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    Chemistry

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    Also known as: 104206-65-7, Orfadin, 2-(2-nitro-4-(trifluoromethyl)benzoyl)cyclohexane-1,3-dione, Nitisone, Ntbc, 2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione
    Molecular Formula
    C14H10F3NO5
    Molecular Weight
    329.23  g/mol
    InChI Key
    OUBCNLGXQFSTLU-UHFFFAOYSA-N
    FDA UNII
    K5BN214699
    Nitisinone
    Nitisinone is a synthetic reversible inhibitor of 4-hydroxyphenylpyruvate dioxygenase. It is used in the treatment of hereditary tyrosinemia type 1. It is sold under the brand name Orfadin.
    Nitisinone is a 4-Hydroxyphenyl-Pyruvate Dioxygenase Inhibitor. The mechanism of action of nitisinone is as a Hydroxyphenylpyruvate Dioxygenase Inhibitor, and Cytochrome P450 2C9 Inhibitor, and Cytochrome P450 2E1 Inducer, and Organic Anion Transporter 1 Inhibitor, and Organic Anion Transporter 3 Inhibitor.
    1 2D Structure

    Nitisinone

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[2-nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione
    2.1.2 InChI
    InChI=1S/C14H10F3NO5/c15-14(16,17)7-4-5-8(9(6-7)18(22)23)13(21)12-10(19)2-1-3-11(12)20/h4-6,12H,1-3H2
    2.1.3 InChI Key
    OUBCNLGXQFSTLU-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CC(=O)C(C(=O)C1)C(=O)C2=C(C=C(C=C2)C(F)(F)F)[N+](=O)[O-]
    2.2 Other Identifiers
    2.2.1 UNII
    K5BN214699
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-(2-nitro-4-(trifluoromethyl)benzoyl)cyclohexane-1,3-dione

    2. 2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione

    3. Ntbc Cpd

    4. Orfadin

    2.3.2 Depositor-Supplied Synonyms

    1. 104206-65-7

    2. Orfadin

    3. 2-(2-nitro-4-(trifluoromethyl)benzoyl)cyclohexane-1,3-dione

    4. Nitisone

    5. Ntbc

    6. 2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione

    7. 2-[2-nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione

    8. 2-(2-nitro-4-trifluoromethylbenzoyl)cyclohexane-1,3-dione

    9. Sc 0735

    10. Sc-0735

    11. 2-(alpha,alpha,alpha-trifluoro-2-nitro-p-tuluoyl)-1,3-cyclohexanedione

    12. 1,3-cyclohexanedione, 2-[2-nitro-4-(trifluoromethyl)benzoyl]-

    13. 2-{[2-nitro-4-(trifluoromethyl)phenyl]carbonyl}cyclohexane-1,3-dione

    14. Chembl1337

    15. Chebi:50378

    16. 1,3-cyclohexanedione, 2-(2-nitro-4-(trifluoromethyl)benzoyl)-

    17. Mfcd01752192

    18. Sc0735

    19. K5bn214699

    20. Nitisinone [inn]

    21. Nitisinone [usan:inn]

    22. Nitisinona

    23. Nitisinonum

    24. Smr002529592

    25. Orfadin (tn)

    26. Nitisinone (jan/usan/inn)

    27. Unii-k5bn214699

    28. Nityr

    29. Fe-0200

    30. 2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione

    31. Nitisinone [mi]

    32. Nitisinone [jan]

    33. Nitisinone [usan]

    34. Nitisinone [vandf]

    35. Nitisinone [mart.]

    36. Nitisinone [who-dd]

    37. Bidd:pxr0129

    38. Mls004774025

    39. Mls006011955

    40. Nitisinone [ema Epar]

    41. Schembl338795

    42. Ambz0071

    43. Gtpl6834

    44. Dtxsid9042673

    45. Nitisinone [orange Book]

    46. Nitisinone, >=95% (hplc)

    47. Schembl15996621

    48. Hms3740a15

    49. Hms3870k03

    50. Bcp15276

    51. Hy-b0607

    52. Bdbm50088804

    53. Nsc773149

    54. Rb3134

    55. S5325

    56. Akos015891363

    57. Akos015994590

    58. Zinc100014475

    59. Am62666

    60. Ccg-222085

    61. Db00348

    62. Ex-6233

    63. Nsc-773149

    64. Sb19017

    65. Ncgc00185778-01

    66. Ncgc00185778-02

    67. Ncgc00185778-04

    68. Ncgc00185778-07

    69. Ac-26934

    70. Sy047291

    71. Db-014936

    72. Ft-0672739

    73. D05177

    74. A800922

    75. Sr-01000940576

    76. J-505680

    77. Q3877355

    78. Sr-01000940576-2

    79. Ntbc; Nitisone; Sc0735; Sc 0735; Sc-0735

    80. Z1514110653

    81. 1,3-cyclohexanedione,2-[2-nitro-4-(trifluoromethyl)benzoyl]-

    82. 2-(2-nitro-4-(trifluoromethyl)-benzoyl)cyclohexane-1,3-dione

    83. 2-[2-nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione;nitisinone

    84. 2-(.alpha.,.alpha.,.alpha.-trifluoro-2-nitro-p-tuluoyl)-1,3-cyclohexanedione

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 329.23 g/mol
    Molecular Formula C14H10F3NO5
    XLogP32.3
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count2
    Exact Mass329.05110691 g/mol
    Monoisotopic Mass329.05110691 g/mol
    Topological Polar Surface Area97 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity524
    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 Information
    1 of 2  
    Drug NameOrfadin
    PubMed HealthNitisinone (By mouth)
    Drug ClassesGastrointestinal Agent
    Drug LabelOrfadin contains nitisinone, which is a hydroxyphenyl-pyruvate dioxygenase inhibitor indicated as an adjunct to dietary restriction of tyrosine and phenylalanine in the treatment of hereditary tyrosinemia type 1 (HT-1). Nitisinone occurs as white to...
    Active IngredientNitisinone
    Dosage FormCapsule
    RouteOral
    Strength5mg; 2mg; 10mg
    Market StatusPrescription
    CompanySwedish Orphan

    2 of 2  
    Drug NameOrfadin
    PubMed HealthNitisinone (By mouth)
    Drug ClassesGastrointestinal Agent
    Drug LabelOrfadin contains nitisinone, which is a hydroxyphenyl-pyruvate dioxygenase inhibitor indicated as an adjunct to dietary restriction of tyrosine and phenylalanine in the treatment of hereditary tyrosinemia type 1 (HT-1). Nitisinone occurs as white to...
    Active IngredientNitisinone
    Dosage FormCapsule
    RouteOral
    Strength5mg; 2mg; 10mg
    Market StatusPrescription
    CompanySwedish Orphan

    4.2 Drug Indication

    Used as an adjunct to dietary restriction of tyrosine and phenylalanine in the treatment of hereditary tyrosinemia type 1.

    FDA Label

    Hereditary tyrosinemia type 1 (HT 1)

    Orfadin is indicated for the treatment of adult and paediatric (in any age range) patients with confirmed diagnosis of hereditary tyrosinemia type 1 (HT 1) in combination with dietary restriction of tyrosine and phenylalanine.

    Alkaptonuria (AKU)

    Orfadin is indicated for the treatment of adult patients with alkaptonuria (AKU).

    Treatment of adult and paediatric patients with confirmed diagnosis of hereditary tyrosinemia type 1 (HT-1) in combination with dietary restriction of tyrosine and phenylalanine.

    Treatment of adult and paediatric (in any age range) patients with confirmed diagnosis of hereditary tyrosinemia type 1 (HT 1) in combination with dietary restriction of tyrosine and phenylalanine.

    Treatment of tyrosinemia type 1

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Hereditary tyrosinemia type 1 occurs due to a deficiency in fumarylacetoacetase (FAH), the final enzyme in the tyrosine catabolic pathway. Nitisinone inhibits catabolism of tyrosine by preventing the catabolic intermediates. In patients with HT-1, these catabolic intermediates are converted to the toxic metabolites succinylacetone and succinylacetoacetate, which are responsible for the observed liver and kidney toxicity. Succinylacetone can also inhibit the porphyrin synthesis pathway leading to the accumulation of 5-aminolevulinate, a neurotoxin responsible for the porphyric crises characteristic of HT-1.

    5.2 MeSH Pharmacological Classification

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    NITISINONE
    5.3.2 FDA UNII
    K5BN214699
    5.3.3 Pharmacological Classes
    Cytochrome P450 2C9 Inhibitors [MoA]; Cytochrome P450 2E1 Inducers [MoA]; Hydroxyphenylpyruvate Dioxygenase Inhibitors [MoA]; Organic Anion Transporter 1 Inhibitors [MoA]; Organic Anion Transporter 3 Inhibitors [MoA]; 4-Hydroxyphenyl-Pyruvate Dioxygenase Inhibitor [EPC]
    5.4 ATC Code

    A16AX04

    A16AX04

    A16AX04

    A - Alimentary tract and metabolism

    A16 - Other alimentary tract and metabolism products

    A16A - Other alimentary tract and metabolism products

    A16AX - Various alimentary tract and metabolism products

    A16AX04 - Nitisinone

    5.5 Absorption, Distribution and Excretion

    Absorption

    The capsule and liquid formulations are bioequivalent in both the plasma concentration-time curve and maximum plasma concentration (Cmax).

    5.6 Biological Half-Life

    ~54 hours

    5.7 Mechanism of Action

    Nitisinone is a competitive inhibitor of 4-hydroxyphenyl-pyruvate dioxygenase, an enzyme upstream of fumarylacetoacetate hydrolyase (FAH) in the tyrosine catabolic pathway. By inhibiting the normal catabolism of tyrosine in patients with hereditary tyrosinemia type 1 (HT-1), nitisinone prevents the accumulation of the catabolic intermediates maleylacetoacetate and fumarylacetoacetate.

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    About the Company : Biophore, founded in 2007, has established itself as a reliable partner in the development and manufacturing of niche and complex pharmaceutical products. With 4 USFDA and EU-appro...

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    About the Company : Established in 2012, Nuray Chemicals Pvt Ltd is an API manufacturer for highly regulated markets. Its manufacturing facility with state-of-the-art R&D is located near Chennai in th...

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    About the Company : HRV Global is a leading global manufacturer, seller & exporter of a wide range of APIs, advanced intermediates, pellets, food grade chemicals, food additives & food ingredients. It...

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    About the Company : Omgene Life Sciences Private Limited is an R&D-driven biopharmaceutical company specializing in biopharmaceuticals, peptides, semi-synthetic, and synthetic actives. As a vertically...

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    Alven Laboratories

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    About the Company : Alven strengths lie in the development of highly complex molecules, technological leadership and efficiency in production. All our R&D work is driven by basic rule – the result o...

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    About the Company : Danesh Kimia Pharmed Co. was established on 2011 by industrial and university researchers in order to invest on the production of new pharmaceutical molecules and their ready to us...

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    About the Company : Established in the early 90’s SCL offers a wide range of Active Pharmaceutical Ingredients and Intermediates to its customers worldwide. SCL’s products are exported to Europe, ...

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    [{"dataSource":"API Export","activeIngredients":"","year":"2022","qtr":"Q1","strtotime":1648492200,"product":"NITISINONE (IN HOUSE) BATCH.NO.NTN-WSA21","address":"PLOT NO. 370. IND. AREA PHASE 2,PA NCHKULA","city":"PANCHKULA,HARYANA","supplier":"SAURAV CHEMICALS","supplierCountry":"INDIA","foreign_port":"BOGOTA","customer":"COLOMPACK S.A.","customerCountry":"COLOMBIA","quantity":"0.00","actualQuantity":"0.002","unit":"KGS","unitRateFc":"350000","totalValueFC":"669.1","currency":"USD","unitRateINR":25500000,"date":"29-Mar-2022","totalValueINR":"51000","totalValueInUsd":"669.1","indian_port":"DELHI AIR","hs_no":"29147990","bill_no":"9296432","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"COLOMBIA","selfForZScoreResived":"Pharma Grade","supplierPort":"DELHI AIR","supplierAddress":"PLOT NO. 370. IND. AREA PHASE 2,PA NCHKULA, PANCHKULA,HARYANA","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2023","qtr":"Q1","strtotime":1673893800,"product":"NITISINONE (IN-HOUSE)(OTHER VEG ALKALOID","address":"PLOT NO. 370. IND. AREA PHASE 2,PA NCHKULA","city":"PANCHKULA,HARYANA","supplier":"SAURAV CHEMICALS","supplierCountry":"INDIA","foreign_port":"LONDON METROPOLITAN","customer":"TO THE ORDER OF","customerCountry":"UNITED KINGDOM","quantity":"0.04","actualQuantity":"0.04","unit":"KGS","unitRateFc":"120000","totalValueFC":"4757.9","currency":"USD","unitRateINR":9725000,"date":"17-Jan-2023","totalValueINR":"389000","totalValueInUsd":"4757.9","indian_port":"DELHI AIR","hs_no":"29147990","bill_no":"7034917","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED KINGDOM","selfForZScoreResived":"Pharma Grade","supplierPort":"DELHI AIR","supplierAddress":"PLOT NO. 370. IND. AREA PHASE 2,PA NCHKULA, PANCHKULA,HARYANA","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2023","qtr":"Q2","strtotime":1683657000,"product":"NITISINONE IN HOUSE OTHR VEG ALKALOIDSNTRL OR RPRDCD BY SYNTHS THR SALTS ESTRSETHERSAND OTHER DRVTVS","address":"PLOT NO. 370. IND. AREA PHASE 2,PA NCHKULA","city":"PANCHKULA,HARYANA","supplier":"SAURAV CHEMICALS","supplierCountry":"INDIA","foreign_port":"LONDON HEATHROW","customer":"TO THE ORDER","customerCountry":"UNITED KINGDOM","quantity":"0.16","actualQuantity":"0.16","unit":"KGS","unitRateFc":"120000","totalValueFC":"18849.3","currency":"USD","unitRateINR":9693750,"date":"10-May-2023","totalValueINR":"1551000","totalValueInUsd":"18849.3","indian_port":"DELHI AIR","hs_no":"29147990","bill_no":"0","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED KINGDOM","selfForZScoreResived":"Pharma Grade","supplierPort":"DELHI AIR","supplierAddress":"PLOT NO. 370. IND. AREA PHASE 2,PA NCHKULA, PANCHKULA,HARYANA","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1719772200,"product":"NITISINONE (IN-HOUSE) (OTHER VEG ALKALOIDS NTRL OR RPRDCD BY SYNTHIS , THR SALTSESTRS ETHERSAND OTHER DRVTS)","address":"SCF.287, MOTOR MARKET,","city":"CHANDIGARH.","supplier":"SAURAV CHEMICALS","supplierCountry":"INDIA","foreign_port":"LONDON - HEATHROW","customer":"TO THE ORDER OF","customerCountry":"UNITED KINGDOM","quantity":"1.23","actualQuantity":"1.23","unit":"KGS","unitRateFc":"120000","totalValueFC":"145712.7","currency":"USD","unitRateINR":9902668.2926829271,"date":"01-Jul-2024","totalValueINR":"12180282","totalValueInUsd":"145712.7","indian_port":"Delhi Air","hs_no":"29147990","bill_no":"2081342","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED KINGDOM","selfForZScoreResived":"Pharma Grade","supplierPort":"Delhi Air","supplierAddress":"SCF.287, MOTOR MARKET,, CHANDIGARH.","customerAddress":""}]
    29-Mar-2022
    01-Jul-2024
    KGS
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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