - Topical - 0.05%
Dữ Kiện Thương Mại
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Picato
  • Công ty : LEO Pharma
    Sản phẩm biệt dược : Picato gel
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB05013
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=6918670
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=12015710
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D09393
ChemSpider
http://www.chemspider.com/Chemical-Structure.5293863.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/50222-503-47
Wikipedia
http://en.wikipedia.org/wiki/Ingenol_mebutate
RxList
http://www.rxlist.com/picato-drug.htm
Drugs.com
http://www.drugs.com/ppa/ingenol-mebutate.html
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