Leconotide

Leconotide

Clinical data
Routes of administration	IV
ATC code	None
Identifiers
IUPAC name (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2R)-2-[(2S)-6-amino-2-[(2S)-2-{2-[(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-[(2R)-2-amino-3-sulfanylpropanamido]hexanamido]-3-hydroxypropanamido]hexanamido]acetamido}propanamido]hexanamido]-3-sulfanylpropanamido]-3-hydroxypropanamido]hexanamido]-4-methylpentanamido]-4-(methylsulfanyl)butanamido]-3-(4-hydroxyphenyl)propanamido]-3-{[(1R)-1-{[(R)-{[(1S)-1-[({[(1S)-1-{[(R)-{[(1S)-1-[({[(1S,2R)-1-{[(1S)-1-[({[(1S)-4-carbamimidamido-1-{[(R)-carbamoyl(methanethioyl)methyl]carbamoyl}butyl]carbamoyl}methyl)carbamoyl]-2-methylpropyl]carbamoyl}-2-hydroxypropyl]carbamoyl}methyl)carbamoyl]-2-hydroxyethyl]carbamoyl}(methanethioyl)methyl]carbamoyl}-2-hydroxyethyl]carbamoyl}methyl)carbamoyl]-2-hydroxyethyl]carbamoyl}(methanethioyl)methyl]carbamoyl}-2-sulfanylethyl]carbamoyl}propanoic acid
Synonyms	H-Cys-Lys-Ser-Lys-Gly-Ala-Lys-Cys-Ser-Lys-Leu-Met-Tyr-Asp-Cys-Cys-Ser-Gly-Ser-Cys-Ser-Gly-Thr-Val-Gly-Arg-Cys-NH2
CAS Number	247207-64-3
PubChem (CID)	16132255
ChemSpider	17288914
UNII	2P1P5JB93S
Chemical and physical data
Formula	C107H179N35O36S7
Molar mass	2756.234 g/mol
3D model (Jmol)	Interactive image
SMILES CSCC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CS)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CS)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CS)C(=O)N[C@@H](C=S)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](C=S)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C=S)C(N)=O
InChI InChI=1S/C107H179N35O36S7/c1-51(2)33-64(129-91(163)62(20-11-15-30-111)127-100(172)71(44-147)135-103(175)73(47-181)137-93(165)60(18-9-13-28-109)124-85(157)53(5)121-77(150)36-117-87(159)58(17-8-12-27-108)126-99(171)70(43-146)134-92(164)61(19-10-14-29-110)125-86(158)57(112)45-179)95(167)128-63(26-32-185-7)94(166)130-65(34-55-22-24-56(149)25-23-55)96(168)131-66(35-81(154)155)97(169)138-76(50-184)104(176)140-75(49-183)102(174)133-67(40-143)88(160)118-37-79(152)123-69(42-145)98(170)139-74(48-182)101(173)132-68(41-144)89(161)119-39-80(153)141-83(54(6)148)106(178)142-82(52(3)4)105(177)120-38-78(151)122-59(21-16-31-116-107(114)115)90(162)136-72(46-180)84(113)156/h22-25,46,48-49,51-54,57-76,82-83,143-149,179,181,184H,8-21,26-45,47,50,108-112H2,1-7H3,(H2,113,156)(H,117,159)(H,118,160)(H,119,161)(H,120,177)(H,121,150)(H,122,151)(H,123,152)(H,124,157)(H,125,158)(H,126,171)(H,127,172)(H,128,167)(H,129,163)(H,130,166)(H,131,168)(H,132,173)(H,133,174)(H,134,164)(H,135,175)(H,136,162)(H,137,165)(H,138,169)(H,139,170)(H,140,176)(H,141,153)(H,142,178)(H,154,155)(H4,114,115,116)/t53-,54+,57-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,82-,83-/m0/s1 Key:HBMCYCKNGADUQP-CFIKXUEXSA-N

Leconotide (INN) (code names CNSB004, AM336), also known as ω-conotoxin CVID, is an ω-conotoxin peptide isolated from the venom of Conus catus which is under investigation as an analgesic drug for the treatment of pain conditions.^[1][2]

It acts as an N-type voltage-gated calcium channel (Ca_v2.2) blocker, and is highly selective for this channel over the related P/Q-type voltage-gated calcium channel (Ca_v2.1).^[1][2]

Relative to ziconotide, leconotide is advantageous in that it is significantly less toxic, and for that reason can be administered intravenously as opposed to via intrathecal injection.^[3][4][5]

See also

• Ziconotide, an analgesic peptide derived from the toxin of the cone snail species Conus magus
• Lacosamide, an approved small molecule analgesic and anti-epileptic
• Ralfinamide, an investigational small molecule analgesic

References

1. Charlotte Allerton; David Fox (2013). Pain Therapeutics: Current and Future Treatment Paradigms. Royal Society of Chemistry. pp. 225–. ISBN 978-1-84973-645-9.
2. Gary Stephens; Sumiko Mochida (23 April 2013). Modulation of Presynaptic Calcium Channels. Springer Science & Business Media. pp. 326–. ISBN 978-94-007-6334-0.
3. Nervous System Diseases: Advances in Research and Treatment: 2011 Edition. ScholarlyEditions. 9 January 2012. pp. 217–. ISBN 978-1-4649-2221-3.
4. Kolosov, Anton; Goodchild, Colin S.; Cooke, Ian (2010). "CNSB004 (Leconotide) Causes Antihyperalgesia Without Side Effects When Given Intravenously: A Comparison with Ziconotide in a Rat Model of Diabetic Neuropathic Pain". Pain Medicine. 11 (2): 262–273. doi:10.1111/j.1526-4637.2009.00741.x. ISSN 1526-2375.
5. Kolosov, Anton; Aurini, Lucia; Williams, Elizabeth D.; Cooke, Ian; Goodchild, Colin S. (2011). "Intravenous Injection of Leconotide, an Omega Conotoxin: Synergistic Antihyperalgesic Effects with Morphine in a Rat Model of Bone Cancer Pain". Pain Medicine. 12 (6): 923–941. doi:10.1111/j.1526-4637.2011.01118.x. ISSN 1526-2375.