A peptide agonist of the guanylate cyclase C receptor
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Labeled Version(s)
28798Linaclotide-d4
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Linaclotide

Item No. 24085

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
L-cysteinyl-L-cysteinyl-L-α-glutamyl-L-tyrosyl-L-cysteinyl-L-cysteinyl-L-asparaginyl-L-prolyl-L-alanyl-L-cysteinyl-L-threonylglycyl-L-cysteinyl-L-tyrosine, cyclic (1→6),(2→10),(5→13)-tris(disulfide)
CAS Number
851199-59-2
Molecular Formula
C59H79N15O21S6
Formula Weight
1526.7
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH 7.2) (1:4): 0.20 mg/ml
SMILES
N[C@H](C(N[C@]1([H])C(N[C@H](CCC(O)=O)C2=O)=O)=O)CSSC[C@]([H])(NC3=O)C(N[C@@H](CC(N)=O)C(N4[C@@](C(N[C@H](C(N[C@](CSSC1)([H])C(NC([C@H](O)C)C(NCC(N[C@H](C(N[C@@H](CC5=CC=C(O)C=C5)C(O)=O)=O)CSSC[C@]3([H])NC([C@H](CC6=CC=C(O)C=C6)N2)=O)=O)=O)=O)=O)C)=O)([H])CCC4)=O)=O
InChi Code
InChI=1S/C59H79N15O21S6/c1-26-47(82)69-41-25-101-99-22-38-52(87)65-33(13-14-45(80)81)49(84)66-34(16-28-5-9-30(76)10-6-28)50(85)71-40(54(89)72-39(23-97-96-20-32(60)48(83)70-38)53(88)67-35(18-43(61)78)58(93)74-15-3-4-42(74)56(91)63-26)24-100-98-21-37(64-44(79)19-62-57(92)46(27(2)75)73-55(41)90)51(86)68-36(59(94)95)17-29-7-11-31(77)12-8-29/h5-12,26-27,32-42,46,75-77H,3-4,13-25,60H2,1-2H3,(H2,61,78)(H,62,92)(H,63,91)(H,64,79)(H,65,87)(H,66,84)(H,67,88)(H,68,86)(H,69,82)(H,70,83)(H,71,85)(H,72,89)(H,73,90)(H,80,81)(H,94,95)/t26-,27+,32-,33+,34-,35-,36-,37-,38-,39-,40-,41-,42-,46?/m0/s1
InChi Key
KXGCNMMJRFDFNR-VRMHCMCOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    1 mg

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    5 mg

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    10 mg

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    Product Description

    Linaclotide is a peptide agonist of the guanylate cyclase C receptor (Ki = 16.4 nM in a radioligand binding assay using mouse intestinal mucosa).1 Luminal exposure to 5 μg of linaclotide stimulates fluid secretion and cGMP concentration in jejunal loops isolated from wild-type mice but not guanylate cyclase C receptor-null mice. Linaclotide (100 μg/kg) increases intestinal transit rate in wild-type mice. It also reduces the number of phosphorylated ERK-positive dorsal horn neurons in the thoracolumbar spinal cord, a marker of nociceptive signaling, following noxious colorectal distension and mechanical hypersensitivity in a mouse model of TNBS-induced colitis.2 Formulations containing linaclotide have been used for the treatment of constipation and pain associated with irritable bowel syndrome.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bryant, A.P., Busby, R.W., Bartolini, W.P., et al. Linaclotide is a potent and selective guanylate cyclase C agonist that elicits pharmacological effects locally in the gastrointestinal tract. Life Sci. 86(19-20), 760-765 (2010).

    2. Castro, J., Harrington, A.M., Hughes, P.A., et al. Linaclotide inhibits colonic nociceptors and relieves abdominal pain via guanylate cyclase-C and extracellular cyclic guanosine 3',5'-monophosphate. Gastroenterology 145(6), 1334-1346 (2013).