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 | |
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| Formal Charge | 0 |
| Atom Count | 56 |
| Chiral Atom Count | 6 |
| Bond Count | 59 |
| Aromatic Bond Count | 6 |
Chemical Component Summary | |
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| 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 |
| Synonyms | DOXYTETRACYCLINE; 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 |
| Formula | C22 H24 N2 O8 |
| Molecular Weight | 444.435 |
| Type | NON-POLYMER |
Chemical Descriptors | |||
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| Type | Program | Version | Descriptor |
| SMILES | ACDLabs | 10.04 | O=C3C2=C(O)C1(O)C(=O)C(=C(O)C(N(C)C)C1C(O)C2C(c4cccc(O)c34)C)C(=O)N |
| SMILES | CACTVS | 3.341 | C[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 |
| SMILES | OpenEye OEToolkits | 1.5.0 | CC1c2cccc(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 SMILES | CACTVS | 3.341 | 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 SMILES | OpenEye OEToolkits | 1.5.0 | 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 |
| InChI | InChI | 1.03 | 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 |
| InChIKey | InChI | 1.03 | JBIWCJUYHHGXTC-AKNGSSGZSA-N |
Drug Info: DrugBank
| DrugBank ID | DB00254? |
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| Name | Doxycycline |
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| Description | Doxycycline 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] |
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| Indication | Doxycycline 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] |
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| CAS number | 564-25-0 |
Drug Targets
| Name | Target Sequence | Pharmacological Action | Actions |
|---|---|---|---|
| 30S ribosomal protein | - | unknown | inhibitor |
| Cytochrome P450 3A4 | MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI... | unknown | inhibitor |
| Albumin | MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA... | unknown | substrate,binder |
| Solute carrier family 22 member 6 | MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR... | unknown | inhibitor |
| ATP-binding cassette sub-family B member 5 | MENSERAEEMQENYQRNGTAEEQPKLRKEAVGSIEIFRFADGLDITLMIL... | unknown | inducer |
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
