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564-25-0 molecular structure
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(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

ChemBase ID: 139
Molecular Formular: C22H24N2O8
Molecular Mass: 444.43456
Monoisotopic Mass: 444.15326574
SMILES and InChIs

SMILES:
[C@@H]12[C@](C(=C3[C@H]([C@@H]2O)[C@H](c2c(C3=O)c(ccc2)O)C)O)(C(=O)C(=C([C@H]1N(C)C)O)C(=O)N)O
Canonical SMILES:
CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1[C@@H](O)[C@@H]1[C@@H](C)c3cccc(c3C(=O)C1=C2O)O)O)O)C
InChI:
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:
JBIWCJUYHHGXTC-AKNGSSGZSA-N

Cite this record

CBID:139 http://www.chembase.cn/molecule-139.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC 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
IUPAC Traditional name
vibramycin
Brand Name
Alti-Doxycycline
Apo-Doxy
Atridox
Doryx
Doxy 100
Doxy-Caps
Doxy-Lemmon
Doxychel
Doxychel Hyclate
Doxycin
Doxylin
Doxytec
Jenacyclin
Monodox
Novo-Doxylin
Nu-Doxycycline
Periostat
Supracyclin
Vibra-Tabs
Vibramycin
Oracea
Synonyms
Doxcycline anhydrous
Doxycycline Hyclate
Doxycycline Monohydrate
Doxytetracycline
(4R,4aR,5S,5aR,6R,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
6-Deoxy-4-epioxytetracycline
4-Epi Doxycycline (>70%)
Doxycycline
CAS Number
564-25-0
6543-77-7
PubChem SID
160963602
46506491
PubChem CID
5281011
54671203

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
E585900 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa -2.235276  H Acceptors
H Donor LogD (pH = 5.5) -4.28254 
LogD (pH = 7.4) -6.187371  Log P -3.435637 
Molar Refractivity 113.8919 cm3 Polarizability 43.13817 Å3
Polar Surface Area 181.62 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P -0.72  LOG S -2.85 
Solubility (Water) 6.30e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
630 mg/L expand Show data source
Methanol expand Show data source
Pyridine expand Show data source
Apperance
Yellow Solid expand Show data source
Melting Point
>176°C (dec.) expand Show data source
Hydrophobicity(logP)
-0.2 expand Show data source
Storage Condition
Amber Vial, -20°C Freezer, Under Inert Atmosphere expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00254 external link
Item Information
Drug Groups approved; investigational
Description A synthetic tetracycline derivative with similar antimicrobial activity. Animal studies suggest that it may cause less tooth staining than other tetracyclines. It is used in some areas for the treatment of chloroquine-resistant falciparum malaria (malaria, falciparum). [PubChem]
Indication Doxycycline is indicated for use in respiratory tract infections caused by Mycoplasma pneumoniae, Haemophilus influenzae, Streptococcus pneumoniae, Legionella spp., or Klebsiella spp. It is also used for prophylaxis of malaria. Doxycycline is indicated for a variety of bacterial infections, from Mycobacterium fortuitum and M. marinum, to susceptible E. coli and Brucella spp. It can be used as an alternative to treating plague, tetanus, Campylobacter fetus
Pharmacology Doxycycline, a long-acting tetracycline derived from oxytetracycline, is used to inhibit bacterial protein synthesis and treat non-gonococcal urethritis and cervicitis, exacerbations of bronchitis in patients with COPD, and adult periodontitis.
Toxicity Symptoms of overdose include anorexia, nausea, diarrhoea, glossitis, dysphagia, enterocolitis and inflammatory lesions (with monilial overgrowth) in the anogenital region, skin reactions such as maculopapular and erythematous rashes, exfoliative dermatitis, photosensitivity, hypersensitivity reactions such as urticaria, angioneurotic oedema, anaphylaxis, anaphyl-actoid purpura, pericarditis, and exacerbation of systemic lupus erythematosus, benign intracranial hypertension in adults disappearing on discontinuation of the medicine, haematologic abnormalities such as haemolytic anaemia, thrombocytopenia, neutropenia, and eosinophilia. LD50=262 mg/kg (I.P. in rat).
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Hepatic
Absorption Completely absorbed following oral administration.
Half Life 18-22 hours
Protein Binding >90%
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.
References
Dahl EL, Shock JL, Shenai BR, Gut J, DeRisi JL, Rosenthal PJ: Tetracyclines specifically target the apicoplast of the malaria parasite Plasmodium falciparum. Antimicrob Agents Chemother. 2006 Sep;50(9):3124-31. [Pubmed]
Hoerauf A, Mand S, Fischer K, Kruppa T, Marfo-Debrekyei Y, Debrah AY, Pfarr KM, Adjei O, Buttner DW: Doxycycline as a novel strategy against bancroftian filariasis-depletion of Wolbachia endosymbionts from Wuchereria bancrofti and stop of microfilaria production. Med Microbiol Immunol. 2003 Nov;192(4):211-6. Epub 2003 Mar 5. [Pubmed]
Taylor MJ, Makunde WH, McGarry HF, Turner JD, Mand S, Hoerauf A: Macrofilaricidal activity after doxycycline treatment of Wuchereria bancrofti: a double-blind, randomised placebo-controlled trial. Lancet. 2005 Jun 18-24;365(9477):2116-21. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals - E585900 external link
An alternative to doxycycline to control gene expression.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Dahl EL, Shock JL, Shenai BR, Gut J, DeRisi JL, Rosenthal PJ: Tetracyclines specifically target the apicoplast of the malaria parasite Plasmodium falciparum. Antimicrob Agents Chemother. 2006 Sep;50(9):3124-31. Pubmed
  • • Hoerauf A, Mand S, Fischer K, Kruppa T, Marfo-Debrekyei Y, Debrah AY, Pfarr KM, Adjei O, Buttner DW: Doxycycline as a novel strategy against bancroftian filariasis-depletion of Wolbachia endosymbionts from Wuchereria bancrofti and stop of microfilaria production. Med Microbiol Immunol. 2003 Nov;192(4):211-6. Epub 2003 Mar 5. Pubmed
  • • Taylor MJ, Makunde WH, McGarry HF, Turner JD, Mand S, Hoerauf A: Macrofilaricidal activity after doxycycline treatment of Wuchereria bancrofti: a double-blind, randomised placebo-controlled trial. Lancet. 2005 Jun 18-24;365(9477):2116-21. Pubmed
  • • Schiffer, I., et al.: Cancer Res. 63, 7221 (2003)
  • • Eger, K., et al.: Biochem. Biophys. Res. Comm., 323, 979, (2004).
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PATENTS

PATENTS

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