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Chemistry

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Also known as: 28704-27-0, Cop-1, (2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;(2s)-2-aminopentanedioic acid;(2s)-2-aminopropanoic acid;(2s)-2,6-diaminohexanoic acid, Dtxsid50182865
Molecular Formula
C23H41N5O11
Molecular Weight
563.6  g/mol
InChI Key
YLOCGHYTXIINAI-XKUOMLDTSA-N

(2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid
Glatiramer acetate consists of the acetate salts of synthetic polypeptides, containing four naturally occurring amino acids: L-glutamic acid, L-alanine, L-tyrosine, and L-lysine with an average molar fraction of 0.141, 0.427, 0.095, and 0.338, respectively. The average molecular weight of glatiramer acetate is 5,000-9,000 daltons. It is an immunomodulator, licensed in much of the world for reduced frequency of relapses in relapsing-remitting multiple sclerosis.
1 2D Structure

(2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid;(2S)-2-aminopentanedioic acid;(2S)-2-aminopropanoic acid;(2S)-2,6-diaminohexanoic acid
2.1.2 InChI
InChI=1S/C9H11NO3.C6H14N2O2.C5H9NO4.C3H7NO2/c10-8(9(12)13)5-6-1-3-7(11)4-2-6;7-4-2-1-3-5(8)6(9)10;6-3(5(9)10)1-2-4(7)8;1-2(4)3(5)6/h1-4,8,11H,5,10H2,(H,12,13);5H,1-4,7-8H2,(H,9,10);3H,1-2,6H2,(H,7,8)(H,9,10);2H,4H2,1H3,(H,5,6)/t8-;5-;3-;2-/m0000/s1
2.1.3 InChI Key
YLOCGHYTXIINAI-XKUOMLDTSA-N
2.1.4 Canonical SMILES
CC(C(=O)O)N.C1=CC(=CC=C1CC(C(=O)O)N)O.C(CCN)CC(C(=O)O)N.C(CC(=O)O)C(C(=O)O)N
2.1.5 Isomeric SMILES
C[C@@H](C(=O)O)N.C1=CC(=CC=C1C[C@@H](C(=O)O)N)O.C(CCN)C[C@@H](C(=O)O)N.C(CC(=O)O)[C@@H](C(=O)O)N
2.2 Synonyms
2.2.1 Depositor-Supplied Synonyms

1. 28704-27-0

2. Cop-1

3. (2s)-2-amino-3-(4-hydroxyphenyl)propanoic Acid;(2s)-2-aminopentanedioic Acid;(2s)-2-aminopropanoic Acid;(2s)-2,6-diaminohexanoic Acid

4. Dtxsid50182865

2.3 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 563.6 g/mol
Molecular Formula C23H41N5O11
Hydrogen Bond Donor Count11
Hydrogen Bond Acceptor Count16
Rotatable Bond Count13
Exact Mass563.28025714 g/mol
Monoisotopic Mass563.28025714 g/mol
Topological Polar Surface Area337 Ų
Heavy Atom Count39
Formal Charge0
Complexity488
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count4
4 Drug and Medication Information
4.1 Drug Indication

For reduction of the frequency of relapses in patients with Relapsing-Remitting Multiple Sclerosis.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Glatiramer acetate was originally designed to mimic a protein in myelin, called myelin basic protein, with the intention of inducing EAE (an animal model of MS). Quite to the contrary, it was found to suppress the disease and as a result came to be trialed in human MS. There is some evidence that Glatiramer acetate converts the body's immune response from a Th1 type to a Th2 one, promotes suppressor T cells or acts as an altered peptide ligand. Studies in animals and in vitro systems suggest that upon its administration, glatiramer acetate-specific suppressor T-cells are induced and activated in the periphery. Some fraction of the injected material, either intact or partially hydrolyzed, is presumed to enter the lymphatic circulation, enabling it to reach regional lymph nodes, and some may enter the systemic circulation intact.


5.2 Metabolism/Metabolites

Hydrolyzed by proteases


5.3 Mechanism of Action

Glatiramer acetate (GA) exhibits strong and promiscuous binding to MHC molecules (HLA DRB1* variants) and consequent competition with various myelin antigens for their presentation to T cells. A further aspect of its action is potent induction of specific suppressor cells of the T helper 2 (Th2) type that migrate to the brain and lead to in situ bystander suppression. Furthermore, the GA-specific cells in the brain express the anti-inflammatory cytokines IL-10 and transforming growth factor beta, in addition to brain-derived neurotrophic factor, whereas they do not express the inflammatory cytokine IFN-gamma. Recent evidence also suggests that Glatiramer acetate directly inhibits dendritic cells and monocytes - both of which are circulating antigen presenting cells.


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API | Excipient name

Glatiramer

Synonyms

28704-27-0, Cop-1, (2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;(2s)-2-aminopentanedioic acid;(2s)-2-aminopropanoic acid;(2s)-2,6-diaminohexanoic acid, Dtxsid50182865

Cas Number

28704-27-0

About Glatiramer

Glatiramer acetate consists of the acetate salts of synthetic polypeptides, containing four naturally occurring amino acids: L-glutamic acid, L-alanine, L-tyrosine, and L-lysine with an average molar fraction of 0.141, 0.427, 0.095, and 0.338, respectively. The average molecular weight of glatiramer acetate is 5,000-9,000 daltons. It is an immunomodulator, licensed in much of the world for reduced frequency of relapses in relapsing-remitting multiple sclerosis.

(2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid Manufacturers

A (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid, including repackagers and relabelers. The FDA regulates (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

(2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid Suppliers

A (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid supplier is an individual or a company that provides (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid active pharmaceutical ingredient (API) or (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid finished formulations upon request. The (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid suppliers may include (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid API manufacturers, exporters, distributors and traders.

(2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid GMP

(2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid 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 (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid 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 (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid GMP manufacturer or (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid GMP API supplier for your needs.

(2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid CoA

A (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid CoA (Certificate of Analysis) is a formal document that attests to (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid's compliance with (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid specifications and serves as a tool for batch-level quality control.

(2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid CoA mostly includes findings from lab analyses of a specific batch. For each (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid 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.

(2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid may be tested according to a variety of international standards, such as European Pharmacopoeia ((2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid EP), (2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid JP (Japanese Pharmacopeia) and the US Pharmacopoeia ((2S)-2,6-diaminohexanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-aminopentanedioic acid; (2S)-2-aminopropanoic acid 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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