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Calcitonin gene-related peptide

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Calcitonin gene-related peptide is a member of the calcitonin family of peptides consisting of calcitonin, amylin, adrenomedullin, adrenomedullin 2 (intermedin) and calcitonin‑receptor‑stimulating peptide.

Category

Functional Peptides

Catalog number

BAT-013603

CAS number

83652-28-2

Molecular Formula

C163H266N50O50S2

Molecular Weight

3790.28

Specification
Reference Reading

IUPAC Name

(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S,3R)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-4-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(4R,7S,10S,13S,16S,19R)-19-[[(2S)-2-aminopropanoyl]amino]-16-(carboxymethyl)-7,13-bis[(1R)-1-hydroxyethyl]-10-methyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]amino]-3-methylbutanoyl]amino]-3-hydroxybutanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-hydroxypropanoyl]amino]acetyl]amino]acetyl]amino]-3-methylbutanoyl]amino]-3-methylbutanoyl]amino]hexanoyl]amino]-4-oxobutanoyl]amino]-4-oxobutanoyl]amino]-3-phenylpropanoyl]amino]-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoyl]amino]-4-oxobutanoyl]amino]-3-methylbutanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]propanoyl]amino]-3-phenylpropanoic acid

Synonyms

Calcitonin, pro-; CALCA protein, human; CALC1 protein, human; CGRP1 protein, human

Sequence

ACDTATCVTHRLAGLLSRSGGVVKNNFVPTNVGSKAF

InChI

InChI=1S/C163H266N50O50S2/c1-73(2)52-96(185-116(225)65-178-130(231)82(18)182-138(239)97(53-74(3)4)191-136(237)94(44-35-49-175-162(170)171)187-141(242)100(57-91-62-174-72-181-91)197-158(259)128(88(24)220)212-155(256)123(79(13)14)206-150(251)110-71-265-264-70-109(202-129(230)81(17)166)149(250)196-104(61-119(228)229)146(247)210-125(85(21)217)156(257)184-84(20)132(233)209-126(86(22)218)159(260)203-110)139(240)192-98(54-75(5)6)140(241)201-108(69-216)148(249)189-95(45-36-50-176-163(172)173)137(238)200-106(67-214)133(234)179-63-115(224)177-64-118(227)204-121(77(9)10)154(255)207-122(78(11)12)153(254)190-93(43-32-34-48-165)135(236)194-101(58-112(167)221)143(244)195-102(59-113(168)222)142(243)193-99(55-89-38-27-25-28-39-89)144(245)208-124(80(15)16)160(261)213-51-37-46-111(213)151(252)211-127(87(23)219)157(258)198-103(60-114(169)223)145(246)205-120(76(7)8)152(253)180-66-117(226)186-107(68-215)147(248)188-92(42-31-33-47-164)134(235)183-83(19)131(232)199-105(161(262)263)56-90-40-29-26-30-41-90/h25-30,38-41,62,72-88,92-111,120-128,214-220H,31-37,42-61,63-71,164-166H2,1-24H3,(H2,167,221)(H2,168,222)(H2,169,223)(H,174,181)(H,177,224)(H,178,231)(H,179,234)(H,180,253)(H,182,239)(H,183,235)(H,184,257)(H,185,225)(H,186,226)(H,187,242)(H,188,248)(H,189,249)(H,190,254)(H,191,237)(H,192,240)(H,193,243)(H,194,236)(H,195,244)(H,196,250)(H,197,259)(H,198,258)(H,199,232)(H,200,238)(H,201,241)(H,202,230)(H,203,260)(H,204,227)(H,205,246)(H,206,251)(H,207,255)(H,208,245)(H,209,233)(H,210,247)(H,211,252)(H,212,256)(H,228,229)(H,262,263)(H4,170,171,175)(H4,172,173,176)/t81-,82-,83-,84-,85+,86+,87+,88+,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,120-,121-,122-,123-,124-,125-,126-,127-,128-/m0/s1

InChI Key

PBGNJGVTFINXOG-XJVRLEFXSA-N

Canonical SMILES

CC1C(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)N1)C(C)O)CC(=O)O)NC(=O)C(C)N)C(=O)NC(C(C)C)C(=O)NC(C(C)O)C(=O)NC(CC2=CN=CN2)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC(C)C)C(=O)NC(C)C(=O)NCC(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(CO)C(=O)NC(CCCNC(=N)N)C(=O)NC(CO)C(=O)NCC(=O)NCC(=O)NC(C(C)C)C(=O)NC(C(C)C)C(=O)NC(CCCCN)C(=O)NC(CC(=O)N)C(=O)NC(CC(=O)N)C(=O)NC(CC3=CC=CC=C3)C(=O)NC(C(C)C)C(=O)N4CCCC4C(=O)NC(C(C)O)C(=O)NC(CC(=O)N)C(=O)NC(C(C)C)C(=O)NCC(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(C)C(=O)NC(CC5=CC=CC=C5)C(=O)O)C(C)O

1. Calcitonin gene-related peptide and pituitary adenylate cyclase-activating polypeptide in migraine treatment

Rogelio Dominguez-Moreno, Thien Phu Do, Messoud Ashina Curr Opin Endocrinol Diabetes Obes. 2022 Apr 1;29(2):225-231. doi: 10.1097/MED.0000000000000717.

Purpose of review: To review the latest advances in migraine management with a focus on medications specifically developed for the treatment of migraine. Recent findings: Randomized clinical trials demonstrated the efficacy of calcitonin gene-related peptide (CGRP) mAbs for the preventive treatment of migraine and the small molecule CGRP receptor antagonist gepants for acute abortion and prevention of migraine attacks. Pituitary adenylate cyclase-activating polypeptide (PACAP) is another signaling molecule of interest and represents a potential new drug class of mechanism-based migraine medications. Drugs targeting PACAP are currently undergoing clinical trials, and the coming years will reveal whether this class of drugs will expand our therapeutic armamentarium. Summary: Here, we summarize the role of CGRP and PACAP in migraine pathophysiology and discuss novel therapies targeting the CGRP and PACAP signaling pathways.

2. Calcitonin gene-related peptide: physiology and pathophysiology

F A Russell, R King, S-J Smillie, X Kodji, S D Brain Physiol Rev. 2014 Oct;94(4):1099-142. doi: 10.1152/physrev.00034.2013.

Calcitonin gene-related peptide (CGRP) is a 37-amino acid neuropeptide. Discovered 30 years ago, it is produced as a consequence of alternative RNA processing of the calcitonin gene. CGRP has two major forms (α and β). It belongs to a group of peptides that all act on an unusual receptor family. These receptors consist of calcitonin receptor-like receptor (CLR) linked to an essential receptor activity modifying protein (RAMP) that is necessary for full functionality. CGRP is a highly potent vasodilator and, partly as a consequence, possesses protective mechanisms that are important for physiological and pathological conditions involving the cardiovascular system and wound healing. CGRP is primarily released from sensory nerves and thus is implicated in pain pathways. The proven ability of CGRP antagonists to alleviate migraine has been of most interest in terms of drug development, and knowledge to date concerning this potential therapeutic area is discussed. Other areas covered, where there is less information known on CGRP, include arthritis, skin conditions, diabetes, and obesity. It is concluded that CGRP is an important peptide in mammalian biology, but it is too early at present to know if new medicines for disease treatment will emerge from our knowledge concerning this molecule.

3. Calcitonin gene-related peptide (CGRP): a new target for migraine

Andrew F Russo Annu Rev Pharmacol Toxicol. 2015;55:533-52. doi: 10.1146/annurev-pharmtox-010814-124701. Epub 2014 Oct 8.

Migraine is a neurological disorder that manifests as a debilitating headache associated with altered sensory perception. The neuropeptide calcitonin gene-related peptide (CGRP) is now firmly established as a key player in migraine. Clinical trials carried out during the past decade have proved that CGRP receptor antagonists are effective for treating migraine, and antibodies to the receptor and CGRP are currently under investigation. Despite this progress in the clinical arena, the mechanisms by which CGRP triggers migraine remain uncertain. This review discusses mechanisms whereby CGRP enhances sensitivity to sensory input at multiple levels in both the periphery and central nervous system. Future studies on epistatic and epigenetic regulators of CGRP actions are expected to shed further light on CGRP actions in migraine. In conclusion, targeting CGRP represents an approachable therapeutic strategy for migraine.