Oxytetracycline Hydrochloride
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MedKoo CAT#: 318450

CAS#: 2058-46-0 (HCl)

Description: Oxytetracycline Hydrochloride is the hydrochloride salt form of oxytetracycline, a tetracycline derivative produced by Streptomyces rimosus exhibiting antimicrobial activity. Oxytetracycline Hydrochloride is an antibacterial compound isolated from the elaboration products of the actinomycete, Streptomyces rimosus, when grown on a suitable medium. Oxytetracycline hydrochloride interferes with binding of aminoacyl-tRNA to the mRNA-ribosome complex, thereby preventing peptide elongation and inhibiting protein synthesis. It is often used to treat skin conditions.


Chemical Structure

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Oxytetracycline Hydrochloride
CAS# 2058-46-0 (HCl)

Theoretical Analysis

MedKoo Cat#: 318450
Name: Oxytetracycline Hydrochloride
CAS#: 2058-46-0 (HCl)
Chemical Formula: C22H25ClN2O9
Exact Mass: 0.00
Molecular Weight: 496.897
Elemental Analysis: C, 53.18; H, 5.07; Cl, 7.13; N, 5.64; O, 28.98

Price and Availability

Size Price Availability Quantity
5g USD 350 2 Weeks
25g USD 550 2 Weeks
100g USD 950 2 Weeks
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Related CAS #: 2058-46-0 (HCl)   6153-64-6 (dihydrate)  

Synonym: Oxytetracycline Hydrochloride; Oxytetracycline HCl; Biosolvomycin; Oxytetracycline.HCl; Dalinmycin; Dalimycin; Oxytetracycline, Sodium Salt; Sodium Salt Oxytetracycline; Terramycin;

IUPAC/Chemical Name: (4S,4aR,5S,5aR,6S,12aR)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride

InChi Key: SVDOODSCHVSYEK-IFLJXUKPSA-N

InChi Code: InChI=1S/C22H24N2O9.ClH/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;/h4-6,12-14,17,25-26,28,30,32-33H,1-3H3,(H2,23,31);1H/t12-,13-,14+,17+,21-,22+;/m1./s1

SMILES Code: CC1(C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O)O.Cl

Appearance: Light yellow to yellow solid powder.

Purity: >95% (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:

Product Data:
Biological target: Oxytetracycline hydrochloride is an antibiotic belonging to the tetracycline class.
In vitro activity: Through screening, this study identified oxytetracycline, which showed significant inhibition activity of LCSC population without damage on hepatocytes. To determine whether oxytetracycline targets LCSC, this study examined whether oxytetracycline treatment could change the CD133 expression, spheroid forming ability as well as the levels of stem cell-related markers. Treatment of spheroid-forming LCSC with oxytetracycline effectively decreased the spheroid formation and the CD133+ cell population. oxytetracycline could suppress expression of CD133 without changing of expression of other stem cell-related markers. Reference: Sci Rep. 2018 Oct 31;8(1):16100. https://pubmed.ncbi.nlm.nih.gov/30382122/
In vivo activity: The present work was carried out to evaluate the effect of naringenin on antioxidant and lipid peroxidation status in liver of oxytetracycline-intoxicated rats. Intraperitonial administration of oxytetracycline 200 mg/kg for 15 days resulted a significant elevation in serum hepatospecific markers such as aspartate transaminase, alanine transaminase, alkaline phosphatase, lactate dehydrogenase, and bilirubin and the levels of lipid peroxidation markers (thiobarbituric acid reactive substances (TBARS) and lipid hydroperoxides) in liver. Oxytetracycline also caused a significant reduction in the activities of superoxide dismutase, catalase, glutathione peroxidase, reduced glutathione (GSH), vitamin C and vitamin E in liver. Reference: Basic Clin Pharmacol Toxicol. 2006 May;98(5):456-61. https://pubmed.ncbi.nlm.nih.gov/16635103/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 299.5 602.74
Water 99.0 199.24

Preparing Stock Solutions

The following data is based on the product molecular weight 496.90 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
Formulation protocol: 1. Song Y, Kim IK, Choi I, Kim SH, Seo HR. Oxytetracycline have the therapeutic efficiency in CD133+ HCC population through suppression CD133 expression by decreasing of protein stability of CD133. Sci Rep. 2018 Oct 31;8(1):16100. doi: 10.1038/s41598-018-34301-1. PMID: 30382122; PMCID: PMC6208387. 2. Rok J, Wrześniok D, Beberok A, Otręba M, Delijewski M, Buszman E. Phototoxic effect of oxytetracycline on normal human melanocytes. Toxicol In Vitro. 2018 Apr;48:26-32. doi: 10.1016/j.tiv.2017.12.008. Epub 2017 Dec 15. PMID: 29248593. 3. Jayanthi R, Subash P. Antioxidant effect of caffeic Acid on oxytetracycline induced lipid peroxidation in albino rats. Indian J Clin Biochem. 2010 Oct;25(4):371-5. doi: 10.1007/s12291-010-0052-8. Epub 2010 Oct 5. PMID: 21966107; PMCID: PMC2994573. 4. Pari L, Gnanasoundari M. Influence of naringenin on oxytetracycline mediated oxidative damage in rat liver. Basic Clin Pharmacol Toxicol. 2006 May;98(5):456-61. doi: 10.1111/j.1742-7843.2006.pto_351.x. PMID: 16635103.
In vitro protocol: 1. Song Y, Kim IK, Choi I, Kim SH, Seo HR. Oxytetracycline have the therapeutic efficiency in CD133+ HCC population through suppression CD133 expression by decreasing of protein stability of CD133. Sci Rep. 2018 Oct 31;8(1):16100. doi: 10.1038/s41598-018-34301-1. PMID: 30382122; PMCID: PMC6208387. 2. Rok J, Wrześniok D, Beberok A, Otręba M, Delijewski M, Buszman E. Phototoxic effect of oxytetracycline on normal human melanocytes. Toxicol In Vitro. 2018 Apr;48:26-32. doi: 10.1016/j.tiv.2017.12.008. Epub 2017 Dec 15. PMID: 29248593.
In vivo protocol: 1. Jayanthi R, Subash P. Antioxidant effect of caffeic Acid on oxytetracycline induced lipid peroxidation in albino rats. Indian J Clin Biochem. 2010 Oct;25(4):371-5. doi: 10.1007/s12291-010-0052-8. Epub 2010 Oct 5. PMID: 21966107; PMCID: PMC2994573. 2. Pari L, Gnanasoundari M. Influence of naringenin on oxytetracycline mediated oxidative damage in rat liver. Basic Clin Pharmacol Toxicol. 2006 May;98(5):456-61. doi: 10.1111/j.1742-7843.2006.pto_351.x. PMID: 16635103.

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1: Gao C, Liu Z, Chen J, Yan Z. A novel fluorescent assay for oxytetracycline hydrochloride based on fluorescence quenching of water-soluble CdTe nanocrystals. Luminescence. 2013 May-Jun;28(3):378-83. doi: 10.1002/bio.2393. Epub 2012 Jun 19. PubMed PMID: 22715152.

2: López-Jornet P, Camacho-Alonso F, Martinez-Canovas A, Sidrach-Cardona M. Topical 1% oxytetracycline hydrochloride versus placebo in oral mucosa biopsy. Dermatol Surg. 2012 Jul;38(7Pt 1):1054-8. doi: 10.1111/j.1524-4725.2012.02399.x. Epub 2012 Mar 27. PubMed PMID: 22455385.

3: Morales-Nin B, Grau A, Pérez-Mayol S, Pastor E, Palmer M. Oxytetracycline hydrochloride vital labelling revisited: the case of Dicentrarchus labrax and Diplodus puntazzo. J Fish Biol. 2011 Mar;78(3):762-82. doi: 10.1111/j.1095-8649.2010.02887.x. PubMed PMID: 21366571.

4: Berry SL, Read DH, Walker RL, Famula TR. Clinical, histologic, and bacteriologic findings in dairy cows with digital dermatitis (footwarts) one month after topical treatment with lincomycin hydrochloride or oxytetracycline hydrochloride. J Am Vet Med Assoc. 2010 Sep 1;237(5):555-60. doi: 10.2460/javma.237.5.555. PubMed PMID: 20807134.

5: Kim H, Lee BJ, Sah H. Reverse micelle-based microencapsulation of oxytetracycline hydrochloride into poly-d,l-lactide-co-glycolide microspheres. Drug Deliv. 2007 Feb;14(2):95-9. PubMed PMID: 17364873.

6: Osofsky A, Tell LA, Kass PH, Wetzlich SE, Nugent-Deal J, Craigmill AL. Investigation of Japanese quail (Coturnix japonica) as a pharmacokinetic model for cockatiels (Nymphicus hollandicus) and Poicephalus parrots via comparison of the pharmacokinetics of a single intravenous injection of oxytetracycline hydrochloride. J Vet Pharmacol Ther. 2005 Dec;28(6):505-13. PubMed PMID: 16343282.

7: Sun XX, Zhang X, Aboul-Enein HY. Construction and characterization of potentiometric sensor for the determination of oxytetracycline hydrochloride. Farmaco. 2004 Apr;59(4):307-14. PubMed PMID: 15081348.

8: Liebenberg W, de Villiers MM, Wurster DE, Swanepoel E, Dekker TG, Lötter AP. The effect of polymorphism on powder compaction and dissolution properties of chemically equivalent oxytetracycline hydrochloride powders. Drug Dev Ind Pharm. 1999 Sep;25(9):1027-33. PubMed PMID: 10518242.

9: Elsheikh HA, Osman Intisar AM, Eltayeb IB, Salam Abdullah A. Effect of dehydration on the pharmacokinetics of oxytetracycline hydrochloride administered intravenously in goats (Capra hircus). Gen Pharmacol. 1998 Sep;31(3):455-8. PubMed PMID: 9703219.

10: Izer K, Török I, Pintér-Magyar G. Stability of oxytetracycline hydrochloride in eye-drops, prepared in pharmacies. Acta Pharm Hung. 1994 Mar;64(2):63-6. PubMed PMID: 8017210.

11: Faktor JH, Frenkel Y, Mashiach S, Serr DM. Intra-amniotic injection of oxytetracycline hydrochloride for termination of mid-trimester pregnancy. Gynecol Obstet Invest. 1988;26(3):177-80. PubMed PMID: 3240887.

12: Mesiha MS, Aboutaleb AE. The prolonged release of oxytetracycline hydrochloride from ethylcellulose microcapsules. Pharmazie. 1982 Jul;37(7):493-5. PubMed PMID: 7134255.

13: Mueller-Brennecke DL, Reed SJ, Waisner DL. Turbidimetric microbiological determination of oxytetracycline hydrochloride in finished feeds and a feed premix: collaborative study. J Assoc Off Anal Chem. 1980 Sep;63(5):1038-43. PubMed PMID: 7410294.

14: Marković D, Kezele D, Kuburović D, Zivanov-Stankić D. [The action of oxytetracycline hydrochloride under in vitro conditions]. Osterr Z Stomatol. 1978 Jun;75(6):225-8. German. PubMed PMID: 283364.

15: Marković D, Zivanov-Stakić D, Radović Z, Kezele D. [Oxytetracycline and oxytetracycline hydrochloride as components of tooth dentinal calcium]. Stomatol Glas Srb. 1977 Aug-Oct;24(4):239-43. Croatian. PubMed PMID: 288214.

16: de Jong MF, Oosterwoud RA. Treatment with oxytetracycline hydrochloride in the prevention of atrophic rhinitis in baby pigs. Tijdschr Diergeneeskd. 1977 Feb 15;102(4):266-73. Dutch. PubMed PMID: 835133.

17: Markovic D, Sćepan V. [Effects of EDTA and oxytetracycline hydrochloride and their complexes with calcium on microorganisms isolated from the root canals of diseased teeth]. Stomatol Vjesn. 1977;6(3-4):17-9. Croatian. PubMed PMID: 116396.

18: Saavedra FE, Belikov VG, Soloveĭ NV. [Spectrophotometric determination of oxytetracycline hydrochloride]. Farmatsiia. 1976 Jan-Feb;25(1):78-9. Russian. PubMed PMID: 1254013.

19: Renshaw HW, Magonigle RA, Eckblad WP, Frank FW. Immunity to bovine anaplasmosis after elimination of the carrier status with oxytetracycline hydrochloride. Proc Annu Meet U S Anim Health Assoc. 1976;(80):79-88. PubMed PMID: 1078098.

20: Lal OP, Teotia TP. Influence of nine surfactants on the activity of oxytetracycline hydrochloride against Lipaphis erysimi Kalt. J Antibiot (Tokyo). 1975 Dec;28(12):993-6. PubMed PMID: 1206011.