Quinupristin

Thuốc trị ký sinh trùng, chống nhiễm khuẩn

Thuốc Gốc

Small Molecule

CAS: 120138-50-3

CTHH: C₅₃H₆₇N₉O₁₀S

PTK: 1022.218

Quinupristin/dalfopristin is a combination of two antibiotics used to treat infections by staphylococci and by vancomycin-resistant Enterococcus faecium. Dalfopristin inhibits the early phase of protein synthesis in the bacterial ribosome and quinupristin inhibits the late phase of protein synthesis. The combination of the two components acts synergistically and is more effective in vitro than each component alone.

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₅₃H₆₇N₉O₁₀S

Phân tử khối

1022.218

Monoisotopic mass

1021.473160099

InChI

InChI=1S/C53H67N9O10S/c1-6-37-50(68)61-23-11-14-38(61)51(69)59(5)40(26-32-16-18-36(19-17-32)58(3)4)52(70)62-28-35(30-73-43-29-60-24-20-33(43)21-25-60)42(64)27-39(62)47(65)57-45(34-12-8-7-9-13-34)53(71)72-31(2)44(48(66)55-37)56-49(67)46-41(63)15-10-22-54-46/h7-10,12-13,15-19,22,31,33,35,37-40,43-45,63H,6,11,14,20-21,23-30H2,1-5H3,(H,55,66)(H,56,67)(H,57,65)/t31-,35?,37-,38+,39?,40+,43-,44+,45+/m1/s1

InChI Key

InChIKey=WTHRRGMBUAHGNI-MJWHERSYSA-N

IUPAC Name

N-[(3S,6S,12R,15S,16R,19S)-25-{[(3S)-1-azabicyclo[2.2.2]octan-3-ylsulfanyl]methyl}-3-{[4-(dimethylamino)phenyl]methyl}-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0^{6,10}]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide

Traditional IUPAC Name

SMILES

CC[C@H]1NC(=O)[C@@H](NC(=O)C2=NC=CC=C2O)[C@@H](C)OC(=O)[C@@H](NC(=O)C2CC(=O)C(CS[C@@H]3CN4CCC3CC4)CN2C(=O)[C@H](CC2=CC=C(C=C2)N(C)C)N(C)C(=O)[C@@H]2CCCN2C1=O)C1=CC=CC=C1

Độ hòa tan

4.45e-02 g/l

logP

2.18

logS

-4.4

pKa (strongest acidic)

7.45

pKa (Strongest Basic)

8.28

PSA

231.2 Å²

Refractivity

272.84 m³·mol^-1

Polarizability

107.02 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

MDDR-Like Rule

true

Dược Lực Học : Quinupristin is a streptogramin antibiotic, derived from pristinamycin I. By inhibiting the bacterial ribosomal subunits, protein synthesis is inhibited thus leading to eventual bacterial cell death or stasis.

Cơ Chế Tác Dụng : Quinupristin/dalfopristin is a combination of two antibiotics used to treat infections by staphylococci and by vancomycin-resistant Enterococcus faecium. Dalfopristin inhibits the early phase of protein synthesis in the bacterial ribosome and quinupristin inhibits the late phase of protein synthesis. The combination of the two components acts synergistically and is more effective in vitro than each component alone. Quinupristin inhibits the late phase of protein synthesis in the bacterial ribosome. Dalfopristin binds to the 23S portion of the 50S ribosomal subunit, and changes the conformation it, enhancing the binding of quinupristin by a factor of about 100. In addition, it inhibits peptidyl transferase. Quinupristin binds to a nearby site on the 50S ribosomal subunit and prevents elongation of the polypeptide as well as causing incomplete chains to be released.

Dược Động Học :

▧ Protein binding :
Moderate.
▧ Metabolism :
Quinupristin is converted to two conjugated active major metabolites, one with glutathione and one with cysteine.
▧ Half Life :
3.1 hours

Chỉ Định : For the treatment of bacterial infections (usually in combination with dalfopristin).

Tương Tác Thuốc :

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Docetaxel This combination presents an increased risk of toxicity.
Dofetilide This combination presents an increased risk of toxicity
Droperidol This combination presents an increased risk of toxicity
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Etoposide This combination presents an increased risk of toxicity
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Lidocaine This combination presents an increased risk of toxicity
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Verapamil This combination presents an increased risk of toxicity
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Dữ Kiện Thương Mại

Đóng gói

Công ty : DSM Corp.

Website : http://www.dsm.com
Công ty : Gruppo Lepetit SPA
Công ty : Monarch Pharmacy

Website : http://www.monarch-pharmacy.co.uk
Công ty : Sanofi-Aventis Inc.

Website : http://www.sanofi-aventis.com

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB01369

KEGG Compound

http://www.genome.jp/dbget-bin/www_bget?cpd:C08032

KEGG Drug

http://www.genome.jp/dbget-bin/www_bget?drug:D00852

PharmGKB

http://www.pharmgkb.org/drug/PA164749647

Wikipedia

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

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