(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: [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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• 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

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.24295226
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -5.5841894
• LogD (pH = 7.4): -7.485068
• Log P: -4.5983834
• Molar Refractivity: 115.3982 cm^3
• Polarizability: 43.880726 Å^3
• Polar Surface Area: 201.85 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.99
• LOG S: -2.52
• Solubility (Water): 1.40e+00 g/l

PROPERTIES

Physical Property

• Solubility: 0.6 mg/mL (6.9 mg/mL as HCl salt); DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: >178°C (dec.); 182-186 °C (dec.)
• Optical Rotation: [α]20/D -195±3°, c = 1% in 0.1 M HCl
• Hydrophobicity(logP): -1.3

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: QI7875000
• German water hazard class: 2; 3
• Safety Statements: 22-24/25
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (NT)
• Grade: for microbiology
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C22H24N2O9; C22H24N2O9 · 2H2O

DETAILS

DrugBank - DB00595

• 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

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

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

Antibiotic substance isolated from the elaboration products of the actinomycete, Streptomyces rimosus, grown on a suitable medium. Antibacterial.

REFERENCES

• 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