Tìm theo
Ciclopirox
Các tên gọi khác (2) :
  • 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone
  • Ciclopiroxum
antifungal agents
Thuốc Gốc
Small Molecule
CAS: 29342-05-0
ATC: D01AE14, G01AX12
ĐG : Actavis Group , http://www.actavis.com
CTHH: C12H17NO2
PTK: 207.2689
Ciclopirox olamine (used in preparations called Batrafen, Loprox, Mycoster, Penlac and Stieprox) is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. It is most useful against Tinea versicolor. [Wikipedia]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C12H17NO2
Phân tử khối
207.2689
Monoisotopic mass
207.125928793
InChI
InChI=1S/C12H17NO2/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10/h7-8,10,15H,2-6H2,1H3
InChI Key
InChIKey=SCKYRAXSEDYPSA-UHFFFAOYSA-N
IUPAC Name
6-cyclohexyl-1-hydroxy-4-methyl-1,2-dihydropyridin-2-one
Traditional IUPAC Name
ciclopirox
SMILES
CC1=CC(=O)N(O)C(=C1)C1CCCCC1
Độ tan chảy
143
Độ hòa tan
1.41e+00 g/l
logP
2.3
logS
-2.2
pKa (strongest acidic)
6.84
pKa (Strongest Basic)
-6.2
PSA
40.54 Å2
Refractivity
60.91 m3·mol-1
Polarizability
23.12 Å3
Rotatable Bond Count
1
H Bond Acceptor Count
2
H Bond Donor Count
1
Physiological Charge
-1
Number of Rings
2
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Ciclopirox is a broad-spectrum antifungal medication that also has antibacterial and anti-inflammatory properties. Its main mode of action is thought to be its high affinity for trivalent cations, which inhibit essential co-factors in enzymes. Ciclopirox exhibits either fungistatic or fungicidal activity in vitro against a broad spectrum of fungal organisms, such as dermatophytes, yeasts, dimorphic fungi, eumycetes, and actinomycetes. In addition to its broad spectrum of action, ciclopirox also exerts antibacterial activity against many Gram-positive and Gram-negative bacteria. Furthermore, the anti-inflammatory effects of ciclopirox have been demonstrated in human polymorphonuclear cells, where ciclopirox has inhibited the synthesis of prostaglandin and leukotriene. Ciclopirox can also exhibit its anti-inflammatory effects by inhibiting the formation of 5-lipoxygenase and cyclooxygenase.
Cơ Chế Tác Dụng : Ciclopirox olamine (used in preparations called Batrafen, Loprox, Mycoster, Penlac and Stieprox) is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. It is most useful against Tinea versicolor. [Wikipedia] Unlike antifungals such as itraconazole and terbinafine, which affect sterol synthesis, ciclopirox is thought to act through the chelation of polyvalent metal cations, such as Fe3+ and Al3+. These cations inhibit many enzymes, including cytochromes, thus disrupting cellular activities such as mitochondrial electron transport processes and energy production. Ciclopirox also appears to modify the plasma membrane of fungi, resulting in the disorganization of internal structures. The anti-inflammatory action of ciclopirox is most likely due to inhibition of 5-lipoxygenase and cyclooxygenase. ciclopirox may exert its effect by disrupting DNA repair, cell division signals and structures (mitotic spindles) as well as some elements of intracellular transport.
Dược Động Học :
▧ Absorption :
Rapidly absorbed after oral administration. Mean absorption of ciclopirox after application to nails of all twenty digits and adjacent 5 millimeters of skin once daily for 6 months in patients with dermatophytic onychomycoses was less than 5% of the applied dose. Ciclopirox olamine also penetrates into hair and through the epidermis and hair follicles into sebaceous glands and dermis.
▧ Protein binding :
Protein binding is 94-97% following topical administration.
▧ Metabolism :
Glucuronidation is the main metabolic pathway of ciclopirox.
▧ Route of Elimination :
Most of the compound is excreted either unchanged or as glucuronide. After oral administration of 10 mg of radiolabeled drug (14C-ciclopirox) to healthy volunteers, approximately 96% of the radioactivity was excreted renally within 12 hours of administration. Ninety-four percent of the renally excreted radioactivity was in the form of glucuronides.
▧ Half Life :
1.7 hours for 1% topical solution.
Độc Tính : Oral LD50 in rat is >10 ml/kg. Symptoms of overexposure include drowsiness and headache.
Chỉ Định : Used as a topical treatment in immunocompetent patients with mild to moderate onychomycosis of fingernails and toenails without lunula involvement, due to Trichophyton rubrum.
Liều Lượng & Cách Dùng : Cream - Topical
Lotion - Topical
Shampoo - Topical
Solution - Topical
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Sanofi
    Sản phẩm biệt dược : Batrafen
  • Công ty :
    Sản phẩm biệt dược : Ciclodan
  • Công ty :
    Sản phẩm biệt dược : CNL8
  • Công ty : Sanofi
    Sản phẩm biệt dược : Loprox
  • Công ty : Pierre Fabre
    Sản phẩm biệt dược : Mycoster
  • Công ty : Sanofi
    Sản phẩm biệt dược : Penlac
  • Công ty : Stiefel
    Sản phẩm biệt dược : Stieprox
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01188
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=2749
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506333
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D01364
ChemSpider
http://www.chemspider.com/Chemical-Structure.2647.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50231223
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0066-8008-01
PharmGKB
http://www.pharmgkb.org/drug/PA164747060
Wikipedia
http://en.wikipedia.org/wiki/Ciclopirox
RxList
http://www.rxlist.com/cgi/generic3/penlac.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/lop1236.shtml
Drugs.com
http://www.drugs.com/cdi/ciclopirox-cream.html
... loading
... loading