| Size | Price | Stock | Qty |
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| 2g |
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| 5g |
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| 10g |
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| 25g |
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| Other Sizes |
Purity: ≥98%
Tetracycline HCl (NSC-108579, Sumycin among others) is a potent and broad-spectrum antibiotic used to treat a number of infections such as gram-positive and gram-negative bacteria. This includes acne, cholera, brucellosis, plague, malaria, and syphilis. It possesses some level of bacteriostatic activity against almost all medically relevant aerobic and anaerobic bacterial genera, both Gram-positive and Gram-negative.
| Targets |
Tetracycline
Tetracycline inhibits bacterial protein synthesis by binding to the 30S ribosomal subunit and preventing the attachment of aminoacyl-tRNA to the ribosomal acceptor (A) site. Studies suggest that the binding pocket involves protein S7 and 16S rRNA bases including G693, A892, U1052, C1054, G1300, and G1338. The active drug species that binds to the ribosome is a magnesium-tetracycline complex [1]. |
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| ln Vitro |
Tetracyclines are broad-spectrum antibiotics that work against a variety of gram-positive and gram-negative bacteria, as well as protozoan parasites and atypical organisms like chlamydiae, mycoplasmas, and rickettsiae. Tetracyclines stop aminoacyl-tRNA from attaching itself to the bacterial ribosome, which inhibits the synthesis of proteins by bacteria. Through the OmpF and OmpC porin channels, tetracyclines enter gram-negative enteric bacteria's outer membrane as positively charged cations (likely magnesium)-tetracycline coordination complexes [1].
Antibacterial Activity: Tetracycline is a broad-spectrum antibiotic, exhibiting activity against a wide range of gram-positive and gram-negative bacteria, as well as atypical organisms such as chlamydiae, mycoplasmas, and rickettsiae. Its effect is primarily bacteriostatic [1]. |
| ln Vivo |
Tetracyclines are useful for treating infections in pigs, sheep, cattle, and poultry. In certain situations, such as when treating a large number of commercially farmed chickens therapeutically, antibiotics can be given as aerosols or added straight to feed or water. Tetracyclines may be utilized to enhance or promote growth. In aquaculture, tetracyclines are used to manage infections in lobsters, salmon, and catfish[2].
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| ADME/Pharmacokinetics |
Absorption: Tetracycline is usually administered orally. Absorption occurs largely in the stomach and proximal small intestine. It is influenced by the presence of food, milk, or divalent cations (particularly calcium), with which tetracyclines form nonabsorbable chelates. Serum levels after normal oral dosing are in the range of 2-5 μg/mL [1].
Distribution: Tetracycline generally penetrates moderately well into body fluids and tissues. It can achieve levels in sputum about 20% of those in serum, explaining its role in treating respiratory tract infections. It also penetrates into sebum and is excreted in perspiration, contributing to its usefulness in acne management [1]. Excretion: Tetracycline is excreted in the urine [1]. Dosing Regimen: Most tetracyclines have relatively short elimination half-lives and need to be given four times daily to maintain therapeutic serum concentrations. However, later-generation tetracyclines like doxycycline and minocycline have longer half-lives, permitting once- or twice-daily dosing [1]. |
| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation
◉ Overview of Use During Lactation Some reviews suggest that tetracycline is contraindicated during lactation because it may stain infant tooth enamel or deposit in bone. However, a careful review of existing literature indicates that short-term use of tetracycline during lactation is unlikely to cause harm, as the concentration of tetracycline in breast milk is low and the calcium in breast milk inhibits the infant's absorption of tetracycline. Short-term use of tetracycline in lactating women is acceptable. As a theoretical precaution, prolonged or repeated use during lactation should be avoided. Closely monitor the infant for rashes and potential effects on the gut microbiota, such as diarrhea or candidiasis (thrush, diaper rash). ◉ Effects on Breastfed Infants No adverse reactions were observed in breastfed infants whose mothers took 1, 1.5, or 2 grams of tetracycline orally daily for 3 days. The infant's age and the extent of breastfeeding were not considered. In one study, five infants were breastfed while their mothers were taking 500 mg tetracycline four times daily, and no adverse reactions were observed. In an observational study of 251 women, 23.8% of lactating mothers took tetracycline while breastfeeding. No serious adverse reactions were observed in any of the breastfed infants. ◉ Effects on lactation and breast milk: As of the revision date, no relevant published information was found. The review notes that tetracyclines are generally associated with an absence of major adverse side effects. However, some specific toxicities are mentioned in the context of the drug class, though not specifically for tetracycline HCl. The review also discusses the widespread emergence of bacterial resistance to tetracycline, which has limited its clinical utility. Resistance mechanisms include efflux proteins (e.g., Tet(A-E), Tet(K), Tet(L)) and ribosomal protection proteins (e.g., Tet(M), Tet(O)). Resistance rates vary geographically and temporally; for instance, in a 1969 Boston hospital, 61% of E. coli isolates were resistant to tetracyclines [1]. |
| References | |
| Additional Infomation |
Tetracycline hydrochloride (oral) may cause developmental toxicity, depending on state or federal labeling requirements. It is a naphthocycloene antibiotic that inhibits the binding of aminoacyl-tRNA during protein synthesis. See also: Tetracycline hydrochloride (note moved to).
Tetracycline was discovered in 1953 (trade name Achromycin) and is a first-generation member of the tetracycline class. It is a product of Streptomyces aureofaciens, S. rimosus, and S. viridofaciens. Its molecular structure comprises a linear fused tetracyclic nucleus. The simplest structure that displays detectable antibacterial activity is 6-deoxy-6-demethyltetracycline, which can be regarded as the minimum pharmacophore. Key features for antibacterial activity include the maintenance of the linear fused tetracycline ring system, specific stereochemical configurations at positions 4a, 12a, and 4, and conservation of the keto-enol system near the phenolic D ring. Tetracycline and other tetracyclines are strong chelating agents, a property that influences both their antimicrobial and pharmacokinetic properties. The emergence of bacterial resistance, particularly through efflux and ribosomal protection mechanisms, has significantly reduced the clinical utility of tetracycline and other first- and second-generation tetracyclines, leading to the development of newer analogs like the glycylcyclines [1]. |
| Exact Mass |
480.129
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|---|---|
| Elemental Analysis |
C, 54.95; H, 5.24; Cl, 7.37; N, 5.83; O, 26.62
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| CAS # |
64-75-5
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| Related CAS # |
Tetracycline;60-54-8
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| PubChem CID |
54704426
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| Appearance |
Light yellow to yellow solid powder
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| Boiling Point |
799.4ºC at 760 mmHg
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| Melting Point |
220-223 °C(lit.)
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| Flash Point |
437.3ºC
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| Vapour Pressure |
5.82E-27mmHg at 25°C
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| Index of Refraction |
-253 ° (C=0.5, 0.1mol/L HCl)
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| LogP |
1.287
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| Hydrogen Bond Donor Count |
7
|
| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
33
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| Complexity |
971
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| Defined Atom Stereocenter Count |
5
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| SMILES |
C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O.Cl
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| InChi Key |
XMEVHPAGJVLHIG-FMZCEJRJSA-N
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| InChi Code |
InChI=1S/C22H24N2O8.ClH/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)1H/t9-,10-,15-,21+,22-/m0./s1
|
| Chemical Name |
(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride
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| Synonyms |
Achromycin V; Hostacyclin; Sustamycin; Tetrabid; Tetracycline; Topicycline;Tetracycline HCl; Achromycin;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : 62.5~96 mg/mL ( 129.96 ~199.62 mM)
Water : 50~80 mg/mL (~103.97 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.33 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (4.33 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.08 mg/mL (4.33 mM) |
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT01628549 | COMPLETEDWITH RESULTS | Drug: 50 mg P005672-HCl Drug: Placebo Drug: 100 mg P005672-HCl |
Acne Vulgaris | Almirall, S.A. | 2012-06-30 | Phase 2 |
| NCT01279187 | TERMINATEDWITH RESULTS | Drug: Teriparatide Drug: Placebo |
Implant | University of Michigan | 2011-02 | Phase 2 |
| NCT00712413 | WITHDRAWN | Drug: OBMT | Helicobacter Pylori Infection | Forest Laboratories | 2008-08 | Phase 3 |
| NCT04716426 | COMPLETEDWITH RESULTS | Drug: Tetracycline hydrochloride 3% Drug: Placebo |
COVID-19 | University of Nove de Julho | 2021-01-28 | Not Applicable |
| NCT00091247 | COMPLETED | Drug: tetracycline hydrochloride Other: placebo |
Unspecified Adult Solid Tumor, Protocol Specific |
Alliance for Clinical Trials in Oncology | 2004-12 | Not Applicable |
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