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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/11/30 22:52:10」(JST)

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Cefdinir is a third-generation oral cephalosporin antibiotic sold under the brand names Cefzon and Omnicef.

As of 2008, cefdinir, as Omnicef, was the highest-selling cephalosporin antibiotic in the United States, with more than US$585 million in retail sales of its generic versions alone.^[1] Cephalosporin antibiotic structurally similar to cefixime.

It was discovered by Fujisawa Pharmaceutical Co., Ltd. (now Astellas) and introduced in 1991 under the brand name Cefzon.^[2]^[3] Warner-Lambert licensed this cephalosporin for marketing in US from Fujisawa.^[4] Abbott obtained U.S. marketing rights to Omnicef (cefdinir) in December 1998 through an agreement with Warner-Lambert Company.^[5] It was approved by FDA on Dec 4, 1997.^[6] It is available in US as Omnicef by Abbott Laboratories and in India as Cednir by Abbott, Kefnir by Glenmark, Cefdair by Xalra Pharma and Cefdiel by Ranbaxy.

Mechanism of action

Indications

Therapeutic uses of cefdinir include otitis media, soft tissue infections, and respiratory tract infections, including sinusitis, strep throat (note: no documented resistance of Group A Streptococcus to penicillin has ever been reported, and penicillin or amoxicillin is the first line treatment), community-acquired pneumonia, and acute exacerbations of bronchitis.

Susceptible organisms

Cefdinir is a bacteriocidal antibiotic. It can be used to treat infections caused by several Gram-negative and Gram-positive bacteria.

Spectrum of bacterial susceptibility and resistance

Cefdinir is a broad-spectrum antibiotic and has been used to treat infections of the respiratory tract including pneumonia, sinusitis, and bronchitis. The following represents MIC susceptibility data for a few medically significant microorganisms.^[7]

Haemophilus influenzae: 0.05 - 4 μg/ml
Streptococcus pneumoniae: 0.006 - 64 μg/ml
Streptococcus pyogenes: ≤0.004 - 2 μg/ml

Side effects

Side effects include diarrhea, vaginal infections or inflammation, nausea, headache, and abdominal pain."^[8]

Available forms

Cefdinir is administered orally. It is available as capsules and a suspension. Dosage, schedule, and duration of therapy varies according to the type of infection.

"Blood" in the stool

The pediatric version of cefdinir can bind to iron in the digestive tract; in rare cases, this causes a rust or red discoloration of the stool. Blood typically appears dark brown or black in stool, and testing may confirm which is present. If the reddish stool is accompanied by abdominal pain, weight loss, diarrhea, etc., a Clostridium difficile infection caused by the antibiotic could be signified. Special caution required for pediatric dry powder; it may take longer for proper mixing.

Synthesis

Cefdinir synthesis:^[9]^[10]^[11] Improved prepn:^[12]

Acylation of the primary amine 1 with 4-bromo-3-oxobutanoyl bromide (2) leads to the amide (3). The active methylene group in that product is then nitrosated with sodium nitrite; the initial product spontaneously tautomerizes to afford the oxime (4). The bromoketone array in that intermediate constitutes a classical starting function for construction of thiazoles. Reaction of 4 with thiourea thus leads to formation of an aminothiazole moiety. Thus there is obtained the antibiotic cefdinir (5).

References

^ "2008 Top 200 generic drugs by retail dollars" PDF (399.4 KB). Drug Topics (May 26, 2009). Retrieved on July 24, 2009.
^ "2005 News Releases - Astellas Pharma Inc.". astellas.com.
^ Cabri, Walter; Ghetti, Paolo; Pozzi, Giovanni; Alpegiani, Marco (2007). "Polymorphisms and Patent, Market, and Legal Battles: Cefdinir Case Study". Organic Process Research & Development 11: 64. doi:10.1021/op0601060.
^ "Document". elsevierbi.com.
^ "Medicis.com - Medicis Pharmaceutical Corporation". globenewswire.com.
^ "Cefdinir medical facts from Drugs.com". drugs.com.
^ "Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). October 14, 2015. Retrieved October 2015.
^ "Omnicef capsules Patient Information" (PDF). Abbott Laboratories. February 2004. Archived from the original (PDF) on 2006-11-18. Retrieved 2006-11-24.
^ T. Takaya et al., BE 897864 ; eidem, U.S. Patent 4,559,334 (1984, 1985 both to Fujisawa).
^ Inamoto, Y; Chiba, T; Kamimura, T; Takaya, T (1988). "FK 482, a new orally active cephalosporin synthesis and biological properties". The Journal of antibiotics 41 (6): 828–30. PMID 3255303.
^ Kamachi, H; Narita, Y; Okita, T; Abe, Y; Iimura, S; Tomatsu, K; Yamasaki, T; Okumura, J; Naito, T; Oki, T (1988). "Synthesis and biological activity of a new cephalosporin, BMY-28232 and its prodrug-type esters for oral use". The Journal of antibiotics 41 (11): 1602–16. PMID 3198494.
^ González, M; Rodríguez, Z; Tolón, B; Rodríguez, J. C.; Velez, H; Valdés, B; López, M. A.; Fini, A (2003). "An alternative procedure for preparation of cefdinir". Il Farmaco 58 (6): 409–18. doi:10.1016/S0014-827X(03)00063-6. PMID 12767379.

External links

Medline Plus: Cefdinir

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 小児における急性中耳炎：治療 acute otitis media in children treatment
2. 1ヶ月以上の乳児および若齢幼児における尿路感染症：急性期マネージメント、画像検査、および予後 urinary tract infections in infants older than one month and young children acute management imaging and prognosis
3. 急性膀胱炎：2歳以上の小児および思春期におけるマネージメントおよび予後 acute cystitis management and prognosis in children older than two years and adolescents
4. 小児における市中肺炎：外来治療 community acquired pneumonia in children outpatient treatment
5. セフェム系 cephalosporins

English Journal

Evaluating Cost Awareness Education in US Pediatric Emergency Medicine Fellowships.

Lee JA, Chernick L, Sawaya R, Roskind CG, Pusic M.SourceFrom the *Pediatric Emergency Medicine, SUNY Downstate Medical Center, Brooklyn; and †Pediatric Emergency Medicine, Columbia University Medical Center, New York, NY.
Pediatric emergency care.Pediatr Emerg Care.2012 Jul;28(7):655-75.
OBJECTIVES: The Accreditation Council for Graduate Medical Education mandates pediatric emergency medicine (PEM) fellowships to incorporate medical care cost teaching into the curriculum; however, there are no studies evaluating cost awareness of PEM fellows. Our objectives were to evaluate cost edu
PMID 22743747

Cyclooxygenase inhibitor improved an exudative lesion of choroidal neovascularization in age-related macular degeneration.

Suzuki M, Suzuki T, Nagano A, Hirasawa M, Sakuyama K, Mizuki N.SourceDepartment of Ophthalmology and Visual Sciences, Yokohama City University Graduate School of Medicine, Yokohama, Kanagawa, Japan.
European journal of ophthalmology.Eur J Ophthalmol.2012 May-Jun;22(3):495-8. doi: 10.5301/ejo.5000032.
PURPOSE: To report a case in which a nonselective cyclooxygenase (COX) inhibitor improved an exudative lesion in age-related macular degeneration.METHODS/RESULTS: A 64-year-old man had a complaint of metamorphopsia in the left eye. Visual acuity was 0.5 in the left eye. Fluorescein angiography and i
PMID 21928264

Japanese Journal

局所麻酔薬による遅延型アレルギーの一例

大野忠男,谷山貴一,隅田佐知,芝規良,澁谷徹
松本歯学 39(1), 12-15, 2013-06-30
… 2%lidocaine for surface anesthesia, 2% lidocaine with adrenaline, acetaminophen and cefdinir were safely used. …
NAID 120005316686

複雑性尿路感染症の既往のある小児に対するセフジニルの予防内服についての検討

大石智洋,UENO Kazuyuki,FUKUMOTO Kyoko,MATSUI Kou,TSUKANO Shinya,TAGUCHI Tetsuo,UCHIYAMA Makoto
Pediatrics international : official journal of the Japan Pediatric Society 53(1), 57-61, 2011-02-01
NAID 10029557120

急性単純性膀胱炎に対するセフジニルの臨床的検討

小田眞平,沢田雄一郎,柳原豊 [他],佐々木豊和,菊川忠彦,西田智保,島本憲司,青木克徳,丹司望,横山雅好,池田哲大,池田稔,越智達正,稲田浩二,黒光浩一
西日本泌尿器科 72(11), 658-663, 2010-11-20
NAID 10027731078

Related Pictures

Cefdinir: Uses, Side Effects, Dosage and Reviews – Drug Details Cefdinir Oral : Uses, Side Effects, Interactions, Pictures, Warnings & Dosing - WebMD Pillbox - National Library of Medicine Cefdinir side effects in adults : Tetracycline hydrochloride for humans Cefdinir 300 mg capsules side effects / Tradaxin cetirizina para que sirve Antibiotic, Antifungal - AntiParasitic : Cefdinir 300 Cefdinir Suspension - patient information, description, dosage and directions.

★リンクテーブル★

リンク元	「セファロスポリン系抗菌薬」「第三世代セフェム」「セフジニル」

「セファロスポリン系抗菌薬」

Cefdinir
Systematic (IUPAC) name
	8-[2-(2-amino-1,3-thiazol-4-yl)-1-hydroxy-2-nitroso-; ethenyl]amino-4-ethenyl-7-oxo-2-thia-6-; azabicyclo[4.2.0]oct-4-ene-5-carboxylic acid
Clinical data
Trade names	Cefzon
AHFS/Drugs.com	monograph
MedlinePlus	a698001
Pregnancy; category	US: B (No risk in non-human studies); ;
Legal status	US: ℞-only;
Routes of; administration	Oral
Pharmacokinetic data
Bioavailability	16% to 21% (dose-dependent)
Protein binding	60% to 70%
Metabolism	Negligible
Biological half-life	1.7 ± 0.6 hours
Excretion	Renal
Identifiers
CAS Number	91832-40-5
ATC code	J01DD15
PubChem	CID: 6915944
DrugBank	DB00535
ChemSpider	5291705
UNII	CI0FAO63WC
KEGG	D00917
ChEBI	CHEBI:3485
ChEMBL	CHEMBL927
Chemical data
Formula	C14H13N5O5S2
Molecular mass	395.416 g/mol
	SMILES O=C2N1/C(=C(/C=C)CS[C@@H]1[C@@H]2NC(=O)C(=N\O)/c3nc(sc3)N)C(=O)O ;
	InChI InChI=1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1 ; Key:RTXOFQZKPXMALH-GHXIOONMSA-N ;
(what is this?) (verify)

　　[★]

英: cephalosporin antibiotics, cephalosporin, cephalosporins
同: セフェム系抗菌薬？、セフェム系抗生物質？ cephem antibiotic？ cephem antibiotics
関: 抗菌薬、βラクタム系抗菌薬、第三世代抗生物質

特徴

抗菌スペクトルが広い

グラム陽性菌、グラム陰性菌

酸に対して安定である
ペニシリナーゼに対して安定である

構造

副作用

過敏症(ペニシリン系抗菌薬と同様であるが、頻度はペニシリン系に比べ低い)
(1)ジスルフィラム様作用、(2)ビタミンK依存性の凝固因子の産生低下(cefotetanとcefoperazoneに特徴的。共通点はN-methylthiotetrazole(NMTT) side chainを持つこと)。(PPC.612)

セフェム系抗菌薬

第三世代セフェム

セフォタキシム	cefotaxime
セフトリアキソン	ceftriaxone
セフジニル	cefdinir
セフジトレンピボキシル	cefditoren pivoxil
セフチブテン	ceftibuten
セフポドキシムプロキセチル	cefpodoxime proxetil
セフチゾキシム	ceftizoxime
セフォペラゾン	cefoperazone
セフタジジム	ceftazidime

「第三世代セフェム」

　　[★]

同: 第3世代セフェム、第三世代抗生物質 antibiotics of third generation、第三世代セフェム系抗生物質 cephem antibiotics of third generation、第3世代セファロスポリン
関: セファロスポリン系抗菌薬

特徴

第３世代セフェム以上は口腔内嫌気性細菌をカバーできる　・・・　わざわざABPC/SBTを選択しなくて良い。

第三世代セフェム

セフォタキシム	cefotaxime
セフトリアキソン	ceftriaxone
セフジニル	cefdinir
セフジトレンピボキシル	cefditoren pivoxil
セフチブテン	ceftibuten
セフポドキシムプロキセチル	cefpodoxime proxetil
セフチゾキシム	ceftizoxime
セフォペラゾン	cefoperazone
セフタジジム	ceftazidime

「セフジニル」

　　[★]

英: cefdinir
商: セフゾン, Omnicef、セフニール

第3世代セフェム系抗菌薬
経口抗菌薬
7位に2-アミノチアゾリルヒドロキシイミノ基を有する構造

内服後約4時間で最高血中濃度に達し、半減期約1.7時間で主として尿中に排泄される。

各種β-ラクタマーゼに安定
特にグラム陽性菌に対する抗菌力を増したことで、グラム陰性菌・陽性菌にバランスのとれた抗菌力を示す。

[1] "2008 Top 200 generic drugs by retail dollars" PDF (399.4 KB). Drug Topics (May 26, 2009). Retrieved on July 24, 2009.

[2] "2005 News Releases - Astellas Pharma Inc.". astellas.com.

[3] Cabri, Walter; Ghetti, Paolo; Pozzi, Giovanni; Alpegiani, Marco (2007). "Polymorphisms and Patent, Market, and Legal Battles: Cefdinir Case Study". Organic Process Research & Development 11: 64. doi:10.1021/op0601060.

[4] "Document". elsevierbi.com.

[5] "Medicis.com - Medicis Pharmaceutical Corporation". globenewswire.com.

[6] "Cefdinir medical facts from Drugs.com". drugs.com.

[7] "Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). October 14, 2015. Retrieved October 2015.

[8] "Omnicef capsules Patient Information" (PDF). Abbott Laboratories. February 2004. Archived from the original (PDF) on 2006-11-18. Retrieved 2006-11-24.

[9] T. Takaya et al., BE 897864 ; eidem, U.S. Patent 4,559,334 (1984, 1985 both to Fujisawa).

[10] Inamoto, Y; Chiba, T; Kamimura, T; Takaya, T (1988). "FK 482, a new orally active cephalosporin synthesis and biological properties". The Journal of antibiotics 41 (6): 828–30. PMID 3255303.

[11] Kamachi, H; Narita, Y; Okita, T; Abe, Y; Iimura, S; Tomatsu, K; Yamasaki, T; Okumura, J; Naito, T; Oki, T (1988). "Synthesis and biological activity of a new cephalosporin, BMY-28232 and its prodrug-type esters for oral use". The Journal of antibiotics 41 (11): 1602–16. PMID 3198494.

[12] González, M; Rodríguez, Z; Tolón, B; Rodríguez, J. C.; Velez, H; Valdés, B; López, M. A.; Fini, A (2003). "An alternative procedure for preparation of cefdinir". Il Farmaco 58 (6): 409–18. doi:10.1016/S0014-827X(03)00063-6. PMID 12767379.

匿名

検索

案内

案内

cefdinir

Wikipedia preview

wiki en

Contents

Mechanism of action

Indications

Susceptible organisms

Spectrum of bacterial susceptibility and resistance

Side effects

Available forms

"Blood" in the stool

Synthesis

References

External links

UpToDate Contents

English Journal

Japanese Journal

Related Links

Related Pictures

★リンクテーブル★

「セファロスポリン系抗菌薬」

特徴

構造

副作用

セフェム系抗菌薬

第三世代セフェム

「第三世代セフェム」

特徴

第三世代セフェム

「セフジニル」