Tìm theo
Tetracycline
Các tên gọi khác (11 ) :
  • (4S,4AS,5as,12as)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
  • Abramycin
  • Achromycin
  • Anhydrotetracycline
  • Deschlorobiomycin
  • Liquamycin
  • Tetracyclin
  • TETRACYCLINE
  • Tetracyclinum
  • Tetrazyklin
  • Tsiklomitsin
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 60-54-8
ATC: A01AB13, D06AA04, J01AA07, S01AA09, S02AA08, S03AA02, A01AB21, S01AA02, J01AA09, D06AA02, J01AA03
ĐG : Advanced Pharmaceutical Services Inc.
CTHH: C22H24N2O8
PTK: 444.4346
Tetracycline is a broad spectrum polyketide antibiotic produced by the Streptomyces genus of Actinobacteria. It exerts a bacteriostatic effect on bacteria by binding reversible to the bacterial 30S ribosomal subunit and blocking incoming aminoacyl tRNA from binding to the ribosome acceptor site. It also binds to some extent to the bacterial 50S ribosomal subunit and may alter the cytoplasmic membrane causing intracellular components to leak from bacterial cells.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C22H24N2O8
Phân tử khối
444.4346
Monoisotopic mass
444.153265754
InChI
InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1
InChI Key
InChIKey=OFVLGDICTFRJMM-WESIUVDSSA-N
IUPAC Name
(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
Traditional IUPAC Name
tetracycline
SMILES
[H][C@@]12C[C@@]3([H])C(=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C)C(=O)C1=C(O)C=CC=C1[C@@]3(C)O
Độ tan chảy
172.5 dec °C
Độ hòa tan
231 mg/L (at 25 °C)
logP
-1.30
logS
-3.12
pKa (strongest acidic)
-2.2
pKa (Strongest Basic)
8.24
PSA
181.62 Å2
Refractivity
114.19 m3·mol-1
Polarizability
43.03 Å3
Rotatable Bond Count
2
H Bond Acceptor Count
9
H Bond Donor Count
6
Physiological Charge
-1
Number of Rings
4
Bioavailability
1
pKa
3.3 (at 25 °C)
Dược Lực Học : Tetracycline is a short-acting antibiotic that inhibits bacterial growth by inhibiting translation. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. It also binds to some extent to the 50S ribosomal subunit. This binding is reversible in nature. Additionally tetracycline may alter the cytoplasmic membrane of bacteria causing leakage of intracellular contents, such as nucleotides, from the cell.
Cơ Chế Tác Dụng : Tetracycline is a broad spectrum polyketide antibiotic produced by the Streptomyces genus of Actinobacteria. It exerts a bacteriostatic effect on bacteria by binding reversible to the bacterial 30S ribosomal subunit and blocking incoming aminoacyl tRNA from binding to the ribosome acceptor site. It also binds to some extent to the bacterial 50S ribosomal subunit and may alter the cytoplasmic membrane causing intracellular components to leak from bacterial cells. Tetracycline passively diffuses through porin channels in the bacterial membrane and reversibly binds to the 30S ribosomal subunit, preventing binding of tRNA to the mRNA-ribosome complex, and thus interfering with protein synthesis.
Dược Động Học :
▧ Absorption :
Bioavailability is less than 40% when administered via intramuscular injection, 100% intravenously, and 60-80% orally (fasting adults). Food and/or milk reduce GI absorption of oral preparations of tetracycline by 50% or more.
▧ Protein binding :
20 - 67% protein bound
▧ Metabolism :
Not metabolized
▧ Route of Elimination :
They are concentrated by the liver in the bile and excreted in the urine and feces at high concentrations in a biologically active form.
▧ Half Life :
6-12 hours
Độc Tính : LD50=808mg/kg (orally in mice)
Chỉ Định : Used to treat bacterial infections such as Rocky Mountain spotted fever, typhus fever, tick fevers, Q fever, rickettsialpox and Brill-Zinsser disease. May be used to treat infections caused by Chlamydiae spp., B. burgdorferi (Lyme disease), and upper respiratory infections caused by typical (S. pneumoniae, H. influenzae, and M. catarrhalis) and atypical organisms (C. pneumoniae, M. pneumoniae, L. pneumophila). May also be used to treat acne. Tetracycline may be an alternative drug for people who are allergic to penicillin.
Tương Tác Thuốc :
  • Acenocoumarol Tetracycline may increase the anticoagulant effect of acenocoumarol.
  • Acitretin Increased risk of intracranial hypertension
  • Aluminium Formation of non-absorbable complexes
  • Amoxicillin Possible antagonism of action
  • Ampicillin Possible antagonism of action
  • Anisindione Tetracycline may increase the anticoagulant effect of anisindione.
  • Atovaquone Tetracycline may decrease the effect of atovaquone.
  • Attapulgite Formation of non-absorbable complexes
  • Azlocillin Possible antagonism of action
  • Aztreonam Possible antagonism of action
  • Bacampicillin Possible antagonism of action
  • Benzylpenicillin Possible antagonism of action
  • Bexarotene Tetracycline may enhance the adverse/toxic effect of Retinoic Acid Derivatives. Due to the risk of developing pseudotumor cerebri (also known as intracranial hypertension), avoid this combination of drugs if possible. If used concomitantly, monitor for evidence of this interaction (eg, dizziness, diplopia, headache).
  • Bismuth Subsalicylate Formation of non-absorbable complexes
  • Calcium Formation of non-absorbable complexes
  • Calcium Acetate Calcium salts such as calcium acetate may decrease the serum concentration of tetracycline derivatives such as tetracycline. In general, the coadministration of oral calcium salts and oral tetracycline derivatives should be avoided. Interactions may be able to be minimized by administering oral calcium preparations several hours before or after the dose of the oral tetracycline derivatives. Even with dose separation, therapy may still be compromised. Monitor for decreased therapeutic effect of oral tetracycline derivatives.
  • Calcium Chloride Calcium salts such as calcium chloride may decrease the serum concentration of tetracycline derivatives such as tetracycline. In general, the coadministration of oral calcium salts and oral tetracycline derivatives should be avoided. Interactions may be able to be minimized by administering oral calcium preparations several hours before or after the dose of the oral tetracycline derivatives. Even with dose separation, therapy may still be compromised. Monitor for decreased therapeutic effect of oral tetracycline derivatives.
  • Carbenicillin Possible antagonism of action
  • Clavulanate Possible antagonism of action
  • Cloxacillin Possible antagonism of action
  • Colesevelam Bile acid sequestrants such as colesevelam may decrease the absorption of Tetracycline Derivatives. Monitor for decreased therapeutic effects of tetracycline derivatives if coadministered with a bile acid sequestrant. If these agents are used concomitantly, separate doses 2 or more hours to minimize the interaction. The manufacturer of colesevelam suggests that drugs should be administered at least 1 hour before or 4 hours after colesevelam.
  • Cyclacillin Possible antagonism of action
  • Dicloxacillin Possible antagonism of action
  • Dicoumarol Tetracycline may increase the anticoagulant effect of dicumarol.
  • Dihydroxyaluminium Formation of non-absorbable complexes
  • Ethinyl Estradiol This anti-infectious agent could decrease the effect of the oral contraceptive
  • Etretinate Increased risk of intracranial hypertension
  • Flucloxacillin Possible antagonism of action
  • Hetacillin Possible antagonism of action
  • Iron Formation of non-absorbable complexes
  • Iron Dextran Formation of non-absorbable complexes
  • Isotretinoin Increased risk of intracranial hypertension
  • Magnesium Formation of non-absorbable complexes
  • Magnesium salicylate Formation of non-absorbable complexes
  • Mestranol This anti-infectious agent could decrease the effect of the oral contraceptive
  • Methicillin Acyl-Serine Possible antagonism of action
  • Methotrexate Tetracycline may increase methotrexate toxicity.
  • Methoxyflurane Tetracycline may increase the renal toxicity of methoxyflurane.
  • Mezlocillin Possible antagonism of action
  • Nafcillin Possible antagonism of action
  • Oxacillin Possible antagonism of action
  • Penicillin V Possible antagonism of action
  • Piperacillin Possible antagonism of action
  • Pivampicillin Possible antagonism of action
  • Pivmecillinam Possible antagonism of action
  • Quinapril Quinapril may decrease the absorption of tetracycline.
  • Tamsulosin Tetracycline, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Tetracycline is initiated, discontinued, or dose changed.
  • Tazobactam Possible antagonism of action
  • Ticarcillin Tetracycline may reduce the effect of Ticarcillin by inhibiting bacterial growth. Ticarcillin exerts its effects on actively growing bacteria. To achieve synergism, Ticarcillin should be administered at least 2 hours prior to using Tetracycline.
  • Tolterodine Tetracycline may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
  • Tramadol Tetracycline may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
  • Trazodone The CYP3A4 inhibitor, Tetracycline, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Tetracycline is initiated, discontinued or dose changed.
  • Tretinoin Demeclocycline may increase the adverse effects of oral Tretinoin. Increase risk of pseudotumour cerebri. Concurrent therapy should be avoided.
  • Trisalicylate-choline Formation of non-absorbable complexes
  • Warfarin Tetracycline may increase the anticoagulant effect of warfarin.
  • Zinc Formation of non-absorbable complexes
Liều Lượng & Cách Dùng : Capsule - Oral
Ointment - Ophthalmic
Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Achromycin
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00759
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5280962
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506693
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C06570
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00201
ChemSpider
http://www.chemspider.com/Chemical-Structure.4510286.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0172-2416-60
PharmGKB
http://www.pharmgkb.org/drug/PA451640
Wikipedia
http://en.wikipedia.org/wiki/Tetracycline
RxList
http://www.rxlist.com/cgi/generic2/tetcycl2.htm
Drugs.com
http://www.drugs.com/tetracycline.html
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