エタンブトール
WordNet
- a complex consisting of an organic base in association with hydrogen chloride
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/05/31 21:35:08」(JST)
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Ethambutol
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| Names |
| Other names
(2S,2’S)-2,2’-(Ethane-1,2-diyldiimino)dibutan-1-ol[1]
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| Identifiers |
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CAS Number
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74-55-5 Y |
| ChEBI |
CHEBI:4877 Y |
| ChEMBL |
ChEMBL44884 Y |
| ChemSpider |
13433 Y |
| DrugBank |
DB00330 Y |
| EC Number |
200-810-26 |
| Jmol 3D model |
Interactive image |
| KEGG |
D07925 Y |
| MeSH |
Ethambutol |
| PubChem |
14052 |
| UNII |
8G167061QZ Y |
InChI
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InChI=1S/C10H24N2O2/c1-3-9(7-13)11-5-6-12-10(4-2)8-14/h9-14H,3-8H2,1-2H3/t9-,10-/m0/s1 Y
Key: AEUTYOVWOVBAKS-UWVGGRQHSA-N Y
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SMILES
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CC[C@@H](CO)NCCN[C@@H](CC)CO
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| Properties |
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Chemical formula
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C10H24N2O2 |
| Molar mass |
204.31 g·mol−1 |
| Appearance |
White crystals |
| Odor |
Odourless |
| log P |
−0.291 |
| Pharmacology |
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ATC code
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J04AK02 (WHO) |
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Pregnancy
category
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Routes of
administration
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Oral |
| Pharmacokinetics: |
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Protein binding
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20–30% |
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Metabolism
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Hepatic |
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Biological half-life
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3–4 hours |
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Excretion
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Renal |
| Related compounds |
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Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references |
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Ethambutol (commonly abbreviated EMB or simply E) is a medication primarily used to treat tuberculosis.[2] It is usually given in combination with other tuberculosis drugs, such as isoniazid, rifampicin and pyrazinamide. It may also be used to treat Mycobacterium avium complex, and Mycobacterium kansasii.[3]
It can cause problems with vision, liver problems and allergies among other side effects.[3] It is pregnancy category C in the United States due to concerns with eye issues and category A in Australia meaning that they did not find evidence of harm after being taken by many pregnant women.[3][4] It is reasonable to use during breast feeding if required.[3]
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.[5] It is sold under the trade names Myambutol and Servambutol.
Contents
- 1 Medical uses
- 2 Adverse effects
- 3 Mechanism of action
- 4 Pharmacokinetics
- 5 References
- 6 External links
Medical uses
Ethambutol is used along with other medications to treat a number of infections including: tuberculosis, Mycobacterium avium complex, and Mycobacterium kansasii.[3]
Adverse effects
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This section needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (May 2014) (Learn how and when to remove this template message) |
- Optic neuritis[6] (hence contraindicated in children below six years of age)
- Red-green color blindness[7]
- Peripheral neuropathy
- Arthralgia
- Hepatotoxicity
- Hyperuricaemia
- Vertical nystagmus
- Milk skin reaction
Mechanism of action
Ethambutol is bacteriostatic against actively growing TB bacilli. It works by obstructing the formation of cell wall. Mycolic acids attach to the 5'-hydroxyl groups of D-arabinose residues of arabinogalactan and form mycolyl-arabinogalactan-peptidoglycan complex in the cell wall. It disrupts arabinogalactan synthesis by inhibiting the enzyme arabinosyl transferase. Disruption of the arabinogalactan synthesis inhibits the formation of this complex and leads to increased permeability of the cell wall.
Pharmacokinetics
It is well absorbed from the gastrointestinal tract and well distributed in body tissues and fluids. 50% is excreted unchanged in urine.
References
- ^ "ethambutol (CHEBI:4877)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 18 August 2010. Main. Retrieved 26 April 2012.
- ^ Yendapally R, Lee RE (March 2008). "Design, synthesis, and evaluation of novel ethambutol analogues". Bioorg. Med. Chem. Lett. 18 (5): 1607–11. doi:10.1016/j.bmcl.2008.01.065. PMC 2276401. PMID 18242089.
- ^ a b c d e "Ethambutol Hydrochloride". The American Society of Health-System Pharmacists. Retrieved 24 April 2014.
- ^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Retrieved 22 April 2014.
- ^ "WHO Model List of Essential Medicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
- ^ Lim SA (April 2006). "Ethambutol-associated optic neuropathy" (PDF). Ann. Acad. Med. Singap. 35 (4): 274–8. PMID 16710500.
- ^ Tripathi, K D (August 2015). Essentials of MEDICAL PHARMACOLOGY (Seventh ed.). India: JAYPEE BROTHERS MEDICAL PUBLISHERS. p. 769. ISBN 978-93-5025-937-5.
External links
- Medline Plus drug information
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Antimycobacterials, including tuberculosis treatment and leprostatic agents (J04)
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| Nucleic acid inhibitor |
Rifamycins/
RNA polymerase inhibitor |
- Rifampicin#
- Rifabutin
- Rifapentine
- Rifalazil§
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| Antifolates/DSI |
- Dapsone#
- Acedapsone
- Aldesulfone sodium
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| ASA |
- 4-Aminosalicylic acid# (Calcium aminosalicylate
- Sodium aminosalicylate)
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| Protein synthesis inhibitor |
| Aminoglycosides |
- Amikacin#
- Capreomycin#
- Kanamycin#
- Streptomycin#
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| Oxazolidone |
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| Cell envelope antibiotic |
| Peptidoglycan layer |
- Alanine analogue: Cycloserine#
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| Arabinogalactan layer |
- Ethylenediamine/arabinosyltransferase inhibitor: Ethambutol#
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| Mycolic acid layer |
- Hydrazides/mycolic acid synth. inhibition: Isoniazid#
- Thiocarbamides: Ethionamide#
- Prothionamide
- Thiocarlide
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| Other/unknown |
- Phenazine (Clofazimine)#
- Pyrazine (Pyrazinamide#, Morinamide)
- Isoxazole (Terizidone)
- Bedaquiline
- Metronidazole (delamanid)
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| Combinations |
- Rifampicin/isoniazid/pyrazinamide
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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UpToDate Contents
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English Journal
- Nationwide survey of anti-tuberculosis drug resistance in Japan.
- Tuberculosis Research Committee (RYOKEN), Tokyo, Japan.
- The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease.Int J Tuberc Lung Dis.2015 Feb;19(2):157-62. doi: 10.5588/ijtld.13.0905.
- OBJECTIVE: To determine the prevalence of anti-tuberculosis drug resistance in Japan.DESIGN: A nationwide drug resistance survey was conducted by convenience sampling based on a voluntary hospital consortium. Mycobacterium tuberculosis isolates (n = 2292) were collected from August 2007 to July 2008
- PMID 25574913
- Clofazimine shortens the duration of the first-line treatment regimen for experimental chemotherapy of tuberculosis.
- Tyagi S1, Ammerman NC2, Li SY1, Adamson J3, Converse PJ1, Swanson RV4, Almeida DV5, Grosset JH5.
- Proceedings of the National Academy of Sciences of the United States of America.Proc Natl Acad Sci U S A.2015 Jan 5. pii: 201416951. [Epub ahead of print]
- A key drug for the treatment of leprosy, clofazimine has recently been associated with highly effective and significantly shortened regimens for the treatment of multidrug-resistant tuberculosis (TB). Consequently, we hypothesized that clofazimine may also shorten the duration of treatment for drug-
- PMID 25561537
- Classical against molecular-genetic methods for susceptibility testing of antituberculotics.
- Porvaznik I1, Mokry J, Solovic I.
- Advances in experimental medicine and biology.Adv Exp Med Biol.2015;835:15-22. doi: 10.1007/5584_2014_28.
- Tuberculosis currently belongs to rare respiratory diseases in Slovakia. However, the emergence and spread of multi-drug resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB) are major challenges for global tuberculosis control, since the treatment of resistant forms c
- PMID 25252893
Japanese Journal
- A Patient with Fulminant Influenza-Related Bacterial Pneumonia Due to Streptococcus pneumoniae Followed by Mycobacterium tuberculosis Infection
- 皮疹を契機に扁桃結核が判明した結節性結核性静脈炎の1例
- 西日本皮膚科 = The Nishinihon journal of dermatology 67(3), 239-242, 2005-06-01
- NAID 10026634366
Related Links
- Ethambutol Dosage and Administration Ethambutol hydrochloride should not be used alone, in initial treatment or in retreatment. Ethambutol hydrochloride should be administered on a once every 24-hour basis only. Absorption is not ...
- Ethambutol dihydrochloride antimycobacterial Synonym: 2,2′-(1,2-Ethanediyldiimino)bis-1-butanol dihydrochloride, Emb SDS Similar Products CAS Number 1070-11-7 Empirical Formula (Hill Notation) C 10 H 24 N 2 O 2 · 2HCl ...
★リンクテーブル★
[★]
- 英
- ethambutol EB EMB
- 化
- 塩酸エタンブトール ethambutol hydrochloride
- 商
- エサンブトール、エブトール
- 関
- 抗結核薬、結核
特徴
- 結核菌に特異的に強い抗菌力を有する
- 他の抗結核薬と交差耐性を示さない。
- 多剤併用により耐性菌の発生を防ぐことができる
構造
作用機序
薬理作用
- 1. 結核菌に対して強い抗菌力を示し、人型結核菌H37Rv株に対し、1％小川培地、Dubos液体培地では2.5～5μg／mLで発育を阻止する8～10)。
- 2. イソニアジド、ストレプトマイシン等の他の抗結核薬との間に交叉耐性はない8～10)。
- 3. 結核菌の核酸合成を阻害し、細胞分裂を抑制することが認められている8～10)。
抗菌スペクトル
動態
- エブトール１２５ｍｇ錠／エブトール２５０ｍｇ錠
1. 血中濃度
- エブトール125mg錠を経口投与(4錠、エタンブトール塩酸塩500mg)した結果、最高血中濃度(Cmax)は1.7μg／mL(血漿中)、最高血中濃度到達時間(Tmax)は2.8時間であった (健康成人男子、空腹時投与) 1)。
- また、エタンブトール塩酸塩は血漿タンパクとはほとんど結合しない (in vitro )。なお、エタンブトール塩酸塩250mg経口投与時の血球内濃度は血清内濃度に比して高値を示した (肺結核患者) 2)。
2. 分布
- エタンブトール塩酸塩0.5g経口投与後、肺組織中濃度は血清中濃度に比して同等ないしは高値を示した (肺結核患者) 3)。
- 25mg／kg経口投与後、喀痰中に高濃度のエタンブトール塩酸塩が認められた (肺結核患者) 4)。
3. 代謝・排泄
- 14C-エタンブトール塩酸塩25mg／kg経口投与後の尿中累積排泄率は、24時間後54～61％、48時間後60～67％であった。糞中には48時間後までに12～19％が排泄された。
- 尿中代謝物の大部分が未変化体で、一部は酸化物であるアルデヒド体並びに酸であった (肺結核患者) 5)。
- (注) 本剤の承認された用量は1日量0.75～1gを1～2回に分けて経口投与である。
効能又は効果
- エブトール１２５ｍｇ錠／エブトール２５０ｍｇ錠
適応菌種
適応症
注意
禁忌
- エブトール１２５ｍｇ錠／エブトール２５０ｍｇ錠
原則禁忌
- エブトール１２５ｍｇ錠／エブトール２５０ｍｇ錠
- 1. 視神経炎のある患者［視力障害が増強するおそれがある(「眼障害予防の具体的方法」の(2)の項参照)。］
- 2. 糖尿病患者、アルコール中毒患者［既に視神経障害を起こしている場合があり、症状が増悪するおそれがある。］
- 3. 乳・幼児［視力障害の早期発見が極めて困難である。］
副作用
- 視力障害は用量依存性で、投与量50mg/kg/dayの患者では15%、投与量25mg/kg/dayの患者では5%、投与量10mg/kg/dayの患者では1%にみられる。視力障害の程度は投与期間と関連がある。副作用の発見するために定期的な視力検査と色覚検査を行う。エタンブトールの使用中止により視力障害から回復する。
添付文書
- http://www.info.pmda.go.jp/go/pack/6225001F1036_1_10/6225001F1036_1_10?view=body
[★]
塩酸塩、ハイドロクロライド
[★]
エタンブトール EB EMB