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6153-64-6 molecular structure
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(4S,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

ChemBase ID: 477
Molecular Formular: C22H24N2O9
Molecular Mass: 460.43396
Monoisotopic Mass: 460.14818036
SMILES and InChIs

SMILES:
[C@H]12[C@](C(=C3[C@H]([C@@H]1O)[C@](c1c(C3=O)c(ccc1)O)(C)O)O)(C(=O)C(=C([C@H]2N(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]1C(=C2O)C(=O)c2c([C@@]1(C)O)cccc2O)O)O)C
InChI:
InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1
InChIKey:
IWVCMVBTMGNXQD-PXOLEDIWSA-N

Cite this record

CBID:477 http://www.chembase.cn/molecule-477.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(4S,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
IUPAC Traditional name
oxytetracycline
Brand Name
Oxytetracycline anhydrous
Oxytetracycline HCl
Terramycin
Synonyms
Oxytetracycline
Oxytetracycline dihydrate
OGYE Selective Supplement
Oxytetracycline
Oxytetra Selective Supplement
[4S-(4α,4aα,5α,5aα,6β,12aα]-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide Dihydrate
5-Hydroxytetracycline Dihydrate
Oxytetracycline Dihydrate
CAS Number
6153-64-6
79-57-2
EC Number
201-212-8
MDL Number
MFCD00003700
Beilstein Number
2714587
PubChem SID
46507025
160963940
PubChem CID
5280972
54675779

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 0.24295226  H Acceptors 10 
H Donor LogD (pH = 5.5) -5.5841894 
LogD (pH = 7.4) -7.485068  Log P -4.5983834 
Molar Refractivity 115.3982 cm3 Polarizability 43.880726 Å3
Polar Surface Area 201.85 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P -0.99  LOG S -2.52 
Solubility (Water) 1.40e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
0.6 mg/mL (6.9 mg/mL as HCl salt) expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Apperance
Pale Yellow Solid expand Show data source
Melting Point
>178°C (dec.) expand Show data source
182-186 °C (dec.) expand Show data source
Optical Rotation
[α]20/D -195±3°, c = 1% in 0.1 M HCl expand Show data source
Hydrophobicity(logP)
-1.3 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
RTECS
QI7875000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
3 expand Show data source
Safety Statements
22-24/25 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥98.0% (NT) expand Show data source
Grade
for microbiology expand Show data source
Certificate of Analysis
Download expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Empirical Formula (Hill Notation)
C22H24N2O9 expand Show data source
C22H24N2O9 · 2H2O expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00595 external link
Item Information
Drug Groups approved
Description A tetracycline analog isolated from the actinomycete streptomyces rimosus and used in a wide variety of clinical conditions. [PubChem]
Indication Oxytetracycline is indicated for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae (respiratory infections), and Diplococcus pneumoniae.
Pharmacology Oxytetracycline is known as a broad-spectrum antibiotic due to its activity against such a wide range of infections. It was the second of the tetracyclines to be discovered. Oxytetracycline, like other tetracyclines, is used to treat many infections common and rare. Its better absorption profile makes it preferable to tetracycline for moderately severe acne, but alternatives sould be sought if no improvement occurs by 3 months.
Toxicity Adverse effects may include stomach or bowel upsets and rarely allergic reactions. Very rarely severe headache and vision problems may be signs of dangerous intracranial hypertenion.
Affected Organisms
Enteric bacteria and other eubacteria
Absorption Readily absorbed following oral administration.
External Links
Wikipedia
RxList
Sigma Aldrich - 75965 external link
Biochem/physiol Actions
Antibiotic produced by Streptomyces rimosus.Mode of Action: Inhibits protein synthesis (elongation) by preventing binding of aminoacyl-tRNA to the 30S subunit.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.Mode of Resistance: Active efflux, ribosome protection, tetracycline inactivation.
Sigma Aldrich - 51239 external link
Components
(per vial sufficient for 500 ml medium) Oxytetracycline 50.0 mg
Biochem/physiol Actions
Oxytetracycline is a protein synthesis inhibitor 2.
Features and Benefits
Added to OGY-Agar (Fluka 75310) Oxytetracycline suppresses the growth of accompanying bacterial flora during culturing yeasts and moulds.
Application
Oxytetracycline is used as an antibacterial selective agent in microbiology studies 1. It is a broad spectrum antibiotic that is active against a wide variety of bacteria. When added to OGY-Agar (Fluka 75310) Oxytetracycline suppresses the growth of accompanying bacterial flora during culturing yeasts and molds.
Toronto Research Chemicals - O877501 external link
Antibiotic substance isolated from the elaboration products of the actinomycete, Streptomyces rimosus, grown on a suitable medium. Antibacterial.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Finlay, et al.: Science, 111, 85 (1950)
  • • Weiss, et al.: Antibiot. Chemother., 7, 374 (1950)
  • • Kruse, H., et al.: Microb. Drug. Resist., 5, 135, (1950)
  • • van den Bogaard, A., et al.: J. Antimicrob. Chemother., 45, 663 (1950)
  • • Nwosu, V., et al.: Res. Microbio
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PATENTS

PATENTS

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INTERNET

INTERNET

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