Tìm theo
Chloramphenicol
Các tên gọi khác (18 ) :
  • Chloramex
  • Chloramphenicol
  • Chloramphenicolum
  • Chlornitromycin
  • Chlorocid
  • Chlorocol
  • Chloromycetin
  • Cloramfenicol
  • D-(-)-2,2-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-P-nitrophenylethyl)acetamide
  • D-(-)-threo-1-P-Nitrophenyl-2-dichloroacetylamino-1,3-propanediol
  • Fenicol
  • Globenicol
  • Halomycetin
  • Laevomycetinum
  • Levomicetina
  • Levomycetin
  • Oleomycetin
  • Sificetina
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 56-75-7
ATC: D06AX02, D10AF03, G01AA05, J01BA01, S01AA01, S02AA01, S03AA08
ĐG : Akorn Inc. , http://www.akorn.com
CTHH: C11H12Cl2N2O5
PTK: 323.129
An antibiotic first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. It has a relatively simple structure and was the first broad-spectrum antibiotic to be discovered. It acts by interfering with bacterial protein synthesis and is mainly bacteriostatic. (From Martindale, The Extra Pharmacopoeia, 29th ed, p106)
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C11H12Cl2N2O5
Phân tử khối
323.129
Monoisotopic mass
322.012326918
InChI
InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1
InChI Key
InChIKey=WIIZWVCIJKGZOK-RKDXNWHRSA-N
IUPAC Name
2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
Traditional IUPAC Name
chloramphenicol
SMILES
OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C(C=C1)[N+]([O-])=O
Độ tan chảy
171
Độ hòa tan
2500 mg/L (at 25 °C)
logP
1.14
logS
-2.11
pKa (strongest acidic)
7.49
pKa (Strongest Basic)
-2.8
PSA
115.38 Å2
Refractivity
73.2 m3·mol-1
Polarizability
28.08 Å3
Rotatable Bond Count
6
H Bond Acceptor Count
5
H Bond Donor Count
3
Physiological Charge
0
Number of Rings
1
Bioavailability
1
Rule of Five
true
Ghose Filter
true
caco2 Permeability
-4.69
Dược Lực Học : Chloramphenicol is a broad-spectrum antibiotic that was derived from the bacterium Streptomyces venezuelae and is now produced synthetically. Chloramphenicol is effective against a wide variety of microorganisms, but due to serious side-effects (e.g., damage to the bone marrow, including aplastic anemia) in humans, it is usually reserved for the treatment of serious and life-threatening infections (e.g., typhoid fever). Chloramphenicol is bacteriostatic but may be bactericidal in high concentrations or when used against highly susceptible organisms. Chloramphenicol stops bacterial growth by binding to the bacterial ribosome (blocking peptidyl transferase) and inhibiting protein synthesis.
Cơ Chế Tác Dụng : An antibiotic first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. It has a relatively simple structure and was the first broad-spectrum antibiotic to be discovered. It acts by interfering with bacterial protein synthesis and is mainly bacteriostatic. (From Martindale, The Extra Pharmacopoeia, 29th ed, p106) Chloramphenicol is lipid-soluble, allowing it to diffuse through the bacterial cell membrane. It then reversibly binds to the L16 protein of the 50S subunit of bacterial ribosomes, where transfer of amino acids to growing peptide chains is prevented (perhaps by suppression of peptidyl transferase activity), thus inhibiting peptide bond formation and subsequent protein synthesis.
Dược Động Học :
▧ Absorption :
Rapidly and completely absorbed from gastrointestinal tract following oral administration (bioavailability 80%). Well absorbed following intramuscular administration (bioavailability 70%). Intraocular and some systemic absorption also occurs after topical application to the eye.
▧ Protein binding :
Plasma protein binding is 50-60% in adults and 32% is premature neonates.
▧ Metabolism :
Hepatic, with 90% conjugated to inactive glucuronide.
▧ Half Life :
Half-life in adults with normal hepatic and renal function is 1.5 - 3.5 hours. In patients with impaired renal function half-life is 3 - 4 hours. In patients with severely impaired hepatic function half-life is 4.6 - 11.6 hours. Half-life in children 1 month to 16 years old is 3 - 6.5 hours, while half-life in infants 1 to 2 days old is 24 hours or longer and is highly variable, especially in low birth-weight infants.
Độc Tính : Oral, mouse: LD50 = 1500 mg/kg; Oral, rat: LD50 = 2500 mg/kg. Toxic reactions including fatalities have occurred in the premature and newborn; the signs and symptoms associated with these reactions have been referred to as the gray syndrome. Symptoms include (in order of appearance) abdominal distension with or without emesis, progressive pallid cyanosis, vasomotor collapse frequently accompanied by irregular respiration, and death within a few hours of onset of these symptoms.
Chỉ Định : Used in treatment of cholera, as it destroys the vibrios and decreases the diarrhea. It is effective against tetracycline-resistant vibrios. It is also used in eye drops or ointment to treat bacterial conjunctivitis.
Tương Tác Thuốc :
  • Acetohexamide Chloramphenicol may increase the effect of sulfonylurea, acetohexamide.
  • Butalbital Barbiturates such as butalbital may increase the metabolism of Chloramphenicol. Chloramphenicol may decrease the metabolism of Barbiturates. Monitor for decreased serum concentrations/therapeutic effects of chloramphenicol if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. In addition, monitor for increased effects of barbiturates if chloramphenicol is initiated/dose increased, or decreased effects if chloramphenicol is discontinued/dose decreased.
  • Chlorpropamide Chloramphenicol may increase the effect of sulfonylurea, chlorpropamide.
  • Cyclosporine Chloramphenicol may increase the effect of cyclosporine.
  • Ethotoin Increases phenytoin, modifies chloramphenicol
  • Fosphenytoin Increases phenytoin, modifies chloramphenicol
  • Gliclazide Chloramphenicol may increase the effect of sulfonylurea, gliclazide.
  • Glipizide Chloramphenicol may increase the effect of sulfonylurea, glipizide.
  • Glisoxepide Chloramphenicol may increase the effect of sulfonylurea, glisoxepide.
  • Glyburide Chloramphenicol may increase the effect of sulfonylurea, glibenclamide.
  • Glycodiazine Chloramphenicol may increase the effect of sulfonylurea, glycodiazine.
  • Lurasidone Concomitant therapy with a strong CYP3A4 inhibitor will increase level or effect of lurasidone. Coadministration with lurasidone is contraindicated.
  • Mephenytoin Increases phenytoin, modifies chloramphenicol
  • Phenytoin Increases phenytoin, modifies chloramphenicol
  • Rifampicin Rifampin decreases the effect of chloramphenicol
  • Silodosin Chloramphenicol is a strong inhibitor of CYP3A4 may increase the serum concentration of silodosin by decreasing its metabolism thus increases the potential for adverse side effects. Combination therapy is contraindicated.
  • Tacrolimus Chloramphenicol may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Chloramphenicol therapy is initiated, discontinued or altered.
  • Thiopental Chloramphenicol may increase the serum concentration of Thiopental by decreasing Thiopental metabolism. Thiopental may decrease the serum concentration of Chloramphenicol by increasing Chloramphenicol metabolism. Monitor for changes in therapeutic effects of both agents if concomitant therapy is initiated, discontinued or doses are adjusted.
  • Tolazamide Chloramphenicol may increase the effect of sulfonylurea, tolazamide.
  • Tolbutamide Chloramphenicol may increase the effect of sulfonylurea, tolbutamide.
Liều Lượng & Cách Dùng : Liquid - Ophthalmic
Ointment - Ophthalmic
Powder, for solution - Intramuscular
Solution - Ophthalmic
Solution / drops - Ophthalmic
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Sanofi-Aventis
    Sản phẩm biệt dược : Brochlor
  • Công ty : Actavis
    Sản phẩm biệt dược : Chloramex
  • Công ty : Egyt
    Sản phẩm biệt dược : Chlorocid
  • Công ty :
    Sản phẩm biệt dược : Chlorocol
  • Công ty : Pfizer
    Sản phẩm biệt dược : Chloromycetin
  • Công ty : Sigma
    Sản phẩm biệt dược : Chlorsig
  • Công ty : Alcon
    Sản phẩm biệt dược : Fenicol
  • Công ty :
    Sản phẩm biệt dược : Globenicol
  • Công ty : Wabosan
    Sản phẩm biệt dược : Halomycetin
  • Công ty :
    Sản phẩm biệt dược : Oleomycetin
  • Công ty : SIFI
    Sản phẩm biệt dược : Sificetina
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00446
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C00918
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00104
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50028502
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/61570-331-31
PharmGKB
http://www.pharmgkb.org/drug/PA448927
Wikipedia
http://en.wikipedia.org/wiki/Chloramphenicol
RxList
http://www.rxlist.com/cgi/generic3/chloramphenicol.htm
Drugs.com
http://www.drugs.com/mtm/chloramphenicol-ophthalmic.html
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