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MedKoo Cat#: 314227 | Name: Linaclotide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Linaclotide is an peptide agonist of guanylate cyclase 2C that is undergoing clinical trials for use in treating abdominal pain in patients with irritable bowel syndrome (IBS) accompanied by constipation. The drug also has promising outlooks for the treatment of gastroparesis, ulcerative colitis, chronic intestinal pseudo-obstruction (CIPO), and inertia coli as well. (Source: http://en.wikipedia.org/wiki/Linaclotide)

Chemical Structure

Linaclotide
Linaclotide
CAS#851199-59-2 (free base)

Theoretical Analysis

MedKoo Cat#: 314227

Name: Linaclotide

CAS#: 851199-59-2 (free base)

Chemical Formula: C59H79N15O21S6

Exact Mass: 1525.3899

Molecular Weight: 1526.75

Elemental Analysis: C, 46.41; H, 5.22; N, 13.76; O, 22.01; S, 12.60

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 650.00 2 Weeks
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Related CAS #
851199-60-5 (acetate) 851199-59-2 (free base)
Synonym
MM-416775; MM 416775; MM416775; MD-1100 acetate; Linaclotide; Linaclotide acetate; Linzess; Constela
IUPAC/Chemical Name
2-(32-amino-40-(2-amino-2-oxoethyl)-26-(2-carboxyethyl)-23-(4-hydroxybenzyl)-9-(1-hydroxyethyl)-3-methyl-1,4,7,10,13,22,25,28,31,38,41,47-dodecaoxotetracontahydro-1H-37,20-(epiminomethano)-6,29-(methanodithiomethano)pyrrolo[2,1-s][1,2,27,28,5,8,11,14,17,20,23,32,35,38,41]tetrathiaundecaazacyclotritetracontine-15-carboxamido)-3-(4-hydroxyphenyl)propanoic acid
InChi Key
KXGCNMMJRFDFNR-UHFFFAOYSA-N
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)
SMILES Code
CC(C1NC(C2CSSCC3NC(C(CSSCC(C(NC(C(N4CCCC4C(NC(C(N2)=O)C)=O)=O)CC(N)=O)=O)NC(C(NC(C(NC(C(NC3=O)CCC(O)=O)=O)CC5=CC=C(C=C5)O)=O)CSSCC(C(NC(C(O)=O)CC6=CC=C(C=C6)O)=O)NC(CNC1=O)=O)=O)N)=O)=O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#-T7R10C25
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Linaclotide is a potent and selective guanylate cyclase C agonist.
In vitro activity:
Linaclotide induced accumulation of cGMP in both human colonic cell lines in a concentration‐dependent manner (Fig. 2C) and importantly, more strongly enhanced phosphorylation of VASPSer239 compared to the cGMP analog 8‐Br‐cGMP, in both C2BBe (Fig. 2D) and T84 cells (Fig. 2E). These data confirm that linaclotide activates cGKII by phosphorylation in its downstream signaling pathway. Reference: Physiol Rep. 2017 Jun;5(11):e13299. https://pubmed.ncbi.nlm.nih.gov/28592587/
In vivo activity:
Linaclotide decreased the plasma levels of TMAO (trimethylamine-N-oxide) at a clinically used low dose of 10 μg/kg in the adenine-induced RF mouse model. At a high concentration of 100 μg/kg, linaclotide clearly improved renal function and reduced the levels of various uremic toxins. Reference: Nephrol Dial Transplant. 2020 Feb 1;35(2):250-264. https://pubmed.ncbi.nlm.nih.gov/31411705/
Solvent mg/mL mM comments
Solubility
DMF 30.0 19.65
DMSO 40.0 26.20
DMSO:PBS (pH 7.2) (1:4) 0.2 0.13
Water 16.7 10.92
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,526.75 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Ahsan MK, Tchernychev B, Kessler MM, Solinga RM, Arthur D, Linde CI, Silos-Santiago I, Hannig G, Ameen NA. Linaclotide activates guanylate cyclase-C/cGMP/protein kinase-II-dependent trafficking of CFTR in the intestine. Physiol Rep. 2017 Jun;5(11):e13299. doi: 10.14814/phy2.13299. PMID: 28592587; PMCID: PMC5471438. 2. Bryant AP, Busby RW, Bartolini WP, Cordero EA, Hannig G, Kessler MM, Pierce CM, Solinga RM, Tobin JV, Mahajan-Miklos S, Cohen MB, Kurtz CB, Currie MG. Linaclotide is a potent and selective guanylate cyclase C agonist that elicits pharmacological effects locally in the gastrointestinal tract. Life Sci. 2010 May 8;86(19-20):760-5. doi: 10.1016/j.lfs.2010.03.015. Epub 2010 Mar 20. PMID: 20307554. 3. Nanto-Hara F, Kanemitsu Y, Fukuda S, Kikuchi K, Asaji K, Saigusa D, Iwasaki T, Ho HJ, Mishima E, Suzuki T, Suzuki C, Tsukimi T, Matsuhashi T, Oikawa Y, Akiyama Y, Kure S, Owada Y, Tomioka Y, Soga T, Ito S, Abe T. The guanylate cyclase C agonist linaclotide ameliorates the gut-cardio-renal axis in an adenine-induced mouse model of chronic kidney disease. Nephrol Dial Transplant. 2020 Feb 1;35(2):250-264. doi: 10.1093/ndt/gfz126. PMID: 31411705. 4. Ge P, Ren J, Harrington AM, Grundy L, Castro J, Brierley SM, Hannig G. Linaclotide treatment reduces endometriosis-associated vaginal hyperalgesia and mechanical allodynia through viscerovisceral cross-talk. Pain. 2019 Nov;160(11):2566-2579. doi: 10.1097/j.pain.0000000000001657. PMID: 31335750.
In vitro protocol:
1. Ahsan MK, Tchernychev B, Kessler MM, Solinga RM, Arthur D, Linde CI, Silos-Santiago I, Hannig G, Ameen NA. Linaclotide activates guanylate cyclase-C/cGMP/protein kinase-II-dependent trafficking of CFTR in the intestine. Physiol Rep. 2017 Jun;5(11):e13299. doi: 10.14814/phy2.13299. PMID: 28592587; PMCID: PMC5471438. 2. Bryant AP, Busby RW, Bartolini WP, Cordero EA, Hannig G, Kessler MM, Pierce CM, Solinga RM, Tobin JV, Mahajan-Miklos S, Cohen MB, Kurtz CB, Currie MG. Linaclotide is a potent and selective guanylate cyclase C agonist that elicits pharmacological effects locally in the gastrointestinal tract. Life Sci. 2010 May 8;86(19-20):760-5. doi: 10.1016/j.lfs.2010.03.015. Epub 2010 Mar 20. PMID: 20307554.
In vivo protocol:
1. Nanto-Hara F, Kanemitsu Y, Fukuda S, Kikuchi K, Asaji K, Saigusa D, Iwasaki T, Ho HJ, Mishima E, Suzuki T, Suzuki C, Tsukimi T, Matsuhashi T, Oikawa Y, Akiyama Y, Kure S, Owada Y, Tomioka Y, Soga T, Ito S, Abe T. The guanylate cyclase C agonist linaclotide ameliorates the gut-cardio-renal axis in an adenine-induced mouse model of chronic kidney disease. Nephrol Dial Transplant. 2020 Feb 1;35(2):250-264. doi: 10.1093/ndt/gfz126. PMID: 31411705. 2. Ge P, Ren J, Harrington AM, Grundy L, Castro J, Brierley SM, Hannig G. Linaclotide treatment reduces endometriosis-associated vaginal hyperalgesia and mechanical allodynia through viscerovisceral cross-talk. Pain. 2019 Nov;160(11):2566-2579. doi: 10.1097/j.pain.0000000000001657. PMID: 31335750.
 

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