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Chemistry

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Also known as: 870281-82-6, Cal-101, Zydelig, Gs-1101, Cal 101, Cal101

Molecular Formula

C₂₂H₁₈FN₇O

Molecular Weight

415.4 g/mol

InChI Key

IFSDAJWBUCMOAH-HNNXBMFYSA-N

FDA UNII

YG57I8T5M0

Idelalisib is an orally bioavailable, small molecule inhibitor of the delta isoform of the 110 kDa catalytic subunit of class I phosphoinositide-3 kinase (PI3K) with potential immunomodulating and antineoplastic activities. Idelalisib inhibits the production of the second messenger phosphatidylinositol-3,4,5-trisphosphate (PIP3), preventing the activation of the PI3K signaling pathway and inhibiting tumor cell proliferation, motility, and survival. Unlike other isoforms of PI3K, PI3K-delta is expressed primarily in hematopoietic lineages. The targeted inhibition of PI3K-delta is designed to preserve PI3K signaling in normal, non-neoplastic cells.

Idelalisib is a Kinase Inhibitor. The mechanism of action of idelalisib is as a Kinase Inhibitor, and Cytochrome P450 3A Inhibitor.

1 2D Structure

Idelalisib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-fluoro-3-phenyl-2-[(1S)-1-(7H-purin-6-ylamino)propyl]quinazolin-4-one

2.1.2 InChI

InChI=1S/C22H18FN7O/c1-2-15(28-20-18-19(25-11-24-18)26-12-27-20)21-29-16-10-6-9-14(23)17(16)22(31)30(21)13-7-4-3-5-8-13/h3-12,15H,2H2,1H3,(H2,24,25,26,27,28)/t15-/m0/s1

2.1.3 InChI Key

IFSDAJWBUCMOAH-HNNXBMFYSA-N

2.1.4 Canonical SMILES

CCC(C1=NC2=C(C(=CC=C2)F)C(=O)N1C3=CC=CC=C3)NC4=NC=NC5=C4NC=N5

2.1.5 Isomeric SMILES

CC[C@@H](C1=NC2=C(C(=CC=C2)F)C(=O)N1C3=CC=CC=C3)NC4=NC=NC5=C4NC=N5

2.2 Other Identifiers

2.2.1 UNII

YG57I8T5M0

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cal 101

2. Cal-101

3. Cal101

4. Gs-1101

5. Zydelig

2.3.2 Depositor-Supplied Synonyms

1. 870281-82-6

2. Cal-101

3. Zydelig

4. Gs-1101

5. Cal 101

6. Cal101

7. (s)-2-(1-((9h-purin-6-yl)amino)propyl)-5-fluoro-3-phenylquinazolin-4(3h)-one

8. 1146702-54-6

9. Idelalisib (cal-101)

10. Cal-101 (idelalisib, Gs-1101)

11. Gs 1101

12. (s)-2-(1-(9h-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3h)-one

13. 5-fluoro-3-phenyl-2-((s)-1-(9h-purin-6-ylamino)-propyl)-3h-quinazolin-4-one

14. Yg57i8t5m0

15. Chembl2216870

16. Chebi:82701

17. Idelalisib; Cal-101

18. 5-fluoro-3-phenyl-2-((1s)-1-(9h-purin-6-ylamino)propyl)-4(3h)-quinazolinone

19. 5-fluoro-3-phenyl-2-[(1s)-1-(7h-purin-6-ylamino)propyl]quinazolin-4-one

20. 5-fluoro-3-phenyl-2-[(1s)-1-(3h-purin-6-ylamino)propyl]quinazolin-4(3h)-one

21. 5-fluoro-3-phenyl-2-[(1s)-1-(7h-purin-6-ylamino)propyl]quinazolin-4(3h)-one

22. 1453810-72-4

23. Idelalisib [inn]

24. Idelalisib [usan:inn]

25. Unii-yg57i8t5m0

26. Idealisib

27. Zydelig (tn)

28. Idelalisib [mi]

29. Idelalisib [jan]

30. Idelalisib [usan]

31. Idelalisib [vandf]

32. Idelalisib [who-dd]

33. Mls006010985

34. Idelalisib (jan/usan/inn)

35. Schembl356400

36. Gtpl6741

37. Idelalisib [orange Book]

38. Schembl16782604

39. Hsdb 8408

40. Amy9239

41. Cal-101/cal101

42. Ex-a330

43. Gs-11cal-101

44. Bcpp000307

45. Dtxsid701007266

46. Bcp02532

47. Ex-a1242

48. Bdbm50403068

49. Mfcd19443647

50. Nsc759224

51. Nsc762828

52. Nsc800771

53. S2226

54. Zinc13986658

55. Akos022186334

56. Idelalisib (cal-101,gs-1101)

57. Bcp9000471

58. Ccg-264949

59. Cs-0256

60. Db09054

61. Nsc-759224

62. Nsc-762828

63. Nsc-800771

64. Cal-101 (gs-1101)

65. Ncgc00262603-01

66. Ncgc00262603-02

67. Ncgc00262603-04

68. Ac-28394

69. Ac-36641

70. Hy-13026

71. Ic489666

72. Smr004702787

73. Sw219823-1

74. A-1138

75. D10560

76. J-517532

77. Q5908266

78. Brd-k60866521-001-01-4

79. (s)-5-fluoro-3-phenyl-2-[1-(9h-purin-6-ylamino)-propyl]-3h-quinazolin-4-one

80. 4(3h)-quinazolinone, 5-fluoro-3-phenyl-2-((1s)-1-(1h-purin-6-ylamino)propyl)-

81. 4(3h)-quinazolinone, 5-fluoro-3-phenyl-2-((1s)-1-(9h-purin-6-ylamino)propyl)-

82. 4(3h)-quinazolinone,5-fluoro-3-phenyl-2-[(1s)-1-(1h-purin-6-ylamino)propyl]-

83. 40l

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₁₈FN₇O
Molecular Weight	415.4 g/mol
XLogP3	3.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	5
Exact Mass	415.15568639 g/mol
Monoisotopic Mass	415.15568639 g/mol
Topological Polar Surface Area	99.2 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	685
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Zydelig
PubMed Health	Idelalisib (Oral route)
Drug Classes	Antineoplastic Agent
Drug Label	Idelalisib is an inhibitor of phosphatidylinositol 3-kinase, PI3K.The chemical name for idelalisib is 5-fluoro-3-phenyl-2-[(1S)-1-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one. It has a molecular formula of C22H18FN7O and a molecular weight of 41...
Active Ingredient	Idelalisib
Dosage Form	Tablet
Route	Oral
Strength	150mg; 100mg
Market Status	Prescription
Company	Gilead Sciences

2 of 2
Drug Name	Zydelig
PubMed Health	Idelalisib (Oral route)
Drug Classes	Antineoplastic Agent
Drug Label	Idelalisib is an inhibitor of phosphatidylinositol 3-kinase, PI3K.The chemical name for idelalisib is 5-fluoro-3-phenyl-2-[(1S)-1-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one. It has a molecular formula of C22H18FN7O and a molecular weight of 41...
Active Ingredient	Idelalisib
Dosage Form	Tablet
Route	Oral
Strength	150mg; 100mg
Market Status	Prescription
Company	Gilead Sciences

4.2 Therapeutic Uses

Antineoplastic Agents; Enzyme Inhibitors

National Library of Medicine's Medical Subject Headings. Idelalisib. Online file (MeSH, 2018). Available from, as of March 7, 2018: https://meshb.nlm.nih.gov/search

/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Idelalisib is included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of March 7, 2018: https://clinicaltrials.gov/

Zydelig is indicated, in combination with rituximab, for the treatment of patients with relapsed chronic lymphocytic leukemia (CLL) for whom rituximab alone would be considered appropriate therapy due to other co-morbidities. /Included in US product label/

NIH; DailyMed. Current Medication Information for Zydelig (Idelalisib) Tablet, Film-coated (Updated: February 8, 2017). Available from, as of March 28, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=efbdafa9-d18c-4e85-b4a2-1e620fc74e50

Zydelig is indicated for the treatment of patients with relapsed follicular B-cell non-Hodgkin lymphoma (FL) who have received at least two prior systemic therapies. Accelerated approval was granted for this indication based on Overall Response Rat. An improvement in patient survival or disease related symptoms has not been established. Continued approval for this indication may be contingent upon verification of clinical benefit in confirmatory trials. /Included in US product label/

Zydelig is indicated for the treatment of patients with relapsed small lymphocytic lymphoma (SLL) who have received at least two prior systemic therapies. /Included in US product label/

4.3 Drug Warning

/BOXED WARNING/ WARNING: FATAL AND SERIOUS TOXICITIES: HEPATIC. Fatal and/or serious hepatotoxicity occurred in 16% to 18% of Zydelig-treated patients. Monitor hepatic function prior to and during treatment. Interrupt and then reduce or discontinue Zydelig as recommended.

/BOXED WARNING/ WARNING: FATAL AND SERIOUS TOXICITIES: SEVERE DIARRHEA, COLITIS. Fatal and/or serious and severe diarrhea or colitis occurred in 14% to 20% of Zydelig-treated patients. Monitor for the development of severe diarrhea or colitis. Interrupt and then reduce or discontinue Zydelig as recommended.

/BOXED WARNING/ WARNING: FATAL AND SERIOUS TOXICITIES: PNEUMONITIS. Fatal and/or serious pneumonitis occurred in 4% of Zydelig-treated patients. Monitor for pulmonary symptoms and bilateral interstitial infiltrates. Interrupt or discontinue Zydelig as recommended.

/BOXED WARNING/ WARNING: FATAL AND SERIOUS TOXICITIES: INFECTIONS. Fatal and/or serious infections occurred in 21% to 48% of Zydelig-treated patients. Monitor for signs and symptoms of infection. Interrupt Zydelig if infection is suspected.

For more Drug Warnings (Complete) data for Idelalisib (20 total), please visit the HSDB record page.

4.4 Drug Indication

Idelalisib is indicated in the treatment of chronic lymphocytic leukemia (CLL), relapsed follicular B-cell non-Hodgkin lymphoma (FL), and relapsed small lymphocytic lymphoma (SLL). For the treatment of relapsed CLL, it is currently indicated as a second-line agent in combination with rituximab in patients for whom rituximab alone would be considered appropriate therapy due to other co-morbidities, while in the treatment of FL and SLL it is intended to be used in patients who have received at least two prior systemic therapies.

FDA Label

Zydelig is indicated in combination with an antiCD20 monoclonal antibody (rituximab or ofatumumab) for the treatment of adult patients with chronic lymphocytic leukaemia (CLL):

- who have received at least one prior therapy, or

- as first line treatment in the presence of 17p deletion or TP53 mutation in patients who are not eligible for any other therapies.

Zydelig is indicated as monotherapy for the treatment of adult patients with follicular lymphoma (FL) that is refractory to two prior lines of treatment.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antineoplastic Agents

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

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.)

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

IDELALISIB

5.2.2 FDA UNII

YG57I8T5M0

5.2.3 Pharmacological Classes

Kinase Inhibitor [EPC]; Kinase Inhibitors [MoA]; Cytochrome P450 3A Inhibitors [MoA]

5.3 ATC Code

L01XX47

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01E - Protein kinase inhibitors

L01EM - Phosphatidylinositol-3-kinase (pi3k) inhibitors

L01EM01 - Idelalisib

5.4 Absorption, Distribution and Excretion

Absorption

Following oral administration, the median Tmax was observed at 1.5 hours.

Route of Elimination

Following a single dose of 150 mg of [14C] idelalisib, 78% and 14% of the radioactivity was excreted in feces and urine, respectively. GS-563117, idelalisib's major metabolite, accounted for 49% of the radioactivity in the urine and 44% in the feces.

Volume of Distribution

23 L

Clearance

14.9 L/hr

Following oral administration of a single 150-mg dose of radiolabeled idelalisib, 78% of the dose was recovered in feces and 14% was recovered in urine; GS-563117 accounted for 44% of the dose recovered in feces and 49% of the dose recovered in urine.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 1175

The administration of a single dose of Zydelig with a high-fat meal (900 calories: 525 calories fat, 250 calories carboydrates, and 125 calories protein) increased idelalisib AUC 1.4-fold relative to fasting conditions. Zydelig can be administered without regard to food.

The median time to peak concentration (Tmax) was observed at 1.5 hours.

5.5 Metabolism/Metabolites

Idelalisib is metabolized by aldehyde oxidase and CYP3A to its major metabolite GS-563117, which is inactive against P110. Idelalisib is also metabolized to a minor extent by UGT1A4.

Idelalisib, a potent phosphatidylinositol-3-kinase delta (PI3Kd) inhibitor, is metabolized primarily by aldehyde oxidase to form GS-563117 and to a lesser extent by cytochrome P450 (CYP) 3A and uridine 5'-diphospho-glucuronosyltransferase 1A4. In vitro, idelalisib inhibits P-glycoprotein (P-gp) and organic anion transporting polypeptides 1B1 and 1B3, and GS-563117 is a time-dependent CYP3A inhibitor. This study enrolled 24 healthy subjects and evaluated (1) the effect of idelalisib on the pharmacokinetics (PK) of digoxin, a P-gp probe substrate, rosuvastatin, a breast cancer resistance protein, and OATP1B1/OATP1B3 substrate, and midazolam, a CYP3A substrate; and (2) the effect of a strong inducer, rifampin, on idelalisib PK. On treatment, the most common clinical adverse events (AEs) were headache and pyrexia. Grade 3 transaminase increases were observed in 5 of 24 subjects and were reversible. Two subjects had serious AEs after treatment completion (grade 3 pyrexia and/or drug-induced liver injury). Idelalisib coadministration did not affect digoxin and rosuvastatin PK. Coadministration with idelalisib increased plasma exposures of midazolam (138% and 437% for maximum observed plasma concentration (Cmax) and area under the plasma concentration-time curve from time 0 extrapolated to infinity (AUCinf), respectively), consistent with the in vitro finding of CYP3A inhibition by GS-563117. Rifampin caused a substantial decrease in idelalisib (58% and 75%, Cmax and AUCinf , respectively) and GS-563117 exposures, indicating an enhanced contribution of CYP3A to idelalisib metabolism under a strongly induced state.

PMID:25760671 Jin F et al; J Clin Pharmacol 55 (8): 909-19 (2015)

Idelalisib is more than 84% bound to plasma proteins. Idelalisib is metabolized to its major metabolite, GS-563117, principally by cytochrome P-450 (CYP) isoenzyme 3A and aldehyde oxidase; the drug is metabolized only to a minor extent by uridine diphosphate-glucuronosyl transferase (UGT) 1A4.1 GS-563117 is inactive against PI3Kdelta in vitro.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 1175

Idelalisib is metabolized via aldehyde oxidase and CYP3A with additional minor metabolism by UGT1A4.

5.6 Biological Half-Life

The terminal elimination half-life is 8.2 hours.

The mean terminal half-life of idelalisib is 8.2 hours.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 1175

5.7 Mechanism of Action

Idelalisib specifically inhibits P110, the delta isoform of the enzyme phosphatidylinositol-4,5-bisphosphate 3-kinase, also known as PI-3K. The PI-3Ks are a family of enzymes involved in cellular functions such as cell growth, proliferation, differentiation, motility, survival and intracellular trafficking, which in turn are involved in cancer. In contrast to the other class IA PI3Ks p110 and p110, p110 is principally expressed in leukocytes (white blood cells) and is important for the function of T cells, B cell, mast cells and neutrophils. By inhibiting this enzyme, idelalisib induces apoptosis of malignant cells and inhibits several cell signaling pathways, including B-cell receptor (BCR) signaling and C-X-C chemokine receptors type 5 and type 4 signalling, which are involved in trafficking and homing of B-cells to the lymph nodes and bone marrow. Treatment of lymphoma cells with idelalisib has been shown to result in inhibition of chemotaxis and adhesion, and reduced cell viability.

Idelalisib is an inhibitor of PI3Kdelta kinase, which is expressed in normal and malignant B-cells. Idelalisib induced apoptosis and inhibited proliferation in cell lines derived from malignant B-cells and in primary tumor cells. Idelalisib inhibits several cell signaling pathways, including B-cell receptor (BCR) signaling and the CXCR4 and CXCR5 signaling, which are involved in trafficking and homing of B-cells to the lymph nodes and bone marrow. Treatment of lymphoma cells with idelalisib resulted in inhibition of chemotaxis and adhesion, and reduced cell viability.

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