(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编号: 141
• 分子式: C29H38N4O10
• 平均质量: 602.63282
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: limeciclina
• 商标名: 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
• 别名: Chlorotetracycline; Chlortetracyclinium chloride; Chlortetracycline hydrochloride; Chlortetracycline; Chlortetracyclin; Chlorotetracycline hydrochloride; CLTC; 7-Chlorotetracycline; Lymecycline

登记号

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

理论计算性质

JChem

• Acid pKa: 0.4019689
• 质子受体: 13
• 质子供体: 9
• LogD (pH = 5.5): -8.334031
• LogD (pH = 7.4): -8.35059
• Log P: -8.298649
• 摩尔折射率: 154.5096 cm^3
• 极化性: 59.682735 Å^3
• 极化表面积: 242.98 Å^2
• 可自由旋转的化学键: 10
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: -0.27
• LOG S: -2.66
• 溶解度: 1.31e+00 g/l

分子性质

理化性质

• 溶解度: Soluble (at all physiological pH values)
• 疏水性(logP): 0.3

详细说明

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

参考文献

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