Methacycline (BioDeep_00000006568)
Secondary id: BioDeep_00000599933
human metabolite blood metabolite Chemicals and Drugs
代谢物信息卡片
化学式: C22H22N2O8 (442.1376)
中文名称: 甲环素
谱图信息:
最多检出来源 Homo sapiens(blood) 72.73%
分子结构信息
SMILES: C=C1c2cccc(c2C(=O)C2=C([C@]3([C@H]([C@@H](C(=C(C3=O)C(=O)N)O)N(C)C)[C@H]([C@H]12)O)O)O)O
InChI: 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/h4-6,10,14-15,17,25-27,30,32H,1H2,2-3H3,(H2,23,31)/t10-,14-,15+,17+,22+/m1/s1
描述信息
Methacycline is only found in individuals that have used or taken this drug. It is a broad-spectrum semisynthetic antibiotic related to tetracycline but excreted more slowly and maintaining effective blood levels for a more extended period. [PubChem]Methacycline, a tetracycline antibiotic, is a protein synthesis inhibitors, inhibiting the binding of aminoacyl-tRNA to the mRNA-ribosome complex. Methacycline inhibits cell growth by inhibiting translation. It binds to the 16S part of the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. The binding is reversible in nature. Tetracyclines also have been found to inhibit matrix metalloproteinases. This mechanism does not add to their antibiotic effects, but has led to extensive research on chemically modified tetracyclines or CMTs (like incyclinide) for the treatmet of rosacea, acne, and various types of neoplasms.
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01A - Tetracyclines > J01AA - Tetracyclines
C784 - Protein Synthesis Inhibitor > C1595 - Tetracycline Antibiotic
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents
C254 - Anti-Infective Agent > C258 - Antibiotic
同义名列表
数据库引用编号
17 个数据库交叉引用编号
- ChEBI: CHEBI:6805
- KEGG: C07654
- KEGGdrug: D04972
- PubChem: 54675785
- HMDB: HMDB0015066
- Metlin: METLIN66704
- DrugBank: DB00931
- ChEMBL: CHEMBL249837
- Wikipedia: Metacycline
- MeSH: Methacycline
- chemspider: 26329510
- CAS: 914-00-1
- PMhub: MS000019630
- PubChem: 9856
- NIKKAJI: J7.166H
- RefMet: Methacycline
- KNApSAcK: 6805
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
文献列表
- Chengyu Dong, Ningning Lu, Ying Liu. Binding of methacycline to human serum albumin at subdomain IIA using multispectroscopic and molecular modeling methods.
Luminescence : the journal of biological and chemical luminescence.
2013 Nov; 28(6):933-41. doi:
10.1002/bio.2462
. [PMID: 23233363] - Na Zhang, Jin-Kai Liu, Chong-Qiu Jiang. Lysozyme-enhanced europium(III)-metacycline luminescence and its application to the determination of metacycline.
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.
2005 May; 21(5):541-4. doi:
10.2116/analsci.21.541
. [PMID: 15913144] - M C Mahedero, D Bohoyo, F Salinas, T Ardila, D Airado, B Roldán. Improvements in europium sensitized fluorimetric determination of demeclocycline and methacycline.
Journal of pharmaceutical and biomedical analysis.
2005 Apr; 37(5):1101-4. doi:
10.1016/j.jpba.2004.10.040
. [PMID: 15862691] - A Takadate, M Irikura, Y Ohkubo, S Goya, M Otagiri, K Uekama. Interaction between methacycline and human serum albumin.
Chemical & pharmaceutical bulletin.
1984 May; 32(5):1898-903. doi:
10.1248/cpb.32.1898
. [PMID: 6467471] - J Brodie. Antibiotics and the Aberdeen typhoid outbreak in 1964.
The Journal of hygiene.
1976 Apr; 76(2):191-203. doi:
10.1017/s0022172400055091
. [PMID: 1063214] - S Hirsch, J Januszko. [Acute non-inflammatory renal failure following therapeutic doses of rondomycin].
Wiadomosci lekarskie (Warsaw, Poland : 1960).
1976 Mar; 29(5):429-31. doi:
. [PMID: 1258481]
- E Mascitelli-Coriandoli, E Cavalieri, V Clini, A Jerano, E Zannini. [Toxicity of antibiotics in animals under suboptimal conditions. III. Toxicity in animals with experimental thyrotoxicosis].
Bollettino chimico farmaceutico.
1975 Oct; 114(10):582-9. doi:
"
. [PMID: 1220716] - Z Sajewicz. [Acute renal failure caused by an allergic-toxic reaction to rondomycin].
Polski tygodnik lekarski (Warsaw, Poland : 1960).
1975 Apr; 30(15):639-40. doi:
NULL
. [PMID: 1135018] - I L Kahán, H Hammer. The parenteral application of a new metacycline preparation, tri-metacycline.
Arzneimittel-Forschung.
1975 Feb; 25(2):234-7. doi:
NULL
. [PMID: 804312] - I L Kahán, H Hammer. In vitro and in vivo study of the biological effects of tri-tetracyclines (new tetracycline complexes).
Chemotherapy.
1974; 20(3):148-55. doi:
10.1159/000221804
. [PMID: 4852380] - P A Mårdh, S Colleen. Lysozyme in seminal fluid of healthy males and patients with prostatitis and in tissues of the male uro-genital tract.
Scandinavian journal of urology and nephrology.
1974; 8(3):179-83. doi:
10.3109/00365597409132126
. [PMID: 4610730] - V P Iakovlev. [A comparative study of the circulation of oxytetracycline and its derivatives--methacycline and doxycycline--in the bodies of animals].
Antibiotiki.
1973 Nov; 18(11):1041-6. doi:
NULL
. [PMID: 4799125] - J R Perez, J Y Gillenwater. Clinical evaluation of testing immediate antibiotic disk sensitivities in bacteriuria.
The Journal of urology.
1973 Oct; 110(4):452-6. doi:
10.1016/s0022-5347(17)60248-9
. [PMID: 4582474] - H Macdonald, R G Kelly, E S Allen, J F Noble, L A Kanegis. Pharmacokinetic studies on minocycline in man.
Clinical pharmacology and therapeutics.
1973 Sep; 14(5):852-61. doi:
10.1002/cpt1973145852
. [PMID: 4199710] - H Gnarpe. Treatment of experimental L-phase infections of the urinary tract.
Journal of medical microbiology.
1973 Feb; 6(1):53-7. doi:
10.1099/00222615-6-1-53
. [PMID: 4570480] - S T Madsen. Trimethoprim + sulphamethoxazole in urinary tract infections. A double blind trial.
Scandinavian journal of urology and nephrology.
1973; 7(2):184-6. doi:
10.3109/00365597309133700
. [PMID: 4586340] - A Michalopoulos. A clinical and laboratory study of doxycycline ('Vibramycin'): a broad-spectrum antibiotic.
Current medical research and opinion.
1973; 1(8):445-55. doi:
10.1185/03007997309111706
. [PMID: 4589631] - P G Popov, K I Vaptzarova, G P Kossekova, T K Nikolov. Fluorometric study of tetracycline--bovine serum albumin interaction. The tetracyclines--a new class of fluorescent probes.
Biochemical pharmacology.
1972 Sep; 21(17):2363-72. doi:
10.1016/0006-2952(72)90388-7
. [PMID: 4630490] - J J Timmes, N J Demos, S Chong. Lung tissue and serum levels of methacycline.
Clinical pharmacology and therapeutics.
1971 Nov; 12(6):920-2. doi:
10.1002/cpt1971126920
. [PMID: 5002640] - B Bernard, E J Yin, H J Simon. Clinical pharmacologic studies with minocycline.
The Journal of clinical pharmacology and new drugs.
1971 Sep; 11(5):332-48. doi:
NULL
. [PMID: 4998431] - T Lipska-Rodziewicz, T Radomański. [Fluorescence of urinary sediment following administration of rondomycin in women with genital neoplasms].
Wiadomosci lekarskie (Warsaw, Poland : 1960).
1971 Jun; 24(12):1159-62. doi:
NULL
. [PMID: 5561271] - J Fabre, E Milek, P Kalfopoulos, G Mérier. [Tetracycline kinetics in man. Digestive absorption and serum concentration].
Schweizerische medizinische Wochenschrift.
1971 May; 101(17):593-8. doi:
NULL
. [PMID: 4995974] - V P Iăkovlev, A V Kosolapova. [Binding of some tetracyclines and polysynthetic penicillins by blood serum proteins].
Antibiotiki.
1971; 16(4):354-9. doi:
NULL
. [PMID: 4998599] - I S Iarmolinskiĭ, T A Vasina, T I Navolotskaia, V A Goriaĭnov, L V Butylina. [Use of some compounds of the tetracycline series in patients with chronic renal insufficiency].
Antibiotiki.
1970 Dec; 15(12):1125-8. doi:
NULL
. [PMID: 4925643] - G V Skurkovich, T A Vasina, L I Tolkacheva, V I Kilachitskaia. [Dynamics of the distribution of rifocin in patients with chronic tonsillitis at different methods of administration].
Antibiotiki.
1970 Dec; 15(12):1117-20. doi:
NULL
. [PMID: 4925642] - E M Ory. The tetracyclines.
The Medical clinics of North America.
1970 Sep; 54(5):1173-86. doi:
10.1016/s0025-7125(16)32585-8
. [PMID: 4248510] - D N Holvey, R L Iles, J C LaPiana. Serum concentrations and recovery in urine of four tetracycline analogues.
Current therapeutic research, clinical and experimental.
1970 Aug; 12(8):536-44. doi:
NULL
. [PMID: 4988843] - H G Genster, P O Madsen. Urinary tract infections following transurethral prostatectomy: with special reference to the use of antimicrobials.
The Journal of urology.
1970 Jul; 104(1):163-8. doi:
10.1016/s0022-5347(17)61692-6
. [PMID: 4193409] - T Nurakawa, M Nishida. [Binding of penicillins with serum protein. 3. Relationship between protein-binding of penicillins and other antibiotics and gel affinity].
The Japanese journal of antibiotics.
1970 Jun; 23(3):223-7. doi:
NULL
. [PMID: 5312208] - H Gnarpe. Experimental spheroplast infections in the urinary tract treated with metacycline.
Acta pathologica et microbiologica Scandinavica. Section B: Microbiology and immunology.
1970; 78(2):271-2. doi:
NULL
. [PMID: 5275096] - J T Doluisio, L W Dittert. Influence of repetitive dosing of tetracyclines on biologic half-life in serum.
Clinical pharmacology and therapeutics.
1969 Sep; 10(5):690-701. doi:
10.1002/cpt1969105690
. [PMID: 4980112] - M S von Wittenau. The oral absorption of doxycycline by man.
Internationale Zeitschrift fur klinische Pharmakologie, Therapie, und Toxikologie. International journal of clinical pharmacology, therapy, and toxicology.
1969 Jan; 2(1):52-5. doi:
NULL
. [PMID: 4979040] - NULL. Targets for tetracyclines.
Food and cosmetics toxicology.
1968 Dec; 6(6):788-90. doi:
NULL
. [PMID: 4979854] - F L Laurencet, J P Fabre. [Effect of renal insufficiency on the action of doxycycline].
Journal d'urologie et de nephrologie.
1968 Dec; 74(12):1038-47. doi:
NULL
. [PMID: 4886359] - R Schilliro. [Methylenecycline in urology (rondomycin)].
Journal d'urologie et de nephrologie.
1968 Jun; 74(6):498-501. doi:
NULL
. [PMID: 4971213] - N H Steigbigel, C W Reed, M Finland. Absorption and excretion of five tetracycline analogues in normal young men.
The American journal of the medical sciences.
1968 May; 255(?):296-312. doi:
10.1097/00000441-196805000-00005
. [PMID: 4967837] - S Morita, M Takano, A Tarumizu, Y Goto, Y Tsutsumi. [Laboratory and clinical studies on methacycline (Rondomycin Pfizer)].
The Journal of antibiotics. Ser. B.
1967 Oct; 20(5):335-7. doi:
NULL
. [PMID: 4967138] - R Fujii, M Konno, S Uno, K Okada. [Clinical evaluation of methacycline (Rondomycin 'Pfizer') in pediatrics].
The Journal of antibiotics. Ser. B.
1967 Aug; 20(4):262-5. doi:
NULL
. [PMID: 5299959] - J Fabre, J de Freudenreich, A Duckert, J S Pitton, M Rudhardt, C Virieux. Influence of renal insufficiency on the excretion of chloroquine, phenobarbital, phenothiazines and methacycline.
Helvetica medica acta.
1967 Jan; 33(4):307-16. doi:
. [PMID: 6062922]
- J Sternberg. Effect of tetracyclines on the turnover of calcium-45 in young rats.
The International journal of applied radiation and isotopes.
1966 Sep; 17(9):497-512. doi:
10.1016/0020-708x(66)90111-6
. [PMID: 5971204] - A V Bo, D Poggiolini. [Serum and tissue levels of two antibiotics in operated patients].
Antibiotica.
1966 Sep; 4(3):210-7. doi:
NULL
. [PMID: 5300214] - L J Bononi, G Pagnini, C Scioli, E Genazzani. [Reactive groups of serum albumin responsible for the binding of 6-methylene-5-hydroxytetracycline].
Antibiotica.
1966 Jun; 4(2):105-13. doi:
NULL
. [PMID: 5965434] - J Fabre, M Rudhardt, A Duckert, J de Freudenreich, J S Pitton. [Influence of renal insufficiency on the excretion of diverse drugs (chloroquine, sedatives, methacycline)].
Helvetica medica acta. Supplementum.
1966 May; 46(?):132-3. doi:
. [PMID: 5286254]
- M Schach von Wittenau, C S Delahunt. The distribution of tetracyclines in tissues of dogs after repeated oral administration.
The Journal of pharmacology and experimental therapeutics.
1966 Apr; 152(1):164-9. doi:
NULL
. [PMID: 4957064] - J S Pitton, P Roch. Serum levels of methacycline.
Chemotherapy.
1966; 11(6):331-7. doi:
10.1159/000220469
. [PMID: 5969683] - V Jadevaia, D Poggiolini, M G Reale. [Determination of serum and tissue levels following the administration of the association: 6-methylene-5-hydroxytetracycline-oleandomycin].
Antibiotica.
1965 Dec; 3(4):299-308. doi:
. [PMID: 5870802]
- A SCRIABINE, M SCHACHVONWITTENAU, M YU, J FURMAN. COMPARATIVE RENAL CLEARANCE STUDIES WITH OXYTETRACYCLINE, DEMETHYLCHLORTETRACYCLINE AND METHACYCLINE IN THE DOG.
Chemotherapia.
1964 ; 20(?):85-94. doi:
10.1159/000220299
. [PMID: 14164296] - C M KUNIN. Comparative serum binding, distribution and excretion of tetracycline and a new analogue, methacycline.
Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.).
1962 Jun; 110(?):311-5. doi:
10.3181/00379727-110-27501
. [PMID: 14460572] - J S REMINGTON, M FINLAND. Antibacterial activity of serum after oral doses of tetracycline, demethylchlortetracycline, and 6-methyleneoxytetracycline.
Clinical pharmacology and therapeutics.
1962 May; 3(?):284-304. doi:
10.1002/cpt196233284
. [PMID: 14491396]