(4S,4aR,5S,5aR,12aS)-4-(dimethylamino)-5,10,12,12a-tetrahydroxy-6-methylidene-1,3,11-trioxo-1,2,3,4,4a,5,5a,6,11,12a-decahydrotetracene-2-carboxamide

• ChemBase ID: 807
• Molecular Formular: C22H22N2O8
• Molecular Mass: 442.41868
• Monoisotopic Mass: 442.13761567
• SMILES: O[C@@]12[C@@H]([C@@H](O)[C@H]3C(=C1O)C(=O)c1c(C3=C)cccc1O)[C@H](N(C)C)C(=O)C(C2=O)C(=O)N
• Canonical SMILES: CN([C@@H]1C(=O)C(C(=O)N)C(=O)[C@@]2([C@H]1[C@@H](O)[C@@H]1C(=C)c3cccc(c3C(=O)C1=C2O)O)O)C
• InChI: InChI=1S/C22H22N2O8/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/h4-6,10,13-15,17,25,27,29,32H,1H2,2-3H3,(H2,23,31)/t10-,13?,14-,15+,17+,22+/m1/s1
• InChIKey: IWFHNYCDKMICPE-LKTMJOCVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aR,5S,5aR,12aS)-4-(dimethylamino)-5,10,12,12a-tetrahydroxy-6-methylidene-1,3,11-trioxo-1,2,3,4,4a,5,5a,6,11,12a-decahydrotetracene-2-carboxamide
• IUPAC Traditional name: (4S,4aR,5S,5aR,12aS)-4-(dimethylamino)-5,10,12,12a-tetrahydroxy-6-methylidene-1,3,11-trioxo-4,4a,5,5a-tetrahydro-2H-tetracene-2-carboxamide
• Brand Name: Rondomycin
• Synonyms: Metacycline; Methacyclin; Methacycline

Database IDs

• CAS Number: 914-00-1
• PubChem SID: 160964270
• PubChem CID: 70789199

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.804618
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.7223067
• LogD (pH = 7.4): -4.6435947
• Log P: -2.371993
• Molar Refractivity: 111.5711 cm^3
• Polarizability: 42.74239 Å^3
• Polar Surface Area: 178.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.39
• LOG S: -2.78
• Solubility (Water): 7.32e-01 g/l

PROPERTIES

Physical Property

• Solubility: 7.55 mg/mL at 21 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Hydrophobicity(logP): -0.3

DETAILS

DrugBank - DB00931

• Drug Groups: approved
• Description: A broad-spectrum semisynthetic antibiotic related to tetracycline but excreted more slowly and maintaining effective blood levels for a more extended period. [PubChem]
• Indication: For the treatment of acute bacterial exacerbations of chronic bronchitis
• Pharmacology: Methacycline is a tetracycline antibiotic. Similar to other tetracyclines, it has a wide spectrum of antimicrobial action. It is active against most Gram-positive bacteria (pneumococci, streptococci, staphylococci) and Gram-negative bacteria (E. coli, salmonella, shigella, etc.), and towards agents causing onithosis, psittacosis, trachoma, and some Protozoa. Like other tetracyclines, the general usefulness of methacycline has been reduced with the onset of bacterial resistance.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: 58% absorbed
• Half Life: 14 hours
• Protein Binding: 75-78% protein bound
• References: Agwuh KN, MacGowan A: Pharmacokinetics and pharmacodynamics of the tetracyclines including glycylcyclines. J Antimicrob Chemother. 2006 Aug;58(2):256-65. Epub 2006 Jul 1. [Pubmed] ; Li J, Chen L, Wang X, Jin H, Ding L, Zhang K, Zhang H: Determination of tetracyclines residues in honey by on-line solid-phase extraction high-performance liquid chromatography. Talanta. 2008 Jun 15;75(5):1245-52. Epub 2008 Jan 20. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Agwuh KN, MacGowan A: Pharmacokinetics and pharmacodynamics of the tetracyclines including glycylcyclines. J Antimicrob Chemother. 2006 Aug;58(2):256-65. Epub 2006 Jul 1. Pubmed
• Li J, Chen L, Wang X, Jin H, Ding L, Zhang K, Zhang H: Determination of tetracyclines residues in honey by on-line solid-phase extraction high-performance liquid chromatography. Talanta. 2008 Jun 15;75(5):1245-52. Epub 2008 Jan 20. Pubmed