Doxycycline Hyclate | CAS#24390-14-5 | Antimicrobial Tetracycline

MedKoo Cat#: 317752 | Name: Doxycycline Hyclate

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Description:

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

Doxycycline is a synthetic tetracycline derivative with similar antimicrobial activity. Doxycycline inhibits bacterial protein synthesis by binding to the 30S ribosomal subunit. Doxycycline has bacteriostatic activity against a broad range of Gram-positive and Gramnegative bacteria. Doxycycline has been shown to be active against most isolates of the following microorganisms, both in vitro and in clinical infections.

Chemical Structure

Doxycycline Hyclate

CAS#24390-14-5 (hyclate)

Theoretical Analysis

MedKoo Cat#: 317752

Name: Doxycycline Hyclate

CAS#: 24390-14-5 (hyclate)

Chemical Formula: C46H58Cl2N4O18

Exact Mass: 0.0000

Molecular Weight: 1025.88

Elemental Analysis: C, 53.86; H, 5.70; Cl, 6.91; N, 5.46; O, 28.07

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 weeks
2g	USD 400.00	2 weeks
5g	USD 750.00	2 weeks

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Related CAS #

17086-28-1 (hydrate) 564-25-0 (free) 83038-87-3 (fosfatex) 24390-14-5 (hyclate) 10592-13-9 (HCl)

Synonym

Doxycycline Hyclate; Vivox; Doxy-Lemmon; Doxychel Hyclate; Atridox; Periostat; Oracea; Periostat; Vibra Tabs; Vibra-Tabs; Vibramycin; Vibramycin Novum; VibraTabs; Vibravenos;

IUPAC/Chemical Name

(4S,5S,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide compound with ethanol (2:1) dihydrochloride hydrate

InChi Key

HALQELOKLVRWRI-ZVACAFRPSA-N

InChi Code

InChI=1S/2C22H24N2O8.C2H6O.2ClH.H2O/c2*1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29;1-2-3;;;/h2*4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31);3H,2H2,1H3;2*1H;1H2/t2*7-,10?,14?,15-,17-,22-;;;;/m00..../s1

SMILES Code

OC1=C2C([C@@H](C3C(C2=O)=C([C@]4(C([C@H]3O)[C@@H](C(O)=C(C4=O)C(N)=O)N(C)C)O)O)C)=CC=C1.CCO.OC5=C6C([C@@H](C7C(C6=O)=C([C@]8(C([C@H]7O)[C@@H](C(O)=C(C8=O)C(N)=O)N(C)C)O)O)C)=CC=C5.Cl.O.Cl

Appearance

Solid powder

Purity

>98% (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

Product Data

Certificate of Analysis

View CoA: current batch, Lot# T22C01I26

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Doxycycline hyclate, an antibiotic, is an orally active and broad-spectrum metalloproteinase (MMP) inhibitor.

In vitro activity:

Doxycycline treatment decreased NLRP3 formation in PC3 and A549 cells compared to untreated and LPS only treated cells (p < 0.05). Doxycycline also decreased proliferation and caused cell death through apoptosis, a response that differed to the LPS-Nigericin mediated pyroptosis. Reference: Pharmaceuticals (Basel). 2021 Aug 26;14(9):852. https://pubmed.ncbi.nlm.nih.gov/34577552/

In vivo activity:

The results described above showed that doxycycline has an antiatherogenic effect associated with a decrease in gelatinolytic activity, MMP-2 expression, and ROS levels in the aortas of ApoE-⁄-/OVX animals. The results are supported by the existence of positive correlations between increased gelatinolytic activity and ROS levels (r2 = 0.72, p = 0.0004, Figure 5A), as well as by the increase in MMP-2 expression and ROS levels (r2 = 0.65, p = 0.0014, Figure 5B) in the aortas of ApoE-⁄-/OVX mice, suggesting that MMP-2 is related to the increase in ROS in these animals. Reference: Int J Mol Sci. 2022 Feb 25;23(5):2532. https://pubmed.ncbi.nlm.nih.gov/35269673/

	Solvent	mg/mL	mM
Solubility
	DMF	1.0	1.95
	DMSO	97.3	94.82
	PBS (pH 7.2)	3.0	2.92
	Water	91.0	88.73

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 1,025.88 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.

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. Chen SH, Lin YJ, Wang LC, Tsai HY, Yang CH, Teng YT, Hsu SM. Doxycycline Ameliorates the Severity of Experimental Proliferative Vitreoretinopathy in Mice. Int J Mol Sci. 2021 Oct 28;22(21):11670. doi: 10.3390/ijms222111670. PMID: 34769100; PMCID: PMC8584209. 2. Alsaadi M, Tezcan G, Garanina EE, Hamza S, McIntyre A, Rizvanov AA, Khaiboullina SF. Doxycycline Attenuates Cancer Cell Growth by Suppressing NLRP3-Mediated Inflammation. Pharmaceuticals (Basel). 2021 Aug 26;14(9):852. doi: 10.3390/ph14090852. PMID: 34577552; PMCID: PMC8466018. 3. Robinson BD, Isbell CL, Melge AR, Lomas AM, Shaji CA, Mohan CG, Huang JH, Tharakan B. Doxycycline prevents blood-brain barrier dysfunction and microvascular hyperpermeability after traumatic brain injury. Sci Rep. 2022 Mar 30;12(1):5415. doi: 10.1038/s41598-022-09394-4. PMID: 35354869; PMCID: PMC8967830. 4. Rodrigues KE, Azevedo A, Gonçalves PR, Pontes MHB, Alves GM, Oliveira RR, Amarante CB, Issa JPM, Gerlach RF, Prado AF. Doxycycline Decreases Atherosclerotic Lesions in the Aorta of ApoE-⁄- and Ovariectomized Mice with Correlation to Reduced MMP-2 Activity. Int J Mol Sci. 2022 Feb 25;23(5):2532. doi: 10.3390/ijms23052532. PMID: 35269673; PMCID: PMC8910467.

In vitro protocol:

In vivo protocol:

1. Robinson BD, Isbell CL, Melge AR, Lomas AM, Shaji CA, Mohan CG, Huang JH, Tharakan B. Doxycycline prevents blood-brain barrier dysfunction and microvascular hyperpermeability after traumatic brain injury. Sci Rep. 2022 Mar 30;12(1):5415. doi: 10.1038/s41598-022-09394-4. PMID: 35354869; PMCID: PMC8967830. 2. Rodrigues KE, Azevedo A, Gonçalves PR, Pontes MHB, Alves GM, Oliveira RR, Amarante CB, Issa JPM, Gerlach RF, Prado AF. Doxycycline Decreases Atherosclerotic Lesions in the Aorta of ApoE-⁄- and Ovariectomized Mice with Correlation to Reduced MMP-2 Activity. Int J Mol Sci. 2022 Feb 25;23(5):2532. doi: 10.3390/ijms23052532. PMID: 35269673; PMCID: PMC8910467.

1: Ghasemi K, Ghasemi K. A Brief look at antitumor effects of doxycycline in the treatment of colorectal cancer and combination therapies. Eur J Pharmacol. 2021 Dec 30:174593. doi: 10.1016/j.ejphar.2021.174593. Epub ahead of print. PMID: 34973952. 2: Ali AS, ASattar MA, Karim S, Kutbi D, Aljohani H, Bakhshwin D, Alsieni M, Alkreathy HM. Pharmacological basis for the potential role of Azithromycin and Doxycycline in management of COVID-19. Arab J Chem. 2021 Mar;14(3):102983. doi: 10.1016/j.arabjc.2020.102983. Epub 2021 Jan 10. PMID: 34909062; PMCID: PMC7797177. 3: Cárdenas Sierra RS, Zúñiga-Benítez H, Peñuela GA. Elimination of cephalexin and doxycycline under low frequency ultrasound. Ultrason Sonochem. 2021 Nov;79:105777. doi: 10.1016/j.ultsonch.2021.105777. Epub 2021 Oct 7. PMID: 34649167; PMCID: PMC8517921. 4: Bidell MR, Lodise TP. Use of oral tetracyclines in the treatment of adult outpatients with skin and skin structure infections: Focus on doxycycline, minocycline, and omadacycline. Pharmacotherapy. 2021 Nov;41(11):915-931. doi: 10.1002/phar.2625. Epub 2021 Oct 5. PMID: 34558677. 5: Patel RS, Parmar M. Doxycycline Hyclate. 2021 Aug 10. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2021 Jan–. PMID: 32310348. 6: Zhao J, Zou Y, Li K, Huang X, Niu C, Wang Z, Zhao S, Zhang Y, Song C, Xie Y. Doxycycline and minocycline in Helicobacter pylori treatment: A systematic review and meta-analysis. Helicobacter. 2021 Oct;26(5):e12839. doi: 10.1111/hel.12839. Epub 2021 Jul 28. PMID: 34318971. 7: Paghdar S, Khan TM, Patel NP, Chandrasekaran S, De Sousa JFM, Tsouklidis N. Doxycycline Therapy for Abdominal Aortic Aneurysm: Inhibitory Effect on Matrix Metalloproteinases. Cureus. 2021 May 11;13(5):e14966. doi: 10.7759/cureus.14966. PMID: 34123662; PMCID: PMC8191685. 8: Manna S, Bageac DV, Berenstein A, Sinclair CF, Kirke D, De Leacy R. Bleomycin sclerotherapy following doxycycline lavage in the treatment of ranulas: A retrospective analysis and review of the literature. Neuroradiol J. 2021 Oct;34(5):449-455. doi: 10.1177/19714009211008790. Epub 2021 Apr 8. PMID: 33832375; PMCID: PMC8559021. 9: Campetti D, Kelly A, Diaz K. Doxycycline-induced idiopathic intracranial hypertension in a patient with Lyme disease. JAAPA. 2021 Mar 1;34(3):35-37. doi: 10.1097/01.JAA.0000731504.17394.29. PMID: 33600108. 10: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Doxycycline. 2021 Jan 18. PMID: 29999621. 11: Narendrakumar L, Joseph I, Thomas S. Potential effectiveness and adverse implications of repurposing doxycycline in COVID-19 treatment. Expert Rev Anti Infect Ther. 2021 Aug;19(8):1001-1008. doi: 10.1080/14787210.2021.1865803. Epub 2020 Dec 24. PMID: 33322952. 12: Nath S, Pulikkotil SJ, Dharmarajan L, Arunachalam M, Jing KT. Effect of locally delivered doxycycline as an adjunct to scaling and root planing in the treatment of periodontitis in smokers: A systematic review of randomized controlled trials with meta-analysis and trial sequential analysis. Dent Res J (Isfahan). 2020 Aug 14;17(4):235-243. PMID: 33282148; PMCID: PMC7688043. 13: Nykytyuk S, Boyarchuk O, Klymnyuk S, Levenets S. The Jarisch-Herxheimer reaction associated with doxycycline in a patient with Lyme arthritis. Reumatologia. 2020;58(5):335-338. doi: 10.5114/reum.2020.99143. Epub 2020 Oct 3. PMID: 33227092; PMCID: PMC7667941. 14: Amores-Martín E, Melé-Ninot G, Del Alcázar Viladomiu E, Fernández-Figueras MT. Successful Treatment of White Sponge Nevus With Oral Doxycycline: A Case Report and Review of the Literature. Actas Dermosifiliogr (Engl Ed). 2021 May;112(5):463-466. English, Spanish. doi: 10.1016/j.ad.2019.10.009. Epub 2020 Nov 18. PMID: 33220312. 15: Yates PA, Newman SA, Oshry LJ, Glassman RH, Leone AM, Reichel E. Doxycycline treatment of high-risk COVID-19-positive patients with comorbid pulmonary disease. Ther Adv Respir Dis. 2020 Jan-Dec;14:1753466620951053. doi: 10.1177/1753466620951053. PMID: 32873175; PMCID: PMC7476338. 16: Hadjimichael AC, Foukas AF, Savvidou OD, Mavrogenis AF, Psyrri AK, Papagelopoulos PJ. The anti-neoplastic effect of doxycycline in osteosarcoma as a metalloproteinase (MMP) inhibitor: a systematic review. Clin Sarcoma Res. 2020 Apr 30;10:7. doi: 10.1186/s13569-020-00128-6. PMID: 32377334; PMCID: PMC7193389. 17: Lees KA, Orlandi RR, Oakley G, Alt JA. The Role of Macrolides and Doxycycline in Chronic Rhinosinusitis. Immunol Allergy Clin North Am. 2020 May;40(2):303-315. doi: 10.1016/j.iac.2019.12.005. Epub 2020 Jan 18. PMID: 32278453. 18: Clemens DL, Duryee MJ, Hall JH, Thiele GM, Mikuls TR, Klassen LW, Zimmerman MC, Anderson DR. Relevance of the antioxidant properties of methotrexate and doxycycline to their treatment of cardiovascular disease. Pharmacol Ther. 2020 Jan;205:107413. doi: 10.1016/j.pharmthera.2019.107413. Epub 2019 Oct 15. PMID: 31626869. 19: Wangrangsimakul T, Phuklia W, Newton PN, Richards AL, Day NPJ. Scrub Typhus and the Misconception of Doxycycline Resistance. Clin Infect Dis. 2020 May 23;70(11):2444-2449. doi: 10.1093/cid/ciz972. PMID: 31570937; PMCID: PMC7245148. 20: Grant JS, Stafylis C, Celum C, Grennan T, Haire B, Kaldor J, Luetkemeyer AF, Saunders JM, Molina JM, Klausner JD. Doxycycline Prophylaxis for Bacterial Sexually Transmitted Infections. Clin Infect Dis. 2020 Mar 3;70(6):1247-1253. doi: 10.1093/cid/ciz866. PMID: 31504345; PMCID: PMC7319058.