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Synopsis

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Chemistry

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Also known as: Primaquine diphosphate, 63-45-6, Primaquine bisphosphate, Primaquine (diphosphate), Malquine, 1,4-pentanediamine, n4-(6-methoxy-8-quinolinyl)-, phosphate (1:2)

Molecular Formula

C₁₅H₂₇N₃O₉P₂

Molecular Weight

455.34 g/mol

InChI Key

GJOHLWZHWQUKAU-UHFFFAOYSA-N

FDA UNII

H0982HF78B

An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404)

1 2D Structure

Primaquine Diphosphate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine;phosphoric acid

2.1.2 InChI

InChI=1S/C15H21N3O.2H3O4P/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14;2*1-5(2,3)4/h4,6,8-11,18H,3,5,7,16H2,1-2H3;2*(H3,1,2,3,4)

2.1.3 InChI Key

GJOHLWZHWQUKAU-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(CCCN)NC1=C2C(=CC(=C1)OC)C=CC=N2.OP(=O)(O)O.OP(=O)(O)O

2.2 Other Identifiers

2.2.1 UNII

H0982HF78B

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Diphosphate, Primaquine

2. Phosphate, Primaquine

3. Primacin

4. Primaquine

5. Primaquine Diphosphate

2.3.2 Depositor-Supplied Synonyms

1. Primaquine Diphosphate

2. 63-45-6

3. Primaquine Bisphosphate

4. Primaquine (diphosphate)

5. Malquine

6. 1,4-pentanediamine, N4-(6-methoxy-8-quinolinyl)-, Phosphate (1:2)

7. Primaquine Phosphate;primaquine Bisphosphate

8. N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine Bis(phosphate)

9. H0982hf78b

10. Nsc-149765

11. N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine; Bis(phosphoric Acid)

12. Primaquine Bis(phosphate)

13. Wr 2975

14. Dsstox_cid_25248

15. Dsstox_rid_80773

16. Dsstox_gsid_45248

17. Ccris 1946

18. Sr-05000001864

19. Ncgc00178754-06

20. Einecs 200-560-8

21. Nsc 149765

22. Primaquine Phosphate [usp]

23. Unii-h0982hf78b

24. Primaquine (tn)

25. Prestwick_406

26. Primaquini Diphosphas

27. Camden

28. Sn13272 Diphosphate

29. 8-((4-amino-1-methylbutyl)amino)-6-methoxyquinoline Diphosphate

30. Cas-63-45-6

31. Ncgc00016284-01

32. 8-((4-amino-1-methylbutyl)amino)-6-methoxyquinoline Phosphate (1:2)

33. Primachine Phosphate

34. Schembl41096

35. Chembl43128

36. Primaquine Bisphosphate, 98%

37. Spectrum1500500

38. Dtxsid6045248

39. Hms502i08

40. Primaquine Phosphate (jan/usp)

41. 8-(4-amino-1-methylbutylamino)-6-methoxyquinoline Diphosphate

42. 8-(4-amino-1-methylbutylamino)-6-methoxyquinolinediphosphate

43. Hms1569o14

44. Hms1920j18

45. Hms2092a19

46. Hms2096o14

47. Hms3652b19

48. Hms3713o14

49. Primaquine Phosphate [jan]

50. Primaquine Diphosphate [mi]

51. Ibscreen-bb Bb_sc-03079

52. Primaquine Phosphate [vandf]

53. Tox21_110350

54. Ccg-40283

55. Mfcd00013166

56. Primaquine Phosphate [mart.]

57. S4237

58. Primaquine Phosphate [usp-rs]

59. Primaquine Phosphate [who-dd]

60. (+-)-8-((4-amino-1-methylbutyl)amino)-6-methoxyquinoline Phosphate (1:2)

61. 1,4-pentanediamine, N(sup 4)-(6-methoxy-8-quinolinyl)-, Phosphate (1:2)

62. Akos026749962

63. Quinoline, 8-((4-amino-1-methylbutyl)amino)-6-methoxy-, Phosphate (1:2)

64. Tox21_110350_1

65. Cs-3875

66. Primaquine Diphosphate [who-ip]

67. 1,4-pentanediamine, N(sup 4)-(6-methoxy-8-quinolinyl)-, (+-)-, Phosphate (1:2)

68. Ncgc00094767-01

69. Ncgc00094767-02

70. As-13148

71. Hy-12651

72. Primaquine Phosphate [orange Book]

73. Db-054488

74. Primaquine Phosphate [usp Monograph]

75. Primaquine Diphosphate [ep Monograph]

76. Primaquini Diphosphas [who-ip Latin]

77. Sw196647-3

78. D02126

79. E75742

80. 013p166

81. Sr-05000001864-1

82. Sr-05000001864-3

83. Sr-05000001864-7

84. Q27279400

85. N4-(6-methoxyquinolin-8-yl)pentane-1,4-diaminebis(phosphate)

86. 8-(4-amino-1-methylbutylamino)-6-methoxyquinoline Diphosphate Salt

87. 1,4-pentanediamine, N^4-(6-methoxy-8-quinolinyl)-, Phosphate (1:2)

88. 8-?(4-?amino-?1-?methylbutylamino)?-?6-?methoxyquinoline Diphosphate Salt

89. Primaquine Diphosphate, European Pharmacopoeia (ep) Reference Standard

90. Primaquine Phosphate, United States Pharmacopeia (usp) Reference Standard

91. Quinoline, 8-((4-amino-1-methylbutyl)amino)-6-methoxy-, Diphosphate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₂₇N₃O₉P₂
Molecular Weight	455.34 g/mol
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	6
Exact Mass	455.12225344 g/mol
Monoisotopic Mass	455.12225344 g/mol
Topological Polar Surface Area	216 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	312
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Primaquine phosphate
Drug Label	Primaquine phosphate is 8-[(4-Amino-1-methylbutyl)amino]-6-methoxyquinoline phosphate, a synthetic compound with potent antimalarial activity. Each tablet contains 26.3 mg of Primaquine phosphate (equivalent to 15 mg of primaquine base). The dosage i...
Active Ingredient	Primaquine phosphate
Dosage Form	Tablet
Route	Oral
Strength	eq 15mg base
Market Status	Prescription
Company	Bayshore Pharms; Alvogen

2 of 2
Drug Name	Primaquine phosphate
Drug Label	Primaquine phosphate is 8-[(4-Amino-1-methylbutyl)amino]-6-methoxyquinoline phosphate, a synthetic compound with potent antimalarial activity. Each tablet contains 26.3 mg of Primaquine phosphate (equivalent to 15 mg of primaquine base). The dosage i...
Active Ingredient	Primaquine phosphate
Dosage Form	Tablet
Route	Oral
Strength	eq 15mg base
Market Status	Prescription
Company	Bayshore Pharms; Alvogen

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antimalarials

Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Antimalarial [EPC]

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API Reference Price

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MELLO ROAD, NEAR G.P.O., MUMBAI,MAHARASHTRA","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2023","qtr":"Q3","strtotime":1688668200,"product":"PRIMAQUINE PHOSPHATE USP BATCH NO: 23001","address":"412-A, CITY CENTER, 570, M.G. ROAD, (OPP, HIGH COURT)","city":"INDORE, M.P.","supplier":"MN GLOBEX PRIVATE ","supplierCountry":"INDIA","foreign_port":"JOHANNESBURG - JOHAN","customer":"DB FINE SPECIALITIES ","customerCountry":"SOUTH AFRICA","quantity":"7.00","actualQuantity":"7","unit":"KGS","unitRateFc":"490","totalValueFC":"3114.7","currency":"USD","unitRateINR":36571.392,"date":"07-Jul-2023","totalValueINR":"255999.744","totalValueInUsd":"3114.7","indian_port":"BOMBAY AIR","hs_no":"29334900","bill_no":"0","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"SOUTH AFRICA","selfForZScoreResived":"Pharma Grade","supplierPort":"BOMBAY AIR","supplierAddress":"412-A, CITY CENTER, 570, M.G. ROAD, (OPP, HIGH COURT), INDORE, M.P.","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2023","qtr":"Q3","strtotime":1689618600,"product":"DRUGS: PRIMAQUINE PHOSPHATE\/PRIMAQUINE D","address":"48 KANDIVLI INDUSTRIAL ESTATE KANDIVLI WEST Contact No: 918928628","city":"MUMBAI","supplier":"IPCA LABORATORIES","supplierCountry":"INDIA","foreign_port":"JAKARTA","customer":"OF","customerCountry":"INDONESIA","quantity":"50.00","actualQuantity":"50","unit":"KGS","unitRateFc":"290","totalValueFC":"13943.4","currency":"USD","unitRateINR":22919.993459999998,"date":"18-Jul-2023","totalValueINR":"1145999.673","totalValueInUsd":"13943.4","indian_port":"BOMBAY AIR","hs_no":"29334900","bill_no":"0","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"INDONESIA","selfForZScoreResived":"Pharma Grade","supplierPort":"BOMBAY AIR","supplierAddress":"48 KANDIVLI INDUSTRIAL ESTATE KANDIVLI WEST Contact No: 918928628, MUMBAI","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2023","qtr":"Q4","strtotime":1697481000,"product":"DRUGS - PRIMAQUINE PHOSPHATE \/ PRIMAQUINE DIPHOSPHATE PH.EUR.","address":"48, KANDIVLI INDUSTRIAL ESTATE,","city":"MUMBAI, MAHARASHTRA.","supplier":"IPCA LABORATORIES","supplierCountry":"INDIA","foreign_port":"LIMASSOL","customer":"OF","customerCountry":"CYPRUS","quantity":"600.00","actualQuantity":"600","unit":"KGS","unitRateFc":"220.3","totalValueFC":"128452.4","currency":"USD","unitRateINR":17818.333333333332,"date":"17-Oct-2023","totalValueINR":"10691000","totalValueInUsd":"128452.4","indian_port":"JNPT","hs_no":"29334900","bill_no":"4690810","productDescription":"API","marketType":"REGULATED MARKET","country":"CYPRUS","selfForZScoreResived":"Pharma Grade","supplierPort":"JNPT","supplierAddress":"48, KANDIVLI INDUSTRIAL ESTATE,, MUMBAI, MAHARASHTRA.","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2023","qtr":"Q4","strtotime":1697481000,"product":"DRUGS - PRIMAQUINE PHOSPHATE \/ PRIMAQUINE DIPHOSPHATE PH.EUR.","address":"48, KANDIVLI INDUSTRIAL ESTATE,","city":"MUMBAI, MAHARASHTRA.","supplier":"IPCA LABORATORIES","supplierCountry":"INDIA","foreign_port":"LIMASSOL","customer":"OF","customerCountry":"CYPRUS","quantity":"600.00","actualQuantity":"600","unit":"KGS","unitRateFc":"220.3","totalValueFC":"128452.4","currency":"USD","unitRateINR":17818.333333333332,"date":"17-Oct-2023","totalValueINR":"10691000","totalValueInUsd":"128452.4","indian_port":"JNPT","hs_no":"29334900","bill_no":"4694372","productDescription":"API","marketType":"REGULATED MARKET","country":"CYPRUS","selfForZScoreResived":"Pharma Grade","supplierPort":"JNPT","supplierAddress":"48, KANDIVLI INDUSTRIAL ESTATE,, MUMBAI, MAHARASHTRA.","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1713724200,"product":"DRUGS: PRIMAQUINE PHOSPHATE \/ PRIMAQUINE DIPHOSPHATE USP","address":"48, KANDIVLI INDUSTRIAL ESTATE,","city":"MUMBAI, MAHARASHTRA.","supplier":"IPCA LABORATORIES","supplierCountry":"INDIA","foreign_port":"MANAGUA","customer":"OF","customerCountry":"NICARAGUA","quantity":"35.00","actualQuantity":"35","unit":"KGS","unitRateFc":"391","totalValueFC":"13552.7","currency":"USD","unitRateINR":32335.700000000001,"date":"22-Apr-2024","totalValueINR":"1131749.5","totalValueInUsd":"13552.7","indian_port":"Bombay Air","hs_no":"29334900","bill_no":"9311436","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"NICARAGUA","selfForZScoreResived":"Pharma Grade","supplierPort":"Bombay Air","supplierAddress":"48, KANDIVLI INDUSTRIAL ESTATE,, MUMBAI, MAHARASHTRA.","customerAddress":""},{"dataSource":"API Import","activeIngredients":"","year":"2021","qtr":"Q3","strtotime":1625596200,"product":"PRIMAQUINE PHOSPHATE","address":"NAIR BAUG, AKURLI ROADKANDIVILI EAST","city":"MUMBAI ,MAHARASHTRA","supplier":"ASUN LABORATORY LTD","supplierCountry":"CHINA","foreign_port":"HONG KONG","customer":"BDH INDUSTRIES LIMITED","customerCountry":"INDIA","quantity":"130.00","actualQuantity":"130","unit":"KGS","unitRateFc":"360","totalValueFC":"47285.6","currency":"USD","unitRateINR":"27108","date":"07-Jul-2021","totalValueINR":"3524040","totalValueInUsd":"47285.6","indian_port":"BOMBAY AIR","hs_no":"29392090","bill_no":"4591772","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"HONG KONG","supplierAddress":"","customerAddress":"NAIR BAUG, AKURLI ROADKANDIVILI EAST"}]

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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ACTIVE PHARMA INGREDIENTS

8 API Suppliers

4 USDMF

1 CEP/COS

3 EU WC

4 NDC API

4 Listed Suppliers

$ API Reference Price

FINISHED DOSAGE FORMULATIONS

12 FDF Dossiers

5 FDA Orange Book

2 Europe

1 Canada

4 Listed Dossiers

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12 BASF

1 Clariant

10 Corel Pharma Chem

4 DFE Pharma

1 Finar

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15 Roquette

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10 Sigachi Industries

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EXCIPIENTS BY APPLICATIONS

55 Fillers, Diluents & Binders

44 Coating Systems & Additives

27 Direct Compression

25 Controlled & Modified Release

20 Thickeners and Stabilizers

15 Solubilizers

15 Co-Processed Excipients

14 Granulation

13 Lubricants & Glidants

11 Topical

11 Film Formers & Plasticizers

10 Disintegrants & Superdisintegrants

9 Parenteral

7 Taste Masking

7 Emulsifying Agents

6 Chewable & Orodispersible Aids

5 Empty Capsules

5 API Stability Enhancers

4 Coloring Agents

4 Rheology Modifiers

4 Vegetarian Capsules

3 Surfactant & Foaming Agents