10118-90-8

10118-90-8结构式
10118-90-8结构式
  • 常用中文名:米诺环素
  • 常用英文名:Minocycline
  • CAS号:10118-90-8
  • 分子式:C23H27N3O7
  • 分子量:457.476
  • 相关类别: 原料药 抗生素类药物 四环素类药
  • 发布时间:2018-07-26 18:29:35
  • 更新时间:2024-01-02 14:12:47
  • 米诺环素是一种口服活性、强效和BBB渗透的半合成四环素抗生素。米诺环素是一种缺氧诱导因子(HIF)-1α抑制剂。米诺环素具有抗癌、抗炎和谷氨酸拮抗作用。米诺环素可减少谷氨酸神经传递,并具有神经保护和抗抑郁作用。米诺环素通过与细菌核糖体的30S亚单位结合抑制细菌蛋白质合成,从而产生抑菌作用[1][2][3][4][5][6][7]。

化源商城直购

中文名 米诺环素
英文名 minocycline
中文别名 4,7-双(二甲氨基)-1,4,4a,5,5a,6,11,12a-八氢-3,10,12,12a-四羟基-1,11-二氧-2-并四苯甲酰胺
二甲胺四环素
7-二甲胺基-6-去甲基-6-去氧四环素
英文别名 (4S,4aS,5aR,12aS)-4,7-Bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracenecarboximidic acid
Minocyclin
Minocin
7-dimethylamino-6-demethyl-6-deoxytetracycline
(4S,4aS,5aR,12aS)-4,7-Bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracenecarboxamide
4S-(4a,4aa,5aa,12aa)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacene carboxamide
Minocyclinum
[4S-(4a,4aa,5aa,12aa)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide
2-Naphthacenecarboximidic acid, 4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)-
Apo-Minocycline
(4S,4aS,5aR,12aR)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
(4S,4aS,5aR,12aS)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)-
Minocycline
Arestin
7-(N,N-dimethylamino)sancycline
Aknemin
Minocyclinum [INN-Latin]
EINECS 237-099-7
Dynacin
Minociclina
MFCD00083669
描述 米诺环素是一种口服活性、强效和BBB渗透的半合成四环素抗生素。米诺环素是一种缺氧诱导因子(HIF)-1α抑制剂。米诺环素具有抗癌、抗炎和谷氨酸拮抗作用。米诺环素可减少谷氨酸神经传递,并具有神经保护和抗抑郁作用。米诺环素通过与细菌核糖体的30S亚单位结合抑制细菌蛋白质合成,从而产生抑菌作用[1][2][3][4][5][6][7]。
相关类别
靶点

L-type calcium channel

体外研究 米诺环素(0-100μM,24-72小时)抑制卵巢癌细胞系(OVCAR-3、SKOV-3和A2780)的增殖和克隆形成活性[3]。米诺环素(0-100μM,24-48小时)通过抑制细胞周期蛋白和抑制DNA掺入来阻止细胞周期[3]。米诺环素(0-100μM,72小时)诱导卵巢癌细胞系中的细胞凋亡[3]。米诺环素显示出直接的神经元保护,这种保护模式可能与线粒体完整性和细胞色素c的保存有关,随后抑制caspase依赖性和caspase非依赖性细胞死亡[2]。米诺环素导致缺氧诱导因子(HIF)-1α的抑制,伴随着p53蛋白水平的上调和AKT/mTOR/p70S6K/4E-BP1途径的失活[6]。细胞增殖试验[3]细胞系:人卵巢癌细胞系(OVCAR-3、SKOV-3和A2780)和原代细胞(HEK-293、HMEC、HUVEC、ATCC)浓度:0、1、10、50和100μM孵育时间:24、48或
体内研究 米诺环素(0-30mg/kg,口服,每日4周)抑制雌性裸鼠OVCAR-3肿瘤生长[3]。在大剂量腹腔注射时,米诺环素(IP)是脑缺血动物模型中的有效神经保护剂[1]。米诺环素(0-40mg/kg,IP,一次)可显著减轻甲基苯丙胺诱导的小鼠过度运动和行为敏化[2]。米诺环素(3和10 mg/kg,静脉注射一次)可有效减少暂时性大脑中动脉闭塞模型(TMCAO)中的梗死面积[1]。二甲胺四环素(3-10 mg/kg,静脉注射一次)的血清水平(3 mg/kg)与标准200 mg剂量后的人体水平相似[1]。米诺环素减轻大鼠缺血诱发的室性心律失常。这种效应可能与PI3K/Akt信号通路、线粒体KATP通道和L型Ca2+通道的激活有关[7]。动物模型:雌性裸鼠(6周龄,每组9只,将OVCAR-3细胞经皮下注射至左侧腹壁
参考文献

[1]. Xu L, et al. Low dose intravenous minocycline is neuroprotective after middle cerebral artery occlusion-reperfusion in rats. BMC Neurol. 2004 Apr 26;4:7.

[2]. Zhang L, et al. Protective effects of minocycline on behavioral changes and neurotoxicity in mice after administration of methamphetamine. Prog Neuropsychopharmacol Biol Psychiatry. 2006 Dec 30;30(8):1381-93.

[3]. Pourgholami MH, et al. Minocycline inhibits growth of epithelial ovarian cancer. Gynecol Oncol. 2012 May;125(2):433-40.

[4]. Molina-Hernández M, et al. Antidepressant-like actions of minocycline combined with several glutamate antagonists. Prog Neuropsychopharmacol Biol Psychiatry. 2008 Feb 15;32(2):380-6.

[5]. Ritchie DJ, et al. A review of intravenous minocycline for treatment of multidrug-resistant Acinetobacter infections. Clin Infect Dis. 2014 Dec 1;59 Suppl 6:S374-80.

[6]. Ataie-Kachoie P, et al. Minocycline attenuates hypoxia-inducible factor-1α expression correlated with modulation of p53 and AKT/mTOR/p70S6K/4E-BP1 pathway in ovarian cancer: in vitro and in vivo studies. Am J Cancer Res. 2015 Jan 15;5(2):575-88.

[7]. Hu X, Wu B, Wang X, Xu C, He B, Cui B, Lu Z, Jiang H. Minocycline attenuates ischemia-induced ventricular arrhythmias in rats. Eur J Pharmacol. 2011 Mar 11;654(3):274-9.

密度 1.6±0.1 g/cm3
沸点 803.3±65.0 °C at 760 mmHg
分子式 C23H27N3O7
分子量 457.476
闪点 439.6±34.3 °C
精确质量 457.184906
PSA 164.63000
LogP -0.65
外观性状 亮黄色-橙色非晶形的固体
蒸汽压 0.0±3.0 mmHg at 25°C
折射率 1.718

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QI7630000
CHEMICAL NAME :
2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro -3,10,12,12a- tetrahydroxy-1,11-dioxo-
CAS REGISTRY NUMBER :
10118-90-8
LAST UPDATED :
199712
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C23-H27-N3-O7
MOLECULAR WEIGHT :
457.53
WISWESSER LINE NOTATION :
L E6 C666 BV FV CU GUTTT&J DQ EQ GMVH HQ IN1&1 ON1&1 RQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
28 mg/kg/2W-I
TOXIC EFFECTS :
Brain and Coverings - changes in circulation (hemorrhage, thrombosis, etc.) Sense Organs and Special Senses (Eye) - visual field changes Behavioral - headache
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
343 mg/kg/17W-I
TOXIC EFFECTS :
Liver - hepatitis (hepatocellular necrosis), diffuse Liver - liver function tests impaired Blood - eosinophilia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
112 mg/kg/4W-I
TOXIC EFFECTS :
Liver - liver function tests impaired Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - body temperature increase
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
100 mg/kg
TOXIC EFFECTS :
Kidney, Ureter, Bladder - interstitial nephritis Kidney, Ureter, Bladder - proteinuria Kidney, Ureter, Bladder - hematuria
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1204 mg/kg/86W-I
TOXIC EFFECTS :
Musculoskeletal - joints
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
730 mg/kg/1Y-I
TOXIC EFFECTS :
Behavioral - anorexia (human) Gastrointestinal - nausea or vomiting Liver - liver function tests impaired
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
310 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
140 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intracerebral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
38 mg/kg
TOXIC EFFECTS :
Behavioral - hallucinations, distorted perceptions Behavioral - excitement Musculoskeletal - changes in teeth and supporting structures

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Human Lymphocyte
DOSE/DURATION :
3750 ug/L
REFERENCE :
BCPHBM British Journal of Clinical Pharmacology. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1974- Volume(issue)/page/year: 16,127,1983 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3732 No. of Facilities: 13 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 7704 (estimated) No. of Female Employees: 7190 (estimated)

~%

10118-90-8结构式

10118-90-8

文献:WO2010/33939 A1, ; Page/Page column 36 ;

~66%

10118-90-8结构式

10118-90-8

文献:The Journal of organic chemistry, , vol. 67, # 14 p. 5025 - 5027
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