914-00-1 (甲烯土霉素,Methacycline)

CAS号:
914-00-1
中文名称:
甲烯土霉素
英文名称:
Methacycline
分子式:
C22H22N2O8
分子量:
442.418686389923
简介:
美他环素又称为“甲烯土霉素”,化学名称为6-亚甲基-4-(二甲氨基)-3,5,10,12.12α-五羟基-1,11-二氧代-1,4,4α,5,5α,6,11,12α-八氢-并四苯甲酰胺,密度为1.66g/cm3,沸点为695.1ºC at 760mmHg,其药品是一种四环素类抗生素。美他环素能与tRNA结合,从而达到抑菌的效果,但长期应用可引起二重感染及肝脏损害。

甲烯土霉素(914-00-1)名称与标识符

名称

中文别名:
甲烯土霉素;美他环素;多西环素EP杂质B;
英文别名:
metacycline;methacycline;6-methylene-oxytetracyclin;6-methyleneoxytetracycline;Adriamicina;bialatan;Cyclobiotic;Germicilclin;Globociclina;gs-2876;methacyclineamphoteric;rondomycin;tri-methacycline;6-deoxy-6-demethyl-6-methylene-5-oxytetracycline;6-methylene-5-hydroxytetracycline;Doxycycline EP impurity B;(4S,4aR,5S,5aR,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide (ACI);2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo- (8CI);2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, [4S-(4α,4aα,5α,5aα,12aα)]- (ZCI);4-Dimethylamino-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide;6-Demethyl-6-deoxy-5-hydroxy-6-methylenetetracycline;6-Deoxy-6-methylene-6-demethyl-5-hydroxytetracycline;GS 2876;MeSH ID: D008690;Oxytetracycline, 6-methylene-;NS00011900;Spectrum_000381;AB00514707;DOXYCYCLINE HYCLATE IMPURITY B [EP IMPURITY];Metacyclinum;SPBio_001416;Prestwick2_000964;CHEMBL249837;Metaciclina [INN-Spanish];KSC-12-231A;XIYOPDCBBDCGOE-IWVLMIASSA-N;(4S,4aR,5S,5aR,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylidene-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide;6-Methylene-5-oxytetracycline;KBio2_000861;D04972;(4S,4aR,5S,5aR,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;Spectrum2_001398;METHACYCLINE [MI];2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, (4S,4aR,5S,5aR,12aS)-;METACYCLINE [WHO-DD];Metacycline [INN];CHEBI:6805;Methacycline [USAN:BAN];AB00053593-03;Q2365033;Methylenecycline;SCHEMBL19555132;DivK1c_000591;NINDS_000591;2-NAPHTHACENECARBOXAMIDE, 4-(DIMETHYLAMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,5,10,12,12A-PENTAHYDROXY-6-METHYLENE-1,11-DIOXO-, (4S-(4.ALPHA.,4A.ALPHA.,5.ALPHA.,5A.ALPHA.,12A.ALPHA.))-;Methacycline base;Metacycline (INN);NCGC00179358-10;NCGC00179358-03;DTXSID2023272;HSDB 3118;BDBM50103629;KUC106428N;BCP24961;SBI-0051637.P002;KBio1_000591;Methacycline (USAN);4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide;DB00931;DOXYCYCLINE IMPURITY B;KBio3_001894;2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, (4S-(4alpha,4aalpha,5alpha,5aalpha,12aalpha))-;BPBio1_001065;Methacyclinum;METHACYCLINE [VANDF];AB00053593_05;SCHEMBL4015;SCHEMBL4014;(4S,4aR,5S,5aR,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide;METHACYCLINE [MART.];AC-13213;UNII-IR235I7C5P;KBio2_005997;(4S,4aR,5S,5aR,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;Prestwick0_000964;KBioSS_000861;KBio2_003429;METHACYCLINE [USAN];BDBM50565697;DOXYCYCLINE MONOHYDRATE IMPURITY B [EP IMPURITY];EN300-7481364;Spectrum5_001576;IR235I7C5P;NCGC00179358-05;Metacyclinum [INN-Latin];SPBio_002888;AB00053593_04;IDI1_000591;NCGC00179358-01;KBioGR_001511;BSPBio_000967;EINECS 213-017-5;AKOS015961140;Methacycline amphoteric;NCGC00179358-06;Prestwick1_000964;MOTC;C07654;Spectrum3_000917;Spectrum4_001016;G76918;Prestwick3_000964;Metaciclina;METHACYCLINE [HSDB];914-00-1;

标识符

InChIKey:
MHIGBKBJSQVXNH-IWVLMIASSA-N
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/h4-6,10,14-15,17,25,27-29,32H,1H2,2-3H3,(H2,23,31)/t10-,14-,15+,17+,22+/m1/s1
SMILES:
O[C@]12C(O)=C3C(C4C(O)=CC=CC=4C([C@H]3[C@H](O)[C@H]1[C@@H](C(=C(C2=O)C(=O)N)O)N(C)C)=C)=O

甲烯土霉素(914-00-1)物化性质

实验特性

  • LogP : 0.26240
  • PSA : 181.62000
  • 折射率 : 1.6500 (estimate)
  • 沸点 : 553.06°C (rough estimate)
  • 闪点 : 374.2°C
  • 密度 : 1.4033 (rough estimate)

计算特性

  • 精确分子量 : 442.13800
  • 氢键供体数量 : 6
  • 氢键受体数量 : 9
  • 可旋转化学键数量 : 2
  • 同位素质量 : 442.138
  • 重原子数量 : 32
  • 复杂度 : 998
  • 同位素原子数量 : 0
  • 确定原子立构中心数量 : 5
  • 不确定原子立构中心数量 : 0
  • 确定化学键立构中心数量 : 0
  • 不确定化学键立构中心数量 : 0
  • 共价键单元数量 : 1
  • 疏水参数计算参考值(XlogP) : 0.3
  • 拓扑分子极性表面积 : 182A^2

甲烯土霉素(914-00-1)生产方法和用途

用途:
用作抗生素类药

甲烯土霉素(914-00-1)参考资料

Reaxys RN:
PubChem CID: