(4S,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride

• ChemBase ID: 133746
• Molecular Formular: C21H22Cl2N2O8
• Molecular Mass: 501.31398
• Monoisotopic Mass: 500.07532103
• SMILES: CN(C)[C@H]1[C@@H]2C[C@@H]3[C@@H](c4c(ccc(c4C(=O)C3=C([C@@]2(C(=O)C(=C1O)C(=O)N)O)O)O)Cl)O.Cl
• Canonical SMILES: CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1C[C@H]1C(=C2O)C(=O)c2c([C@H]1O)c(Cl)ccc2O)O)O)C.Cl
• InChI: InChI=1S/C21H21ClN2O8.ClH/c1-24(2)14-7-5-6-10(16(27)12-9(25)4-3-8(22)11(12)15(6)26)18(29)21(7,32)19(30)13(17(14)28)20(23)31;/h3-4,6-7,14-15,25-26,28-29,32H,5H2,1-2H3,(H2,23,31);1H/t6-,7-,14-,15-,21-;/m0./s1
• InChIKey: GVSJQNRGSCOSNJ-KBHRXELFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride
• IUPAC Traditional name: demeclocycline hydrochloride
• Synonyms: [4S-(4α,4aα,5aα,6β,12aα)]-7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide Monohydrochloride; 6-Demethyl-7-chlorotetracycline Hydrochloride; Demetraciclina; Detravis; Ledermycin Hydrochloride; Meciclin; Demeclocycline Hydrochloride; 7-Chloro-6-demethyltetracycline hydrochloride; Demeclocycline hydrochloride

Database IDs

• CAS Number: 64-73-3
• EC Number: 200-592-2
• MDL Number: MFCD00082371
• Beilstein Number: 3849198
• PubChem SID: 24858709; 24278380; 162228023
• PubChem CID: 54686764

CALCULATED PROPERTIES

• Acid pKa: -2.5592184
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -4.3682384
• LogD (pH = 7.4): -6.1644874
• Log P: -3.2341983
• Molar Refractivity: 114.3549 cm^3
• Polarizability: 43.324028 Å^3
• Polar Surface Area: 181.62 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble20 mg/mL, clear, very deep greenish-yellow; Methanol
• Apperance: powder; Yellow Solid
• Melting Point: >225°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: QI7700000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 43
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC); ≥98.0% (TLC)
• Loss on Drying: ≤4% loss on drying
• Empirical Formula (Hill Notation): C21H21ClN2O8 · HCl

DETAILS

Sigma Aldrich - D6140

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Demeclocycline hydrochloride is a tetracycline antibiotic derived from a strain of Streptomyces aureofaciens. DMC protects neurons from glutamate induced toxicity by suppressing calpain I and II activities.

Sigma Aldrich - 30910

Application
Demeclocycline is used to study mechanisms of bacterial protein synthesis inhibition at the level of the 30S subunit and aminoacy-tRNA A-site binding.

Toronto Research Chemicals - D230725

An antibiotic related to tetracycline and produced by streptomyces aureofaciens. Because it is excreted more slowly than tetracycline, it maintains effective blood levels for longer periods of time.

REFERENCES

• Jilka, R., et al.: J. Clin. Invest., 104, 439 (1999)
• Hauge, E; Bone, 28, 556 (1999)
• Dobnig, H., et al.: J. Clin. Endocrinol. Metab., 90, 3970 (1999)