bis((4S,5S,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide) ethanol hydrate dihydrochloride

• ChemBase ID: 132498
• Molecular Formular: C46H58Cl2N4O18
• Molecular Mass: 1025.87472
• Monoisotopic Mass: 1024.3123164
• SMILES: CCO.C[C@H]1c2cccc(c2C(=O)C2=C([C@]3(C([C@H](C12)O)[C@@H](C(=C(C3=O)C(=O)N)O)N(C)C)O)O)O.C[C@H]1c2cccc(c2C(=O)C2=C([C@]3(C([C@H](C12)O)[C@@H](C(=C(C3=O)C(=O)N)O)N(C)C)O)O)O.O.Cl.Cl
• Canonical SMILES: CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2(C1[C@@H](O)C1[C@@H](C)c3cccc(c3C(=O)C1=C2O)O)O)O)C.CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2(C1[C@@H](O)C1[C@@H](C)c3cccc(c3C(=O)C1=C2O)O)O)O)C.CCO.O.Cl.Cl
• InChI: InChI=1S/2C22H24N2O8.C2H6O.2ClH.H2O/c2*1-7-8-5-4-6-9(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;1-2-3;;;/h2*4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31);3H,2H2,1H3;2*1H;1H2/t2*7-,10?,14?,15-,17-,22-;;;;/m00..../s1
• InChIKey: HALQELOKLVRWRI-ZVACAFRPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis((4S,5S,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide) ethanol hydrate dihydrochloride
• IUPAC Traditional name: bis((4S,5S,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide) ethyl alcohol hydrate dihydrochloride
• Synonyms: Doxycycline hyclate; Doxycycline hydrochloride hemiethanolate hemihydrate; 多西环素盐酸盐半乙醇化物半水合物; 多西环素 单盐酸半乙醇半水合物

Database IDs

• CAS Number: 24390-14-5
• MDL Number: MFCD07357237
• Beilstein Number: 5702728
• PubChem SID: 24278399; 162226775; 24860078
• PubChem CID: 54713024

CALCULATED PROPERTIES

• Acid pKa: -2.235276
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -4.28254
• LogD (pH = 7.4): -6.187371
• Log P: -3.435637
• Molar Refractivity: 113.8919 cm^3
• Polarizability: 43.13817 Å^3
• Polar Surface Area: 181.62 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Do you have solubility information on this product that you would like to share?; H2O: soluble50 mg/mL, clear, yellow-green

Safety Information

• RTECS: QI8925000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98% (TLC); ≥98.0% (TLC)
• Grade: certified reference material; VETRANAL™, analytical standard
• Packaging: pkg of 1 g
• Suitability: suitable for 1694 per US EPA
• Impurities: ≤5% water; ≤7% ethanol
• Pharmacopeia Traceability: traceable to BP 780; traceable to PhEur D3000000; traceable to USP 1226003
• Empirical Formula (Hill Notation): C22H24N2O8 · HCl · 0.5H2O · 0.5C2H6O

DETAILS

Sigma Aldrich - D9891

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Do you have application information on this product that you would like to share?
Doxycycline hyclate is a synthetic oxytetracycline derivative. It has been used to eliminate Borrelia burgdorferi and Anaplasma phagocytophilum in rodent reservoirs and to eliminate Ixodes scapularis ticks1. It is used to inhibit matrix metalloproteinases2 and has been used to inhibit the inflammatory response of Lyme Disease3.
Biochem/physiol Actions
Derivative of oxytetracycline. A broad spectrum inhibitor used to inhibit matrix metallo-proteinases (MMP) such as type 1 collagenase in studies on would healing and tissue remodeling.
Doxycycline hyclate inhibits the inflammatory response to the Lyme Disease Spirochete Borrelia burgdorferi3. It is a broad spectrum inhibitor of matrix metalloproteinases in vivo.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 33429

Biochem/physiol Actions
Doxycycline hyclate inhibits the inflammatory response to the Lyme Disease Spirochete Borrelia burgdorferi1. It is a broad spectrum inhibitor of matrix metalloproteinases in vivo.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 44577

Application
Do you have application information on this product that you would like to share?
Biochem/physiol Actions
Doxycycline hyclate inhibits the inflammatory response to the Lyme Disease Spirochete Borrelia burgdorferi1. It is a broad spectrum inhibitor of matrix metalloproteinases in vivo.

Sigma Aldrich - PHR1145

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.
Biochem/physiol Actions
Doxycycline hyclate inhibits the inflammatory response to the Lyme Disease Spirochete Borrelia burgdorferi1. It is a broad spectrum inhibitor of matrix metalloproteinases in vivo.