13614-98-7 Usage
Description
Minocycline hydrochloride, also known as Minocin, Vectrin, Dynacin, or Solodyn, is a second-generation tetracycline antibiotic derived from minocycline. It is a potent antibiotic obtained by reductive methylation of 7-nitro-6-demethyl-6-deoxytetracycline and was released for use in the United States in 1971. Minocycline hydrochloride is characterized by its yellow crystalline powder form and is stable in acids, making it suitable for pharmaceutical applications. It exhibits broad-spectrum antibacterial and antiprotozoan activity by binding to the 30S and 50S ribosomal sub-units, blocking protein synthesis. Minocycline hydrochloride also displays anti-inflammatory, antiapoptotic, and neuroprotective properties.
Uses
Used in Pharmaceutical Industry:
Minocycline hydrochloride is used as an antibiotic for its broad-spectrum antibacterial and antiprotozoan activity. It is particularly effective against Gram-positive bacteria, such as staphylococci and streptococci, and has been effective against staphylococcal strains resistant to methicillin and other tetracyclines.
Minocycline hydrochloride is used as an anti-inflammatory agent for its ability to reduce inflammation and prevent neuropathic pain in various conditions, such as in a rat sciatic nerve injury model.
Used in Respiratory Infections:
Minocycline hydrochloride is used as a treatment for chronic bronchitis and other upper respiratory tract infections due to its high serum and tissue levels, despite its relatively low renal clearance.
Used in Urinary Tract Infections:
Minocycline hydrochloride is used for the treatment of urinary tract infections, as it has been effective in the eradication of N. meningitidis in asymptomatic carriers.
Used in Neurological Applications:
Minocycline hydrochloride is used as a neuroprotective agent, attenuating disease severity in mouse models of multiple sclerosis and potentially being effective in methotrexate-induced lung fibrosis.
Used in Research and Development:
Minocycline hydrochloride is used in research for its antiapoptotic properties and its ability to reduce MMP-9 activity, which may have implications for various therapeutic applications.
Therapeutic Function
Antibiotic
Biochem/physiol Actions
Minocycline is a broad spectrum antibiotic with bacteriostatic function. Minocycline has anti-inflammatory properties. Minocycline inhibits lipopolysaccharide mediated inflammatory cytokine tumour necrosis factor (TNF-α) secretion by macrophages. Minocycline inhibits macrophage proliferation in a dose dependent manner. Minocycline inhibits neuroinflammation in pre-plaque of Alzheimer′s disease-like amyloid pathology through inhibition of key inflammatory enzymes like inducible nitric oxide synthase (iNOS), matrix metalloproteinase 9 (MMP-9) and 5-lipoxygenase. Minocycline inhibits endothelial cell proliferation and angiogenesis. Minocycline exhibits anti-tumor activity in glioma by inhibiting membrane type 1 matrix metalloproteinase (MT1-MMP). Minocycline increases cognition and neuronal differentiation. zMinocycline effectively reduces neuropathic pain by increasing the functions of nociceptin/orphanin FQ.
Veterinary Drugs and Treatments
Minocycline may be useful for treating Brucellosis (in combination
with aminoglycosides), Lyme disease,
and certain nosocomial infections
where other more commonly used drugs are ineffective.
It has been investigated as adjunctive therapy for treating hemangiosarcomas,
but early results have been disappointing.
References
1) Padi and Kulkarni (2008), Minocycline prevents the development of neuropathic pain, but not acute pain: possible anti-inflammatory and antioxidant mechanisms; Eur. J. Pharmacol., 601 79
2) Dziembowska et al. (2013), High MMP-9 activity levels in fragile X syndrome are lowered by minocycline; Am. J. Med. Genet. A, 161A 1897
3) Brundula et al. (2002), Targeting leukocyte MMPs and transmigration: minocycline as a potential therapy for multiple sclerosis; Brain., 125 1297
4) Tikka et al. (2001), Minocycline, a tetracycline derivative, is neuroprotective against excitotoxicity by inhibiting activation and proliferation of microglia; J. Neurosci., 21 2580
5) Kalemci et al. (2013), The efficacy of minocycline against methotrexate-induced pulmonary fibrosis in mice; Eur. Rev. Med. Pharmacol. Sci., 17 3334
Check Digit Verification of cas no
The CAS Registry Mumber 13614-98-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,6,1 and 4 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 13614-98:
(7*1)+(6*3)+(5*6)+(4*1)+(3*4)+(2*9)+(1*8)=97
97 % 10 = 7
So 13614-98-7 is a valid CAS Registry Number.
InChI:InChI=1/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;/h5-6,9,11,17,27,29-30,33H,7-8H2,1-4H3,(H2,24,32);1H/t9-,11-,17-,23-;/m0./s1
13614-98-7Relevant articles and documents
Synthesis method of minocycline hydrochloride
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, (2021/06/21)
The invention relates to a synthesis method of minocycline hydrochloride, which comprises the following steps of: (1) reacting demeclocycline with an amination reagent in a first organic solvent in the presence of a palladium metal complex to obtain 7-amino-6-demethyltetracycline; (2) carrying out a dehydroxylation reaction on the 7-amino-6-demethyltetracycline in a second organic solvent in the presence of a first acid reagent and a first catalyst, so as to obtain 7-amino-6-demethyl-6-deoxytetracycline; and (3) in a third organic solvent, in the presence of a second acid reagent and a second catalyst, carrying out alkylation reaction on the 7-amino-6-demethyl-6-deoxytetracycline and an alkylation reagent to obtain minocycline hydrochloride. The minocycline hydrochloride prepared by the method disclosed by the invention has the advantages of simple synthesis process, high yield, high purity and easiness in large-scale production.
Synthesis method of minocycline hydrochloride
-
Paragraph 0024; 0052-0053, (2021/03/31)
The invention discloses a preparation method of minocycline hydrochloride. The preparation method is characterized by comprising the following steps: with demeclocycline hydrochloride as an initial raw material, carrying out a dehydroxylation reaction to obtain 6-deoxy-6-demeclocycline (intermediate I for short); carrying out acetyl protection on the intermediate I to obtain 3,10,12,12a-tetraacetyl-6-deoxy-6-demeclocycline (intermediate II for short); carrying out the BuchwaldHartwig reaction on the intermediate II to obtain 3,10,12,12a-tetraacetylminocycline (intermediate III for short); hydrolyzing the intermediate III to obtain minocycline free alkali (intermediate IV for short); and salifying the intermediate IV to obtain minocycline hydrochloride. According to the invention, nitrification, diazotization and azo reactions used in traditional minocycline hydrochloride synthesis processes are avoided, so dangerous factors in the production process are reduced, operation is simple, environmental pollution is avoided, and the method has industrial production prospects.
A robust platform for the synthesis of new tetracycline antibiotics
Sun, Cuixiang,Wang, Qiu,Brubaker, Jason D.,Wright, Peter M.,Lerner, Christian D.,Noson, Kevin,Charest, Mark,Siegel, Dionicio R.,Wang, Yi-Ming,Myers, Andrew G.
supporting information; experimental part, p. 17913 - 17927 (2009/07/18)
Tetracyclines and tetracycline analogues are prepared by a convergent, single-step Michael-Claisen condensation of AB precursor 1 or 2 with D-ring precursors of wide structural variability, followed by removal of protective groups (typically in two steps). A number of procedural variants of the key C-ring-forming reaction are illustrated in multiple examples. These include stepwise deprotonation of a D-ring precursor followed by addition of 1 or 2, in situ deprotonation of a D-ring precursor in mixture with 1 or 2, and in situ lithium-halogen exchange of a benzylic bromide D-ring precursor in the presence of 1 or 2, followed by warming. The AB plus D strategy for tetracycline synthesis by C-ring construction is shown to be robust across a range of different carbocyclic and heterocyclic D-ring precursors, proceeding reliably and with a high degree of stereochemical control. Evidence suggests that Michael addition of the benzylic anion derived from a given D-ring precursor to enones 1 or 2 is quite rapid at -78 °C, while Claisen cyclization of the enolate produced is rate-determining, typically occurring upon warming to 0 °C. The AB plus D coupling strategy is also shown to be useful for the construction of tetracycline precursors that are diversifiable by latter-stage transformations, subsequent to cyclization to form the C ring. Results of antibacterial assays and preliminary data obtained from a murine septicemia model show that many of the novel tetracyclines synthesized have potent antibiotic activities, both in bacterial cell culture and in vivo. The platform for tetracycline synthesis described gives access to a broad range of molecules that would be inaccessible by semisynthetic methods (presently the only means of tetracycline production) and provides a powerful engine for the discovery and, perhaps, development of new tetracycline antibiotics.