| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H24N2O9.2H2O |
| Molecular Weight | 496.4645 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.[H][C@@]12[C@@H](O)[C@@]3([H])C(C(=O)C4=C(O)C=CC=C4[C@@]3(C)O)=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C
InChI
InChIKey=SRRPEXWCHWWJOC-JEKSYDDFSA-N
InChI=1S/C22H24N2O9.2H2O/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);2*1H2/t12-,13-,14+,17+,21-,22+;;/m1../s1
| Molecular Formula | C22H24N2O9 |
| Molecular Weight | 460.434 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
MOL RATIO
2 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Oxytetracycline, a tetracycline analog isolated from the actinomycete streptomyces rimosus, was the second of the broad-spectrum tetracycline group of antibiotics to be discovered The drug is used for the prophylaxis and local treatment of superficial ocular infections due to oxytetracycline- and polymyxin-sensitive organisms for animal use only. These infections include the following: Ocular infections due to streptococci, rickettsiae E. coli, and A. aerogenes (such as conjunctivitis, keratitis, pinkeye, corneal ulcer, and blepharitis in dogs); ocular infections due to secondary bacterial complications associated with distemper in dogs; and ocular infections due to bacterial inflammatory conditions which may occur secondary to other diseases in dogs. Allergic reactions may occasionally occur. Treatment should be discontinued if reactions are severe. If new infections due to nonsensitive bacteria or fungi appear during therapy, appropriate measures should be taken. Oxytetracycline inhibits cell growth by inhibiting translation. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. The binding is reversible in nature. Oxytetracycline is lipophilic and can easily pass through the cell membrane or passively diffuses through porin channels in the bacterial membrane.
Originator
Approval Year
AEs
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| yes [Inhibition 5 uM] | ||||
| yes [Inhibition 500 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes |
Sourcing
| Vendor/Aggregator | ID | URL |
|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Acute renal failure following overdosage of oxyterracin]. | 1970 Jan |
|
| Azotaemia aggravated by tetracycline. | 1970 Jan 3 |
|
| Azotaemia aggravated by oxytetracycline. | 1971 Nov 16 |
|
| Case report: coma due to oxytetracycline. | 1977 |
|
| Oxytetracycline nephrotoxicosis in two dogs. | 1980 Mar 15 |
|
| Screening for new compounds with antiherpes activity. | 1984 Oct |
|
| Inhibition of HIV-1 RNA-dependent DNA polymerase and cellular DNA polymerases alpha, beta and gamma by phosphonoformic acid and other drugs. | 1988 Feb |
|
| In vitro cultivation of Cryptosporidium parvum and screening for anticryptosporidial drugs. | 1990 Aug |
|
| Contact allergies to topical corticosteroids. | 1993 Mar |
|
| Cholestatic hepatitis associated with flucloxacillin. | 1993 May 3 |
|
| Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro. | 1996 Dec |
|
| Minocycline-induced chronic interstitial nephritis? | 1996 Mar |
|
| Oxytetracycline-induced nephrotoxicosis in dogs after intravenous administration for experimental bone labeling. | 1996 Oct |
|
| Identification of HIV-1 integrase inhibitors via three-dimensional database searching using ASV and HIV-1 integrases as targets. | 2000 Oct |
|
| Human organic anion transporters mediate the transport of tetracycline. | 2002 Jan |
|
| In vitro effects of oxytetracycline on matrix metalloproteinase-1 mRNA expression and on collagen gel contraction by cultured myofibroblasts obtained from the accessory ligament of foals. | 2004 Apr |
|
| Risk of cholestatic liver disease associated with flucloxacillin and flucloxacillin prescribing habits in the UK: cohort study using data from the UK General Practice Research Database. | 2005 Jul |
|
| Drug treatment during pregnancy and isolated orofacial clefts in hungary. | 2007 Mar |
|
| Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. | 2010 Jul |
|
| Impact of isoflupredone acetate treatment on clinical signs and weight gain in weanling heifers with experimentally induced Mannheimia haemolytica bronchopneumonia. | 2011 Dec |
|
| Environmental impact on vascular development predicted by high-throughput screening. | 2011 Nov |
|
| Effect of pharmaceuticals exposure on acetylcholinesterase (AchE) activity and on the expression of AchE gene in the monogonont rotifer, Brachionus koreanus. | 2013 Nov |
|
| Molecular and Cellular Effects Induced in Mytilus galloprovincialis Treated with Oxytetracycline at Different Temperatures. | 2015 |
Patents
Sample Use Guides
For Animal Use Only: topically to the eye 2–4 times daily.
Route of Administration:
Other
It was investigated the possible toxic mechanism of oxytetracycline (OTC) on the human red blood cells (hRBCs). The experimental results indicate that OTC can cause a decline in the function of the antioxidant defense system of hRBCs, resulting in oxidative stress. OTC can bring about morphological changes to hRBCs, and further leads to hemolysis, when the concentration of OTC is over 8×10(-5) M (about 164 µg/ml). At a low OTC concentration, below 4×10(-5) M (82 µg/ml), OTC can enhance the activity of ATP enzyme of hRBCs, known as hormesis. However, at a high concentration, above 4×10(-5) M (about 82 µg/ml), the ATP enzymatic activity was inhibited, affecting the function of hRBCs.
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
WHO-ATC | D06AA03 | ||
|
WHO-VATC | QG51AG06 | ||
|
WHO-VATC | QG01AA07 | ||
|
NCI_THESAURUS | C1595 | ||
|
CFR | 21 CFR 556.500 | ||
|
CFR | 21 CFR 520.1660 | ||
|
WHO-VATC | QS01AA04 | ||
|
WHO-ATC | S01AA04 | ||
|
WHO-ATC | J01AA56 | ||
|
CFR | 21 CFR 520.1660D | ||
|
CFR | 21 CFR 520.1660A | ||
|
CFR | 21 CFR 524.1662A | ||
|
CFR | 21 CFR 522.1660A | ||
|
WHO-VATC | QG51AA01 | ||
|
CFR | 21 CFR 558.455 | ||
|
WHO-VATC | QD06AA03 | ||
|
CFR | 21 CFR 524.1662B | ||
|
CFR | 21 CFR 333.120 | ||
|
CFR | 21 CFR 558.450 | ||
|
WHO-VATC | QD06AA53 | ||
|
NDF-RT | N0000175505 | ||
|
WHO-ATC | G01AA07 | ||
|
LIVERTOX | NBK547920 | ||
|
WHO-VATC | QJ01AA06 | ||
|
CFR | 21 CFR 522.1660B | ||
|
WHO-VATC | QJ51AA06 | ||
|
WHO-ATC | J01AA20 | ||
|
CFR | 21 CFR 524.1662 | ||
|
CFR | 21 CFR 522.1660 | ||
|
WHO-ATC | J01AA06 | ||
|
CFR | 21 CFR 522.1664 |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
266974 | PRIMARY | |||
|
2041 | PRIMARY | |||
|
SUB03601MIG | PRIMARY | |||
|
1491004 | PRIMARY | |||
|
DB00595 | PRIMARY | |||
|
X20I9EN955 | PRIMARY | |||
|
133011 | PRIMARY | |||
|
OXYTETRACYCLINE | PRIMARY | Description: A pale yellow, crystalline powder; odourless. Solubility: Very slightly soluble in water; sparingly soluble in ethanol (~750 g/l) TS; freely soluble in dilute acids and alkalis. Category: Antibacterial drug. Storage: Oxytetracycline dihydrate should be kept in a tightly closed container, protected from light.Labelling: The designation sterile Oxytetracycline dihydrate indicates that the substance complies with the additional requirements for sterile Oxytetracycline dihydrate and may be used for parenteral administration or for other sterile applications.Additional information: Oxytetracycline dihydrate darkens on exposure to strong sunlight. It deteriorates in solutions having a pH below 2 and is rapidly destroyed by alkali hydroxide solutions.Definition: Oxytetracycline dihydrate contains not less than 920 International Units of Oxytetracycline per mg, calculated withreference to the anhydrous substance. | ||
|
6153-64-6 | PRIMARY | |||
|
DTXSID4023412 | PRIMARY | |||
|
oxytetracycline | PRIMARY | |||
|
100000085515 | PRIMARY | |||
|
D010118 | PRIMARY | |||
|
757262 | PRIMARY | |||
|
Oxytetracycline | PRIMARY | |||
|
OXYTETRACYCLINE | PRIMARY | |||
|
C61872 | PRIMARY | |||
|
X20I9EN955 | PRIMARY | |||
|
7821 | ALTERNATIVE | |||
|
CHEMBL1517 | PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
|
||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
|
||
|
ANHYDROUS->SOLVATE | |||
|
|
PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
(eluting on the tail of the principal peak): not more than 4 times the area of the peak due to impurity A in the chromatogram obtained with reference solution (e)
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |