Oxytetracycline hydrochloride
[CAS# 2058-46-0]

Identification

• Classification: API >> Antibiotics >> Tetracycline
• Name: Oxytetracycline hydrochloride
• Synonyms: 5-Hydroxytetracycline hydrochloride; [4S-(4alpha,4aalpha,5alpha,5aalpha,6beta,12aalpha)]-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 monohydrochloride
• Molecular Formula: C₂₂H₂₄N₂O₉.HCl
• Molecular Weight: 496.90
• CAS Registry Number: 2058-46-0
• EC Number: 218-161-2
• SMILES: CN(C)[C@@H]1C(O)=C(C(N)=O)C(=O)[C@@]2(O)C(O)=C3C(=O)c4c(O)cccc4[C@@](C)(O)[C@H]3[C@H](O)[C@@H]12.Cl.Cl

Properties

• Melting point: 180 °C
• Water solubility: >100 g/L

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Warning
• Risk Statements: H319-H361-H361d-H362-H400-H410
• Safety Statements: P203-P260-P263-P264-P264+P265-P270-P273-P280-P305+P351+P338-P318-P337+P317-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Repr.	2	H361
Eye irritation	Eye Irrit.	2	H319
Reproductive toxicity	Lact.	-	H362
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Reproductive toxicity	Repr.	2	H361d
Skin sensitization	Skin Sens.	1	H317
Reproductive toxicity	Repr.	1B	H360
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	4	H302
Respiratory sensitization	Resp. Sens.	1	H334
Acute toxicity	Acute Tox.	3	H311

Discovery and Applications

Oxytetracycline hydrochloride is a broad-spectrum antibiotic belonging to the tetracycline class, which is widely used in both human and veterinary medicine. It is an antimicrobial agent that works by inhibiting protein synthesis in bacteria, thereby preventing their growth and replication. Oxytetracycline hydrochloride was first introduced in the 1950s as a treatment for bacterial infections, offering a valuable alternative to penicillin and other early antibiotics.

The compound is synthesized through a fermentation process involving the bacterium *Streptomyces rimosus*, which naturally produces oxytetracycline. The hydrochloride form of oxytetracycline is the salt form of the antibiotic, making it more stable and easier to formulate into various pharmaceutical products, including tablets, ointments, and injectable solutions. This stability allows for its widespread use in treating a variety of infections, including respiratory infections, urinary tract infections, and certain skin infections.

Oxytetracycline hydrochloride has a wide range of applications. In human medicine, it is used to treat bacterial infections caused by both Gram-positive and Gram-negative bacteria. It is also effective against atypical bacteria, including certain mycoplasmas and rickettsiae. The antibiotic is commonly prescribed for infections such as acne, chlamydia, and respiratory tract infections. It is also used as part of the treatment for Lyme disease and certain eye infections.

In veterinary medicine, oxytetracycline hydrochloride is used to treat infections in animals, particularly in livestock, poultry, and pets. It is effective in controlling a variety of bacterial infections in animals, including those affecting the respiratory system, digestive tract, and reproductive organs. The compound is frequently administered in feed or drinking water to treat or prevent infections in large groups of animals, making it an important tool in agriculture and animal husbandry.

Oxytetracycline hydrochloride has also found use in aquaculture for the treatment of bacterial infections in fish and other aquatic organisms. Its effectiveness in controlling diseases such as furunculosis and columnaris has made it an essential tool in the maintenance of healthy fish populations in commercial aquaculture.

Despite its broad-spectrum activity, the use of oxytetracycline hydrochloride is associated with certain limitations and concerns. Like other tetracyclines, it can cause side effects such as gastrointestinal upset, allergic reactions, and, in rare cases, liver toxicity. Additionally, the overuse of oxytetracycline in both human and veterinary medicine has led to concerns about the development of antibiotic-resistant bacteria. To mitigate this risk, it is important to use oxytetracycline hydrochloride judiciously and only when prescribed by a healthcare provider or veterinarian.

In conclusion, oxytetracycline hydrochloride remains a valuable antibiotic used in the treatment of a variety of bacterial infections in both humans and animals. Its broad-spectrum activity and effectiveness in controlling infections make it an important tool in medical and agricultural practices. However, its use must be carefully managed to prevent the emergence of antibiotic-resistant bacteria and to minimize potential side effects.

References

2024. Comparison of Oxytetracycline and Sulfamethazine Effects Over Root Elongation in Selected Wild and Crop Plants Commonly Present in the Mediterranean Cropland and Pasture Scenarios. *Archives of Environmental Contamination and Toxicology*, 87(3).
DOI: 10.1007/s00244-024-01104-7

2024. Analysis of binary mixture of oxytetracycline and bromohexine in their combined veterinary formulation by four simple spectrophotometric methods with greenness assessment. *BMC Chemistry*, 18(1).
DOI: 10.1186/s13065-024-01296-y

2024. Eco-friendly electrochemical assay of oxytetracycline and flunixin in their veterinary injections and spiked milk samples. *BMC Chemistry*, 18(1).
DOI: 10.1186/s13065-024-01282-4