MedKoo Cat#: 571551 | Name: Tetracycline
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tetracycline, sold under the brand name Sumycin among others, is an antibiotic used to treat a number of infections. 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.

Chemical Structure

Tetracycline
CAS#60-54-8 (free base)

Theoretical Analysis

MedKoo Cat#: 571551

Name: Tetracycline

CAS#: 60-54-8 (free base)

Chemical Formula: C22H4N2O8

Exact Mass: 444.1533

Molecular Weight: 444.44

Elemental Analysis: C, 59.46; H, 5.44; N, 6.30; O, 28.80

Price and Availability

Size Price Availability Quantity
5g USD 150.00 Ready to ship
10g USD 250.00 Ready to ship
100g USD 610.00 2 weeks
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Synonym
Mericycline; Micycline; Neocycline; NSC 108579; NSC-108579; NSC108579
IUPAC/Chemical Name
2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S,4aS,5aS,6S,12aS)-
InChi Key
OFVLGDICTFRJMM-WESIUVDSSA-N
InChi Code
InChI=1S/C22H24N2O8/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)/t9-,10-,15-,21+,22-/m0/s1
SMILES Code
O=C(C(C1=O)=C(O)[C@@H](N(C)C)[C@]2([H])C[C@]3([H])[C@](C)(O)C4=C(C(C3=C(O)[C@@]21O)=O)C(O)=CC=C4)N
Appearance
Solid powder
Purity
>90% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Certificate of Analysis
Safety Data Sheet (SDS)
Biological target:
Tetracycline is a broad-spectrum antibiotic with oral activity.
In vitro activity:
As shown in Fig. 1A , co-incubation of β 1-42 with tetracycline for 5 days (Fig. 1B) markedly reduced the amyloid fibrils formation as detected by EM in comparison with the control (Fig. 1A). This was confirmed by the measurement of specific binding of thioflavine T to amyloid fibrils formed by β 1-42, tetracyclines increasing ratios progressively reduced amyloid formation (Fig. 1C). Reference: FEBS Lett. 2001 Jan 5;487(3):404-7. https://pubmed.ncbi.nlm.nih.gov/11163366/
In vivo activity:
The results demonstrated that the concentration (LC50 = 125.25 μg/ml) of antibiotics Tetracycline leads to kills half of the individuals. These data indicate that the high concentrations of Tetracycline have a significant effect on the histological composition of the cells of the midgut of honeybee larvae. Antibiotic exposure can negatively impact the health of honey bees, especially Tetracycline because it is the most used antibiotic in apiculture. Reference: Saudi J Biol Sci. 2022 Mar;29(3):1477-1486. https://pubmed.ncbi.nlm.nih.gov/35280597/
Solvent mg/mL mM comments
Solubility
DMSO 107.0 240.75
Ethanol 22.0 49.50
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 444.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Pfaller MA, Li L, Liu Q, Zhang J, Huband MD, Lindley JM, Mendes RE. In vitro activity of a novel aminomethylcycline antibacterial (KBP-7072), a third-generation tetracycline, against clinical isolates with molecularly characterized tetracycline resistance mechanisms. JAC Antimicrob Resist. 2021 Dec 14;3(4):dlab177. doi: 10.1093/jacamr/dlab177. PMID: 34917942; PMCID: PMC8669227. 2. Forloni G, Colombo L, Girola L, Tagliavini F, Salmona M. Anti-amyloidogenic activity of tetracyclines: studies in vitro. FEBS Lett. 2001 Jan 5;487(3):404-7. doi: 10.1016/s0014-5793(00)02380-2. PMID: 11163366. 3. Aljedani DM. Antibiotic treatment (Tetracycline) effect on bio-efficiency of the larvae honey bee (Apis mellifera jemenatica). Saudi J Biol Sci. 2022 Mar;29(3):1477-1486. doi: 10.1016/j.sjbs.2021.11.024. Epub 2021 Nov 22. PMID: 35280597; PMCID: PMC8913381. 4. Peukert K, Steinhagen F, Fox M, Feuerborn C, Schulz S, Seeliger B, Schuss P, Schneider M, Frede S, Sauer A, Putensen C, Latz E, Wilhelm C, Bode C. Tetracycline ameliorates silica-induced pulmonary inflammation and fibrosis via inhibition of caspase-1. Respir Res. 2022 Feb 7;23(1):21. doi: 10.1186/s12931-022-01937-7. PMID: 35130879; PMCID: PMC8822850.
In vitro protocol:
1. Pfaller MA, Li L, Liu Q, Zhang J, Huband MD, Lindley JM, Mendes RE. In vitro activity of a novel aminomethylcycline antibacterial (KBP-7072), a third-generation tetracycline, against clinical isolates with molecularly characterized tetracycline resistance mechanisms. JAC Antimicrob Resist. 2021 Dec 14;3(4):dlab177. doi: 10.1093/jacamr/dlab177. PMID: 34917942; PMCID: PMC8669227. 2. Forloni G, Colombo L, Girola L, Tagliavini F, Salmona M. Anti-amyloidogenic activity of tetracyclines: studies in vitro. FEBS Lett. 2001 Jan 5;487(3):404-7. doi: 10.1016/s0014-5793(00)02380-2. PMID: 11163366.
In vivo protocol:
1. Aljedani DM. Antibiotic treatment (Tetracycline) effect on bio-efficiency of the larvae honey bee (Apis mellifera jemenatica). Saudi J Biol Sci. 2022 Mar;29(3):1477-1486. doi: 10.1016/j.sjbs.2021.11.024. Epub 2021 Nov 22. PMID: 35280597; PMCID: PMC8913381. 2. Peukert K, Steinhagen F, Fox M, Feuerborn C, Schulz S, Seeliger B, Schuss P, Schneider M, Frede S, Sauer A, Putensen C, Latz E, Wilhelm C, Bode C. Tetracycline ameliorates silica-induced pulmonary inflammation and fibrosis via inhibition of caspase-1. Respir Res. 2022 Feb 7;23(1):21. doi: 10.1186/s12931-022-01937-7. PMID: 35130879; PMCID: PMC8822850.
1: Chon JW, Lee SK, Yoon Y, Yoon KS, Kwak HS, Joo IS, Seo KH. Quantitative prevalence and characterization of Campylobacter from chicken and duck carcasses from poultry slaughterhouses in South Korea. Poult Sci. 2018 May 10. doi: 10.3382/ps/pey120. [Epub ahead of print] PubMed PMID: 29757448. 2: Saidani M, Messadi L, Soudani A, Daaloul-Jedidi M, Châtre P, Ben Chehida F, Mamlouk A, Mahjoub W, Madec JY, Haenni M. Epidemiology, Antimicrobial Resistance, and Extended-Spectrum Beta-Lactamase-Producing Enterobacteriaceae in Clinical Bovine Mastitis in Tunisia. Microb Drug Resist. 2018 May 14. doi: 10.1089/mdr.2018.0049. [Epub ahead of print] PubMed PMID: 29757079. 3: Tadesse HA, Gidey NB, Workelule K, Hailu H, Gidey S, Bsrat A, Taddele H. Antimicrobial Resistance Profile of E. coli Isolated from Raw Cow Milk and Fresh Fruit Juice in Mekelle, Tigray, Ethiopia. Vet Med Int. 2018 Mar 19;2018:8903142. doi: 10.1155/2018/8903142. eCollection 2018. PubMed PMID: 29755727; PubMed Central PMCID: PMC5884018. 4: Okado JB, Avaca-Crusca JS, Oliveira AL, Dabul ANG, da Cunha Camargo ILB. Daptomycin and vancomycin heteroresistance revealed among CC5-SCCmecII MRSA clone and in vitro evaluation of treatment alternatives. J Glob Antimicrob Resist. 2018 May 9. pii: S2213-7165(18)30085-7. doi: 10.1016/j.jgar.2018.05.001. [Epub ahead of print] PubMed PMID: 29753135. 5: Xu N, Meng L, Li HW, Lu DY, Wu Y. Polyethyleneimine capped bimetallic Au/Pt nanoclusters are a viable fluorescent probe for specific recognition of chlortetracycline among other tetracycline antibiotics. Mikrochim Acta. 2018 May 11;185(6):294. doi: 10.1007/s00604-018-2828-0. PubMed PMID: 29752570. 6: Hu J, Zhao F, Zhang XX, Li K, Li C, Ye L, Li M. Metagenomic profiling of ARGs in airborne particulate matters during a severe smog event. Sci Total Environ. 2018 Feb 15;615:1332-1340. doi: 10.1016/j.scitotenv.2017.09.222. Epub 2017 Oct 17. PubMed PMID: 29751438. 7: Wang L, Ben W, Li Y, Liu C, Qiang Z. Behavior of tetracycline and macrolide antibiotics in activated sludge process and their subsequent removal during sludge reduction by ozone. Chemosphere. 2018 May 3;206:184-191. doi: 10.1016/j.chemosphere.2018.04.180. [Epub ahead of print] PubMed PMID: 29751244. 8: Zhu JJ, Jiang JG. Pharmacological and Nutritional Effects of Natural Coumarins and Their Structure-Activity Relationships. Mol Nutr Food Res. 2018 May 11:e1701073. doi: 10.1002/mnfr.201701073. [Epub ahead of print] Review. PubMed PMID: 29750855. 9: Botelho ACN, Oliveira JG, Damasco AP, Santos KTB, Ferreira AFM, Rocha GT, Marinho PS, Bornia RBG, Pinto TCA, Américo MA, Fracalanzza SEL, Teixeira LM. Streptococcus agalactiae carriage among pregnant women living in Rio de Janeiro, Brazil, over a period of eight years. PLoS One. 2018 May 11;13(5):e0196925. doi: 10.1371/journal.pone.0196925. eCollection 2018. PubMed PMID: 29750801. 10: Liu C, Feng J, Zhang D, Xie Y, Li A, Wang J, Su Y. Clustering Analysis of Antibiograms and Antibiogram Types of Streptococcus agalactiae Strains from Tilapia in China. Microb Drug Resist. 2018 May 11. doi: 10.1089/mdr.2017.0350. [Epub ahead of print] PubMed PMID: 29750585. 11: Bhardwaj N, Mathur P, Behera B, Mathur K, Kapil A, Misra MC. Antimicrobial resistance in beta-haemolytic streptococci in India: A four-year study. Indian J Med Res. 2018 Jan;147(1):81-87. doi: 10.4103/ijmr.IJMR_1517_16. PubMed PMID: 29749365. 12: Yang GH, Bao DD, Zhang DQ, Wang C, Qu LL, Li HT. Removal of Antibiotics From Water with an All-Carbon 3D Nanofiltration Membrane. Nanoscale Res Lett. 2018 May 10;13(1):146. doi: 10.1186/s11671-018-2555-9. PubMed PMID: 29748741. 13: Judge MS, Miller JM, Lyons M 3rd. Green Bone: Minocycline-Induced Discoloration of Bone Rarely Reported in Foot and Ankle. J Foot Ankle Surg. 2018 May 7. pii: S1067-2516(17)30646-4. doi: 10.1053/j.jfas.2017.11.009. [Epub ahead of print] PubMed PMID: 29748107. 14: Kim MJ, Ku S, Kim SY, Lee HH, Jin H, Kang S, Li R, Johnston TV, Park MS, Ji GE. Safety Evaluations of Bifidobacterium bifidum BGN4 and Bifidobacterium longum BORI. Int J Mol Sci. 2018 May 9;19(5). pii: E1422. doi: 10.3390/ijms19051422. PubMed PMID: 29747442. 15: Khan T, Azad I, Ahmad R, Raza S, Dixit S, Joshi S, Khan AR. Synthesis, characterization, computational studies and biological activity evaluation of Cu, Fe, Co and Zn complexes with 2-butanone thiosemicarbazone and 1,10-phenanthroline ligands as anticancer and antibacterial agents. EXCLI J. 2018 Mar 29;17:331-348. doi: 10.17179/excli2017-984. eCollection 2018. PubMed PMID: 29743867; PubMed Central PMCID: PMC5938540. 16: Ankrapp D, Schaus B, Clements L, Klein F, Rice J, Rejman J. Validation of the BetaStar(®) Advanced for Tetracyclines Test Kit for the Screening of Bulk Tank and Tanker Truck Milks for the Presence of Tetracycline Drug Residues. J AOAC Int. 2018 May 9. doi: 10.5740/jaoacint.18-0082. [Epub ahead of print] PubMed PMID: 29743134. 17: Zatta M, Di Bella S, Busetti M, Michelacci V, Owczarek S, Luzzi I, Luzzati R. Emergence of quinolone-resistant Shigella flexneri in Italy (March 2017). Int J STD AIDS. 2018 Jan 1:956462418769805. doi: 10.1177/0956462418769805. [Epub ahead of print] PubMed PMID: 29743001. 18: He Y, Huang YY, Xi L, Gelfand JA, Hamblin MR. Tetracyclines function as dual-action light-activated antibiotics. PLoS One. 2018 May 9;13(5):e0196485. doi: 10.1371/journal.pone.0196485. eCollection 2018. PubMed PMID: 29742128. 19: Chen D, Zou W, Xie S, Kong L, Chen Y, Zhang X, Li J, Wang H, Cheng G, Qin Y, Mu X, Yang X. Serotype and Antimicrobial Resistance of Escherichia coli Isolated from Feces of Wild Giant Pandas ( Ailuropoda melanoleuca) in Sichuan Province, China. J Wildl Dis. 2018 May 9. doi: 10.7589/2017-07-165. 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