| Revision as of 11:54, 28 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL').← Previous edit |
Latest revision as of 05:46, 7 May 2024 edit undoPikaBoo (talk | contribs)Extended confirmed users1,491 editsNo edit summaryTag: Visual edit |
| (41 intermediate revisions by 31 users not shown) |
| Line 1: |
Line 1: |
|
|
{{Short description|Chemical compound}} |
|
{{Drugbox |
|
{{Drugbox |
|
|
| Verifiedfields = changed |
|
|
| Watchedfields = changed |
|
|
| verifiedrevid = 457805069 |
|
| IUPAC_name = 6-diazo-2-{6-diazo-5-oxo-2-hexanamido}-5-oxohexanoic acid |
|
| IUPAC_name = 6-diazo-2-{6-diazo-5-oxo-2-hexanamido}-5-oxohexanoic acid |
|
| image = alazopeptin.png |
|
| image = Alazopeptin Structure.svg |
|
| alt = |
|
| alt = |
|
|
|
|
|
<!--Clinical data--> |
|
<!--Clinical data--> |
|
| tradename = |
|
| tradename = |
|
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
|
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
|
| pregnancy_US = <!-- A / B / C / D / X --> |
|
| pregnancy_US = <!-- A / B / C / D / X --> |
|
| pregnancy_category = |
|
| pregnancy_category = |
|
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
|
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
|
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> |
|
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> |
|
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM --> |
|
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM --> |
|
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
|
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
|
| legal_status = |
|
| legal_status = |
|
| routes_of_administration = |
|
| routes_of_administration = |
|
|
|
|
|
<!--Pharmacokinetic data--> |
|
<!--Pharmacokinetic data--> |
|
| bioavailability = |
|
| bioavailability = |
|
| protein_bound = |
|
| protein_bound = |
|
| metabolism = |
|
| metabolism = |
|
| elimination_half-life = |
|
| elimination_half-life = |
|
| excretion = |
|
| excretion = |
|
|
|
|
|
<!--Identifiers--> |
|
<!--Identifiers--> |
|
|
| CAS_number_Ref = {{cascite|changed|??}} |
|
| CAS_number = |
|
|
| ATCvet = |
|
| CAS_number = 1397-84-8 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
| UNII = H2QL5CU7EQ |
|
|
| ATCvet = |
|
| ATC_prefix = None |
|
| ATC_prefix = None |
|
| ATC_suffix = |
|
| ATC_suffix = |
|
| PubChem = |
|
| PubChem = 5486654 |
|
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank = |
|
| DrugBank = |
|
| ChEMBL = <!-- blanked - oldvalue: 92957 --> |
|
|
|
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
|
| chemical_formula = C15 H20 N6 O5 |
|
|
|
| ChEMBL = 92957 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
|
| ChemSpiderID = 16735646 |
|
|
|
|
|
|
<!--Chemical data--> |
|
| molecular_weight = 364.4 |
|
|
|
| C=15 | H=20 | N=6 | O=5 |
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChI = 1S/C15H20N6O5/c1-2-7-18-12(5-3-10(22)8-19-16)14(24)21-13(15(25)26)6-4-11(23)9-20-17/h2,8-9,12-13,18H,1,3-7H2,(H2-2,21,22,23,24,25,26)/b10-8-,11-9- |
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChIKey = RCQIFJCPIWRTAF-WGEIWTTOSA-N |
|
|
| smiles = C=CCNC(CCC(=C#N))C(=O)NC(CCC(=C#N))C(=O)O |
|
}} |
|
}} |
|
|
|
|
|
|
'''Alazopeptin''' is an ], with moderate anti-]l<ref name="IshiyamaOtoguro2008">{{cite journal | vauthors = Ishiyama A, Otoguro K, Namatame M, Nishihara A, Furusawa T, Masuma R, Shiomi K, Takahashi Y, Ichimura M, Yamada H, Omura S | display-authors = 6 | title = In vitro and in vivo antitrypanosomal activitiy of two microbial metabolites, KS-505a and alazopeptin | journal = The Journal of Antibiotics | volume = 61 | issue = 10 | pages = 627–632 | date = October 2008 | pmid = 19168977 | doi = 10.1038/ja.2008.83 | doi-access = free }}</ref> and ] activity.<ref name="HataUmezawa1973">{{cite journal | vauthors = Hata T, Umezawa I, Iwai Y, Katagiri M, Awaya J | title = Studies on the antitumor activity of an alazopeptin isolated from a new strain of Streptomyces | journal = The Journal of Antibiotics | volume = 26 | issue = 3 | pages = 181–183 | date = March 1973 | pmid = 4205875 | doi = 10.7164/antibiotics.26.181 | doi-access = free }}</ref> It was originally isolated from '']'', sourced from soil near ].<ref>{{cite journal | vauthors = Patterson EL, Johnson BL, DeVoe SE, Bohonos N | title = Structure of the antitumor antibiotic alazopeptin | journal = Antimicrobial Agents and Chemotherapy | volume = 5 | pages = 115–118 | year = 1965 | pmid = 5883414 }}</ref> It is also isolated from ''Kitasatospora azatica''<ref name="HataUmezawa1973" /> It is still largely produced via fermentation broths of that ]. Structurally, alazopeptin is a tripeptide and contains 2 molecules of ] and one molecule of L-alanine.<ref>{{cite journal | vauthors = De Voe SE, Rigler NE, Shay AJ, Martin JH, Boyd TC, Backus EJ, Mowat JH, Bohonos N | display-authors = 6 | title = Alazopeptin; production, isolation, and chemical characteristics | journal = Antibiotics Annual | pages = 730–735 | date = 1956–1957 | pmid = 13425456 | url = https://pubmed.ncbi.nlm.nih.gov/13425456/ }}</ref><ref>{{cite journal | vauthors = Patterson EL, Johnson BL, DeVoe SE, Bohonos N | title = Structure of the antitumor antibiotic alazopeptin | journal = Antimicrobial Agents and Chemotherapy | volume = 5 | pages = 115–118 | date = 1965 | pmid = 5883414 | url = https://pubmed.ncbi.nlm.nih.gov/5883414/ }}</ref> In 2021 the biosynthetic pathway of alazopeptin was elucidated.<ref>{{cite journal | vauthors = Kawai S, Sugaya Y, Hagihara R, Tomita H, Katsuyama Y, Ohnishi Y | title = Complete Biosynthetic Pathway of Alazopeptin, a Tripeptide Consisting of Two Molecules of 6-Diazo-5-oxo-l-norleucine and One Molecule of Alanine | journal = Angewandte Chemie | volume = 60 | issue = 18 | pages = 10319–10325 | date = April 2021 | pmid = 33624374 | doi = 10.1002/anie.202100462 | s2cid = 232039107 }}</ref><ref>{{cite journal | vauthors = Kawai S, Katsuyama Y, Ohnishi Y | title = The α/β Hydrolase AzpM Catalyzes Dipeptide Synthesis in Alazopeptin Biosynthesis Using Two Molecules of Carrier Protein-Tethered Amino Acid | journal = ChemBioChem | volume = 23 | issue = 7 | pages = e202100700 | date = April 2022 | pmid = 35132756 | doi = 10.1002/cbic.202100700 | s2cid = 246651326 }}</ref> |
|
'''Alazopeptin''' is an ] antibiotic, produced by '']''. It is sourced from soil near WIlliamsburg, Iowa.<ref>{{cite journal | last1 = Patterson | first1 = E.L. | journal = Antimicrob. Agents Chemotherapy | pages = 115 | year = 1965 }}</ref> |
|
|
|
|
|
|
==References== |
|
== References == |
|
{{Reflist}} |
|
{{Reflist}} |
|
|
|
|
|
] |
|
] |
|
|
] |
|
|
|
|
|
] |
|
|
] |
|
|
|
|
|
{{antineoplastic-drug-stub}} |
|
{{antineoplastic-drug-stub}} |
|
|
<blockquote></blockquote> |