| Revision as of 21:49, 10 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validation|Chem/Drugbox← Previous edit |
Latest revision as of 01:15, 11 October 2023 edit undoWhywhenwhohow (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers48,667 edits →top: update atc |
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{{Short description|Chemical compound}} |
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{{drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 444144628 |
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| image = Halofuginone.png |
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| width = 180 |
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| image2 = Halofuginone molecule ball.png |
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| width2 = 240 |
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| alt2 = Ball-and-stick model of the halofuginone molecule |
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<!--Clinical data--> |
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| tradename = Halocur |
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| Drugs.com = {{drugs.com|international|halofuginone}} |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_category = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_EU = Rx-only |
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| legal_status = |
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| routes_of_administration = |
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| ATCvet = yes |
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| ATC_prefix = P51 |
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| ATC_suffix = BX01 |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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| index_label = |
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| index2_label = |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 55837-20-2 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 1199540 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = L31MM1385E |
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| UNII = L31MM1385E |
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| PubChem = 400772 |
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| verifiedrevid = 443219269 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| IUPAC_name = 7-Bromo-6-chloro-3--2-oxopropyl]-4-quinazolinone |
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| ChemSpiderID = 355164 |
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| image = halofuginone.png |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| CAS_number = 55837-20-2 |
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| StdInChI = 1S/C16H17BrClN3O3/c17-11-6-13-10(5-12(11)18)16(24)21(8-20-13)7-9(22)4-14-15(23)2-1-3-19-14/h5-6,8,14-15,19,23H,1-4,7H2/t14-,15+/m0/s1 |
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| ATCvet = yes |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| ATC_prefix = P51 |
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| StdInChIKey = LVASCWIMLIKXLA-LSDHHAIUSA-N |
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| ATC_suffix = AX08 |
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| PubChem = 62891 |
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<!--Chemical data--> |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| IUPAC_name = 7-Bromo-6-chloro-3--2-oxopropyl]-4-quinazolinone |
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| DrugBank = |
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| chemical_formula = |
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| C=16 | H=17 | Br=1 | Cl=1 | N=3 | O=3 |
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| C=16 | H=17 | Br=1 | Cl=1 | N=3 | O=3 |
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| smiles = O=C(CN3C=NC2=CC(Br)=C(Cl)C=C2C3=O)C1NCCC1O |
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| molecular_weight = 414.68 g/mol |
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|drug_name=|alt=|caption=|type=|MedlinePlus=|licence_EU=|licence_US=}} |
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| smiles = O=C(CN3C=NC2=CC(Br)=C(Cl)C=C2C3=O)C1NCCC1O |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category= |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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}} |
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'''Halofuginone''' is a ] used in veterinary medicine. It is a synthetic ]ated derivative of ], a natural ] alkaloid which can be found in the Chinese herb '']'' (Chang Shan).<ref name=drugdictionary>, NCI Drug Dictionary</ref> Collgard Biopharmaceuticals is developing halofuginone for the treatment of ] and it has received ] designation from the ].<ref>, March 10, 2000</ref> |
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'''Halofuginone''', sold under the brand name '''Halocur''', is a ] used in veterinary medicine. It is a synthetic ]ated derivative of ], a natural ] alkaloid which can be found in the Chinese herb '']'' (Chang Shan).<ref name=drugdictionary>{{cite web | url = http://www.cancer.gov/drugdictionary/?CdrID=38485 | title = Halofuginone hydrobromide | work = NCI Drug Dictionary | publisher = National Cancer Institute, National Institutes of Health, U.S. Department of Health and Human Services }}</ref> Collgard Biopharmaceuticals is developing halofuginone for the treatment of ] and it has received ] designation from the ].<ref>{{cite web | url = http://www.pslgroup.com/dg/18dff6.htm | title = Halofuginone Receives FDA Orphan Drug Status For Scleroderma | archive-url = https://web.archive.org/web/20120304235043/http://www.pslgroup.com/dg/18dff6.htm | archive-date= 4 March 2012 | url-status = dead | date = 10 March 2000 | work = WebCite }}</ref> |
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Halofuginone inhibits the development of ]s, immune cells that play an important players in autoimmune disease, but it does not affect other kinds of T cells which involved in normal immune function.<ref>{{cite journal | last1 = Sundrud | first1 = M. S. | last2 = Koralov | first2 = S. B. | last3 = Feuerer | first3 = M. | last4 = Calado | first4 = D. P. | last5 = Kozhaya | first5 = A. E. | last6 = Rhule-Smith | first6 = A. | last7 = Lefebvre | first7 = R. E. | last8 = Unutmaz | first8 = D. | last9 = Mazitschek | first9 = R. | title = Halofuginone Inhibits TH17 Cell Differentiation by Activating the Amino Acid Starvation Response | journal = Science | volume = 324 | issue = 5932 | pages = 1334 | year = 2009 | pmid = 19498172 | pmc = 2803727 | doi = 10.1126/science.1172638}}</ref> Halofuginone therefore has potential for the treatment of autoimmune disorders.<ref>, June 4, 2009</ref> |
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Halofuginone inhibits the development of ]s, immune cells that play an important role in autoimmune disease, but it does not affect other kinds of T cells which are involved in normal immune function.<ref>{{cite journal | vauthors = Sundrud MS, Koralov SB, Feuerer M, Calado DP, Kozhaya AE, Rhule-Smith A, Lefebvre RE, Unutmaz D, Mazitschek R, Waldner H, Whitman M, Keller T, Rao A | display-authors = 6 | title = Halofuginone inhibits TH17 cell differentiation by activating the amino acid starvation response | journal = Science | volume = 324 | issue = 5932 | pages = 1334–8 | date = June 2009 | pmid = 19498172 | pmc = 2803727 | doi = 10.1126/science.1172638 | bibcode = 2009Sci...324.1334S }}</ref> Halofuginone therefore has potential for the treatment of autoimmune disorders.<ref name="pmid19498172">{{cite journal | vauthors = Sundrud MS, Koralov SB, Feuerer M, Calado DP, Kozhaya AE, Rhule-Smith A, Lefebvre RE, Unutmaz D, Mazitschek R, Waldner H, Whitman M, Keller T, Rao A | title = Halofuginone inhibits TH17 cell differentiation by activating the amino acid starvation response | journal = Science | volume = 324 | issue = 5932 | pages = 1334–8 | date = June 2009 | pmid = 19498172 | pmc = 2803727 | doi = 10.1126/science.1172638 | bibcode = 2009Sci...324.1334S}} |
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* {{cite press release |date=4 June 2009 |title=A new lead for autoimmune disease |website=EurekAlert! |url=http://www.eurekalert.org/pub_releases/2009-06/chb-anl060109.php}}</ref> |
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Halofuginone is also an inhibitor of ] gene expression and as a consequence it may inhibit tumor cell growth.<ref name=drugdictionary/> Halofuginone exerts its effects by acting as a high affinity inhibitor of the enzyme glutamyl-prolyl tRNA synthetase. Inhibition of prolyl tRNA charging leads to the accumulation of uncharged prolyl tRNAs, which serve as a signal to initiate the ], which in turn exerts anti-inflammatory and anti-fibrotic effects.<ref>{{cite journal | vauthors = Keller TL, Zocco D, Sundrud MS, Hendrick M, Edenius M, Yum J, Kim YJ, Lee HK, Cortese JF, Wirth DF, Dignam JD, Rao A, Yeo CY, Mazitschek R, Whitman M | display-authors = 6 | title = Halofuginone and other febrifugine derivatives inhibit prolyl-tRNA synthetase | journal = Nature Chemical Biology | volume = 8 | issue = 3 | pages = 311–7 | date = February 2012 | pmid = 22327401 | pmc = 3281520 | doi = 10.1038/nchembio.790 }}</ref> |
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Halofuginine is also an inhibitor of ] gene expression and as a consequence it may inhibit tumor cell growth.<ref name=drugdictionary/> |
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==References== |
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== References == |
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