13614-98-7 Usage
Description
Minocycline HCl (13614-98-7) displays antiapoptotic, anti-inflammatory1 activity. Prevents neuropathic pain in a rat sciatic nerve injury model.1 Reduces MMP-9 activity.2 Attenuates disease severity in mouse models of multiple sclerosis.3 Displays neuroprotective activity.4 Minocycline HCl may be effective in methotrexate-induced lung fibrosis.5?Orally active and brain penetrant.
Chemical Properties
Yellow Crystalline Powder
Uses
Different sources of media describe the Uses of 13614-98-7 differently. You can refer to the following data:
1. Second generation tetracycline antibiotic. Antibacterial.
2. antiinflammatory
3. Minocycline hydrochloride is a salt prepared from minocycline, taking advantage of the two basic dimethylamino groups which protonate and readily form a salt from hydrochloric acid solutions. The hydrochloride is the preferred formulation for pharmaceutical applications. Like all tetracyclines, minocycline shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal sub-units, blocking protein synthesis.
Brand name
Dynacin (Medicis); Minocin (Lederle); Minocin (Triax);
Solodyn (Medicis).
Therapeutic Function
Antibiotic
General Description
Minocycline, 7-dimethylamino-6-demethyl-6-deoxytetracycline(Minocin, Vectrin), the most potent tetracycline currentlyused in therapy, is obtained by reductive methylationof 7-nitro-6-demethyl-6-deoxytetracycline. It was releasedfor use in the United States in 1971. Because minocycline,like doxycycline, lacks the 6-hydroxyl group, it is stablein acids and does not dehydrate or rearrange to anhydroor lactone forms. Minocycline is well absorbed orally togive high plasma and tissue levels. It has a very long serumhalf-life, resulting from slow urinary excretion and moderateprotein binding. Doxycycline and minocycline, alongwith oxytetracycline, show the least in vitro calcium bindingof the clinically available tetracyclines. The improved distributionproperties of the 6-deoxytetracyclines have been attributedto greater lipid solubility.Perhaps the most outstanding property of minocyclineis its activity toward Gram-positive bacteria, especiallystaphylococci and streptococci. In fact, minocycline hasbeen effective against staphylococcal strains that are resistantto methicillin and all other tetracyclines, includingdoxycycline. Although it is doubtful that minocyclinewill replace bactericidal agents for the treatment of lifethreateningstaphylococcal infections, it may become auseful alternative for the treatment of less serious tissueinfections. Minocycline has been recommended for thetreatment of chronic bronchitis and other upper respiratorytract infections. Despite its relatively low renal clearance,partially compensated for by high serum and tissuelevels, it has been recommended for the treatment of urinary tract infections. It has been effective in the eradicationof N. meningitidis in asymptomatic carriers.
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
Preparation method of 7-amino-6-demethylation-6-deoxy tetracycline and minocycline hydrochloride
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Paragraph 0326-0329; 0336; 0337, (2021/04/14)
The invention relates to a preparation method of 7-amido-6-demethylation-6-deoxy tetracycline and minocycline hydrochloride, and particularly provides a preparation method of 7-amido-6-demethylation-6-deoxy tetracycline. The preparation method comprises the following steps: (1) carrying out chlorination reaction on 6- preparation method-6-deoxy tetracycline and a chlorination reagent, and obtaining a chlorination product; carrying out azo reaction on the chlorination product and an azo reagent to obtain a reaction solution containing 7-p-benzenesulfonic acid azo group-11a-chloro-6-demethylation-6-deoxy tetracycline; and (2) adding a reducing reagent into the reaction solution containing the 7-p-benzenesulfonic acid azo group-11a-chloro-6-demethylation-6-deoxy tetracycline obtained in the step (1), and carrying out a reaction to obtain the 7-amido-6-demethylation-6-deoxy tetracycline. The synthesis method of minocycline hydrochloride has the advantages of simple synthesis process, high yield, high purity, easiness in large-scale production and the like.
Synthesis method of minocycline hydrochloride
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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.
