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]

References[edit]

^ ^a ^b Charlotte Allerton; David Fox (2013). Pain Therapeutics: Current and Future Treatment Paradigms. Royal Society of Chemistry. pp. 225–. ISBN 978-1-84973-645-9.
^ ^a ^b Gary Stephens; Sumiko Mochida (23 April 2013). Modulation of Presynaptic Calcium Channels. Springer Science & Business Media. pp. 326–. ISBN 978-94-007-6334-0.
^ Nervous System Diseases: Advances in Research and Treatment: 2011 Edition. ScholarlyEditions. 9 January 2012. pp. 217–. ISBN 978-1-4649-2221-3.
^ 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.
^ 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.

This analgesic-related article is a stub. You can help Wikipedia by expanding it.

[AllertonFox2013-1] Charlotte Allerton; David Fox (2013). Pain Therapeutics: Current and Future Treatment Paradigms. Royal Society of Chemistry. pp. 225–. ISBN 978-1-84973-645-9.

[StephensMochida2013-2] 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.

[KolosovGoodchild2010-4] 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.

[KolosovAurini2011-5] 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.

[1]

[2]

[3]

[4]

[5]

v t e Neuropathic pain and fibromyalgia pharmacotherapies

Monoaminergics	SNRIs (e.g., duloxetine, milnacipran) TCAs (e.g., amitriptyline, nortriptyline, dosulepin) Tapentadol Tramadol

Ion channel blockers	Anticonvulsants (e.g., gabapentin, pregabalin, carbamazepine, oxcarbazepine, lacosamide, lamotrigine) Local anesthetics (e.g., lidocaine) Mexiletine TCAs (e.g., amitriptyline, nortriptyline, desipramine) Ziconotide

Others	Alpha lipoic acid Benfotiamine Botulinum toxin A Bupropion Cannabinoids (e.g., cannabis, dronabinol, nabilone) NMDAR antagonists (e.g., ketamine, dextromethorphan, methadone) Opioids (e.g., hydrocodone, morphine, oxycodone, methadone, buprenorphine, tramadol, tapentadol) Sodium oxybate (GHB)

Leconotide

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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