(2E,4S,4aS,5aR,12aS)-2-[amino(hydroxy)methylidene]-4,7-bis(dimethylamino)-10,11,12a-trihydroxy-1,2,3,4,4a,5,5a,6,12,12a-decahydrotetracene-1,3,12-trione

• ChemBase编号: 890
• 分子式: C23H27N3O7
• 平均质量: 457.47638
• 单一同位素质量: 457.18490022
• SMILES: O[C@@]12[C@@H](C[C@H]3C(=C(O)c4c(C3)c(N(C)C)ccc4O)C1=O)[C@H](N(C)C)C(=O)/C(=C(\O)/N)/C2=O
• Canonical SMILES: CN([C@@H]1C(=O)/C(=C(\O)/N)/C(=O)[C@@]2([C@H]1C[C@@H]1Cc3c(ccc(c3C(=C1C2=O)O)O)N(C)C)O)C
• InChI: InChI=1S/C23H27N3O7/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28/h5-6,9,11,17,27-28,32-33H,7-8,24H2,1-4H3/b22-16+/t9-,11-,17-,23-/m0/s1
• InChIKey: CUJCFMVUUMIFDR-XVLNIUNCSA-N

名称和登记号

名称

• IUPAC标准名: (2E,4S,4aS,5aR,12aS)-2-[amino(hydroxy)methylidene]-4,7-bis(dimethylamino)-10,11,12a-trihydroxy-1,2,3,4,4a,5,5a,6,12,12a-decahydrotetracene-1,3,12-trione
• IUPAC传统名: minocycline hcl
• 商标名: Alti-Minocycline; Apo-Minocycline; Arestin; Dynacin; Gen-Minocycline; Klinomycin; Minociclina [INN-Spanish]; Minocin; Minocyclin; Minocycline HCl; Minocyclinum [INN-Latin]; Minocyn; Minomycin; Novo-Minocycline; Vectrin; Solodyn
• 别名: minocycline; Minocycline

登记号

• CAS号: 10118-90-8
• PubChem SID: 160964353
• PubChem CID: 54675783

理论计算性质

JChem

• Acid pKa: 2.6824608
• 质子受体: 10
• 质子供体: 5
• LogD (pH = 5.5): -1.2131377
• LogD (pH = 7.4): -2.0282679
• Log P: -1.1025907
• 摩尔折射率: 131.5263 cm^3
• 极化性: 45.539722 Å^3
• 极化表面积: 164.63 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.3
• LOG S: -2.14
• 溶解度: 3.31e+00 g/l

分子性质

理化性质

• 溶解度: 52 mg/mL
• 疏水性(logP): 0.5

详细说明

DrugBank - DB01017

• Drug Groups: approved; investigational
• Description: A tetracycline analog, having a 7-dimethylamino and lacking the 5 methyl and hydroxyl groups, which is effective against tetracycline-resistant staphylococcus infections. [PubChem]
• Indication: For the treatment of infections caused by susceptible strains of microorganisms, such as Rocky Mountain spotted fever, typhus fever and the typhus group, Q fever, rickettsial pox and tick fevers caused by Rickettsiae, upper respiratory tract infections caused by Streptococcus pneumoniae and for the treatment of asymptomatic carriers of Neisseria meningitidis.
• Pharmacology: Minocycline, the most lipid soluble and most active tetracycline antibiotic, is, like doxycycline, a long-acting tetracycline. Minocycline's effects are related to the inhibition of protein synthesis. Although minocycline's broader spectrum of activity, compared to other members of the group, includes activity against Neisseria meningitidis, its use as a prophylaxis is no longer recomended because of side effects (dizziness and vertigo). Current research is examining the possible neuroprotective effects of minocycline against progression of Huntington's Disease, an inherited neurodegenerative disorder. The neuroprotective action of minocycline may include its inhibitory effect on 5-lipoxygenase, an inflammatory enzyme associated with brain aging.
• Toxicity: Minocycline has been observed to cause a dark discoloration of the thyroid in experimental animals (rats, minipigs, dogs and monkeys). In the rat, chronic treatment with minocycline has resulted in goiter accompanied by elevated radioactive iodine uptake and evidence of thyroid tumor production. Minocycline has also been found to produce thyroid hyperplasia in rats and dogs. LD₅₀=2380 mg/kg (rat, oral), LD₅₀=3600 mg/kg (mouse, oral)
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic.
• Absorption: Rapidly absorbed from the gastrointestinal tract and absorption is not significantly impaired by ingestion of food or milk. Oral bioavailability is 100%.
• Half Life: 11-22 hours
• Protein Binding: 55% to 76%
• References: [Link] ; [Link] ; Gough A, Chapman S, Wagstaff K, Emery P, Elias E: Minocycline induced autoimmune hepatitis and systemic lupus erythematosus-like syndrome. BMJ. 1996 Jan 20;312(7024):169-72. [Pubmed] ; Chen M, Ona VO, Li M, Ferrante RJ, Fink KB, Zhu S, Bian J, Guo L, Farrell LA, Hersch SM, Hobbs W, Vonsattel JP, Cha JH, Friedlander RM: Minocycline inhibits caspase-1 and caspase-3 expression and delays mortality in a transgenic mouse model of Huntington disease. Nat Med. 2000 Jul;6(7):797-801. [Pubmed] ; Tikka TM, Koistinaho JE: Minocycline provides neuroprotection against N-methyl-D-aspartate neurotoxicity by inhibiting microglia. J Immunol. 2001 Jun 15;166(12):7527-33. [Pubmed] ; Nirmalananthan N, Greensmith L: Amyotrophic lateral sclerosis: recent advances and future therapies. Curr Opin Neurol. 2005 Dec;18(6):712-9. [Pubmed] ; Song Y, Wei EQ, Zhang WP, Zhang L, Liu JR, Chen Z: Minocycline protects PC12 cells from ischemic-like injury and inhibits 5-lipoxygenase activation. Neuroreport. 2004 Oct 5;15(14):2181-4. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

参考文献

• Chen M, Ona VO, Li M, Ferrante RJ, Fink KB, Zhu S, Bian J, Guo L, Farrell LA, Hersch SM, Hobbs W, Vonsattel JP, Cha JH, Friedlander RM: Minocycline inhibits caspase-1 and caspase-3 expression and delays mortality in a transgenic mouse model of Huntington disease. Nat Med. 2000 Jul;6(7):797-801. Pubmed
• Tikka TM, Koistinaho JE: Minocycline provides neuroprotection against N-methyl-D-aspartate neurotoxicity by inhibiting microglia. J Immunol. 2001 Jun 15;166(12):7527-33. Pubmed
• Nirmalananthan N, Greensmith L: Amyotrophic lateral sclerosis: recent advances and future therapies. Curr Opin Neurol. 2005 Dec;18(6):712-9. Pubmed
• Song Y, Wei EQ, Zhang WP, Zhang L, Liu JR, Chen Z: Minocycline protects PC12 cells from ischemic-like injury and inhibits 5-lipoxygenase activation. Neuroreport. 2004 Oct 5;15(14):2181-4. Pubmed
• Gough A, Chapman S, Wagstaff K, Emery P, Elias E: Minocycline induced autoimmune hepatitis and systemic lupus erythematosus-like syndrome. BMJ. 1996 Jan 20;312(7024):169-72. Pubmed
• Link
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