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Modimelanotide

January 23, 2023

Modimelanotide (INN) (code names AP-214, ABT-719, ZP-1480) is a melanocortinergic peptide drug derived from α-melanocyte-stimulating hormone (α-MSH) which was under development by, at different times, Action Pharma, Abbott Laboratories, AbbVie, and Zealand for the treatment of acute kidney injury.[1][2] It acts as a non-selective melanocortin receptor agonist, with IC50 values of 2.9 nM, 1.9 nM, 3.7 nM, and 110 nM at the MC1, MC3, MC4, and MC5 receptors.[3] Modimelanotide failed clinical trials for acute kidney injury despite showing efficacy in animal models,[4][5] and development was not further pursued.[1][2]

Modimelanotide
Clinical data
Other namesAcetylhexa-L-lysyl-α-MSH
ATC code
  • None
Identifiers
  • N2-acetyl-L-lysyl-L-lysyl-L-lysyl-L-lysyl-L-lysyl-L-lysyl-L-seryl-L-tyrosyl-L-seryl-L-methionyl-L-alpha-glutamyl-L-histidyl-L-phenylalanyl-L-arginyl-L-tryptophylglycyl-L-lysyl-L-prolyl-L-valinamide
CAS Number
  • 926277-68-1
PubChem CID
  • 72941953
ChemSpider
  • 34988374
UNII
  • 96C1EBE9CG
Chemical and physical data
FormulaC113H181N33O25S
Molar mass2433.96 g·mol−1
3D model (JSmol)
  • Interactive image
  • [H]/N=C(\N)/NCCC[C@@H](C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N3CCC[C@H]3C(=O)N[C@@H](C(C)C)C(=O)N)NC(=O)[C@H](Cc4ccccc4)NC(=O)[C@H](Cc5c[nH]cn5)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CO)NC(=O)[C@H](Cc6ccc(cc6)O)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)C
  • InChI=1S/C113H181N33O25S/c1-66(2)94(95(121)154)145-111(170)91-38-25-54-146(91)112(171)84(36-16-23-52-120)130-92(151)62-127-96(155)87(58-70-60-126-74-29-9-8-28-73(70)74)141-102(161)81(37-24-53-125-113(122)123)136-106(165)85(56-68-26-6-5-7-27-68)139-108(167)88(59-71-61-124-65-128-71)142-104(163)82(43-44-93(152)153)137-105(164)83(45-55-172-4)138-109(168)89(63-147)144-107(166)86(57-69-39-41-72(150)42-40-69)140-110(169)90(64-148)143-103(162)80(35-15-22-51-119)135-101(160)79(34-14-21-50-118)134-100(159)78(33-13-20-49-117)133-99(158)77(32-12-19-48-116)132-98(157)76(31-11-18-47-115)131-97(156)75(129-67(3)149)30-10-17-46-114/h5-9,26-29,39-42,60-61,65-66,75-91,94,126,147-148,150H,10-25,30-38,43-59,62-64,114-120H2,1-4H3,(H2,121,154)(H,124,128)(H,127,155)(H,129,149)(H,130,151)(H,131,156)(H,132,157)(H,133,158)(H,134,159)(H,135,160)(H,136,165)(H,137,164)(H,138,168)(H,139,167)(H,140,169)(H,141,161)(H,142,163)(H,143,162)(H,144,166)(H,145,170)(H,152,153)(H4,122,123,125)/t75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,94-/m0/s1
  • Key:WHRVKPBBRZHWTN-ZHHKRVSMSA-N

See also

References

  1. ^ a b Ramos AM, González-Guerrero C, Sanz A, Sanchez-Niño MD, Rodríguez-Osorio L, Martín-Cleary C, et al. (May 2015). "Designing drugs that combat kidney damage". Expert Opinion on Drug Discovery. 10 (5): 541–56. doi:10.1517/17460441.2015.1033394. PMID 25840605. S2CID 24191324.
  2. ^ a b Montero-Melendez T (May 2015). "ACTH: The forgotten therapy". Seminars in Immunology. 27 (3): 216–26. doi:10.1016/j.smim.2015.02.003. PMID 25726511.
  3. ^ "Renal-Urologic drugs". Drug Data Reports. Prous Science. 29 (1): 42. 2007. ISSN 0379-4121.
  4. ^ Doi K, Hu X, Yuen PS, Leelahavanichkul A, Yasuda H, Kim SM, et al. (June 2008). "AP214, an analogue of alpha-melanocyte-stimulating hormone, ameliorates sepsis-induced acute kidney injury and mortality". Kidney International. 73 (11): 1266–74. doi:10.1038/ki.2008.97. PMC 2398767. PMID 18354376.
  5. ^ Simmons MN, Subramanian V, Crouzet S, Haber GP, Colombo JR, Ukimura O, et al. (April 2010). "Alpha-melanocyte stimulating hormone analogue AP214 protects against ischemia induced acute kidney injury in a porcine surgical model". The Journal of Urology. 183 (4): 1625–9. doi:10.1016/j.juro.2009.12.007. PMID 20172543.

External links

  • Modimelanotide - AdisInsight
  • ZP1480 (ABT-719) Publications - Zealand Pharma
 

This drug article relating to the genito-urinary system is a stub. You can help Wikipedia by expanding it.

January 23, 2023
modimelanotide, code, names, 1480, melanocortinergic, peptide, drug, derived, from, melanocyte, stimulating, hormone, which, under, development, different, times, action, pharma, abbott, laboratories, abbvie, zealand, treatment, acute, kidney, injury, acts, se. Modimelanotide INN code names AP 214 ABT 719 ZP 1480 is a melanocortinergic peptide drug derived from a melanocyte stimulating hormone a MSH which was under development by at different times Action Pharma Abbott Laboratories AbbVie and Zealand for the treatment of acute kidney injury 1 2 It acts as a non selective melanocortin receptor agonist with IC50 values of 2 9 nM 1 9 nM 3 7 nM and 110 nM at the MC1 MC3 MC4 and MC5 receptors 3 Modimelanotide failed clinical trials for acute kidney injury despite showing efficacy in animal models 4 5 and development was not further pursued 1 2 ModimelanotideClinical dataOther namesAcetylhexa L lysyl a MSHATC codeNoneIdentifiersIUPAC name N2 acetyl L lysyl L lysyl L lysyl L lysyl L lysyl L lysyl L seryl L tyrosyl L seryl L methionyl L alpha glutamyl L histidyl L phenylalanyl L arginyl L tryptophylglycyl L lysyl L prolyl L valinamideCAS Number926277 68 1PubChem CID72941953ChemSpider34988374UNII96C1EBE9CGChemical and physical dataFormulaC 113H 181N 33O 25SMolar mass2433 96 g mol 13D model JSmol Interactive imageSMILES H N C N NCCC C H C O N C H Cc1c nH c2c1cccc2 C O NCC O N C H CCCCN C O N3CCC C H 3C O N C H C C C C O N NC O C H Cc4ccccc4 NC O C H Cc5c nH cn5 NC O C H CCC O O NC O C H CCSC NC O C H CO NC O C H Cc6ccc cc6 O NC O C H CO NC O C H CCCCN NC O C H CCCCN NC O C H CCCCN NC O C H CCCCN NC O C H CCCCN NC O C H CCCCN NC O CInChI InChI 1S C113H181N33O25S c1 66 2 94 95 121 154 145 111 170 91 38 25 54 146 91 112 171 84 36 16 23 52 120 130 92 151 62 127 96 155 87 58 70 60 126 74 29 9 8 28 73 70 74 141 102 161 81 37 24 53 125 113 122 123 136 106 165 85 56 68 26 6 5 7 27 68 139 108 167 88 59 71 61 124 65 128 71 142 104 163 82 43 44 93 152 153 137 105 164 83 45 55 172 4 138 109 168 89 63 147 144 107 166 86 57 69 39 41 72 150 42 40 69 140 110 169 90 64 148 143 103 162 80 35 15 22 51 119 135 101 160 79 34 14 21 50 118 134 100 159 78 33 13 20 49 117 133 99 158 77 32 12 19 48 116 132 98 157 76 31 11 18 47 115 131 97 156 75 129 67 3 149 30 10 17 46 114 h5 9 26 29 39 42 60 61 65 66 75 91 94 126 147 148 150H 10 25 30 38 43 59 62 64 114 120H2 1 4H3 H2 121 154 H 124 128 H 127 155 H 129 149 H 130 151 H 131 156 H 132 157 H 133 158 H 134 159 H 135 160 H 136 165 H 137 164 H 138 168 H 139 167 H 140 169 H 141 161 H 142 163 H 143 162 H 144 166 H 145 170 H 152 153 H4 122 123 125 t75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 94 m0 s1Key WHRVKPBBRZHWTN ZHHKRVSMSA NSee also EditAfamelanotide BMS 470 539 Bremelanotide Melanotan II PF 00446687 SetmelanotideReferences Edit a b Ramos AM Gonzalez Guerrero C Sanz A Sanchez Nino MD Rodriguez Osorio L Martin Cleary C et al May 2015 Designing drugs that combat kidney damage Expert Opinion on Drug Discovery 10 5 541 56 doi 10 1517 17460441 2015 1033394 PMID 25840605 S2CID 24191324 a b Montero Melendez T May 2015 ACTH The forgotten therapy Seminars in Immunology 27 3 216 26 doi 10 1016 j smim 2015 02 003 PMID 25726511 Renal Urologic drugs Drug Data Reports Prous Science 29 1 42 2007 ISSN 0379 4121 Doi K Hu X Yuen PS Leelahavanichkul A Yasuda H Kim SM et al June 2008 AP214 an analogue of alpha melanocyte stimulating hormone ameliorates sepsis induced acute kidney injury and mortality Kidney International 73 11 1266 74 doi 10 1038 ki 2008 97 PMC 2398767 PMID 18354376 Simmons MN Subramanian V Crouzet S Haber GP Colombo JR Ukimura O et al April 2010 Alpha melanocyte stimulating hormone analogue AP214 protects against ischemia induced acute kidney injury in a porcine surgical model The Journal of Urology 183 4 1625 9 doi 10 1016 j juro 2009 12 007 PMID 20172543 External links EditModimelanotide AdisInsight ZP1480 ABT 719 Publications Zealand Pharma This drug article relating to the genito urinary system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Modimelanotide amp oldid 993704801, wikipedia, wiki, book, books, library,

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