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Safety Information

SML3710

Sigma-Aldrich

Linaclotide

≥95% (HPLC)

Synonym(s):

CCEFCCNPACTGCF-OH cyclo(1-6),(2-10),(5-13)-tris(disulfide), Cys-Cys-Glu-Tyr-Cys-Cys-Asn-Pro-Ala-Cys-Thr-Gly-Cys-Tyr-OH cyclo(1-6),(2-10),(5-13)-tris(disulfide), 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-OH cyclo(1-6),(2-10),(5-13)-tris(disulfide)

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About This Item

Empirical Formula (Hill Notation):
C59H79N15O21S6
CAS Number:
851199-59-2
Molecular Weight:
1526.74
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

(Powder or Lyophilized powder or film)

storage condition

desiccated

color

white to off-white

storage temp.

-10 to -25°C

SMILES string

S1SC[C@@H]2NC(=O)[C@@H](NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)[C@H]4NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CSSC4)N)C1)CCC(=O)O)Cc6ccc(cc6)O)CSSC[C@H](NC(=O)CNC(=O)C(NC2=O)[C@H](O)C)C(=O)N[C@@H](Cc5ccc(cc5)O)C(=O)O)CC(=O)N)C

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-

InChI key

KXGCNMMJRFDFNR-IURAOCFRSA-N

Biochem/physiol Actions

Linaclotide is an orally active guanylate cyclase-C (GC-C) agonist that competes against bacterial STa enterotoxin binding to intestinal mucosal membranes from wild-type, but not GC-C null, mice (Ki = 16.4 nM). Linaclotide stimulates fluid secretion, upregulates cGMP accumulation in the intestinal lumen (5 μg/100 μL via injection into surgically ligated intestinal loops), and significantly increases the rate of gastrointestinal transit when administered orally in mice in vivo (100 μg/kg p.o.).

Caution

Hygroscopic

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000378035
0000378035
0000239578
0000242552
0000242552

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Alexander P Bryant et al.
Life sciences, 86(19-20), 760-765 (2010-03-24)
Linaclotide is an orally administered 14-amino acid peptide being developed for the treatment of constipation-predominant irritable bowel syndrome (IBS-C) and chronic constipation. We determined the stability of linaclotide in the intestine, measured the oral bioavailability, and investigated whether the pharmacodynamic
John Cuppoletti et al.
BMC pharmacology, 12, 3-3 (2012-05-05)
Linaclotide has been proposed as a treatment for the same gastrointestinal indications for which lubiprostone has been approved, chronic idiopathic constipation and irritable bowel syndrome with constipation. Stressors damage the epithelial cell barrier and cellular homeostasis leading to loss of
Robert W Busby et al.
European journal of pharmacology, 649(1-3), 328-335 (2010-09-25)
Linaclotide is a first-in-class, orally administered 14-amino acid peptide that is in development for the treatment of irritable bowel syndrome with constipation and chronic constipation. We have characterized the solution structure of linaclotide, the in vitro binding and agonist activity

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