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    Also known as: 150824-47-8, (e)-nitenpyram, 120738-89-8, Niterndipoine, Bestguard, Capstar
    Molecular Formula
    C11H15ClN4O2
    Molecular Weight
    270.71  g/mol
    InChI Key
    CFRPSFYHXJZSBI-DHZHZOJOSA-N
    FDA UNII
    3A837VZ81Y
    Nitenpyram
    nitenpyram is a natural product found in Streptomyces canus with data available.
    1 2D Structure

    Nitenpyram

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (E)-1-N'-[(6-chloropyridin-3-yl)methyl]-1-N'-ethyl-1-N-methyl-2-nitroethene-1,1-diamine
    2.1.2 InChI
    InChI=1S/C11H15ClN4O2/c1-3-15(11(13-2)8-16(17)18)7-9-4-5-10(12)14-6-9/h4-6,8,13H,3,7H2,1-2H3/b11-8+
    2.1.3 InChI Key
    CFRPSFYHXJZSBI-DHZHZOJOSA-N
    2.1.4 Canonical SMILES
    CCN(CC1=CN=C(C=C1)Cl)C(=C[N+](=O)[O-])NC
    2.1.5 Isomeric SMILES
    CCN(CC1=CN=C(C=C1)Cl)/C(=C/[N+](=O)[O-])/NC
    2.2 Other Identifiers
    2.2.1 UNII
    3A837VZ81Y
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (1e)-n-((6-chloro-3-pyridinyl)methyl)-n-ethyl-n'-methyl-2-nitro-1,1-ethenediamine

    2. (e)-n-(6-chloro-3-pyridylmethyl)-n-ethyl-n'-methyl-2-nitrovinylidenediamine

    2.3.2 Depositor-Supplied Synonyms

    1. 150824-47-8

    2. (e)-nitenpyram

    3. 120738-89-8

    4. Niterndipoine

    5. Bestguard

    6. Capstar

    7. (e)-n-((6-chloropyridin-3-yl)methyl)-n-ethyl-n'-methyl-2-nitroethene-1,1-diamine

    8. Nitenpyram [iso]

    9. Ti 304

    10. Chebi:39170

    11. (1e)-n-((6-chloro-3-pyridinyl)methyl)-n-ethyl-n'-methyl-2-nitro-1,1-ethenediamine

    12. N-((6-chloropyridin-3-yl)methyl)-n-ethyl-n-methyl-2-nitroethene-1,1-diamine

    13. (e)-n-[(6-chloropyridin-3-yl)methyl]-n-ethyl-n'-methyl-2-nitroethene-1,1-diamine

    14. (e)-1-n'-[(6-chloropyridin-3-yl)methyl]-1-n'-ethyl-1-n-methyl-2-nitroethene-1,1-diamine

    15. 3a837vz81y

    16. Ncgc00166149-01

    17. (e)-n-(6-chloro-3-pyridylmethyl)-n-ethyl-n'-methyl-2-nitrovinylidenediamine

    18. N-((6-chloropyridin-3-yl)methyl)-n-ethyl-n'-methyl-2-nitroethene-1,1-diamine

    19. Dsstox_cid_21080

    20. Dsstox_rid_79622

    21. Dsstox_gsid_41080

    22. (1e)-n-[(6-chloro-3-pyridinyl)methyl]-n-ethyl-n'-methyl-2-nitro-1,1-ethenediamine

    23. 1,1-ethenediamine, N-((6-chloro-3-pyridinyl)methyl)-n-ethyl-n'-methyl-2-nitro-, (1e)-

    24. 1,1-ethenediamine, N-[(6-chloro-3-pyridinyl)methyl]-n-ethyl-n'-methyl-2-nitro-, (1e)-

    25. Cas-150824-47-8

    26. Unii-3a837vz81y

    27. N-[(6-chloropyridin-3-yl)methyl]-n-ethyl-n'-methyl-2-nitroethene-1,1-diamine

    28. Nitenpyram [mi]

    29. Schembl25788

    30. Schembl25789

    31. Chembl259728

    32. Nitenpyram [green Book]

    33. Dtxsid8041080

    34. Chebi:39171

    35. Hsdb 8491

    36. Hms3885b06

    37. Hy-b0820

    38. Zinc2381598

    39. Tox21_112342

    40. Bdbm50486236

    41. Mfcd01631161

    42. Ti-304

    43. (e)-n-(6-chloro-3-pyridylmethyl)-n-ethyl-n2-methyl-2-nitrovinylidenediamine

    44. Akos015914907

    45. Nitenpyram 100 Microg/ml In Methanol

    46. Tox21_112342_1

    47. Ccg-267169

    48. Db11438

    49. Ks-5369

    50. (1e)-n-((6-chloro-3-pyridinyl)methyl]-n-ethyl-n2-methyl-2-nitro-1,1-ethenediamine

    51. (e)-n-(6-chloro-3-pyridylmethyl)-n-ethyl-n'-methyl-2-nitroethylene-1,1-diamine

    52. Nitenpyram 1000 Microg/ml In Methanol

    53. Ncgc00166149-02

    54. Nitenpyram 10 Microg/ml In Acetonitrile

    55. Cs-0012837

    56. S4422

    57. Nitenpyram, Pestanal(r), Analytical Standard

    58. A14229

    59. C18511

    60. 738n898

    61. A804578

    62. A809078

    63. Q-201476

    64. Q3817186

    65. Q27119765

    66. N-ethyl-n-[1-(methylamino)-2-nitroethenyl]-6-chloropyridine-3-methanamine

    67. (e)-n-((6-chloro-3-pyridinyl)methyl)-n-ethyl-n'-methyl-2-nitro-1,1-ethenediamine

    68. (e)-n-((6-chloropyridin-3-yl)methyl)-n-ethyl-n-methyl-2-nitroethene-1,1-diamine

    69. [(e)-1-{[(6-chloropyridin-3-yl)methyl](ethyl)amino}-2-nitroethenyl](methyl)amine

    70. 1,1-ethenediamine, N-((6-chloro-3-pyridinyl)methyl)-n-ethyl-n-methyl-2-nitro-

    71. N-[(6-chloro-3-pyridinyl)methyl]-n-ethyl-n'-methyl-2-nitro-1,1-ethenediamine

    72. N1-[(6-chloro-3-pyridyl)methyl]-n1'-ethyl-n1'-methyl-2-nitro-ethene-1,1-diamine

    73. (e)-n1'-[(6-chloro-3-pyridyl)methyl]-n1'-ethyl-n1-methyl-2-nitro-ethene-1,1-diamine;nitenpyram

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 270.71 g/mol
    Molecular Formula C11H15ClN4O2
    XLogP32.4
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count5
    Exact Mass270.0883534 g/mol
    Monoisotopic Mass270.0883534 g/mol
    Topological Polar Surface Area74 Ų
    Heavy Atom Count18
    Formal Charge0
    Complexity306
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    VET: Nitenpyram inhibits the nicotinic acetylcholine receptor. It is used to treat Ctenocephalides spp in dogs and cats ... . It is toxic to fleas for only 24-48 hr and is normally used in combination with an insect growth regulator to provide continuous flea control.

    Kahn, C.M (ed.).; The Merck Veterinary Manual 10th Edition. Merck & Co. Whitehouse Station NJ. 2010, p. 2197

    VET: Nitenpyram is indicated as a flea adulticide in dogs and cats that are, at a minimum, 2 pounds in weight and 4 weeks old. It does not repel fleas or ticks and does not reliably kill ticks, flea eggs, larvae or immature fleas. Nitenpyram may be effective for treating fly larvae (maggots) of various species. Fleas begin to fall from treated animals about 30 minutes after dosing and a single dose can protect animals for 1-2 days.

    Plumb D.C. Veterinary Drug Handbook. 8th ed. (pocket). Ames, IA: Wiley-Blackwell, 2015., p. 1048

    4.2 Drug Warning

    VET: The following adverse events are based on post-approval adverse drug experience reporting. Not all adverse reactions are reported to FDA CVM. It is not always possible to reliably estimate the adverse event frequency or establish a causal relationship to product exposure using this data. The following adverse events are listed in decreasing order of reporting frequency. Cats: hyperactivity, panting, lethargy, itching, vocalization, vomiting, fever, decreased appetite, nervousness, diarrhea, difficulty breathing, salivation, incoordination, seizures, pupil dilation, increased heart rate, and trembling. Dogs: lethargy/depression, vomiting, itching, decreased appetite, diarrhea, hyperactivity, incoordination, trembling, seizures, panting, allergic reactions including hives, vocalization, salivation, fever, and nervousness. The frequency of serious signs, including neurologic signs and death, was greater in animals under 2 pounds of body weight, less than 8 weeks of age, and/or reported to be in poor body condition. In some instances, birth defects and fetal/neonatal loss were reported after treatment of pregnant and/or lactating animals.

    NIH; DailyMed. Current Medication Information for Capstar-nitenpyram capsule (Updated: October 17, 2018). Available from, as of November 27, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=71454d3d-6bd3-49ef-89c2-bd930adcb421

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Insecticides

    Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

    5.2 Absorption, Distribution and Excretion

    Nitenpyram is rapidly and practically completely absorbed after oral administration. Peak levels occur approximately 80 minutes after dosing in dogs; approximately 40 minutes in cats. Elimination half-lives are: approximately 3 hours for dogs; 8 hours for cats. Nitenpyram is excreted primarily as conjugated metabolites in the urine and excretion is complete within 48 hours of dosing. In dogs, approximately 3% of a dose is excreted in feces; in cats approximately 5% is excreted in the feces.

    Plumb D.C. Veterinary Drug Handbook. 8th ed. (pocket). Ames, IA: Wiley-Blackwell, 2015., p. 1048

    Nitenpyram is administered PO in pill form to kill fleas in both dogs and cats. It is absorbed rapidly, with maximal blood concentrations reached within 1.2 hr and 0.6 hr in dogs and cats, respectively. ... The compound is rapidly eliminated, with >90% excreted in the urine within 24-48 hr, primarily as unchanged nitenpyram.

    Kahn, C.M (ed.).; The Merck Veterinary Manual 10th Edition. Merck & Co. Whitehouse Station NJ. 2010, p. 2360

    5.3 Metabolism/Metabolites

    BACKGROUND: Nitenpyram is a member of the economically important neonicotinoid class of insecticides. The in vivo metabolism of nitenpyram is not well characterized, but cytochrome P450 activity is the major mechanism of resistance to neonicotinoids identified in insect pests, and P450s metabolize other neonicotinoids including imidacloprid. RESULTS: Here, we used the GAL4-UAS targeted expression system to direct RNA interference (RNAi) against the cytochrome P450 redox partners to interrupt P450 functions in specific tissues in Drosophila melanogaster. RNAi of the mitochondrial redox partner defective in the avoidance of repellents (dare) in the digestive tissues reduced nitenpyram mortality, suggesting an activation step in the metabolism of nitenpyram carried out by a mitochondrial P450. RNAi of the mitochondrial cytochrome P450 Cyp12a5, which is expressed in the digestive tissues, resulted in the same phenotype, and transgenic overexpression of Cyp12a5 increased nitenpyram sensitivity. CONCLUSION: These results suggest that in vivo metabolism of nitenpyram by the mitochondrial P450 CYP12A5 results in the formation of a product with higher toxicity than the parent compound.

    PMID:29316188 Harrop TW et al; Pest Manag Sci 74 (7): 1616-1622 (2018)

    5.4 Biological Half-Life

    Elimination half-lives /after oral dosing/ are: approximately 3 hours for dogs; 8 hours for cats.

    Plumb D.C. Veterinary Drug Handbook. 8th ed. (pocket). Ames, IA: Wiley-Blackwell, 2015., p. 1048

    5.5 Mechanism of Action

    Nitenpyram is in the class of neonicotinoid insecticides. It enters the systemic circulation of the adult flea after consuming blood from a treated animal. It binds to nicotinic acetylcholine receptors in the postsynaptic membranes and blocks acetylcholine-mediated neuronal transmission causing paralysis and death of the flea. Nitenpyram is 3500x more selective for insect alpha-4beta-2 nicotinic receptors than in vertebrate receptors. It does not inhibit acetylcholinesterase.

    Plumb D.C. Veterinary Drug Handbook. 8th ed. (pocket). Ames, IA: Wiley-Blackwell, 2015., p. 1048

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    NDC Package Code : 62158-0006

    Start Marketing Date : 2021-02-08

    End Marketing Date : 2025-12-31

    Dosage Form (Strength) : POWDER (1kg/kg)

    Marketing Category : BULK INGREDIENT

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    [{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1722450600,"product":"VOSY-NYNY-C066-N NITENPYRAM","address":"B2-B 10TH FLAT PLOT NO.27,SECTOR-1","city":"DWARKA NEW DELHI,DELHI","supplier":"XXLIXXXHARXXCEUXXCALXXRIVXXE LXXITEX","supplierCountry":"CHINA","foreign_port":"PUDONG\/SHANGHAI, 31","customer":"FELIX GENERICS PRIVATE ","customerCountry":"INDIA","quantity":"30.00","actualQuantity":"30","unit":"KGS","unitRateFc":"2200","totalValueFC":"66528.3","currency":"USD","unitRateINR":"186010","date":"01-Aug-2024","totalValueINR":"5580300","totalValueInUsd":"66528.3","indian_port":"Indore-EPZ\/SEZ","hs_no":"29333990","bill_no":"1005616","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"PUDONG\/SHANGHAI, 31","supplierAddress":"N\/A","customerAddress":"B2-B 10TH FLAT PLOT NO.27,SECTOR-1"}]
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    ABOUT THIS PAGE

    Nitenpyram Manufacturers

    A Nitenpyram manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Nitenpyram, including repackagers and relabelers. The FDA regulates Nitenpyram manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Nitenpyram 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 Nitenpyram manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Nitenpyram Suppliers

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

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

    Nitenpyram 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 Nitenpyram as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for Nitenpyram 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 Nitenpyram 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 Nitenpyram and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Nitenpyram NDC to their finished compounded human drug products, they may choose to do so.

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

    Nitenpyram GMP

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

    Nitenpyram CoA

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

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

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