DXT

(4S,4AR,5S,5AR,6R,12AS)-4-(DIMETHYLAMINO)-3,5,10,12,12A-PENTAHYDROXY-6-METHYL-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDROTETRACENE-2-CARBOXAMIDE

Created: 2006-12-27
Last modified:  2020-05-27

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Chemical Details

Formal Charge0
Atom Count56
Chiral Atom Count6
Bond Count59
Aromatic Bond Count6
2D diagram of DXT
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Chemical Component Summary

Name(4S,4AR,5S,5AR,6R,12AS)-4-(DIMETHYLAMINO)-3,5,10,12,12A-PENTAHYDROXY-6-METHYL-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDROTETRACENE-2-CARBOXAMIDE
SynonymsDOXYTETRACYCLINE; DOXYCYCLINE
Systematic Name (OpenEye OEToolkits)(4S,4aR,5S,5aR,6R,12aS)-4-dimethylamino-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
FormulaC22 H24 N2 O8
Molecular Weight444.435
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C3C2=C(O)C1(O)C(=O)C(=C(O)C(N(C)C)C1C(O)C2C(c4cccc(O)c34)C)C(=O)N
SMILESCACTVS3.341C[CH]1[CH]2[CH](O)[CH]3[CH](N(C)C)C(=C(C(N)=O)C(=O)[C]3(O)C(=C2C(=O)c4c(O)cccc14)O)O
SMILESOpenEye OEToolkits1.5.0CC1c2cccc(c2C(=O)C3=C(C4(C(C(C13)O)C(C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O
Canonical SMILESCACTVS3.341 C[C@@H]1[C@H]2[C@H](O)[C@H]3[C@H](N(C)C)C(=C(C(N)=O)C(=O)[C@@]3(O)C(=C2C(=O)c4c(O)cccc14)O)O
Canonical SMILESOpenEye OEToolkits1.5.0 C[C@H]1c2cccc(c2C(=O)C3=C([C@]4([C@@H]([C@H]([C@H]13)O)[C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O
InChIInChI1.03 InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1
InChIKeyInChI1.03 JBIWCJUYHHGXTC-AKNGSSGZSA-N

Drug Info: DrugBank

DrugBank IDDB00254 
NameDoxycycline
Groups
  • approved
  • vet_approved
  • investigational
DescriptionDoxycycline is a broad-spectrum antibiotic synthetically derived from [oxytetracycline].[L42880] It is a second-generation tetracycline that was first discovered in 1967.[A19429] Second-generation tetracyclines exhibit lesser toxicity than first-generation tetracyclines.[A174034] Doxycycline is used to treat a wide variety of gram-positive and gram-negative bacterial infections. It is also used to treat acne and malaria.[A251730]
Synonyms
  • Doxycycline (anhydrous)
  • Doxycycline calcium
  • Anhydrous doxycycline
  • Doxycycline hydrochloride
  • Doxycycline anhydrous
Brand Names
  • Doxycycline Capsules
  • Doxycycline Monohydrate
  • Vibramycin Cap 100mg
  • BenzoDox 30 Kit
  • Apprilon
IndicationDoxycycline is indicated for the treatment of various infections by gram-positive and gram-negative bacteria, aerobes and anaerobes, as well other types of bacteria, including: - Early Lyme disease (as evidenced by erythema migraines) due to _Borrelia burgdorferi_ in adults and pediatric patients 8 years of age and older weighing 45 kg and above [L42875] - Rickettsial infections,[L42870] such as Rocky Mountain spotted fever, typhus fever and the typhus group, Q fever, rickettsialpox, and tick fevers [L42880] - Sexually transmitted infections [L42870] - Respiratory tract infections [L42870] caused by _Mycoplasma pneumoniae_ and _Haemophilus influenzae_ [L42880] - Specific bacterial infections [L42870] after indicative bacteriologic testing. These include infections caused by _Escherichia coli_, _Enterobacter aerogenes_, _Shigella_ species, _Acinetobacter_ species, and _Klebsiella_ species [L42880] - Ophthalmic infections,[L42870] such as inclusion conjunctivitis caused by _Chlamydia trachomatis_ [L42880] - Anthrax, including inhalational anthrax (post-exposure) [L42870] - Alternative treatment for selected infections when [penicillin] is contraindicated [L42870] - Adjunctive therapy in acute intestinal amebiasis and severe acne [L42870, L42880] - Lymphogranuloma venereum caused by _Chlamydia trachomatis_ [L42880] - Psittacosis (ornithosis) caused by _Chlamydophila psittaci_ [L42880] - Trachoma caused by _Chlamydia trachomatis_, although the infectious agent is not always eliminated, as judged by immunofluorescence [L42880] - Uncomplicated urethral, endocervical, or rectal infections in adults caused by _Chlamydia trachomatis_ [L42880] - Nongonococcal urethritis caused by _Ureaplasma urealyticum_ [L42880] - Relapsing fever due to _Borrelia recurrentis_ [L42880] - Prophylaxis of malaria due to _Plasmodium falciparum_ in short-term travelers (<4 months) to areas with chloroquine and/or pyrimethamine-sulfadoxine resistant strains [L42870, L42880] It is also used to treat infections caused by the following gram-negative microorganisms: - Chancroid caused by _Haemophilus ducreyi_ [L42880] - Plague due to _Yersinia pestis_ [L42880] - Tularemia due to _Francisella tularensis_ [L42880] - Cholera caused by _Vibrio cholerae_ [L42880] - Campylobacter fetus infections caused by _Campylobacter fetus_ [L42880] - Brucellosis due to _Brucella_ species (in conjunction with [streptomycin]) [L42880] - Bartonellosis due to _Bartonella bacilliformis_ [L42880] - Granuloma inguinale caused by _Klebsiella granulomatis_ [L42880]
Categories
  • Agents that produce neuromuscular block (indirect)
  • Alimentary Tract and Metabolism
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
ATC-Code
  • J01AA02
  • A01AB22
  • J01AA20
CAS number564-25-0

Drug Targets

NameTarget SequencePharmacological ActionActions
30S ribosomal protein-unknowninhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknowninhibitor
Serum albuminMKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...unknownsubstrate,binder
Solute carrier family 22 member 6MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...unknowninhibitor
ATP-binding cassette sub-family B member 5MENSERAEEMQENYQRNGTAEEQPKLRKEAVGSIEIFRFADGLDITLMIL...unknowninducer
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682