An amylin analog
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Pramlintide (acetate hydrate)

Item No. 24093

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
25-L-proline-28-L-proline-29-L-proline-amylin (human), monoacetate hydrate
CAS Number
196078-30-5
Molecular Formula
C171H267N51O53S2 • XC2H4O2 [XH2O]
Formula Weight
3949.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 10 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
NC([C@@H](NC([C@@]([C@@H](C)O)([H])NC([C@H](CC(N)=O)NC([C@H](CO)NC(CNC([C@H](C(C)C)NC([C@H](CC(N)=O)NC([C@@]([C@@H](C)O)([H])NC([C@@H]1CCCN1C([C@@H]2CCCN2C([C@H](CC(C)C)NC([C@@]([C@H](CC)C)([H])NC([C@@H]3CCCN3C(CNC([C@@H](NC([C@H](CC(N)=O)NC([C@H](CC(N)=O)NC([C@H](CO)NC([C@H](CO)NC([C@@H](NC([C@H](C(C)C)NC([C@H](CC(C)C)NC([C@@H](NC([C@H](CC(N)=O)NC([C@@H](NC([C@H](CC(C)C)NC([C@H](CCCNC(N)=N)NC([C@H](CCC(N)=O)NC([C@@]([C@@H](C)O)([H])NC([C@@H](NC([C@@H](N4)CSSC[C@H](NC([C@H](CCCCN)N[H])=O)C(N[C@@H](CC(N)=O)C(N[C@]([C@@H](C)O)([H])C(N[C@H](C(N[C@]([C@@H](C)O)([H])C4=O)=O)C)=O)=O)=O)=O)C)=O)=O)=O)=O)=O)C)=O)=O)CC5=CC=CC=C5)=O)=O)=O)CC6=CN=CN6)=O)=O)=O)=O)=O)CC7=CC=CC=C7)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)CC8=CC=C(O)C=C8)=O.OC(C)=O.O
InChi Code
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
FVNLNEGMCMHEBF-WFVXIAQHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $72

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    5 mg

    $269

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    10 mg

    $501

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    25 mg

    $1,073

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    Product Description

    Pramlintide is a non-amyloidogenic analog of the antidiabetic peptide hormone amylin (Item Nos. 24274 | 24275) that contains proline residues substituted at positions 25, 28, and 29.1 It stimulates cAMP production in HEK293 cells expressing human amylin receptor 1a (AMY1a), AMY2a, and AMY3a (EC50s = 0.35, 22.9, and 0.89 nM, respectively).2 Pramlintide inhibits human islet amyloid polypeptide fibrilization in a concentration-dependent manner.3 In vivo, pramlintide (200 pg/kg) reduces brain levels of amyloid-β (1-40) (Aβ40; Item No. 21617) and increases spontaneous alternation in the Y-maze in the Tg2576 transgenic mouse model of Alzheimer's disease.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, H., Abedini, A., Ruzsicska, B., et al. Rationally designed, nontoxic, nonamyloidogenic analogues of human islet amyloid polypeptide with improved solubility. Biochemistry 53(37), 5876-5584 (2014).

    2. Gingell, J.J., Burns, E.R., and Hay, D.L. Activity of pramlintide, rat and human amylin but not Aβ1-42 at human amylin receptors. Endocrinology 155(1), 21-26 (2014).

    3. Wang, H., Ridgway, Z., Cao, P., et al. Analysis of the ability of pramlintide to inhibit amyloid formation by human islet amyloid polypeptide reveals a balance between optimal recognition and reduced amyloidogenicity. Biochemistry 54(44), 6704-6711 (2015).

    4. Zhu, H., Wang, X., Wallack, M., et al. Intraperitoneal injection of the pancreatic peptide amylin potently reduces behavioral impairment and brain amyloid pathology in murine models of Alzheimer’s disease. Mol. Psychiatry 20(2), 252-262 (2015).