Tìm theo
Hetacillin
Các tên gọi khác (7 ) :
  • (2S,5R,6R)-6-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • 6beta-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanic acid
  • Hetacilina
  • Hetacillin
  • Hétacilline
  • Hetacillinum
  • Phenazacillin
penicillins
Thuốc Gốc
Small Molecule
CAS: 3511-16-8
ATC: J01CA18
CTHH: C19H23N3O4S
PTK: 389.469
Hetacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Hetacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Hetacillin results from the inhibition of cell wall synthesis and is mediated through Hetacillin binding to penicillin binding proteins (PBPs). Hetacillin has been withdrawn from the market since it has been discovered that it has no therapeutic advantage compared to non-ester derivatives like ampicillin.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C19H23N3O4S
Phân tử khối
389.469
Monoisotopic mass
389.140926929
InChI
InChI=1S/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11-,12-,13+,16-/m1/s1
InChI Key
InChIKey=DXVUYOAEDJXBPY-NFFDBFGFSA-N
IUPAC Name
(2S,5R,6R)-6-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional IUPAC Name
hetacillin
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2N1C(=O)[C@H](NC1(C)C)C1=CC=CC=C1)C(O)=O
Độ tan chảy
190 °C
Độ hòa tan
5.12e-01 g/l
logP
1.3
logS
-2.9
pKa (strongest acidic)
3.63
pKa (Strongest Basic)
5.47
PSA
89.95 Å2
Refractivity
99.9 m3·mol-1
Polarizability
39.58 Å3
Rotatable Bond Count
3
H Bond Acceptor Count
5
H Bond Donor Count
2
Physiological Charge
-1
Number of Rings
4
Bioavailability
1
Rule of Five
true
Dược Lực Học : Hetacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Hetacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Hetacillin results from the inhibition of cell wall synthesis and is mediated through Hetacillin binding to penicillin binding proteins (PBPs).
Cơ Chế Tác Dụng : Hetacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Hetacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Hetacillin results from the inhibition of cell wall synthesis and is mediated through Hetacillin binding to penicillin binding proteins (PBPs). Hetacillin has been withdrawn from the market since it has been discovered that it has no therapeutic advantage compared to non-ester derivatives like ampicillin. Hetacillin is a semisynthetic penicillin prodrug which itself has no antibacterial activity, but is converted in the body to ampicillin and has actions and uses similar to those of ampicillin. Hetacillin is prepared by reacting ampicillin with acetone. Ampicillin rapidly decomposes because of the intramolecular attack of the side chain amino group on the lactam ring. Hetacillin locks up the offending amino group and prevents the decompolsition Hetacillin, once hydrolyzed to ampicillin (and acetone) binds to the penicillin binding proteins found in susceptible bacteria. This inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins. Targets below reflect ampicillin targets.
Dược Động Học :

▧ Metabolism :
Hydrolyzed to active ampicillin via esterases
Chỉ Định : Hetacillin is a beta-lactam antibiotic prodrug used to treat bacterial infections. In the body it gets converted to ampicillin.
Tương Tác Thuốc :
Dữ Kiện Thương Mại
Nhà Sản Xuất
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00739
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=443387
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46504545
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C11729
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D01074
ChemSpider
http://www.chemspider.com/Chemical-Structure.391616.html
PharmGKB
http://www.pharmgkb.org/drug/PA164746559
Wikipedia
http://en.wikipedia.org/wiki/Hetacillin
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