Minocycline | CAS#13614-98-7 | CAS#10118-90-8 | tetracycline antibiotic

MedKoo Cat#: 317115 | Name: Minocycline HCl

Description:

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

Minocycline (INN) is a broad-spectrum tetracycline antibiotic, and has a broader spectrum than the other members of the group. It is a bacteriostatic antibiotic, classified as a long-acting type. As a result of its long half-life it generally has serum levels 2–4 times that of the simple water-soluble tetracyclines (150 mg giving 16 times the activity levels compared with 250 mg of tetracycline at 24–48 hours). Minocycline is the most lipid-soluble of the tetracycline-class antibiotics, giving it the greatest penetration into the prostate and brain. Minocycline is not a naturally-occurring antibiotic, but was synthesized semi-synthetically from natural tetracycline antibiotics by Lederle Laboratories in 1966. (https://en.wikipedia.org/wiki/Minocycline) )

Chemical Structure

Minocycline HCl

CAS#13614-98-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 317115

Name: Minocycline HCl

CAS#: 13614-98-7 (HCl)

Chemical Formula: C23H28ClN3O7

Exact Mass: 0.0000

Molecular Weight: 493.94

Elemental Analysis: C, 55.93; H, 5.71; Cl, 7.18; N, 8.51; O, 22.67

Price and Availability

Size	Price	Availability
100mg	USD 90.00	Ready to ship
500mg	USD 150.00	Ready to ship
1g	USD 250.00	Ready to ship
2g	USD 450.00	Ready to ship
5g	USD 950.00	Ready to ship
10g	USD 1,650.00	Ready to ship
20g	USD 2,650.00	Ready to ship
50g	USD 4,650.00	Ready to ship
100g	USD 6,450.00	2 Weeks

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Related CAS #

13614-98-7 (HCl) 10118-90-8 (free base) 128420-71-3 (HCl hydrate)

Synonym

Minocycline HCl; NSC 141993; Mynocine hydrochloride; Periocline; Klinomycin; Minocin; Solodyn; Tri-mino; Vectrin; Ximino;

IUPAC/Chemical Name

(4S,4aR,5aS,12aR,E)-2-(amino(hydroxy)methylene)-4,7-bis(dimethylamino)-10,11,12a-trihydroxy-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione hydrochloride

InChi Key

KDLQIOPKJDNQIM-YKWOUSISSA-N

InChi Code

InChI=1S/C23H27N3O7.ClH/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28;/h5-6,9,11,17,27-28,32-33H,7-8,24H2,1-4H3;1H/b22-16+;/t9-,11-,17+,23-;/m1./s1

SMILES Code

O=C([C@@]1(O)[C@@](C[C@]2([H])C(C1=O)=C(O)C3=C(O)C=CC(N(C)C)=C3C2)([H])[C@@H]4N(C)C)/C(C4=O)=C(N)/O.[H]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#B7B11C07

QC Data

View QC data: current batch, Lot#B7B11C07

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Minocycline hydrochloride is a broad-spectrum tetracycline antibiotic, acting by binding to the bacterial 30S ribosomal subunit and inhibiting protein synthesis.

In vitro activity:

The activity of caspases was detected during cytometric analysis with the use of caspase-specific fluorochrome-labelled inhibitors. The obtained results, presented in Figure 10, show the increased activity of all tested caspases in melanoma cells treated with minocycline for 24 h and 48 h. The activity growth, in almost all cases, was proportional to the time of incubation as well as to the concentration of the tested drug. Slightly different relationships were observed for caspase 9. A high increase in cells with active caspase 9, ca. 50%, was noticed for 100 µM of minocycline after 48 h as well as for 200 µM of the drug, regardless of the incubation time. After one-day treatment, minocycline in a concentration of 100 µM caused the activation of all caspases in ca. 20% of melanoma cells. The analysis of caspase 8 indicates that the use of a higher concentration of the drug is associated with an almost two-fold increase in the enzyme activity for both incubation times. In turn, the most significant rise of a number of cells with active executioner caspases 3/7 (ca. 52%) was noticed after 48 h treatment with 200 µM of minocycline. Reference: Int J Mol Sci. 2020 Sep; 21(18): 6917. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7555712/

In vivo activity:

Minocycline treatment significantly alleviated myocardial cell damage, accompanied by unbroken myocardial muscle fibers, ordered myocardial cells, reduced erythrocyte leakage and leukocyte infiltration, and no granular degeneration and lipoid degeneration. Rat cardiac function was evaluated via transthoracic echocardiography (Fig. 1c), and LVEF output was significantly lower in the I/R model group than in the sham control group, while rats treated with minocycline showed increased LVEF (61.05 ± 16.32% vs 86.00 ± 2.86%; P < 0.05). Furthermore, I/R injury resulted in significantly reduced LVFS compared to the sham control group, while treatment with minocycline improved LVFS (34.60 ± 11.91% vs 54.43 ± 5.42%; P < 0.01), although not to the level observed in the sham control group. These data suggested that minocycline plays a protective role following myocardial I/R infarction. Reference: Acta Pharmacol Sin. 2019 Aug; 40(8): 1019–1028. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6786388/

	Solvent	mg/mL	mM
Solubility
	DMSO	0.5	0.99
	Water	6.5	13.16

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 493.94 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. Rok J, Rzepka Z, Beberok A, Pawlik J, Wrześniok D. Cellular and Molecular Aspects of Anti-Melanoma Effect of Minocycline-A Study of Cytotoxicity and Apoptosis on Human Melanotic Melanoma Cells. Int J Mol Sci. 2020 Sep 21;21(18):6917. doi: 10.3390/ijms21186917. PMID: 32967177; PMCID: PMC7555712. 2. Puty B, Nogueira ICDC, Nogueira LS, Vasconcelos CP, Araújo TMC, Bittencourt LO, Ferreira RO, Oliveira EHC, Leal WG, Lima RR. Genotoxic effect of non-lethal concentrations of minocycline in human glial cell culture. Biomed Pharmacother. 2020 Aug;128:110285. doi: 10.1016/j.biopha.2020.110285. Epub 2020 May 30. PMID: 32485569. 3. Liao YT, Wang SM, Chen SH. Anti-inflammatory and antiviral effects of minocycline in enterovirus 71 infections. Biomed Pharmacother. 2019 Oct;118:109271. doi: 10.1016/j.biopha.2019.109271. Epub 2019 Aug 1. PMID: 31377467. 4. Yi Q, Tan FH, Tan JA, Chen XH, Xiao Q, Liu YH, Zhang GP, Luo JD. Minocycline protects against myocardial ischemia/reperfusion injury in rats by upregulating MCPIP1 to inhibit NF-κB activation. Acta Pharmacol Sin. 2019 Aug;40(8):1019-1028. doi: 10.1038/s41401-019-0214-z. Epub 2019 Feb 21. PMID: 30792486; PMCID: PMC6786388.

In vitro protocol:

In vivo protocol:

1. Liao YT, Wang SM, Chen SH. Anti-inflammatory and antiviral effects of minocycline in enterovirus 71 infections. Biomed Pharmacother. 2019 Oct;118:109271. doi: 10.1016/j.biopha.2019.109271. Epub 2019 Aug 1. PMID: 31377467. 2. Yi Q, Tan FH, Tan JA, Chen XH, Xiao Q, Liu YH, Zhang GP, Luo JD. Minocycline protects against myocardial ischemia/reperfusion injury in rats by upregulating MCPIP1 to inhibit NF-κB activation. Acta Pharmacol Sin. 2019 Aug;40(8):1019-1028. doi: 10.1038/s41401-019-0214-z. Epub 2019 Feb 21. PMID: 30792486; PMCID: PMC6786388.

1: Doughty MJ. On the prescribing of oral doxycycline or minocycline by UK optometrists as part of management of chronic Meibomian Gland Dysfunction (MGD). Cont Lens Anterior Eye. 2015 Sep 4. pii: S1367-0484(15)30020-5. doi: 10.1016/j.clae.2015.08.002. [Epub ahead of print] Review. PubMed PMID: 26347083. 2: Dean OM, Maes M, Ashton M, Berk L, Kanchanatawan B, Sughondhabirom A, Tangwongchai S, Ng C, Dowling N, Malhi GS, Berk M. Protocol and Rationale-The Efficacy of Minocycline as an Adjunctive Treatment for Major Depressive Disorder: A Double Blind, Randomised, Placebo Controlled Trial. Clin Psychopharmacol Neurosci. 2014 Dec;12(3):180-188. Epub 2014 Dec 26. Review. PubMed PMID: 25598820; PubMed Central PMCID: PMC4293162. 3: Ritchie DJ, Garavaglia-Wilson A. A review of intravenous minocycline for treatment of multidrug-resistant Acinetobacter infections. Clin Infect Dis. 2014 Dec 1;59 Suppl 6:S374-80. doi: 10.1093/cid/ciu613. Review. PubMed PMID: 25371513. 4: Sheu J, Saavedra AP, Mostaghimi A. Rapid response of tattoo-associated cutaneous sarcoidosis to minocycline: case report and review of the literature. Dermatol Online J. 2014 Aug 17;20(8). pii: 13030/qt6dd1m2j9. Review. PubMed PMID: 25148277. 5: Oya K, Kishi T, Iwata N. Efficacy and tolerability of minocycline augmentation therapy in schizophrenia: a systematic review and meta-analysis of randomized controlled trials. Hum Psychopharmacol. 2014 Sep;29(5):483-91. Review. PubMed PMID: 25087702. 6: Zhang L, Zhao J. Profile of minocycline and its potential in the treatment of schizophrenia. Neuropsychiatr Dis Treat. 2014 Jun 17;10:1103-11. doi: 10.2147/NDT.S64236. eCollection 2014. Review. PubMed PMID: 24971013; PubMed Central PMCID: PMC4069141. 7: Hovens JE, Onderwater TA. [Minocycline for schizophrenia: a brief overview]. Tijdschr Psychiatr. 2014;56(6):402-6. Review. Dutch. PubMed PMID: 24953514. 8: Chen JS, Chan WK, Yang PC. Intrapleural minocycline pleurodesis for the treatment of primary spontaneous pneumothorax. Curr Opin Pulm Med. 2014 Jul;20(4):371-6. doi: 10.1097/MCP.0000000000000067. Review. PubMed PMID: 24852327. 9: Neonakis IK, Spandidos DA, Petinaki E. Is minocycline a solution for multidrug-resistant Acinetobacter baumannii? Future Microbiol. 2014;9(3):299-305. doi: 10.2217/fmb.13.167. Review. PubMed PMID: 24762305. 10: Nakajima T, Taniwaka K, Yoshioka T, Abe S, Kamei T, Goto H. [A case of carcinomatous cardiac tamponade caused by breast cancer treated with instillation of paclitaxel and minocycline]. Gan To Kagaku Ryoho. 2014 Jan;41(1):87-9. Review. Japanese. PubMed PMID: 24423958. 11: Nakamura J, Sugawara H, Ishii A, Tsukahara R, Demitsu T, Sanayama H, Watanabe T, Nokubi M. [Case report; a case of minocycline-induced polyarteritis nodosa with fever, arthralgia, and erythema on bilateral lower extremities]. Nihon Naika Gakkai Zasshi. 2013 Aug 10;102(8):2053-6. Review. Japanese. PubMed PMID: 24167867. 12: Cunha BA. Minocycline, often forgotten but preferred to trimethoprim-sulfamethoxazole or doxycycline for the treatment of community-acquired meticillin-resistant Staphylococcus aureus skin and soft-tissue infections. Int J Antimicrob Agents. 2013 Dec;42(6):497-9. doi: 10.1016/j.ijantimicag.2013.08.006. Epub 2013 Sep 13. Review. PubMed PMID: 24126085. 13: Li C, Yuan K, Schluesener H. Impact of minocycline on neurodegenerative diseases in rodents: a meta-analysis. Rev Neurosci. 2013;24(5):553-62. doi: 10.1515/revneuro-2013-0040. Review. PubMed PMID: 24077620. 14: Liao TV, Forehand CC, Hess DC, Fagan SC. Minocycline repurposing in critical illness: focus on stroke. Curr Top Med Chem. 2013;13(18):2283-90. Review. PubMed PMID: 24059465. 15: Parr K, Mahmoudizad R, Grimwood R. Resolution of radiation-induced acneform eruption following treatment with tretinoin and minocycline: a case report. Cutis. 2013 Jul;92(1):27-8. Review. PubMed PMID: 23961521. 16: Hashimoto K, Ishima T, Fujita Y, Zhang L. [Antibiotic drug minocycline: a potential therapeutic drug for methamphetamine-related disorders]. Nihon Arukoru Yakubutsu Igakkai Zasshi. 2013 Apr;48(2):118-25. Review. Japanese. PubMed PMID: 23808319. 17: Lenert P, Icardi M, Dahmoush L. ANA (+) ANCA (+) systemic vasculitis associated with the use of minocycline: case-based review. Clin Rheumatol. 2013 Jul;32(7):1099-106. doi: 10.1007/s10067-013-2245-z. Epub 2013 Apr 21. Review. PubMed PMID: 23604593. 18: Garrido-Mesa N, Zarzuelo A, Gálvez J. Minocycline: far beyond an antibiotic. Br J Pharmacol. 2013 May;169(2):337-52. doi: 10.1111/bph.12139. Review. PubMed PMID: 23441623; PubMed Central PMCID: PMC3651660. 19: Kerbleski GJ, Hampton TT, Cornejo A. Black bone disease of the foot: a case study and review of literature demonstrating a correlation of long-term minocycline therapy and bone hyperpigmentation. J Foot Ankle Surg. 2013 Mar-Apr;52(2):239-41. doi: 10.1053/j.jfas.2012.10.018. Epub 2013 Jan 9. Review. PubMed PMID: 23312403. 20: Zur E. Recurrent aphthous stomatitis: topical treatment with minocycline and other evidence-based agents. Int J Pharm Compd. 2012 Nov-Dec;16(6):462-9. Review. PubMed PMID: 23259361.