Tìm theo
Calanolide A
Các tên gọi khác (2) :
  • (+)-calanolide A
  • (+/-)-calanolide A
anti hiv agents, reverse transcriptase inhibitors
Thuốc Gốc
Small Molecule
CAS: 142632-32-4
CTHH: C22H26O5
PTK: 370.4388
Calanolide A is a new non-nucleoside reverse transcriptase inhibitor (NNRTI) derived from a plant found in the Malaysian rain forest. A related compound, calanolide B, also has anti-HIV activity. Both drugs are being developed by Sarawak Pharmaceuticals. A preliminary dosing study among HIV-infected individuals showed a significant antiviral effect compared with placebo.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C22H26O5
Phân tử khối
370.4388
Monoisotopic mass
370.178023942
InChI
InChI=1S/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3/t11-,12-,18+/m1/s1
InChI Key
InChIKey=NIDRYBLTWYFCFV-FMTVUPSXSA-N
IUPAC Name
(10R,11S,12S)-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-6,10,11,12-tetrahydro-2H-1,5,9-trioxatriphenylen-2-one
Traditional IUPAC Name
calanolide A
SMILES
CCCC1=CC(=O)OC2=C1C1=C(C=CC(C)(C)O1)C1=C2[C@@H](O)[C@H](C)[C@@H](C)O1
Độ hòa tan
1.78e-02 g/l
logP
3.79
logS
-4.3
pKa (strongest acidic)
13.63
pKa (Strongest Basic)
-3.4
PSA
64.99 Å2
Refractivity
104.11 m3·mol-1
Polarizability
40.99 Å3
Rotatable Bond Count
2
H Bond Acceptor Count
4
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
4
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Calanolide A is a new non-nucleoside reverse transcriptase inhibitor (NNRTI) derived from a plant found in the Malaysian rain forest. A related compound, calanolide B, also has anti-HIV activity. Both drugs are being developed by Sarawak Pharmaceuticals. The drug is metabolised by cytochrome P450 CYP3A, and its developers have suggested that drug levels may be enhanced if co-administered with ritonavir (Norvir). The drug is active in the test tube against HIV with the two most common NNRTI-related mutations, K103N and Y181C, and selects for a mutation which does not cause cross-resistance with any other NNRTIs currently under investigation. A substitution at codon Y188H of reverse transcriptase has been associated with 30-fold resistance to calanolide A in vitro (Quan 1999). The compound is essentially inactive against strains of the less common HIV type 2.
Cơ Chế Tác Dụng : Calanolide A is a new non-nucleoside reverse transcriptase inhibitor (NNRTI) derived from a plant found in the Malaysian rain forest. A related compound, calanolide B, also has anti-HIV activity. Both drugs are being developed by Sarawak Pharmaceuticals. A preliminary dosing study among HIV-infected individuals showed a significant antiviral effect compared with placebo. Viral life-cycle studies indicate that calanolide A acts early in the infection process, similar to the known HIV reverse transcriptase (RT) inhibitor 2', 3'-dideoxycytidine. In enzyme inhibition assays, calanolide A potently and selectively inhibits recombinant HIV type 1 RT but not cellular DNA polymerases or HIV type 2 RT within the concentration range tested.
Dược Động Học :

▧ Metabolism :
Hepatic.
▧ Half Life :
20 hours for 800mg
Chỉ Định : For use in combination treatment of HIV infection (AIDS).
Liều Lượng & Cách Dùng : Capsule - Oral
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB04886
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=64972
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=11339
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C09147
ChemSpider
http://www.chemspider.com/Chemical-Structure.58497.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50002662
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