ChemicalBook > CAS DataBase List > Minocycline hydrochloride

Minocycline hydrochloride

Product Name
Minocycline hydrochloride
CAS No.
13614-98-7
Chemical Name
Minocycline hydrochloride
Synonyms
MINOCYCLINE HCL;Arestin;Dynacin;minocyclinechloride;[4S-(4alpha,4aalpha,5aalpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxonaphthacene-2-carboxamide monohydrochloride;minocyn;MINOCIN;tri-mino;MYNOCINE;Minomycin
CBNumber
CB6472139
Molecular Formula
C23H28ClN3O7
Formula Weight
493.94
MOL File
13614-98-7.mol
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Minocycline hydrochloride Property

Melting point:
205-210° (dec)
Boiling point:
813℃
Flash point:
>110°(230°F)
storage temp. 
2-8°C
solubility 
Sparingly soluble in water, slightly soluble in ethanol (96 per cent). It dissolves in solutions of alkali hydroxides and carbonates.
form 
crystalline
color 
yellow
Water Solubility 
Freely soluble in water
Merck 
14,6202
Stability:
Light Sensitive
InChIKey
GLMUAFMGXXHGLU-VQAITOIOSA-N
SMILES
[C@@]12([H])C[C@@]3([H])C(C(=O)C4C(O)=CC=C(N(C)C)C=4C3)=C(O)[C@]1(O)C(=O)C(C(=O)N)=C(O)[C@H]2N(C)C.Cl |&1:0,3,21,31,r|
LogP
0.808 (est)
CAS DataBase Reference
13614-98-7(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
RIDADR 
3249
WGK Germany 
3
RTECS 
QI7630500
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29413020
Toxicity
human,TDLo,oral,14286ug/kg/10 (14.286mg/kg),LUNGS, THORAX, OR RESPIRATION: RESPIRATORY OBSTRUCTIONLUNGS, THORAX, OR RESPIRATION: DYSPNEASKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE",Archives of Internal Medicine. Vol. 154, Pg. 1633, 1994.
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H303May be harmfulif swallowed

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H335May cause respiratory irritation

H360May damage fertility or the unborn child

H362May cause harm to breast-fed children

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P263Avoid contact during pregnancy/while nursing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
1444004
Product name
Minocycline hydrochloride
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
350mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
M2288
Product name
Minocycline Hydrochloride
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$171
Updated
2024/03/01
TCI Chemical
Product number
M2288
Product name
Minocycline Hydrochloride
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$556
Updated
2024/03/01
Alfa Aesar
Product number
J66429
Product name
Minocycline hydrochloride, 890-950 μg/mg
Packaging
500mg
Price
$234
Updated
2024/03/01
Alfa Aesar
Product number
J66429
Product name
Minocycline hydrochloride, 890-950 μg/mg
Packaging
1g
Price
$359
Updated
2024/03/01
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Minocycline hydrochloride Chemical Properties,Usage,Production

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

Originator

Minocin,Lederle ,US,1971

Uses

Second generation tetracycline antibiotic. Antibacterial.

Uses

antiinflammatory

Uses

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.

Manufacturing Process

Preparation of 7-(N,N'-Dicarbobenzyloxyhydrazino)-6-Demethyltetracycline: A1.0 g portion of 6-demethyltetracycline was dissolved in a mixture of 9.6 ml oftetrahydrofuran and 10.4 ml of methanesulfonic acid at -10°C. The mixturewas allowed to warm to 0°C. A solution of 0.86 g of dibenzyl azodicarboxylatein 0.5 ml of tetrahydrofuran was added dropwise and the mixture was stirredfor 2 hours while the temperature was maintained at 0°C. The reactionmixture was added to ether. The product was filtered off, washed with etherand then dried. The 7-(N,N'-dicarbobenzyloxyhydrazino)-6-demethyltetracycline was identified by paper chromatography.
Reductive Methylation of 7-(N,N'-Dicarbobenzyloxyhydrazino)-6-Demethyl-6-Deoxytetracycline to 7-Dimethylamino-6-Demethyl-6-Deoxytetracycline: Asolution of 100 mg of 7(N,N'-dicarbobenzyloxyhydrazino)-6-demethyl-6-deoxytetracycline in 2.6 ml of methanol, 0.4 ml of 40% aqueous ormaldehyde solution and 50 mg of 5% palladium on carbon catalyst washydrogenated at room temperature and two atmospheres pressure. Uptake ofthe hydrogen was complete in 3 hours. The catalyst was filtered off and thesolution was taken to dryness under reduced pressure. The residue wastriturated with ether and then identified as 7-dimethylamino-6-demethyl-6-deoxytetracycline by comparison with an authentic sample, according to USPatent 3,483,251.

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.

Side effects

Common side effects of Minocycline hydrochloride include: nausea, vomiting, diarrhoea, dizziness, lightheadedness or spinning sensation. Individuals may experience symptoms of serious adverse reactions such as gingival hyperpigmentation, pain/difficulty swallowing, tinnitus or hearing loss, joint stiffness/pain/swelling, nephrotoxicity (elevated urea nitrogen, interstitial nephritis), hepatotoxicity (hyperbilirubinaemia, hepatic cholestasis, elevated liver enzymes, fatal hepatic failure, and jaundice), and hypersensitivity reactions. It rarely causes elevated pressure around the brain (intracranial hypertension - IH). The risk of this side effect is greater in women of childbearing age who are overweight or who have had IH in the past. Serious intestinal disorders including: non-stop diarrhoea, abdominal or stomach pain/cramps, and blood/mucus in the stool are less common.

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.

storage

+4°C

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

Minocycline hydrochloride Preparation Products And Raw materials

Raw materials

Minocycline demeclocycline hydrochloride,hemihydrate

Preparation Products

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View Lastest Price from Minocycline hydrochloride manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Minocycline hydrochloride 13614-98-7
Price
US $200.00-85.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-04-23
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Minocycline hydrochloride 13614-98-7
Price
US $0.00/g/Bag
Min. Order
100g
Purity
890-950ug/mg; USP41
Supply Ability
400kg/month
Release date
2021-06-04
Hebei Weibang Biotechnology Co., Ltd
Product
Minocycline hydrochloride 13614-98-7
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-19

13614-98-7, Minocycline hydrochlorideRelated Search:

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  • (4S,4aS,5aR,12aS)-4,7-Bis(diMethylaMino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxaMide hydrochloride
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  • 2-(Amino-hydroxy-methylidene)-4,7-bis(dimethylamino)-10,11,12a-trihydroxy-4,4a,5,5a,6,12a-hexahydrotetracene-1,3,12-trione hydrochloride
  • minocyclinechloride
  • minocyclinehydrochloridehydrate
  • minocyn
  • 2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, monohydrochloride, (4S,4aS,5aR,12aS)-
  • 2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, monohydrochloride (8CI)
  • 2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, monohydrochloride, (4S,4aS,5aR,12aS)- (9CI)
  • 2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, monohydrochloride, [4S-(4a,4aa,5aa,12aa)]-
  • Klinomycin
  • minocyline hydrochloride
  • Minomycin
  • NSC 141993
  • Periocline
  • 7-Dimethylamino-6-demethyl-6-deoxytetracyline
  • [4S-(4alpha,4aalpha,5aalpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxonaphthacene-2-carboxamide monohydrochloride
  • Coupelacin
  • Minostacin
  • Periofeel
  • [4S-(4α,4aα,5aα,12aα)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a,tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide
  • Minocycline Hydrochloride (200 mg)
  • Minocycline Hydrochloride (350 mg)
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  • tri-minocycline
  • MYNOCINE
  • MINOCYCLINE HYDROCHLORIDE
  • MINOCYCLINE HCL
  • MINOCIN
  • Minocyclinhydrochloride
  • 7-DIMETHYLAMINO-6-DEMETHYL-6-DEOXYTETRACYCLINE, HCL
  • 7-DIMETHYLAMINO-6-DEMETHYL-6-DEOXYTETRACYCLINE HYDROCHLORIDE
  • [4S-(4a,4aa,5aa,12aa)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydro-1,11-dioxo-2-naphthacenecarboxamide Hydrochloride
  • Arestin
  • Dynacin
  • Klinomyci
  • [4S-(4α,4aα,5aα,12aα)]-4,7-Bis(diMethylaMino)-1,4,4a,5,5a,6,11,12a -octahydro-3,10,12,12a-tetrahydro-1,11-dioxo-2-naphthacenecarboxaMide Hydrochloride
  • Minocycline, Minocycline Hcl
  • 10,12,12a-tetrahydroxy-1,11-dioxo--
  • KlinoMycin, Minocycline chloride
  • Minocycline Hydrochloride Pack:150G X 2
  • Minocycillin
  • 2-[amino(hydroxy)methylidene]-4,7-bis(dimethylamino)-10,11,12a-trihydroxy-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione hydrochloride
  • Minocycline, Hydrochloride - CAS 13614-98-7 - Calbiochem
  • Omadacycline intermediate
  • Minocycline hydrochloride salt
  • MinocyclineHydrochloride&gt
  • Minocycline hydrochloride CRS
  • [4S-(4α,4aα,5aα,12aα)]-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxonaphthacene-2-carboxamide monohydrochloride
  • Minocycline hydrochloride USP/EP/BP
  • Minocycline Hydrochloride DihydrateV
  • Minocycline hydrochloride / Minocycline hcl