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an antibiotic used to treat gonorrhea

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/11/17 12:50:16」(JST)

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Spectinomycin is an antibiotic useful for the treatment of the bacterial infection, gonorrhea.^[1]

It is marketed as the hydrochloride salt spectinomycin hydrochloride under the trade name Trobicin. It is in aminocyclitol class, closely related to the aminoglycosides, produced by the bacterium Streptomyces spectabilis. Spectinomycin is produced in nature by many organisms including cyanobacteria and various plant species. It is present in the genome or plastome of many plastids as the spc operon, which is usually 2–10 amino acids long (this has been known to vary). The difference in size may be due to the elimination of obsolete genes or the takeover of its function by nuclear genes. Spectinomycin is mainly produced by organisms as a defence mechanism against predators.

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.^[2]

Medical uses

It is given by injection to treat gonorrhea, especially in patients who are allergic to penicillins.

This antibiotic is no longer available in the United States. A resistance-conferring gene for spectinomycin can also be used as a selection marker in bacteria for molecular cloning purposes. Furthermore, Spectinomycin is used as a selection agent for transformed plant cells that contain the selectable marker gene Spcr.^[3]

Side effects

Side effects include itching, chills, stomach-ache, and red rash.

Mechanism of action

Spectinomycin binds to the 30S subunit of the bacterial ribosome and interrupts protein synthesis.

One form of resistance has emerged in the 16S ribosomal RNA in Pasteurella multocida.^[4]

Biosynthetic Mechanism of Spectinomycin

Proposed Spectinomycin Biosynthesis

Biosynthesis of spectinomycin begins similar to all aminoglycosides, with the formation of an inositol ring. The difference is the initial modification that form the inositol ring of spectinomycin. The process begins with a glucose-6-phosphate (1a), which is reduced by NADH to form a ketone at C2 (2a). This ketone is then formed into a primary amine group through PLP and glutamine transamination (3a). This process is repeated again at C4 to form a second primary amine (4a). Once these two amines are present, the glucose ring is ready to be methylated through two SAM (S-adenosyl methionine) molecules (5a). With this methylation, the glucose ring is finally ready to be converted into an inositol ring through inositol cyclase (6a). This can then be hydrolyzed to get rid of the phosphate group, making the inositol ring necessary for spectinomycin (7a).

While all this happens, an alternate pathway is occurring creating the sugar functional group from a similar starting product. In this pathway, glucose-1-phosphate is used as the starting product (1b). This is converted into a TDP glucose through TDP synthase (2b). TDP glucose then has the hydroxyl removed from C6 through a hydratase enzyme (3b), which is then reduced through NADH at C4 creating a new product (4b). With this ketone present, PLP and glutamine can come in to convert it to a primary amine (5b) which can then be removed through a deaminase (6b). This conversion to 6b is also accompanied by a double reduction at C4 and C3 through two more NADH molecules. Giving the final product necessary to form the aminoglycoside. With this, products 7a and 6b can come together, removing the TDP functional group and combining with the sugar molecule to form the aminoglycoside Spectinomycin.^[5]

History

There was a disruption in the supply in 2001.^[6]

References

^ "Spectinomycin Hydrochloride". The American Society of Health-System Pharmacists. Retrieved Apr 24, 2014.
^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014.
^ "Spectinomycin Hydrochloride" (pdf). Toku-E. 2010-10-10. Retrieved 2012-06-11.
^ Kehrenberg C, Schwarz S (June 2007). "Mutations in 16S rRNA and ribosomal protein S5 associated with high-level spectinomycin resistance in Pasteurella multocida". Antimicrob. Agents Chemother. 51 (6): 2244–6. doi:10.1128/AAC.00229-07. PMC 1891365. PMID 17371823.
^ Dewick, Paul M. (4 Feb 2009). Medicinal Natural Products: A Biosynthetic Approach, 3rd Edition. Wiley Online Library: Wiley. pp. 485–508. ISBN 9780470741689. Retrieved 29 May 2014.
^ "From the Centers for Disease Control and Prevention. Update on spectinomycin availability in the United States". JAMA 286 (11): 1308–9. September 2001. doi:10.1001/jama.286.11.1308. PMID 11575327.

UpToDate Contents

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1. 合併症のない淋菌感染の治療 treatment of uncomplicated gonococcal infections
2. アミノグリコシド aminoglycosides
3. 成人男性における尿道炎 urethritis in adult men
4. 急性子宮頚管炎 acute cervicitis
5. ペスト（Yersinia pestis感染症）の臨床症状、診断、および治療 clinical manifestations diagnosis and treatment of plague yersinia pestis infection

English Journal

Metabolomic approach to optimizing and evaluating antibiotic treatment in the axenic culture of cyanobacterium Nostoc flagelliforme.

Han PP1, Jia SR, Sun Y, Tan ZL, Zhong C, Dai YJ, Tan N, Shen SG.
World journal of microbiology & biotechnology.World J Microbiol Biotechnol.2014 Sep;30(9):2407-18. doi: 10.1007/s11274-014-1666-4. Epub 2014 May 16.
The application of antibiotic treatment with assistance of metabolomic approach in axenic isolation of cyanobacterium Nostoc flagelliforme was investigated. Seven antibiotics were tested at 1-100 mg L(-1), and order of tolerance of N. flagelliforme cells was obtained as kanamycin > ampicillin
PMID 24832956

Re-identification of Aeromonas isolates from rainbow trout and incidence of class 1 integron and β-lactamase genes.

Vega-Sánchez V1, Latif-Eugenín F2, Soriano-Vargas E1, Beaz-Hidalgo R2, Figueras MJ3, Aguilera-Arreola MG4, Castro-Escarpulli G5.
Veterinary microbiology.Vet Microbiol.2014 Aug 27;172(3-4):528-33. doi: 10.1016/j.vetmic.2014.06.012. Epub 2014 Jun 22.
Forty-eight Aeromonas isolates from rainbow trout previously identified by the 16S rDNA-RFLP technique were re-identified using 2 housekeeping genes (gyrB and rpoD). After sequencing the prevalences of the species were A. veronii (29.2%), A. bestiarum (20.8%), A. hydrophila (16.7%), A. sobria (10.4%
PMID 25008317

Antimicrobial susceptibility monitoring of respiratory tract pathogens isolated from diseased cattle and pigs across Europe: The VetPath study.

de Jong A1, Thomas V2, Simjee S3, Moyaert H4, El Garch F5, Maher K6, Morrissey I6, Butty P7, Klein U8, Marion H9, Rigaut D10, Vallé M11.
Veterinary microbiology.Vet Microbiol.2014 Aug 6;172(1-2):202-15. doi: 10.1016/j.vetmic.2014.04.008. Epub 2014 Apr 21.
VetPath is an ongoing pan-European antibiotic susceptibility monitoring programme collecting pathogens from diseased antimicrobial non-treated cattle, pigs and poultry. In the current study, 1001 isolates from cattle and pig respiratory tract infections were tested for their antimicrobial susceptibi
PMID 24837878

Japanese Journal

Biosynthetic approach for the production of new aminoglycoside derivative(BIOCHEMICAL ENGINEERING)

Nepal Keshav Kumar,Yoo Jin Cheol,Sohng Jae Kyung
Journal of bioscience and bioengineering 110(1), 109-112, 2010-07
… Here, we report a biosynthetic approach for the fusion of spectinomycin and kanamycin biosynthetic gene clusters to yield the new aminoglycoside derivative, oxykanamycinC, in a non-aminoglycoside producing heterologous host. …
NAID 110007681455

An RNA helicase, CrhR, regulates the low-temperature-inducible expression of heat-shock genes groES, groEL1 and groEL2 in Synechocystis sp. PCC 6803

Prakash Jogadhenu S. S.,Krishna Pilla Sankara,Sirisha Kodru,Kanesaki Yu,Suzuki Iwane,Shivaji Sisinthy,Murata Norio,鈴木石根
Microbiology 156(2), 442-451, 2010-02
… In the present study, we replaced the crhR gene with a spectinomycin-resistance gene cassette. …
NAID 120002808044

Related Pictures

★リンクテーブル★

リンク元	「抗菌薬」「スペクチノマイシン」
拡張検索	「spectinomycin hydrochloride」

「抗菌薬」

Spectinomycin
Systematic (IUPAC) name
	(1R,3S,5R,8R,10R,11S,12S,13R,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.03,8]tetradecan-7-one
Clinical data
Trade names	Trobicin
AHFS/Drugs.com	monograph
Pregnancy cat.	US: B;
Legal status	not available in US;
Identifiers
CAS number	1695-77-8
ATC code	J01XX04
PubChem	CID 15541
DrugBank	DB00919
ChemSpider	14785
UNII	93AKI1U6QF
KEGG	D08526
ChEBI	CHEBI:9215
ChEMBL	CHEMBL1167
Synonyms	(2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)decahydro-4H-pyrano[2,3-b][1,4]benzodioxin-4-one
Chemical data
Formula	C14H24N2O7
Mol. mass	332.35 g/mol
	SMILES O=C1[C@@]2(O[C@@H]3[C@@H](NC)[C@@H](O)[C@@H](NC)[C@H](O)[C@H]3O[C@@H]2O[C@@H](C1)C)O;
	InChI InChI=1S/C14H24N2O7/c1-5-4-6(17)14(20)13(21-5)22-12-10(19)7(15-2)9(18)8(16-3)11(12)23-14/h5,7-13,15-16,18-20H,4H2,1-3H3/t5-,7-,8+,9+,10+,11-,12-,13+,14+/m1/s1 ; Key:UNFWWIHTNXNPBV-WXKVUWSESA-N ;
(what is this?) (verify)

　　[★]

英: antibacterial drug, antibacterial
関: 抗生剤、薬理学、抗菌薬一覧、抗細菌薬

first aid step 1 2006 p.165

定義

細菌/微生物に静菌作用、殺菌作用を示す物質。結果として、人において病原性を除去する目的で使用される。
このうち、微生物によって産生される物質を抗生物質と呼ぶ

作用機序による分類

細胞壁合成阻害：βラクタム系抗菌薬(ペニシリン系抗菌薬、セフェム系抗菌薬、モノバクタム系抗菌薬、カルバペネム系抗菌薬)
核酸合成阻害　：ニューキノロン系抗菌薬、メトロニダゾール
タンパク質合成阻害

30S：アミノグリコシド系抗菌薬、テトラサイクリン系抗菌薬
50S：マクロライド系抗菌薬、クリンダマイシン、クロラムフェニコール、ストレプトグラミン系抗菌薬、オキソゾリニドン系抗菌薬(リゾネリド)

代謝拮抗：サルファ剤(サルファメソキサゾール、トリメトプリム)

first aid step 1 2006 p.165

	Mechanism of action	Drugs
1	Block cell wall synthesis by inhibition of peptidoglycan cross-linking	penicillin, ampicillin, ticarcillin, piperacillin, imipenem, aztreonam, cephalosporins
2	Block peptidoglycan synthesis	bacitracin, vancomycin, cycloserine
3	Disrupt bacterial/fungal cell membranes	polymyxins
4	Disrupt fungal cell membranes	amphotericin B, nystatin, fluconazole/azoles
5	Block nucleotide synthesis	sulfonamides, trimethoprim
6	Block DNA topoisomerases	quinolones
7	Block mRNA synthesis	rifampin
8	Block protein synthesis at 50S ribosomal subunit	chloramphenicol, erythromycin/macrolides, lincomycin, clindamycin, streptogramins (quinupristin, dalfopristin), linezolid
9	Block protein synthesis at 30S ribosomal subunit	aminoglycosides, tetracyclines, spectinomycin 　ATuSi　→　あつし

薬物動態

濃度依存性：アミノグリコシド系抗菌薬、ニューロキノロン系抗菌薬
時間依存性：βラクタム系抗菌薬

治療期間

小児

尾内一信 ; 第 39 回日本小児感染症学会教育講演 2 小児感染症の抗菌薬療法 -耐性菌時代の適正使用-

感染臓器・臨床診断	原因菌	投与期間（抗菌薬）
髄膜炎	インフルエンザ菌	7-10日
	肺炎球菌	10-14日
	髄膜炎菌	7-10日
	GBS，腸内細菌，リステリア	21日
中耳炎	＜2 歳	10日
中耳炎	2 歳≦	5-7日
咽頭炎	A 群連鎖球菌	10日(ペニシリン系薬)
咽頭炎	A 群連鎖球菌	5日(セフェム系薬)
肺炎	肺炎球菌，インフルエンザ菌	解熱後3-4日
	黄色ブドウ球菌	3-4週間
	マイコプラズマ，クラミジア	10-21日
腎臓、膀胱炎、腎盂腎炎	大腸菌，プロテウス，腸球菌	3日
腎臓、膀胱炎、腎盂腎炎	大腸菌，プロテウス，腸球菌	14日
骨髄炎	黄色ブドウ球菌	21日
骨髄炎	連鎖球菌，インフルエンザ菌	14日

主要な感染症の抗菌薬投与期間

感染レジマニュ p.27

骨	骨髄炎		4-6週
耳鼻咽喉	中耳炎		5-7日
	副鼻腔炎		5-14日
	A群溶連菌咽頭炎		10日
肺	肺炎	肺炎球菌	7-10日 or 解熱後3日間
		インフルエンザ菌	10-14日
		マイコプラズマ	14日(7-10日)
		レジオネラ	21日
	肺化膿症		28-42日
心臓	感染性心内膜炎	α連鎖球菌	2-4週
		黄色ブドウ球菌	4-6週
消化管	腸炎	赤痢菌	3日
		チフス	14日(5-7日)
		パラチフス
	腹膜炎	特発性	5日
		二次性	10-14日
胆肝膵	肝膿瘍	細菌性	4-8週
		アメーバ性	10日
尿路	膀胱炎		3日
	急性腎盂腎炎		14日(7-10日)
	急性腎盂腎炎・再発		6週
	慢性前立腺炎		1-3ヶ月
髄腔	髄膜炎	インフルエンザ菌	7-10日
		髄膜炎菌
		肺炎球菌	10-14日
		リステリア	21日
敗血症	敗血症	コアグラーゼ陰性ブドウ球菌	5-7日
		黄色ブドウ球菌	28日(14日)
		グラム陰性桿菌	14日(7-14日)
		カンジダ	血液培養陰性化後, 14日

ソース不明

シャント感染：黄色ブドウ球菌：頭蓋内デバイスの感染の場合、髄液培養陰性+10日間

妊婦に避けるべき抗菌薬

Antibiotics to avoid in pregnancy
Sulfonamides––kernicterus.
Aminoglycosides––ototoxicity.
Fluoroquinolones––cartilage damage.
Erythromycin––acute cholestatic hepatitis in mom

(and clarithromycin––embryotoxic).

Metronidazole––mutagenesis.
Tetracyclines––discolored teeth, inhibition of bone growth.
Ribavirin (antiviral)––teratogenic.
Griseofulvin (antifungal)––teratogenic.
Chloramphenicol––“gray baby.”
SAFE Moms Take Really Good Care.

使っても良い

YN.H-24

βラクタム系
エリスロマイシン、アジスロマイシン

参考

抗菌薬インターネットブック

まとまっていてよい

http://www.antibiotic-books.jp

抗菌薬一覧

「スペクチノマイシン」

　　[★]

英: spectinomycin
化: 塩酸スペクチノマイシン spectinomycin hydrochloride

特徴

構造

作用機序

30Sリボソーム

薬理作用

抗菌スペクトル

動態

適応

注意

禁忌

副作用

「spectinomycin hydrochloride」

　　[★] スペクチノマイシン

[AHFS2014-1] "Spectinomycin Hydrochloride". The American Society of Health-System Pharmacists. Retrieved Apr 24, 2014.

[2] "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014.

[3] "Spectinomycin Hydrochloride" (pdf). Toku-E. 2010-10-10. Retrieved 2012-06-11.

[pmid17371823-4] Kehrenberg C, Schwarz S (June 2007). "Mutations in 16S rRNA and ribosomal protein S5 associated with high-level spectinomycin resistance in Pasteurella multocida". Antimicrob. Agents Chemother. 51 (6): 2244–6. doi:10.1128/AAC.00229-07. PMC 1891365. PMID 17371823.

[5] Dewick, Paul M. (4 Feb 2009). Medicinal Natural Products: A Biosynthetic Approach, 3rd Edition. Wiley Online Library: Wiley. pp. 485–508. ISBN 9780470741689. Retrieved 29 May 2014.

[pmid11575327-6] "From the Centers for Disease Control and Prevention. Update on spectinomycin availability in the United States". JAMA 286 (11): 1308–9. September 2001. doi:10.1001/jama.286.11.1308. PMID 11575327.

匿名

検索

案内

spectinomycin