(2S)-6-[({[(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracen-2-yl]formamido}methyl)amino]-2-aminohexanoic acid

• ChemBase ID: 141
• Molecular Formular: C29H38N4O10
• Molecular Mass: 602.63282
• Monoisotopic Mass: 602.25879344
• SMILES: c1cc(c2c(c1)[C@@]([C@@H]1C(=C([C@]3([C@@H](C1)[C@@H](C(=C(C3=O)C(=O)NCNCCCC[C@H](N)C(=O)O)O)N(C)C)O)O)C2=O)(C)O)O
• Canonical SMILES: N[C@H](C(=O)O)CCCCNCNC(=O)C1=C(O)[C@@H](N(C)C)[C@H]2[C@](C1=O)(O)C(=C1[C@H](C2)[C@](C)(O)c2c(C1=O)c(O)ccc2)O
• InChI: InChI=1S/C29H38N4O10/c1-28(42)13-7-6-9-17(34)18(13)22(35)19-14(28)11-15-21(33(2)3)23(36)20(25(38)29(15,43)24(19)37)26(39)32-12-31-10-5-4-8-16(30)27(40)41/h6-7,9,14-16,21,31,34,36-37,42-43H,4-5,8,10-12,30H2,1-3H3,(H,32,39)(H,40,41)/t14-,15-,16-,21-,28+,29-/m0/s1
• InChIKey: AHEVKYYGXVEWNO-UEPZRUIBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-[({[(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracen-2-yl]formamido}methyl)amino]-2-aminohexanoic acid
• IUPAC Traditional name: limeciclina
• Brand Name: Aureomycin; Acronize; Acronize PD; Aureocarmyl; Aureociclin; Aureociclina; Aureocina; Aureocycline; Aureomicina; Aureomycin monohydrochloride; Aureomycin A-377; Aureomykoin; Aurofac; Aurofac 10; Auxeomycin; B-Aureo; Biomitsin; Biomitsin hydrochloride; Biomycin A; Biomycin hydrochloride; Biovetin; Centraureo; Chrusomykine; Chrysomykine; Clorocipan; Duomycin; Flamycin; Isphamycin; Orospray; Psittacin hydrochloride; Tetra 5; Tetralysal; Tetrlysal 300; Tocopherex; Aureomycin hydrochloride
• Synonyms: Chlorotetracycline; Chlortetracyclinium chloride; Chlortetracycline hydrochloride; Chlortetracycline; Chlortetracyclin; Chlorotetracycline hydrochloride; CLTC; 7-Chlorotetracycline; Lymecycline

Database IDs

• CAS Number: 992-21-2
• PubChem SID: 46505518; 160963604
• PubChem CID: 24757945; 54707177

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.4019689
• H Acceptors: 13
• H Donor: 9
• LogD (pH = 5.5): -8.334031
• LogD (pH = 7.4): -8.35059
• Log P: -8.298649
• Molar Refractivity: 154.5096 cm^3
• Polarizability: 59.682735 Å^3
• Polar Surface Area: 242.98 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.27
• LOG S: -2.66
• Solubility (Water): 1.31e+00 g/l

PROPERTIES

Physical Property

• Solubility: Soluble (at all physiological pH values)
• Hydrophobicity(logP): 0.3

DETAILS

DrugBank - DB00256

• Drug Groups: approved
• Description: A tetracycline with a 7-chloro substitution. [PubChem]
• Indication: For the treatment of infections and to treat acne. It may also be used to treat urinary tract infections, gum disease, and other bacterial infections such as gonorrhea and chlamydia. Lymecycline is also used commonly as a prophylactic treatment for infection by Bacillus anthracis (anthrax). It is also effective against Yersinia pestis and malaria and is also prescribed for the treatment of Lyme disease.
• Pharmacology: Lymecycline is a tetracycline broad-spectrum antibiotic. It is approximately 5000 times more soluble than tetracycline base and is unique amongst tetracyclines in that it is absorbed by the "active transport" process across the intestinal wall, making use of the same fast and efficient mechanism by which carbohydrates are absorbed. It inhibits cell growth by inhibiting translation.
• Toxicity: Adverse effects include nausea, vomiting, diarrhoea, glossitis, enterocolitis, dysphagia, dermatitis, hypersensitivity reactions, proctitis, and vaginitis.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Absorption is fast and efficient. Bioavailability is 100% following oral administration.
• References: [Link] ; Meynadier J, Alirezai M: Systemic antibiotics for acne. Dermatology. 1998;196(1):135-9. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Link
• Meynadier J, Alirezai M: Systemic antibiotics for acne. Dermatology. 1998;196(1):135-9. Pubmed