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Pramlintide

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Pramlintide, a synthetic version of amylin, is the first in a new class of pharmaceutical agents and exhibits high affinity for amylin, CGRP and calcitonin receptors (Ki values are 0.023, 3.8 and 5.1 nM respectively).

Category

Peptide Inhibitors

Catalog number

BAT-010050

CAS number

151126-32-8

Molecular Formula

C171H267N51O53S2

Molecular Weight

3949.42

Specification
Reference Reading

IUPAC Name

(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-4-amino-1-[[(2S)-1-[[2-[(2S)-2-[[(2S,3S)-1-[[(2S)-1-[(2S)-2-[(2S)-2-[[(2S,3R)-1-[[(2S)-4-amino-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-4-amino-1-[[(2S,3R)-1-[[(2S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]carbamoyl]pyrrolidine-1-carbonyl]pyrrolidin-1-yl]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-2-oxoethyl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]-2-[[(2S,3R)-2-[[(2S)-2-[[(4R,7S,10S,13S,16S,19R)-16-(2-amino-2-oxoethyl)-19-[[(2S)-2,6-diaminohexanoyl]amino]-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]propanoyl]amino]-3-hydroxybutanoyl]amino]pentanediamide

Synonyms

AC 0137; AC 137; Symlin; Tripro-Amylin; riproamylin; Pramlintide; LS-181996; LS181996; Amylin

Sequence

KCNTATCATQRLANFLVHSSNNFGPILPPTNVGSNTY

Storage

Store in a cool and dry place (or refer to the Certificate of Analysis).

InChI

InChI=1S/C171H267N51O53S2.C2H4O2.H2O/c1-21-81(12)130(163(268)207-110(56-78(6)7)169(274)222-53-33-42-118(222)170(275)221-52-32-41-117(221)160(265)219-135(89(20)230)167(272)206-109(66-125(180)238)151(256)212-128(79(8)9)161(266)186-68-126(239)192-111(70-223)154(259)203-107(64-123(178)236)152(257)218-134(88(19)229)166(271)195-98(136(181)241)57-92-43-45-94(231)46-44-92)214-159(264)116-40-31-51-220(116)127(240)69-187-141(246)101(58-90-34-24-22-25-35-90)199-148(253)105(62-121(176)234)201-149(254)106(63-122(177)235)202-155(260)112(71-224)209-156(261)113(72-225)208-146(251)103(60-93-67-184-75-188-93)205-162(267)129(80(10)11)213-150(255)100(55-77(4)5)198-145(250)102(59-91-36-26-23-27-37-91)200-147(252)104(61-120(175)233)196-137(242)82(13)189-144(249)99(54-76(2)3)197-142(247)96(39-30-50-185-171(182)183)193-143(248)97(47-48-119(174)232)194-165(270)132(86(17)227)215-138(243)83(14)190-157(262)114-73-276-277-74-115(210-140(245)95(173)38-28-29-49-172)158(263)204-108(65-124(179)237)153(258)217-131(85(16)226)164(269)191-84(15)139(244)216-133(87(18)228)168(273)211-114;1-2(3)4;/h22-27,34-37,43-46,67,75-89,95-118,128-135,223-231H,21,28-33,38-42,47-66,68-74,172-173H2,1-20H3,(H2,174,232)(H2,175,233)(H2,176,234)(H2,177,235)(H2,178,236)(H2,179,237)(H2,180,238)(H2,181,241)(H,184,188)(H,186,266)(H,187,246)(H,189,249)(H,190,262)(H,191,269)(H,192,239)(H,193,248)(H,194,270)(H,195,271)(H,196,242)(H,197,247)(H,198,250)(H,199,253)(H,200,252)(H,201,254)(H,202,260)(H,203,259)(H,204,263)(H,205,267)(H,206,272)(H,207,268)(H,208,251)(H,209,261)(H,210,245)(H,211,273)(H,212,256)(H,213,255)(H,214,264)(H,215,243)(H,216,244)(H,217,258)(H,218,257)(H,219,265)(H4,182,183,185);1H3,(H,3,4);1H2/t81-,82-,83-,84-,85+,86+,87+,88+,89+,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,128-,129-,130-,131-,132-,133-,134-,135-;;/m0../s1

InChI Key

TZIRZGBAFTZREM-MKAGXXMWSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CC(C)C)C(=O)N1CCCC1C(=O)N2CCCC2C(=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(CC(=O)N)C(=O)NC(C(C)O)C(=O)NC(CC3=CC=C(C=C3)O)C(=O)N)NC(=O)C4CCCN4C(=O)CNC(=O)C(CC5=CC=CC=C5)NC(=O)C(CC(=O)N)NC(=O)C(CC(=O)N)NC(=O)C(CO)NC(=O)C(CO)NC(=O)C(CC6=CNC=N6)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC7=CC=CC=C7)NC(=O)C(CC(=O)N)NC(=O)C(C)NC(=O)C(CC(C)C)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCC(=O)N)NC(=O)C(C(C)O)NC(=O)C(C)NC(=O)C8CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N8)C(C)O)C)C(C)O)CC(=O)N)NC(=O)C(CCCCN)N.CC(=O)O.O

1.Hypothalamic Amylin Acts in Concert with Leptin to Regulate Food Intake.

Li Z1, Kelly L1, Heiman M2, Greengard P3, Friedman JM4. Cell Metab. 2015 Dec 1;22(6):1059-67. doi: 10.1016/j.cmet.2015.10.012. Epub 2015 Nov 19.

In this report we evaluated the functions of hypothalamic amylin in vivo and in vitro. Profiling of hypothalamic neurons revealed that islet amyloid polypeptide (Iapp, precursor to amylin) is expressed in neurons in the lateral hypothalamus, arcuate nucleus, medial preoptic area, and elsewhere. Hypothalamic expression of lapp is markedly decreased in ob/ob mice and normalized by exogenous leptin. In slices, amylin and leptin had similar electrophysiologic effects on lateral hypothalamic leptin receptor ObRb-expressing neurons, while the amylin antagonist AC187 inhibited their activity and blunted the effect of leptin. Finally, i.c.v. infusion of AC187 acutely reduced the anorectic effects of leptin. These data show that hypothalamic amylin is transcriptionally regulated by leptin, that it can act directly on ObRb neurons in concert with leptin, and that it regulates feeding. These findings provide a potential mechanism for the increased efficacy of a metreleptin/pramlintide combination therapy for obesity.

2.Immunogenicity associated with metreleptin treatment in patients with obesity or lipodystrophy.

Chan JL1, Koda J2, Heilig JS3, Cochran EK4, Gorden P4, Oral EA5, Brown RJ4. Clin Endocrinol (Oxf). 2015 Nov 21. doi: 10.1111/cen.12980. [Epub ahead of print]

OBJECTIVE: Recombinant human leptin (metreleptin) improves glycemia and hypertriglyceridemia in patients with generalized lipodystrophy; antibody development with in vitro neutralizing activity has been reported. We aimed to characterize anti-metreleptin antibody development, including in vitro neutralizing activity.

3.Impact of Disease Duration on the Effects of Pramlintide in Type 1 Diabetes: A Post Hoc Analysis of Three Clinical Trials.

Herrmann K1, Brunell SC1, Li Y1, Zhou M2, Maggs DG1. Adv Ther. 2016 Apr 12. [Epub ahead of print]

INTRODUCTION: Adjunctive mealtime use of the amylin analog pramlintide improves postprandial hyperglycemia in patients with type 1 diabetes. This post hoc analysis of three randomized trials evaluated whether disease duration affected responses to pramlintide.

4.Amylin-mediated control of glycemia, energy balance, and cognition.

Mietlicki-Baase EG1. Physiol Behav. 2016 Feb 27. pii: S0031-9384(16)30078-6. doi: 10.1016/j.physbeh.2016.02.034. [Epub ahead of print]

Amylin, a peptide hormone produced in the pancreas and in the brain, has well-established physiological roles in glycemic regulation and energy balance control. It improves postprandial blood glucose levels by suppressing gastric emptying and glucagon secretion; these beneficial effects have led to the FDA-approved use of the amylin analog pramlintide in the treatment of diabetes mellitus. Amylin also acts centrally as a satiation signal, reducing food intake and body weight. The ability of amylin to promote negative energy balance, along with its unique capacity to cooperatively facilitate or enhance the intake- and body weight-suppressive effects of other neuroendocrine signals like leptin, have made amylin a leading target for the development of novel pharmacotherapies for the treatment of obesity. In addition to these more widely studied effects, a growing body of literature suggests that amylin may play a role in processes related to cognition, including the neurodegeneration and cognitive deficits associated with Alzheimer's disease (AD).