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MedKoo Cat#: 318852 | Name: Tetracycline HCl
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Description:

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

Tetracyclines are a group of broad-spectrum antibiotics whose general usefulness has been reduced with the onset of antibiotic resistance. Despite this, they remain the treatment of choice for some specific indications. Tetracycline antibiotics are protein synthesis inhibitors, inhibiting the binding of aminoacyl-tRNA to the mRNA-ribosome complex. They do so mainly by binding to the 30S ribosomal subunit in the mRNA translation complex. Tetracyclines also have been found to inhibit matrix metalloproteinases.

Chemical Structure

Tetracycline HCl
CAS#64-75-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 318852

Name: Tetracycline HCl

CAS#: 64-75-5 (HCl)

Chemical Formula: C22H25ClN2O8

Exact Mass: 0.0000

Molecular Weight: 480.90

Elemental Analysis: C, 54.95; H, 5.24; Cl, 7.37; N, 5.83; O, 26.62

Price and Availability

Size Price Availability Quantity
25g USD 250.00 2 weeks
100g USD 550.00 2 weeks
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Related CAS #
64-75-5 (HCl) 60-54-8 (free base)
Synonym
Tetracycline HCl; Achromycin; Achromycin V; Hostacyclin; Sustamycin; Tetrabid; Tetracycline; Topicycline.
IUPAC/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
InChi Key
XMEVHPAGJVLHIG-FMZCEJRJSA-N
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
SMILES Code
[H][C@@]12C[C@]3(C(C(C4=C(C=CC=C4[C@]3(O)C)O)=O)=C([C@@]1(C(C(C(N)=O)=C([C@H]2N(C)C)O)=O)O)O)[H].[H]Cl
Appearance
Solid powder
Purity
>97% (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, not in water
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

Preparing Stock Solutions

The following data is based on the product molecular weight 480.90 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
1: Chatzispyrou IA, Held NM, Mouchiroud L, Auwerx J, Houtkooper RH. Tetracycline Antibiotics Impair Mitochondrial Function and Its Experimental Use Confounds Research. Cancer Res. 2015 Nov 1;75(21):4446-9. doi: 10.1158/0008-5472.CAN-15-1626. Epub 2015 Oct 16. Review. PubMed PMID: 26475870; PubMed Central PMCID: PMC4631686. 2: Lv ZF, Wang FC, Zheng HL, Wang B, Xie Y, Zhou XJ, Lv NH. Meta-analysis: is combination of tetracycline and amoxicillin suitable for Helicobacter pylori infection? World J Gastroenterol. 2015 Feb 28;21(8):2522-33. doi: 10.3748/wjg.v21.i8.2522. Review. PubMed PMID: 25741163; PubMed Central PMCID: PMC4342932. 3: Yeh ES, Vernon-Grey A, Martin H, Chodosh LA. Tetracycline-regulated mouse models of cancer. Cold Spring Harb Protoc. 2014 Oct 1;2014(10):pdb.top069823. doi: 10.1101/pdb.top069823. Review. PubMed PMID: 25275112. 4: Sakai N. Principles for the use of in vivo transgene techniques: overview and an introductory practical guide for the selection of tetracycline-controlled transgenic mice. Methods Mol Biol. 2014;1142:33-40. doi: 10.1007/978-1-4939-0404-4_4. Review. PubMed PMID: 24706272. 5: Nguyen F, Starosta AL, Arenz S, Sohmen D, Dönhöfer A, Wilson DN. Tetracycline antibiotics and resistance mechanisms. Biol Chem. 2014 May;395(5):559-75. doi: 10.1515/hsz-2013-0292. Review. PubMed PMID: 24497223. 6: Emaneini M, Bigverdi R, Kalantar D, Soroush S, Jabalameli F, Noorazar Khoshgnab B, Asadollahi P, Taherikalani M. Distribution of genes encoding tetracycline resistance and aminoglycoside modifying enzymes in Staphylococcus aureus strains isolated from a burn center. Ann Burns Fire Disasters. 2013 Jun 30;26(2):76-80. Review. PubMed PMID: 24133400; PubMed Central PMCID: PMC3793882. 7: Srikumar GP, Sekhar KS, Nischith KG. Mixture tetracycline citric acid and detergent - A root canal irrigant. A review. J Oral Biol Craniofac Res. 2013 Jan-Apr;3(1):31-5. doi: 10.1016/j.jobcr.2012.09.001. Epub 2012 Sep 14. Review. PubMed PMID: 25737877; PubMed Central PMCID: PMC3941632. 8: Li WM, Bao YY, Zhou QX. [Degradation pathways and main degradation products of tetracycline antibiotics: research progress]. Ying Yong Sheng Tai Xue Bao. 2012 Aug;23(8):2300-8. Review. Chinese. PubMed PMID: 23189713. 9: Mullany P, Allan E, Warburton PJ. Tetracycline resistance genes and mobile genetic elements from the oral metagenome. Clin Microbiol Infect. 2012 Jul;18 Suppl 4:58-61. doi: 10.1111/j.1469-0691.2012.03858.x. Review. PubMed PMID: 22647052. 10: Kozlova EN, Berens C. Guiding differentiation of stem cells in vivo by tetracycline-controlled expression of key transcription factors. Cell Transplant. 2012;21(12):2537-54. doi: 10.3727/096368911X637407. Epub 2012 Mar 28. Review. PubMed PMID: 22469517. 11: Onishchenko GG, Sheveleva SA, Khotimchenko SA. [New aspects of safety assessment and food contamination with antibiotics of tetracycline group in the light of harmonization of hygienic standards in Russia and Customs Union with the international standards]. Vopr Pitan. 2012;81(5):4-12. Review. Russian. PubMed PMID: 23461166. 12: Roy SK, Kendrick D, Sadowitz BD, Gatto L, Snyder K, Satalin JM, Golub LM, Nieman G. Jack of all trades: pleiotropy and the application of chemically modified tetracycline-3 in sepsis and the acute respiratory distress syndrome (ARDS). Pharmacol Res. 2011 Dec;64(6):580-9. doi: 10.1016/j.phrs.2011.06.012. Epub 2011 Jun 21. Review. PubMed PMID: 21767646; PubMed Central PMCID: PMC3195907. 13: Greenwald RA. The road forward: the scientific basis for tetracycline treatment of arthritic disorders. Pharmacol Res. 2011 Dec;64(6):610-3. doi: 10.1016/j.phrs.2011.06.010. Epub 2011 Jun 21. Review. PubMed PMID: 21723947. 14: Gu Y, Lee HM, Simon SR, Golub LM. Chemically modified tetracycline-3 (CMT-3): a novel inhibitor of the serine proteinase, elastase. Pharmacol Res. 2011 Dec;64(6):595-601. doi: 10.1016/j.phrs.2011.05.011. Epub 2011 May 31. Review. PubMed PMID: 21651982. 15: Sirangelo I, Irace G. Inhibition of aggregate formation as therapeutic target in protein misfolding diseases: effect of tetracycline and trehalose. Expert Opin Ther Targets. 2010 Dec;14(12):1311-21. doi: 10.1517/14728222.2010.531012. Review. PubMed PMID: 21058920. 16: Griffin MO, Ceballos G, Villarreal FJ. Tetracycline compounds with non-antimicrobial organ protective properties: possible mechanisms of action. Pharmacol Res. 2011 Feb;63(2):102-7. doi: 10.1016/j.phrs.2010.10.004. Epub 2010 Oct 14. Review. PubMed PMID: 20951211; PubMed Central PMCID: PMC3031662. 17: Nishijima H, Yasunari T, Nakayama T, Adachi N, Shibahara K. Improved applications of the tetracycline-regulated gene depletion system. Biosci Trends. 2009 Oct;3(5):161-7. Review. PubMed PMID: 20103842. 18: Thaker M, Spanogiannopoulos P, Wright GD. The tetracycline resistome. Cell Mol Life Sci. 2010 Feb;67(3):419-31. doi: 10.1007/s00018-009-0172-6. Epub 2009 Oct 28. Review. PubMed PMID: 19862477. 19: Korting HC, Schöllmann C. Tetracycline actions relevant to rosacea treatment. Skin Pharmacol Physiol. 2009;22(6):287-94. doi: 10.1159/000235550. Epub 2009 Sep 25. Review. PubMed PMID: 19786821. 20: Oberholzer PA, Nobbe S, Kolm I, Kerl K, Kamarachev J, Trüeb RM. Red scalp disease--a rosacea-like dermatosis of the scalp? Successful therapy with oral tetracycline. Dermatology. 2009;219(2):179-81. doi: 10.1159/000228319. Epub 2009 Jul 8. Review. PubMed PMID: 19590169.