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recategorized from Nitrobenzenes to Nitrobenzene derivatives
 
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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields =
| Verifiedfields =
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| verifiedrevid =
| verifiedrevid =
| IUPAC_name = 3-[(5S,8S,11S)-8-(4-aminobutyl)-5-(carboxymethylcarbamoyl)-16-nitro-7,10,13-trioxo-2-oxa-6,9,12-triazabicyclo[12.4.0]octadeca-1(14),15,17-trien-11-yl]propanoic acid
| IUPAC_name = 3-[(5S,8S,11S)-8-(4-aminobutyl)-5-(carboxymethylcarbamoyl)-16-nitro-7,10,13-trioxo-2-oxa-6,9,12-triazabicyclo[12.4.0]octadeca-1(14),15,17-trien-11-yl]propanoic acid
| image =
| image = Tavilermide_structure.png
| width =
| width = 250


<!--Clinical data-->
<!--Clinical data-->
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| CAS_number = 263251-78-1
| CAS_number = 263251-78-1
| CAS_supplemental =
| CAS_supplemental =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = NMG938VJ6T
| ATC_prefix = None
| ATC_prefix = None
| ATC_suffix =
| ATC_suffix =
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| DrugBank_Ref =
| DrugBank_Ref =
| DrugBank =
| DrugBank =
| KEGG = D11226
| ChemSpiderID_Ref =
| ChemSpiderID_Ref =
| ChemSpiderID = 7984131
| ChemSpiderID = 7984131
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<!--Chemical data-->
<!--Chemical data-->
| C=24 | H=32 | N=6 | O=11
| C=24 | H=32 | N=6 | O=11
| smiles = NCCCC[C@@H]1NC(=O)[C@H](CCC(=O)O)NC(=O)c2cc([N+](=O)[O-])ccc2OCC[C@@H](C(=O)NCC(=O)O)NC1=O
| molecular_weight = 580.54448 g/mol
⚫
| StdInChI = 1S/C24H32N6O11/c25-9-2-1-3-15-23(37)29-17(22(36)26-12-20(33)34)8-10-41-18-6-4-13(30(39)40)11-14(18)21(35)27-16(24(38)28-15)5-7-19(31)32/h4,6,11,15-17H,1-3,5,7-10,12,25H2,(H,26,36)(H,27,35)(H,28,38)(H,29,37)(H,31,32)(H,33,34)/t15-,16-,17-/m0/s1
| smiles = C1COC2=C(C=C(C=C2)[N+](=O)[O-])C(=O)NC(C(=O)NC(C(=O)NC1C(=O)NCC(=O)O)CCCCN)CCC(=O)O
⚫
| StdInChIKey = DVJXNXPFYJIACK-ULQDDVLXSA-N
⚫
| InChI = InChI=1S/C24H32N6O11/c25-9-2-1-3-15-23(37)29-17(22(36)26-12-20(33)34)8-10-41-18-6-4-13(30(39)40)11-14(18)21(35)27-16(24(38)28-15)5-7-19(31)32/h4,6,11,15-17H,1-3,5,7-10,12,25H2,(H,26,36)(H,27,35)(H,28,38)(H,29,37)(H,31,32)(H,33,34)/t15-,16-,17-/m0/s1
⚫
| InChIKey = DVJXNXPFYJIACK-ULQDDVLXSA-N
| StdInChI_Ref =
| StdInChI =
| StdInChIKey_Ref =
| StdInChIKey =
| synonyms =
| synonyms =
}}
}}


'''Tavilermide''' ([[International Nonproprietary Name|INN]]) (developmental code name '''MIM-D3''') is a selective, [[small-molecule]] [[partial agonist]] of [[TrkA]], or a [[nerve growth factor]] (NGF) [[mimetic]].<ref name="MeerovitchTorkildsen2013">{{cite journal|last1=Meerovitch|first1=Karen|last2=Torkildsen|first2=Gail|last3=Lonsdale|first3=John|last4=Goldfarb|first4=Heidi|last5=Lama|first5=Teresa|last6=Cumberlidge|first6=Garth|last7=Ousler III|first7=George W.|title=Safety and efficacy of MIM D3 ophthalmic solutions in a randomized placebo controlled Phase 2 clinical trial in patients with dry eye|journal=Clinical Ophthalmology|year=2013|pages=1275|issn=1177-5483|doi=10.2147/OPTH.S44688}}</ref><ref name="JainLi2011">{{cite journal|last1=Jain|first1=Pooja|last2=Li|first2=Ruihong|last3=Lama|first3=Teresa|last4=Saragovi|first4=H. Uri|last5=Cumberlidge|first5=Garth|last6=Meerovitch|first6=Karen|title=An NGF mimetic, MIM-D3, stimulates conjunctival cell glycoconjugate secretion and demonstrates therapeutic efficacy in a rat model of dry eye|journal=Experimental Eye Research|volume=93|issue=4|year=2011|pages=503–512|issn=00144835|doi=10.1016/j.exer.2011.06.014}}</ref><ref name="VickersGupta2015">{{cite journal|last1=Vickers|first1=Laura A.|last2=Gupta|first2=Preeya K.|title=The Future of Dry Eye Treatment: A Glance into the Therapeutic Pipeline|journal=Ophthalmology and Therapy|year=2015|issn=2193-8245|doi=10.1007/s40123-015-0038-y}}</ref> It was under development by [[Mimetogen Pharmaceuticals]] as an [[ophthalmic solution|ophthalmic (eye drop) solution]] for the treatment of [[dry eyes]], and reached [[Phases of clinical research#Phase III|phase III]] [[clinical trial]]s for this indication, but development appears to have been halted.<ref name="MeerovitchTorkildsen2013" /><ref name="VickersGupta2015" />[http://adisinsight.springer.com/drugs/800033231] Tavilermide is also in [[Phases of clinical research#Phase I|phase I]] clinical trials for the treatment of [[glaucoma]]; studies are ongoing.<ref name="pmid22349567">{{cite journal | vauthors = Chang EE, Goldberg JL | title = Glaucoma 2.0: neuroprotection, neuroregeneration, neuroenhancement | journal = Ophthalmology | volume = 119 | issue = 5 | pages = 979–86 | year = 2012 | pmid = 22349567 | pmc = 3343191 | doi = 10.1016/j.ophtha.2011.11.003 | url = }}</ref>[http://adisinsight.springer.com/drugs/800033231]
'''Tavilermide''' ([[International Nonproprietary Name|INN]]) (developmental code name '''MIM-D3''') is a [[binding selectivity|selective]], [[cyclic peptide|cyclic tripeptide]] [[partial agonist]] of [[TrkA]]. (this class of drugs is sometimes referred to as [[nerve growth factor]] (NGF) [[mimetic]]s)<ref name="MeerovitchTorkildsen2013">{{cite journal | vauthors = Meerovitch K, Torkildsen G, Lonsdale J, Goldfarb H, Lama T, Cumberlidge G, Ousler GW | title = Safety and efficacy of MIM-D3 ophthalmic solutions in a randomized, placebo-controlled Phase 2 clinical trial in patients with dry eye | journal = Clinical Ophthalmology | volume = 7 | pages = 1275–1285 | year = 2013 | pmid = 23836957 | pmc = 3699314 | doi = 10.2147/OPTH.S44688 | doi-access = free }}</ref><ref name="JainLi2011">{{cite journal | vauthors = Jain P, Li R, Lama T, Saragovi HU, Cumberlidge G, Meerovitch K | title = An NGF mimetic, MIM-D3, stimulates conjunctival cell glycoconjugate secretion and demonstrates therapeutic efficacy in a rat model of dry eye | journal = Experimental Eye Research | volume = 93 | issue = 4 | pages = 503–512 | date = October 2011 | pmid = 21726552 | doi = 10.1016/j.exer.2011.06.014 }}</ref><ref name="VickersGupta2015">{{cite journal | vauthors = Vickers LA, Gupta PK | title = The Future of Dry Eye Treatment: A Glance into the Therapeutic Pipeline | journal = Ophthalmology and Therapy | volume = 4 | issue = 2 | pages = 69–78 | date = December 2015 | pmid = 26289997 | pmc = 4675732 | doi = 10.1007/s40123-015-0038-y }}</ref> Tavilermide was first synthesized by Burgess and co-workers at Texas A&M University with the intention of producing TrkA agonists.<ref>{{Cite journal| vauthors = Feng Y, Wang Z, Jin S, Burgess K |date=1998|title=S<sub>N</sub>Ar Cyclizations To Form Cyclic Peptidomimetics of β-Turns|url=https://pubs.acs.org/doi/10.1021/ja981589t|journal=Journal of the American Chemical Society|volume=120|issue=41|pages=10768–10769|doi=10.1021/ja981589t}}</ref><ref>{{Cite journal| vauthors = Feng Y, Burgess K |date=1999|title=Solid-phase S<sub>N</sub>Ar macrocyclizations to give turn-extended-turn peptidomimetics|url=https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/%28SICI%291521-3765%2819991105%295%3A11%3C3261%3A%3AAID-CHEM3261%3E3.0.CO%3B2-H|journal=Chemistry: A European Journal|volume=5|issue=11|pages=3261–3272|doi=10.1002/(SICI)1521-3765(19991105)5:11<3261::AID-CHEM3261>3.0.CO;2-H}}</ref> It is under development by Mimetogen Pharmaceuticals as an [[ophthalmic solution|ophthalmic (eye drop) solution]] for the treatment of [[dry eyes]], and is in [[Phases of clinical research#Phase III|phase III]] [[clinical trial]]s for this indication. Tavilermide is currently being evaluated in two multi-center phase III clinical studies in the United States for the treatment of dry eye disease.[http://www.streetinsider.com/Corporate+News/Allergan+%28AGN%29,+Mimetogen+Pharma+Enter+MIM-D3+D+Development+Collaboration/11033405.html] Tavilermide is also in [[Phases of clinical research#Phase I|phase I]] clinical trials for the treatment of [[glaucoma]]; studies are ongoing.<ref name="pmid22349567">{{cite journal | vauthors = Chang EE, Goldberg JL | title = Glaucoma 2.0: neuroprotection, neuroregeneration, neuroenhancement | journal = Ophthalmology | volume = 119 | issue = 5 | pages = 979–986 | date = May 2012 | pmid = 22349567 | pmc = 3343191 | doi = 10.1016/j.ophtha.2011.11.003 }}</ref><ref>{{cite web |title=Tavilermide | work = AdisInsight |url= http://adisinsight.springer.com/drugs/800033231|publisher=Springer Nature Switzerland AG |access-date=18 August 2016}}</ref>


==See also==
== See also ==
* [[Ciclosporin]]
* [[Cenegermin]]
* [[FX007]]
* [[Tanezumab]]


==References==
== References ==
{{Reflist|2}}
{{Reflist|30em}}


==External links==
== External links ==
* [http://www.mimetogen.com/clinical-development.html Clinical Development - Mimetogen Pharmaceuticals]
* [http://www.mimetogen.com/clinical-development.html Clinical Development - Mimetogen Pharmaceuticals]
* [http://adisinsight.springer.com/drugs/800033231 Tavilermide - AdisInsight]
* [http://adisinsight.springer.com/drugs/800033231 Tavilermide - AdisInsight]
* [http://www.streetinsider.com/Corporate+News/Allergan+%28AGN%29,+Mimetogen+Pharma+Enter+MIM-D3+D+Development+Collaboration/11033405.html MIM-D3 StreetInsider]



{{Antiglaucoma preparations and miotics}}
{{Antiglaucoma preparations and miotics}}
{{Growth factor receptor modulators}}
{{Neurotrophinergics}}


[[Category:Glaucoma]]
[[Category:Glaucoma]]
[[Category:Ophthalmology drugs]]
[[Category:Ophthalmology drugs]]
[[Category:Receptor agonists]]
[[Category:Receptor agonists]]
[[Category:Cyclic peptides]]

[[Category:Nitrobenzene derivatives]]

[[Category:Tripeptides]]
{{pharmacology-stub}}

Latest revision as of 22:08, 3 February 2024

Tavilermide
Clinical data
Routes of
administration		Eye drop
ATC code
  • None
Identifiers
  • 3-[(5S,8S,11S)-8-(4-aminobutyl)-5-(carboxymethylcarbamoyl)-16-nitro-7,10,13-trioxo-2-oxa-6,9,12-triazabicyclo[12.4.0]octadeca-1(14),15,17-trien-11-yl]propanoic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H32N6O11
Molar mass580.551 g·mol−1
3D model (JSmol)
  • NCCCC[C@@H]1NC(=O)[C@H](CCC(=O)O)NC(=O)c2cc([N+](=O)[O-])ccc2OCC[C@@H](C(=O)NCC(=O)O)NC1=O
  • InChI=1S/C24H32N6O11/c25-9-2-1-3-15-23(37)29-17(22(36)26-12-20(33)34)8-10-41-18-6-4-13(30(39)40)11-14(18)21(35)27-16(24(38)28-15)5-7-19(31)32/h4,6,11,15-17H,1-3,5,7-10,12,25H2,(H,26,36)(H,27,35)(H,28,38)(H,29,37)(H,31,32)(H,33,34)/t15-,16-,17-/m0/s1
  • Key:DVJXNXPFYJIACK-ULQDDVLXSA-N

Tavilermide (INN) (developmental code name MIM-D3) is a selective, cyclic tripeptide partial agonist of TrkA. (this class of drugs is sometimes referred to as nerve growth factor (NGF) mimetics)[1][2][3] Tavilermide was first synthesized by Burgess and co-workers at Texas A&M University with the intention of producing TrkA agonists.[4][5] It is under development by Mimetogen Pharmaceuticals as an ophthalmic (eye drop) solution for the treatment of dry eyes, and is in phase III clinical trials for this indication. Tavilermide is currently being evaluated in two multi-center phase III clinical studies in the United States for the treatment of dry eye disease.[1] Tavilermide is also in phase I clinical trials for the treatment of glaucoma; studies are ongoing.[6][7]

See also

[edit]

References

[edit]
  1. ^ Meerovitch K, Torkildsen G, Lonsdale J, Goldfarb H, Lama T, Cumberlidge G, Ousler GW (2013). "Safety and efficacy of MIM-D3 ophthalmic solutions in a randomized, placebo-controlled Phase 2 clinical trial in patients with dry eye". Clinical Ophthalmology. 7: 1275–1285. doi:10.2147/OPTH.S44688. PMC 3699314. PMID 23836957.
  2. ^ Jain P, Li R, Lama T, Saragovi HU, Cumberlidge G, Meerovitch K (October 2011). "An NGF mimetic, MIM-D3, stimulates conjunctival cell glycoconjugate secretion and demonstrates therapeutic efficacy in a rat model of dry eye". Experimental Eye Research. 93 (4): 503–512. doi:10.1016/j.exer.2011.06.014. PMID 21726552.
  3. ^ Vickers LA, Gupta PK (December 2015). "The Future of Dry Eye Treatment: A Glance into the Therapeutic Pipeline". Ophthalmology and Therapy. 4 (2): 69–78. doi:10.1007/s40123-015-0038-y. PMC 4675732. PMID 26289997.
  4. ^ Feng Y, Wang Z, Jin S, Burgess K (1998). "SNAr Cyclizations To Form Cyclic Peptidomimetics of β-Turns". Journal of the American Chemical Society. 120 (41): 10768–10769. doi:10.1021/ja981589t.
  5. ^ Feng Y, Burgess K (1999). "Solid-phase SNAr macrocyclizations to give turn-extended-turn peptidomimetics". Chemistry: A European Journal. 5 (11): 3261–3272. doi:10.1002/(SICI)1521-3765(19991105)5:11<3261::AID-CHEM3261>3.0.CO;2-H.
  6. ^ Chang EE, Goldberg JL (May 2012). "Glaucoma 2.0: neuroprotection, neuroregeneration, neuroenhancement". Ophthalmology. 119 (5): 979–986. doi:10.1016/j.ophtha.2011.11.003. PMC 3343191. PMID 22349567.
  7. ^ "Tavilermide". AdisInsight. Springer Nature Switzerland AG. Retrieved 18 August 2016.
[edit]
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