Tavilermide

Tavilermide
Clinical data
Routes of; administration	Eye drop
ATC code	None;
Identifiers
	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;
CAS Number	263251-78-1;
PubChem CID	9808372;
ChemSpider	7984131;
UNII	NMG938VJ6T;
KEGG	D11226;
CompTox Dashboard (EPA)	DTXSID00180937 ;
Chemical and physical data
Formula	C24H32N6O11
Molar mass	580.551 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	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; 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]

References

^ 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.
^ 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.
^ 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.
^ Feng Y, Wang Z, Jin S, Burgess K (1998). "S_NAr Cyclizations To Form Cyclic Peptidomimetics of β-Turns". Journal of the American Chemical Society. 120 (41): 10768–10769. doi:10.1021/ja981589t.
^ Feng Y, Burgess K (1999). "Solid-phase S_NAr 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.
^ 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.
^ "Tavilermide". AdisInsight. Springer Nature Switzerland AG. Retrieved 18 August 2016.

External links

[MeerovitchTorkildsen2013-1] 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.

[JainLi2011-2] 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.

[VickersGupta2015-3] 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). "S_NAr 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 S_NAr 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.

[pmid22349567-6] 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

See also

References

External links