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    Synopsis

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    Chemistry

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    Also known as: 1257044-40-8, Abt-199, Venclexta, Gdc-0199, Abt199, Abt 199
    Molecular Formula
    C45H50ClN7O7S
    Molecular Weight
    868.4  g/mol
    InChI Key
    LQBVNQSMGBZMKD-UHFFFAOYSA-N
    FDA UNII
    N54AIC43PW
    Venetoclax
    Venetoclax is an orally bioavailable, selective small molecule inhibitor of the anti-apoptotic protein Bcl-2, with potential antineoplastic activity. Venetoclax mimics BH3-only proteins, the native ligands of Bcl-2 and apoptosis activators, by binding to the hydrophobic groove of Bcl-2 proteins thereby repressing Bcl-2 activity and restoring apoptotic processes in tumor cells. Bcl-2 protein is overexpressed in some cancers and plays an important role in the regulation of apoptosis; its expression is associated with increased drug resistance and tumor cell survival. Compared to the Bcl-2 inhibitor navitoclax, this agent does not inhibit bcl-XL and does not cause bcl-XL-mediated thrombocytopenia.
    Venetoclax is a BCL-2 Inhibitor. The mechanism of action of venetoclax is as a P-Glycoprotein Inhibitor. The physiologic effect of venetoclax is by means of Increased Cellular Death.
    1 2D Structure

    Venetoclax

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-N-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonyl-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide
    2.1.2 InChI
    InChI=1S/C45H50ClN7O7S/c1-45(2)15-11-33(39(26-45)31-3-5-34(46)6-4-31)29-51-17-19-52(20-18-51)35-7-9-38(42(24-35)60-36-23-32-12-16-47-43(32)49-28-36)44(54)50-61(57,58)37-8-10-40(41(25-37)53(55)56)48-27-30-13-21-59-22-14-30/h3-10,12,16,23-25,28,30,48H,11,13-15,17-22,26-27,29H2,1-2H3,(H,47,49)(H,50,54)
    2.1.3 InChI Key
    LQBVNQSMGBZMKD-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1(CCC(=C(C1)C2=CC=C(C=C2)Cl)CN3CCN(CC3)C4=CC(=C(C=C4)C(=O)NS(=O)(=O)C5=CC(=C(C=C5)NCC6CCOCC6)[N+](=O)[O-])OC7=CN=C8C(=C7)C=CN8)C
    2.2 Other Identifiers
    2.2.1 UNII
    N54AIC43PW
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)-n-((3-nitro-4-((tetrahydro-2h-pyran-4-ylmethyl)amino)phenyl)sulfonyl)-2-(1h-pyrrolo(2,3-b)pyridin-5-yloxy)benzamide

    2. Abt-199

    3. Benzamide, 4-(4-((2-(4-chlorophenyl)-4,4-dimethyl-1-cyclohexen-1-yl)methyl)-1-piperazinyl)-n-((3-nitro-4-(((tetrahydro-2h-pyran-4-yl)methyl)amino)phenyl)sulfonyl)-2-(1h-pyrrolo(2,3-b)pyridin-5-yloxy)-

    4. Gdc-0199

    5. Rg-7601

    6. Rg7601

    7. Venclexta

    2.3.2 Depositor-Supplied Synonyms

    1. 1257044-40-8

    2. Abt-199

    3. Venclexta

    4. Gdc-0199

    5. Abt199

    6. Abt 199

    7. Rg7601

    8. Venetoclax (abt199)

    9. Gdc 0199

    10. Rg-7601

    11. Venetoclax; Abt-199

    12. 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonyl-2-(1h-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide

    13. Venetoclax (abt-199)

    14. N54aic43pw

    15. Abt-199 (gdc-0199)

    16. 2-(1h-pyrrolo[2,3-b]pyridin-5-yloxy)-4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)-n-(3-nitro-4-((tetrahydro-2h-pyran-4-yl)methy

    17. 4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)-n-((3-nitro-4-((tetrahydro-2h-pyran-4-ylmethyl)amino)phenyl)sulfonyl)-2-(1h-pyrrolo(2,3-b)pyridin-5-yloxy)benzamide

    18. 4-[4-[[2-(4-chlorophenyl)-4,4-dimethyl-1-cyclohexen-1-yl]methyl]-1-piperazinyl]-n-[[3-nitro-4-[[(tetrahydro-2h-pyran-4-yl)methyl]amino]phenyl]sulfonyl]-2-(1h-pyrrolo[2,3-b]pyridin-5-yloxy)-benzamide

    19. Benzamide, 4-(4-((2-(4-chlorophenyl)-4,4-dimethyl-1-cyclohexen-1-yl)methyl)-1-piperazinyl)-n-((3-nitro-4-(((tetrahydro-2h-pyran-4-yl)methyl)amino)phenyl)sulfonyl)-2-(1h-pyrrolo(2,3-b)pyridin-5-yloxy)-

    20. Venclyxto

    21. Bdbm189459

    22. Unii-n54aic43pw

    23. 4-(4-{[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-n-({3-nitro-4-[(oxan-4-ylmethyl)amino]benzene}sulfonyl)-2-{1h-pyrrolo[2,3-b]pyridin-5-yloxy}benzamide

    24. 4-(4-{[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-n-({3-nitro-4-[(tetrahydro-2h-pyran-4-ylmethyl)amino]phenyl}sulfonyl)-2-(1h-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide

    25. 4-{4-[(4'-chloro-5,5-dimethyl[3,4,5,6-tetrahydro[1,1'-biphenyl]]-2-yl)methyl]piperazin-1-yl}-n-(3-nitro-4-{[(oxan-4-yl)methyl]amino}benzene-1-sulfonyl)-2-[(1h-pyrrolo[2,3-b]pyridin-5-yl)oxy]benzamide

    26. Venetoclax [usan:inn]

    27. Venclexta (tn)

    28. Benzamide, 4-[4-[[2-(4-chlorophenyl)-4,4-dimethyl-1-cyclohexen-1-yl]methyl]-1-piperazinyl]-n-[[3-nitro-4-[[(tetrahydro-2h-pyran-4-yl)methyl]amino]phenyl]sulfonyl]-2-(1h-pyrrolo[2,3-b]pyridin-5-yloxy)-

    29. Venetoclax [mi]

    30. Venetoclax(abt-199)

    31. Venetoclax [inn]

    32. Venetoclax [jan]

    33. Venetoclax [usan]

    34. Venetoclax [who-dd]

    35. Mls006010298

    36. Schembl523816

    37. Venetoclax (jan/usan/inn)

    38. Amy343

    39. Gtpl8318

    40. Chembl3137309

    41. Schembl19236295

    42. Venetoclax [orange Book]

    43. Bdbm60828

    44. Dtxsid30154863

    45. Ex-a168

    46. Chebi:133021

    47. Hms3653j06

    48. Hms3745e07

    49. Bcp06811

    50. Bdbm50162774

    51. Mfcd23160052

    52. Nsc766270

    53. Akos025289539

    54. Zinc150338755

    55. Ccg-270543

    56. Cs-1155

    57. Db11581

    58. Ks-1470

    59. Nsc-766270

    60. Sb16499

    61. Ncgc00345789-01

    62. Ncgc00345789-05

    63. Ncgc00345789-10

    64. Ncgc00345789-11

    65. Ac-28754

    66. Da-35360

    67. Hy-15531

    68. Smr004701366

    69. Ft-0699586

    70. S8048

    71. Sw219672-1

    72. J3.516.625d

    73. D10679

    74. Us9174982, 5

    75. A850921

    76. Us9174982, 369

    77. J-005269

    78. Q23671272

    79. 2-((1h-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazin-1-yl)-n-((3-nitro-4-(((tetrahydro-2h-pyran-4-yl)methyl)amino)phenyl)sulfonyl)benzamide

    80. 4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)-n-((3-nitro-4-((tetrahydro-2hpyran-4-ylmethyl) Amino)phenyl)sulfonyl)-2-(1h-pyrrolo(2,3-b)pyridin-5-yloxy)benzamide

    81. 4-[4-[[2-(4-chlorophenyl)-4,4-dimethyl-1-cyclohexen-1-yl]methyl]-1-piperazinyl]-n-[[3-nitro-4-[[(tetrahydro-2h-pyran-4-yl)methyl]amino]phenyl]sulfonyl]-2-(1h-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide

    82. 4-[4-[[2-(4-chlorophenyl)-4,4-dimethyl-cyclohexen-1-yl]methyl]piperazin-1-yl]-n-[3-nitro-4-(tetrahydropyran-4-ylmethylamino)phenyl]sulfonyl-2-(1h-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide

    83. 4-{4-[(4'-chloro-5,5-dimethyl[3,4,5,6-tetrahydro[1,1'-biphenyl]]-2-yl)methyl]piperazin-1-yl}-n-[(3-nitro-4-{[(oxan-4-yl

    2.4 Create Date
    2011-01-31
    3 Chemical and Physical Properties
    Molecular Weight 868.4 g/mol
    Molecular Formula C45H50ClN7O7S
    XLogP38.2
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count12
    Exact Mass867.3180958 g/mol
    Monoisotopic Mass867.3180958 g/mol
    Topological Polar Surface Area183 Ų
    Heavy Atom Count61
    Formal Charge0
    Complexity1640
    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

    A BCL-2 inhibitor indicated for the treatment of patients with chronic lymphocytic leukemia (CLL) or small lymphocytic lymphoma (SLL), with or without 17p deletion, who have received at least one prior therapy.

    FDA Label

    Venclyxto in combination with obinutuzumab is indicated for the treatment of adult patients with previously untreated chronic lymphocytic leukaemia (CLL) (see section 5. 1).

    Venclyxto in combination with rituximab is indicated for the treatment of adult patients with CLL who have received at least one prior therapy.

    Venclyxto monotherapy is indicated for the treatment of CLL:

    - in the presence of 17p deletion or TP53 mutation in adult patients who are unsuitable for or have failed a B cell receptor pathway inhibitor, or

    - in the absence of 17p deletion or TP53 mutation in adult patients who have failed both chemoimmunotherapy and a B-cell receptor pathway inhibitor.

    Venclyxto in combination with a hypomethylating agent is indicated for the treatment of adult patients with newly diagnosed acute myeloid leukaemia (AML) who are ineligible for intensive chemotherapy.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Venetoclax induces rapid and potent onset apoptosis of CLL cells, powerful enough to act within 24h and to lead to tumor lysis syndrome,,. Selective targeting of BCL2 with venetoclax has demonstrated a manageable safety profile and has been shown to induce significant response in patients with relapsed CLL (chronic lymphocytic leukemia) or SLL (small lymphocytic leukemia), including patients with poor prognostic features. This drug is not expected to have a significant impact on the cardiac QT interval. Venetoclax has demonstrated efficacy in various types of lymphoid malignancies, including relapsed/ refractory CLL harboring deletion 17p, with an overall response rate of approximately 80%.

    5.2 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    VENETOCLAX
    5.3.2 FDA UNII
    N54AIC43PW
    5.3.3 Pharmacological Classes
    Increased Cellular Death [PE]; P-Glycoprotein Inhibitors [MoA]; BCL-2 Inhibitor [EPC]
    5.4 ATC Code

    L01XX52

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01X - Other antineoplastic agents

    L01XX - Other antineoplastic agents

    L01XX52 - Venetoclax

    5.5 Absorption, Distribution and Excretion

    Absorption

    Following several oral administrations after a meal, the maximum plasma concentration of venetoclax was reached 5-8 hours after the dose. Venetoclax steady state AUC (area under the curve) increased proportionally over the dose range of 150-800 mg. After a low-fat meal, venetoclax mean ( standard deviation) steady-state Cmax was 2.1 1.1 g/mL and AUC0-24 was 32.8 16.9 gh/mL at the 400 mg once daily dose. When compared with the fasted state, venetoclax exposure increased by 3.4 times when ingested with a low-fat meal and 5.2 times with a high-fat meal. When comparing low versus high fat, the Cmax and AUC were both increased by 50% when ingested with a high-fat meal. The FDA label indicataes that venetoclax should be taken with food,.

    Route of Elimination

    After single oral administration of 200 mg radiolabeled [14C]-venetoclax dose to healthy subjects, >99.9% of the dose was found in feces and <0.1% of the dose was excreted in urine within 9 days, suggesting that hepatic elimination is responsible for the clearance of venetoclax from systemic circulation. Unchanged venetoclax accounted for 20.8% of the radioactive dose excreted in feces.

    Volume of Distribution

    The population estimate for apparent volume of distribution (Vdss/F) of venetoclax ranged from 256-321 L.

    Clearance

    Mainly hepatic.

    5.6 Metabolism/Metabolites

    In vitro studies demonstrated that venetoclax is predominantly metabolized as a substrate of CYP3A4/5,,.

    5.7 Biological Half-Life

    The half-life of venetoclax is reported to be 19-26 hours, after administration of a single 50-mg dose,.

    5.8 Mechanism of Action

    Proteins in the B cell CLL/lymphoma 2 (BCL-2) family are necessary regulators of the apoptotic (anti-cell programmed death) process. This family comprises proapoptotic and prosurvival proteins for various cells. Cancer cells evade apoptosis by inhibiting programmed cell death (apoptosis). The therapeutic potential of directly inhibiting prosurvival proteins was unveiled with the development of navitoclax, a selective inhibitor of both BCL-2 and BCL-2-like 1 (BCL-X(L)), which has demonstrated clinical efficacy in some BCL-2-dependent hematological cancers. Selective inhibition of BCL-2 by venetoclax, sparing BCL-xL enables therapeutic induction of apoptosis without the negative effect of thrombocytopenia,. Venetoclax helps restore the process of apoptosis by binding directly to the BCL-2 protein, displacing pro-apoptotic proteins, leading to mitochondrial outer membrane permeabilization and the activation of caspase enzymes. In nonclinical studies, venetoclax has shown cytotoxic activity in tumor cells that overexpress BCL-2.

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C-24,","city":"HYDERABAD. AP","supplier":"MSN LABORATORIES","supplierCountry":"INDIA","foreign_port":"LARNACA","customer":"REMEDICA LTD","customerCountry":"CYPRUS","quantity":"0.10","actualQuantity":"0.1","unit":"KGS","unitRateFc":"28000","totalValueFC":"2651.8","currency":"USD","unitRateINR":2216690,"date":"30-Jul-2024","totalValueINR":"221669","totalValueInUsd":"2651.8","indian_port":"Hyderabad Air","hs_no":"29337990","bill_no":"2828003","productDescription":"API","marketType":"REGULATED MARKET","country":"CYPRUS","selfForZScoreResived":"Pharma Grade","supplierPort":"Hyderabad Air","supplierAddress":"MSN HOUSE, PLOT NO. C-24,, HYDERABAD. AP","customerAddress":""},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1709836200,"product":"VENETOCLAX","address":"H.NO. 8-2-337,BESIDE TV9 OFFICE","city":"HYDERABAD ANDHRA PRADESH","supplier":"CHANGZHOU PHARMACEUTICAL FACTORY","supplierCountry":"CHINA","foreign_port":"SHANGHAI - PU DONG","customer":"DR. REDDY\\'S LABORATORIES","customerCountry":"INDIA","quantity":"1.00","actualQuantity":"1","unit":"KGS","unitRateFc":"9000","totalValueFC":"9077.4","currency":"USD","unitRateINR":"753750","date":"08-Mar-2024","totalValueINR":"753750","totalValueInUsd":"9077.4","indian_port":"Hyderabad Air","hs_no":"29359090","bill_no":"2488103","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI - PU DONG","supplierAddress":"NO.518, LAO DONG EAST ROAD, CHANGZHOU JIANGSU 213018, CHINA. Changzhou, , China China","customerAddress":"H.NO. 8-2-337,BESIDE TV9 OFFICE"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1716229800,"product":"VENETOCLAX","address":"H.NO. 8-2-337,BESIDE TV9 OFFICE","city":"HYDERABAD ANDHRA PRADESH","supplier":"CHANGZHOU PHARMACEUTICAL FACTORY","supplierCountry":"CHINA","foreign_port":"SHANGHAI - PU DONG","customer":"DR. REDDY\\'S LABORATORIES","customerCountry":"INDIA","quantity":"1.00","actualQuantity":"1","unit":"KGS","unitRateFc":"9000","totalValueFC":"9107.5","currency":"USD","unitRateINR":"759150","date":"21-May-2024","totalValueINR":"759150","totalValueInUsd":"9107.5","indian_port":"Hyderabad Air","hs_no":"29359090","bill_no":"3588882","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI - PU DONG","supplierAddress":"NO.518, LAO DONG EAST ROAD, CHANGZHOU JIANGSU 213018, CHINA. Changzhou, , China China","customerAddress":"H.NO. 8-2-337,BESIDE TV9 OFFICE"}]
    12-Feb-2021
    30-Jul-2024
    KGS
    overview
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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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