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Chemistry

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Also known as: Dolcanatide [usan], Unii-wu977t914k, Gtpl10011, Wu977t914k, Hy-p3499, 1092457-65-2
Molecular Formula
C65H104N18O26S4
Molecular Weight
1681.9  g/mol
InChI Key
NSPHQWLKCGGCQR-HLHYUOOASA-N

Dolcanatide
Dolcanatide is an orally administered analog of the human endogenous natriuretic hormone uroguanylin and guanylate cyclase C (GC-C) agonist, with potential laxative, anti-nociceptive and anti-inflammatory activities. Upon administration, dolcanatide, by mimicking uroguanylin, binds to and activates GC-C locally on endothelial cells in the gastrointestinal (GI) tract, without entering the systemic circulation. Activation of GC-C results in an increase in cyclic guanosine monophosphate (cGMP). Increased concentrations of cGMP lead to the activation of the anion channel cystic fibrosis transmembrane conductance regulator (CFTR). CFTR activation increases the secretion of negatively charged ions, particularly chloride and bicarbonate, into the GI tract lumen, which further drives sodium ions and then water into the lumen. This leads to increased fluid secretion in the GI tract, accelerated transit and changes in stool consistency. In addition, ion channel modulation may decrease muscle contractions and the activity of pain-sensing nerves, thereby decreasing intestinal pain. Also, GC-C may inhibit the secretion of pro-inflammatory cytokines, which may ameliorate GI inflammation. Uroguanylin, a naturally occurring human GI peptide, is a ligand for GC-C and plays a key role in anti-inflammatory processes in the GI tract.
1 2D Structure

Dolcanatide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2R)-2-[[(1R,4S,7S,10S,13S,16R,19S,22S,25R,32S,38R)-10-(2-amino-2-oxoethyl)-25-[[(2S)-4-carboxy-2-[[(2S)-3-carboxy-2-[[(2R)-2,4-diamino-4-oxobutanoyl]amino]propanoyl]amino]butanoyl]amino]-22-(2-carboxyethyl)-32-[(1R)-1-hydroxyethyl]-4-methyl-19-(2-methylpropyl)-3,6,9,12,15,18,21,24,30,33,36-undecaoxo-7,13-di(propan-2-yl)-27,28,40,41-tetrathia-2,5,8,11,14,17,20,23,31,34,37-undecazabicyclo[14.13.13]dotetracontane-38-carbonyl]amino]-4-methylpentanoic acid
2.1.2 InChI
InChI=1S/C65H104N18O26S4/c1-25(2)15-34-55(98)80-41-24-113-110-21-38(58(101)77-37(65(108)109)16-26(3)4)71-44(87)20-69-62(105)50(30(10)84)83-61(104)40(78-51(94)29(9)70-63(106)48(27(5)6)81-57(100)35(18-43(68)86)76-64(107)49(28(7)8)82-60(41)103)23-112-111-22-39(59(102)73-32(53(96)75-34)11-13-45(88)89)79-54(97)33(12-14-46(90)91)72-56(99)36(19-47(92)93)74-52(95)31(66)17-42(67)85/h25-41,48-50,84H,11-24,66H2,1-10H3,(H2,67,85)(H2,68,86)(H,69,105)(H,70,106)(H,71,87)(H,72,99)(H,73,102)(H,74,95)(H,75,96)(H,76,107)(H,77,101)(H,78,94)(H,79,97)(H,80,98)(H,81,100)(H,82,103)(H,83,104)(H,88,89)(H,90,91)(H,92,93)(H,108,109)/t29-,30+,31+,32-,33-,34-,35-,36-,37+,38-,39-,40-,41-,48-,49-,50-/m0/s1
2.1.3 InChI Key
NSPHQWLKCGGCQR-HLHYUOOASA-N
2.1.4 Canonical SMILES
CC1C(=O)NC2CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(NC(=O)CNC(=O)C(NC2=O)C(C)O)C(=O)NC(CC(C)C)C(=O)O)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)C(C)C)CC(=O)N)C(C)C)CC(C)C)CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CC(=O)O)NC(=O)C(CC(=O)N)N
2.1.5 Isomeric SMILES
C[C@H]1C(=O)N[C@H]2CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@H](NC(=O)CNC(=O)[C@@H](NC2=O)[C@@H](C)O)C(=O)N[C@H](CC(C)C)C(=O)O)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)C(C)C)CC(=O)N)C(C)C)CC(C)C)CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@@H](CC(=O)N)N
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Sp-333

2.2.2 Depositor-Supplied Synonyms

1. Dolcanatide [usan]

2. Unii-wu977t914k

3. Gtpl10011

4. Wu977t914k

5. Hy-p3499

6. 1092457-65-2

7. D-leucine, D-asparaginyl-l-alpha-aspartyl-l-alpha-glutamyl-l-cysteinyl-l-alpha-glutamyl-l-leucyl-l-cysteinyl-l-valyl-l-asparaginyl-l-valyl-l-alanyl-l-cysteinyl-l-threonylglycyl-l-cysteinyl-, Cyclic (4->12),(7->15)-bis(disulfide)

8. Cs-0615000

2.3 Create Date
2015-08-15
3 Chemical and Physical Properties
Molecular Weight 1681.9 g/mol
Molecular Formula C65H104N18O26S4
XLogP3-8.2
Hydrogen Bond Donor Count23
Hydrogen Bond Acceptor Count31
Rotatable Bond Count28
Exact Mass1680.6252002 g/mol
Monoisotopic Mass1680.6252002 g/mol
Topological Polar Surface Area819 Ų
Heavy Atom Count113
Formal Charge0
Complexity3490
Isotope Atom Count0
Defined Atom Stereocenter Count16
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Guanylyl Cyclase C Agonists

Compunds that bind to and activate GUANYLYL CYCLASE-C RECEPTORS. (See all compounds classified as Guanylyl Cyclase C Agonists.)


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ABOUT THIS PAGE

Dolcanatide Manufacturers

A Dolcanatide manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Dolcanatide, including repackagers and relabelers. The FDA regulates Dolcanatide manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Dolcanatide API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Dolcanatide Suppliers

A Dolcanatide supplier is an individual or a company that provides Dolcanatide active pharmaceutical ingredient (API) or Dolcanatide finished formulations upon request. The Dolcanatide suppliers may include Dolcanatide API manufacturers, exporters, distributors and traders.

Dolcanatide GMP

Dolcanatide Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Dolcanatide GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Dolcanatide GMP manufacturer or Dolcanatide GMP API supplier for your needs.

Dolcanatide CoA

A Dolcanatide CoA (Certificate of Analysis) is a formal document that attests to Dolcanatide's compliance with Dolcanatide specifications and serves as a tool for batch-level quality control.

Dolcanatide CoA mostly includes findings from lab analyses of a specific batch. For each Dolcanatide CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Dolcanatide may be tested according to a variety of international standards, such as European Pharmacopoeia (Dolcanatide EP), Dolcanatide JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Dolcanatide USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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