Methacycline HCl - ≥99% , CAS No.3963-95-9

CAS: 3963-95-9 Cat. No.: M129888 Molecular Weight: 478.88 Beilstein Registry Number: 5470951 EC Number: 223-568-3

GRADE & PURITY ≥99%

Synonyms

METHACYCLINE HYDROCHLORIDE [USP-RS] | SPECTRUM1501104 | s2527 | Methacycline HCl | 9beta-?Androsta-?4,?6-?diene-?3,?17-?dione | C08029 | NSC356465 | NSC-356465 | HMS1921D15 | METHACYCLINE HYDROCHLORIDE [USP MONOGRAPH] | Physiomycine | D00849 | DTXSID10947

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Methacycline hydrochloride is a tetracycline antibiotic and can inhibits bacterial protein synthesis. Methacycline hydrochloride is a potent epithelial-mesenchymal transition (EMT) inhibitor. Methacycline hydrochloride blocks EMT in vitro and fibrogenesis in vivo without directly affecting TGF-β1 Smad signaling. Methacycline hydrochloride is an antimicrobial and has the potential for pulmonary fibrosis

Specifications

Synonyms

METHACYCLINE HYDROCHLORIDE [USP-RS] | SPECTRUM1501104 | s2527 | Methacycline HCl | 9beta-?Androsta-?4, ?6-?diene-?3, ?17-?dione | C08029 | NSC356465 | NSC-356465 | HMS1921D15 | METHACYCLINE HYDROCHLORIDE [USP MONOGRAPH] | Physiomycine | D00849 | DTXSID10947

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Broad-spectrum antibiotic. Anti-bacterial agent. Active in vivo and in vitro .

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 504771365
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504771365
• Canonical Smiles: CN(C)C1C2C(C3C(=C)C4=C(C(=CC=C4)O)C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O.Cl
• IUPAC Name: (4S,4aR,5S,5aR,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride
• InChIKey: VXPSARQTYDZXAO-CCHMMTNSSA-N
• INCHI: 1S/C22H22N2O8.ClH/c1-7-8-5-4-6-9(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;/h4-6,10,14-15,17,25-27,30,32H,1H2,2-3H3,(H2,23,31);1H/t10-,14-,15+,17+,22+;/m1./s1
• Isomeric SMILES: CN(C)[C@H]1[C@@H]2[C@H]([C@@H]3C(=C)C4=C(C(=CC=C4)O)C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O.Cl
• Molecular Weight: 478.88
• Beilstein: 5470951
• Reaxy-Rn: 25461541
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25461541&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Tetracyclines

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Tetracyclines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Tetracyclines
• Alternative Parents: Naphthols and derivatives 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Cyclohexenones Vinylogous acids Tertiary alcohols Cyclic alcohols and derivatives Secondary alcohols Trialkylamines Polyols Enols Carboximidic acids Organopnictogen compounds Organic oxides Hydrochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Tetracycline - 1-naphthol - Naphthalene - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Cyclohexenone - Benzenoid - Cyclic alcohol - Tertiary alcohol - Vinylogous acid - Ketone - Secondary alcohol - Cyclic ketone - Tertiary aliphatic amine - Tertiary amine - Carboximidic acid - Carboximidic acid derivative - Enol - Polyol - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Amine - Alcohol - Organooxygen compound - Carbonyl group - Hydrocarbon derivative - Hydrochloride - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

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POLB Tchem DNA polymerase beta (23632 Activities)

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NR1I2 Tchem Pregnane X receptor (6667 Activities)

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PLCG1 Tchem Phospholipase C-gamma-1 (184 Activities)

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PLCB3 Tbio Phospholipase C-beta-3 (157 Activities)

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FEN1 Tchem Flap endonuclease 1 (12055 Activities)

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POLK Tbio DNA polymerase kappa (8653 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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POLH Tchem DNA polymerase eta (21678 Activities)

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KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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L3MBTL1 Tchem Lethal(3)malignant brain tumor-like protein 1 (14536 Activities)

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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

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RECQL Tbio ATP-dependent DNA helicase Q1 (5575 Activities)

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GMNN Tbio Geminin (128009 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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BAZ2B Tchem Bromodomain adjacent to zinc finger domain protein 2B (56204 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)

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RAPGEF3 Tchem Rap guanine nucleotide exchange factor 3 (15528 Activities)

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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

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RUNX1 Tbio Runt-related transcription factor 1/Core-binding factor subunit beta (7867 Activities)

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GLS Tchem Glutaminase kidney isoform, mitochondrial (16997 Activities)

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RACGAP1 Tbio Rac GTPase-activating protein 1 (2057 Activities)

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WRN Tbio Werner syndrome ATP-dependent helicase (8824 Activities)

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RAD52 Tchem DNA repair protein RAD52 homolog (856 Activities)

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KPNB1 Tbio Importin subunit beta-1/Snurportin-1 (25097 Activities)

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Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)

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Streptococcus (3973 Activities)

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Escherichia coli (133304 Activities)

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Plasmodium falciparum (966862 Activities)

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Streptococcus sp. 'group A' (3417 Activities)

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ddn Putative uncharacterized protein (49 Activities)

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TGR Thioredoxin glutathione reductase (28579 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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ska Streptokinase A (5805 Activities)

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fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

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NS3 NS3 (1121 Activities)

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Nr1i2 Nuclear receptor subfamily 1 group I member 2 (14 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO 3 mg/mL Water 5 mg/mL Ethanol <1 mg/mL
• Melt Point(°C): >190°C
• Molecular Weight: 478.900 g/mol
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 2
• Exact Mass: 478.114 Da
• Monoisotopic Mass: 478.114 Da
• Topological Polar Surface Area: 182.000 Ų
• Heavy Atom Count: 33
• Formal Charge: 0
• Complexity: 998.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

1. Wanliang Liao, Yang Xu, Dingyun Li, Yixing Ye, Yuhan Ning, Weiping Wang, Ai-jun Wang.  (2022)  Facile room temperature synthesis of a NiFe2O4-based magnetic covalent organic framework for the extraction of tetracycline residues in environmental water samples prior to HPLC.  Analytical Methods,  14  (47): (4938-4946).  [PMID:36421069] [10.1039/D2AY01226J]