ジヒドロプテロイン酸
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/05/09 03:00:42」(JST)
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Dihydropteroate
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Names |
IUPAC name
4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoic acid
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Identifiers |
CAS Number
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2134-76-1 N |
Beilstein Reference
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1226443 |
ChEBI |
CHEBI:4581 Y |
ChemSpider |
165 Y |
Jmol 3D model |
Interactive image
Interactive image |
KEGG |
C00921 N |
PubChem |
170 |
InChI
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InChI=1S/C14H14N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,16H,5-6H2,(H,22,23)(H4,15,17,19,20,21) Y
Key: WBFYVDCHGVNRBH-UHFFFAOYSA-N Y
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InChI=1/C14H14N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,16H,5-6H2,(H,22,23)(H4,15,17,19,20,21)
Key: WBFYVDCHGVNRBH-UHFFFAOYAH
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SMILES
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O=C(O)c1ccc(cc1)NCC/2=N/C=3C(=O)\N=C(/NC=3NC\2)N
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C1C(=NC2=C(N1)NC(=NC2=O)N)CNC3=CC=C(C=C3)C(=O)O
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Properties |
Chemical formula
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C14H14N6O3 |
Molar mass |
314.3 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N verify (what is YN ?) |
Infobox references |
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Dihydropteroate is a pterin created from para-aminobenzoic acid (PABA) by the enzyme dihydropteroate synthase. It is an important intermediate in folate synthesis.
Tetrahydrofolate synthesis pathway
Bacteriostatic agents, such as sulfonamides, target dihydropteroate synthetase. The effect of dihydropteroate synthetase inhibition is comparable to that of dihydrofolate reductase inhibition by trimethoprim, another bacteriostatic agent. Together these two drugs - trimethoprim-sulfamethoxazole [TMP-SMX] - are commonly used to treat recurrent urinary tract, Shigella, Salmonella, and Pneumocystis jivoreci infections.
See also
UpToDate Contents
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English Journal
- Pterin-sulfa conjugates as dihydropteroate synthase inhibitors and antibacterial agents.
- Zhao Y1, Shadrick WR1, Wallace MJ1, Wu Y2, Griffith EC3, Qi J4, Yun MK3, White SW2, Lee RE5.
- Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2016 Aug 15;26(16):3950-4. doi: 10.1016/j.bmcl.2016.07.006. Epub 2016 Jul 4.
- The sulfonamide class of antibiotics has been in continuous use for over 70years. They are thought to act by directly inhibiting dihydropteroate synthase (DHPS), and also acting as prodrugs that sequester pterin pools by forming dead end pterin-sulfonamide conjugates. In this study, eight pterin-sul
- PMID 27423480
- Low prevalence of dihydro folate reductase (dhfr) and dihydropteroate synthase (dhps) quadruple and quintuple mutant alleles associated with SP resistance in Plasmodium vivax isolates of West Bengal, India.
- Das S1, Banik A1, Hati AK2, Roy S3.
- Malaria journal.Malar J.2016 Aug 2;15(1):395. doi: 10.1186/s12936-016-1445-9.
- BACKGROUND: Emergence of chloroquine resistant Plasmodium vivax is a serious obstacle towards malaria control in India. This study elucidates the temporal pattern of antifolate [sulfadoxine-pyrimethamine (SP)] resistance in P. vivax infection by means of genetic polymorphisms, especially analysing t
- PMID 27485211
- Role of Plasmodium vivax Dihydropteroate Synthase Polymorphisms in Sulfa Drug Resistance.
- Pornthanakasem W1, Riangrungroj P2, Chitnumsub P2, Ittarat W2, Kongkasuriyachai D2, Uthaipibull C2, Yuthavong Y2, Leartsakulpanich U1.
- Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2016 Jul 22;60(8):4453-63. doi: 10.1128/AAC.01835-15. Print 2016 Aug.
- Dihydropteroate synthase (DHPS) is a known sulfa drug target in malaria treatment, existing as a bifunctional enzyme together with hydroxymethyldihydropterin pyrophosphokinase (HPPK). Polymorphisms in key residues of Plasmodium falciparum DHPS (PfDHPS) have been characterized and linked to sulfa dru
- PMID 27161627
Japanese Journal
- Longitudinal survey of Plasmodium falciparum infection in Vietnam: characteristics of antimalarial resistance and their associated factors.
- Isozumi Rie,Uemura Haruki,Le Duc Dao,Truong Van Hanh,Nguyen Duc Giang,Ha Viet Vien,Bui Quang Phuc,Nguyen Van Tuan,Nakazawa Shusuke
- Journal of clinical microbiology 48(1), 70-77, 2010-01-00
- … falciparum dihydropteroate synthetase (PfDHPS) was observed in 2002. …
- NAID 120002153040
- ニューモシスチスにおける薬物標的分子の変異と今後の展開
- 高橋 孝
- 日本医真菌学会雑誌 = Japanese journal of medical mycology 50(2), 67-73, 2009-04-30
- … T(サルファメソキサゾールとトリメトプリム)合剤を第1選択として,ペンタミジンやアトバコンなどが第2選択として選択される.<I>Pc</I>に対する薬物標的は,(1)サルファメソキサゾール → dihydropteroate synthase(DHPS),(2)トリメトプリム → dihydrofolate reductase,(3)アトバコン → cytochrome <I>b</I>であり,その耐性機序として標的をコードする遺伝子変異がいわれている.特に,DHPSの活性中心であるア …
- NAID 10024793243
- 沖縄県の豚由来Toxoplasma gondiiの遺伝子型別(短報)(寄生虫病学)
- 座喜味 聡,喜屋 武向子,大城 守 [他],杉本 千尋,藤崎 幸蔵
- The journal of veterinary medical science 68(4), 401-404, 2006-04-25
- … 沖縄県のと畜場から得た有病変豚リンパ節101検体のDNAを抽出後,Toxoplasma gondiiのSAG2遺伝子をターゲットにnested PCRを実施したところ57検体が陽性だった.そのうち49が制限酵素による型別が可能で,22(44.9%)がI型,23(46.9%)がII型,4(8.2%)がIII型だった.またサルファ剤耐性と関連するとされるdihydropteroate synthase遺伝子がnested PCRにより57検体中40で増幅され,制限酵素パターンとシーケンスによるとこれらは全て野生型(感受性)だった. …
- NAID 110004758098
Related Pictures
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- dihydropteroate, dihydropteroic acid
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ジヒドロプテロイン酸合成酵素、ジヒドロプテロイン酸シンターゼ