Tìm theo
Voacamine
Các tên gọi khác (3) :
  • Methyl-12-methoxy-13-(17-methoxy-17-oxovobasan-3alpha-yl)ibogamine-18-carboxylate
  • Voacanginine
  • Vocamine
antimalarials
Thuốc Gốc
Small Molecule
CAS: 3371-85-5
CTHH: C43H52N4O5
PTK: 704.8968
Voacamine is an alkaloid isolated from the bark of the Pescheria fuchsiae folia tree. It is an antimalarial drug approved for use in several African countries. Voacamine is also under investigation for use in modulating multidrug-resistance in tumor cells.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C43H52N4O5
Phân tử khối
704.8968
Monoisotopic mass
704.393770794
InChI
InChI=1S/C43H52N4O5/c1-7-24-15-23-20-43(42(49)52-6)39-27(13-14-47(21-23)40(24)43)29-19-36(50-4)30(17-34(29)45-39)31-16-28-25(8-2)22-46(3)35(37(28)41(48)51-5)18-32-26-11-9-10-12-33(26)44-38(31)32/h8-12,17,19,23-24,28,31,35,37,40,44-45H,7,13-16,18,20-22H2,1-6H3/b25-8-/t23-,24-,28-,31+,35+,37?,40-,43+/m0/s1
InChI Key
InChIKey=VCMIRXRRQJNZJT-XRMSBCOFSA-N
IUPAC Name
methyl (1S,15S,17S,18S)-17-ethyl-6-[(1R,12R,14R,15E)-15-ethylidene-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8-tetraen-12-yl]-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate
Traditional IUPAC Name
methyl (1S,15S,17S,18S)-17-ethyl-6-[(1R,12R,14R,15E)-15-ethylidene-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8-tetraen-12-yl]-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate
SMILES
[H][C@@]12C[C@H](CC)[C@]3([H])N(C1)CCC1=C(NC4=CC(=C(OC)C=C14)[C@@]1([H])C[C@]4([H])C(C(=O)OC)[C@@]([H])(CC5=C1NC1=CC=CC=C51)N(C)C\C4=C\C)[C@@]3(C2)C(=O)OC
Độ hòa tan
3.23e-03 g/l
logP
6.21
logS
-5.3
pKa (strongest acidic)
15.56
pKa (Strongest Basic)
8.53
PSA
99.89 Å2
Refractivity
203.68 m3·mol-1
Rotatable Bond Count
7
H Bond Acceptor Count
5
H Bond Donor Count
2
Physiological Charge
2
Number of Rings
9
Bioavailability
0
MDDR-Like Rule
true
Dược Lực Học : Voacamine is an anti-malarial extracted from the Brazilian tree Peschiera fuchsiaefolia. In one study (PMID: 11180519), the in vivo antiplasmodial activity of voacamine was assessed in a 4-day test. It was shown to exhibit in vivo activity with 25.4% and 43.4% inhibition of parasitaemia with 2.5 and 10 mg/kg, respectively. In synchronized cultures, it was found to act on trophozoite and schizont stages of Plasmodium falciparum. Voacamine is a bisindolic alkaloid under investigation for modulation of multidrug resistance to enhance anticancer drugs such as doxorubicin.
Cơ Chế Tác Dụng : Voacamine is an alkaloid isolated from the bark of the Pescheria fuchsiae folia tree. It is an antimalarial drug approved for use in several African countries. Voacamine is also under investigation for use in modulating multidrug-resistance in tumor cells. Voacamine is possibly a substrate for P-glycoprotein (P-gp), an efflux pump responsible for multidrug resistance in tumor cells. Voacamine may compete with anticancer drugs such as doxorubicin for P-gp transport, decreasing removal of doxorubicin.
Chỉ Định : For the treatment of malaria. Also under investigation for the modulation of multidrug resistance in cancer cells.
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB04877
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=11953931
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=99443228
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C09252
ChemSpider
http://www.chemspider.com/Chemical-Structure.10128230.html
PharmGKB
http://www.pharmgkb.org/drug/PA165958347
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