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    Chemistry

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    Also known as: 415903-37-6, Cj-023423, Aat-007, Cj 023423, Rq-7, Rq-00000007
    Molecular Formula
    C26H29N5O3S
    Molecular Weight
    491.6  g/mol
    InChI Key
    HZVLFTCYCLXTGV-UHFFFAOYSA-N
    FDA UNII
    J9F5ZPH7NB
    Grapiprant
    Grapiprant is an orally bioavailable antagonist of the prostaglandin E receptor subtype 4 (EP4), with potential analgesic, immunomodulating and antineoplastic activities. Upon administration of grapiprant, this agent selectively binds to and inhibits the binding of prostaglandin E2 (PGE2) and prevents the activation of the EP4 receptor. This inhibits PGE2-EP4 receptor-mediated signaling and prevents proliferation in tumor cells in which the PGE2-EP4 signaling pathway is over-activated. In addition, EP4 receptor inhibition modulates the immune system by preventing both interleukin-23 (IL-23) production and the IL-23-mediated expansion of Th17 cells. As EP4 is expressed by peripheral sensory neurons, blockade of EP4-mediated signaling may induce an analgesic effect. EP4, a prostanoid receptor subtype, is a G protein-coupled receptor that is expressed in certain types of cancers; it promotes tumor cell proliferation and invasion.
    1 2D Structure

    Grapiprant

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[2-[4-(2-ethyl-4,6-dimethylimidazo[4,5-c]pyridin-1-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea
    2.1.2 InChI
    InChI=1S/C26H29N5O3S/c1-5-24-29-25-19(4)28-18(3)16-23(25)31(24)21-10-8-20(9-11-21)14-15-27-26(32)30-35(33,34)22-12-6-17(2)7-13-22/h6-13,16H,5,14-15H2,1-4H3,(H2,27,30,32)
    2.1.3 InChI Key
    HZVLFTCYCLXTGV-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCC1=NC2=C(N1C3=CC=C(C=C3)CCNC(=O)NS(=O)(=O)C4=CC=C(C=C4)C)C=C(N=C2C)C
    2.2 Other Identifiers
    2.2.1 UNII
    J9F5ZPH7NB
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-(2-(4-(2-ethyl-4,6-dimethylimidazo(4,5-c)pyridin-1-yl)phenyl)ethyl)-3-(4-methylphenyl)sulfonylurea

    2. Aat-007

    3. Cj 023,423

    4. Cj 023423

    5. Cj-023

    6. Cj-023,423

    7. Cj-023423

    8. Mr-10a7

    9. Mr10a7

    10. N-(((2-(4-(2-ethyl-4,6-dimethyl-1h-imidazo(4,5-c)pyridin-1-yl) Phenyl)ethyl)amino)carbonyl)-4-methylbenzenesulfonamide

    11. Rq-00000007

    12. Rq-7

    2.3.2 Depositor-Supplied Synonyms

    1. 415903-37-6

    2. Cj-023423

    3. Aat-007

    4. Cj 023423

    5. Rq-7

    6. Rq-00000007

    7. Mr-10a7

    8. Cj-023,423

    9. N-((4-(2-ethyl-4,6-dimethyl-1h-imidazo[4,5-c]pyridin-1-yl)phenethyl)carbamoyl)-4-methylbenzenesulfonamide

    10. Cj-023

    11. Mr10a7

    12. J9f5zph7nb

    13. Grapiprant (cj-023423)

    14. 706802-34-8

    15. Cj-023423;rq-00000007;aat-007

    16. 1-[2-[4-(2-ethyl-4,6-dimethylimidazo[4,5-c]pyridin-1-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea

    17. Benzenesulfonamide, N-(((2-(4-(2-ethyl-4,6-dimethyl-1h-imidazo(4,5-c)pyridin-1-yl)phenyl)ethyl)amino)carbonyl)-4-methyl-

    18. Grapiprant [usan:inn]

    19. Unii-j9f5zph7nb

    20. 1-(2-(4-(2-ethyl-4,6-dimethylimidazo(4,5-c)pyridin-1-yl)phenyl)ethyl)-3-(4-methylphenyl)sulfonylurea

    21. N-(((2-(4-(2-ethyl-4,6-dimethyl-1h-imidazo(4,5-c)pyridin-1-yl)phenyl)ethyl)amino)carbonyl)-4-methylbenzenesulfonamide

    22. N-[([2-[4-(2-ethyl-4,6-dimethyl-1h-imidazo[4,5-c]pyridin-1-yl)phenyl]ethyl]amino)carbonyl]-4-methylbenzenesulfonamide

    23. Grapiprant [mi]

    24. Grapiprant [inn]

    25. Grapiprant (usan/inn)

    26. Grapiprant [usan]

    27. Grapiprant [who-dd]

    28. Schembl120428

    29. Gtpl5858

    30. Grapiprant [green Book]

    31. Chembl3039498

    32. Dtxsid60194419

    33. Bcp20570

    34. Ex-a2544

    35. Bdbm50107283

    36. S6694

    37. Zinc38228051

    38. Akos030526811

    39. Aat-007cj-023423

    40. Cs-5392

    41. Db12836

    42. Sb18902

    43. Ac-36123

    44. As-77380

    45. Hy-16781

    46. A15964

    47. D10638

    48. D83673

    49. A900379

    50. Q27077852

    51. B0084-470919

    52. Cj-023423; Rq-00000007; Aat-007

    53. Grapiprant; Rq-00000007; Aat-007; Cj-023423

    54. 2-ethyl-4,6-dimethyl-1-(4-(2-(((((4-methylphenyl)sulfonyl)amino)carbonyl)amino)ethyl)phenyl)-1h-imidazo(4,5-c)pyridine

    55. Benzenesulfonamide,n-[[[2-[4-(2-ethyl-4,6-dimethyl-1h-imidazo[4,5-c]pyridin-1-yl)phenyl]ethyl]amino]carbonyl]-4-methyl-

    56. N-(((2-(4-(2-ethyl-4,6-dimethyl-1h-imidazo(4,5-c)pyridin-1-yl)phenyl)ethyl)amino)carbonyl)-4-methyl-benzenesulfonamide

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 491.6 g/mol
    Molecular Formula C26H29N5O3S
    XLogP34.6
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count7
    Exact Mass491.19911098 g/mol
    Monoisotopic Mass491.19911098 g/mol
    Topological Polar Surface Area114 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity802
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    The effects of grapiprant have been investigated in the area of analgesia and anti-inflammation due to the effects that have been reported about this molecule. This molecule has been approved and widely accepted to be used in veterinary for pain reduction in arthritis. In humans, it has been researched to be used in the control of pain and inflammation associated with osteoarthritis. The effect of grapiprant can be explained through the function of prostaglandin E2 (PGE2) which is a key mediator of swelling redness and pain which are classic signs of inflammation. The effect of PGE2 results from its action through four receptor EP1, EP2, EP3 and EP4 from which the EP4 is the primary mediator of PGE2-driven inflammation.

    For the treatment of pain associated with mild to moderate osteoarthritis in dogs.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Preclinical studies have shown that grapiprant is very effective to reduce acute and chronic pain and inflammation. The effect of grapiprant seems to be dose-dependent and it is comparable to the effect of rofecoxib and piroxicam. The effects of grapiprant have been reported to be effective in the relief from arthritic pain in canine patients.

    5.2 ATC Code

    QM01AX92

    5.3 Absorption, Distribution and Excretion

    Absorption

    Studies in animals (horse) have shown the presence of a concentration >0.005 ng/ml in serum 72 hours after initial administration of a dose of 2 mg/kg. It is rapidly absorbed and the reported Cmax in this reports was 31.9 ng/ml in a Tmax of 1.5 hours and AUC of 2000 ng.hr/ml. In the case of bioavailability, grapiprant presents a mean bioavailability of 39%. The bioavailability, time for peak concentration and maximal concentration has been reported to be significantly reduced after food.

    Route of Elimination

    Following an oral dose, the majority of the dose an within the first 72 hours. Studies in animals (horse) have shown the presence of a concentration >0.005 ng/ml in urine 96 hours after initial administration of a dose of 2 mg/kg. From the excreted dose, 55%, 15% and 19% of the administered dose is excreted in bile, urine, and feces respectively.

    Volume of Distribution

    The reported volume of distribution in animal studies (cats) was reported to be 918 ml/kg.

    Clearance

    The reported clearance rate in animal studies (cats) was reported to be 173.2 ml/hr.kg.

    5.4 Metabolism/Metabolites

    _In vitro_ studies with dog microsomes have reported the identification of four metabolites, an N-deamination metabolite which is the major metabolite in urine and feces, two hydroxylated metabolites and one N-oxidation metabolite.

    5.5 Biological Half-Life

    The reported elimination half-life in animal studies (horse) is of 5.86 hours.

    5.6 Mechanism of Action

    Grapiprant is an EP4 prostaglandin receptor antagonist and thus the activity of this drug is thought to be completely related to the selective blockade of this receptor. It binds to human and other mammals EP4 prostaglandin receptor with high affinity without interfering with other prostaglandin pathways which are important for a variety of physiological functions. The binding of grapiprant blocks PGE2 binding and hence its biological effect related to the signaling pain and inflammation cascade. Grapiprant has been accepted very greatly in veterinary as its mechanism of action is a targeted approach to pain management by not having any interaction with the production of prostanoids and thus, by not interacting with other prostaglandin receptor pathways.

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    ABOUT THIS PAGE

    Grapiprant Manufacturers

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

    click here to find a list of Grapiprant manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Grapiprant Suppliers

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

    click here to find a list of Grapiprant suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

    Grapiprant NDC

    National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Grapiprant as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for Grapiprant API and other APIs are published in this directory by the FDA.

    Unfinished drugs

    The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

    Pharmaceutical companies that manufacture Grapiprant as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

    Compounded drug products

    The NDC directory also contains data on finished compounded human drug products that contain Grapiprant and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Grapiprant NDC to their finished compounded human drug products, they may choose to do so.

    click here to find a list of Grapiprant suppliers with NDC on PharmaCompass.

    Grapiprant GMP

    Grapiprant 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 Grapiprant 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 Grapiprant GMP manufacturer or Grapiprant GMP API supplier for your needs.

    Grapiprant CoA

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

    Grapiprant CoA mostly includes findings from lab analyses of a specific batch. For each Grapiprant 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.

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