CAS 914-00-1|Methacyclin|Methacycline|(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|Rondomycin|(4S,4aR,5...

General Information

Structure

Molecular Formula

C₂₂H₂₂N₂O₈

Molecular Mass

442.41868

Exact Mass

442.13761567

Charge

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

Canonic 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

Isomeric 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

Calculated Properties

JChem

Acid pKa

1.804618

H Acceptors

H Donor

LogD (pH = 5.5)

-2.7223067

LogD (pH = 7.4)

-4.6435947

Log P

-2.371993

Molar Refractivity

111.5711

Polarizability

42.74239

Polar Surface Area

178.46

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

0.39

LOG S

-2.78

Solubility (Water)

7.32e-01 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

MethacyclinMethacyclineMetacycline

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

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

Brand Name

Rondomycin

Names and Identifiers

Registration numbers

CAS Number

914-00-1

PubChem SID

160964270

PubChem CID

70789199

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

-0.3

Solubility

7.55 mg/mL at 21 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

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General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data