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CAS-74381-53-6

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Also known as: Leuprorelin acetate, Lupron, 74381-53-6, Carcinil, Enantone, Lucrin

Molecular Formula

C₆₁H₈₈N₁₆O₁₄

Molecular Weight

1269.4 g/mol

InChI Key

RGLRXNKKBLIBQS-XNHQSDQCSA-N

FDA UNII

37JNS02E7V

A potent synthetic long-acting agonist of GONADOTROPIN-RELEASING HORMONE that regulates the synthesis and release of pituitary gonadotropins, LUTEINIZING HORMONE and FOLLICLE STIMULATING HORMONE.

1 2D Structure

CAS 74381-53-6

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

acetic acid;(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(2S)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide

2.1.2 InChI

InChI=1S/C59H84N16O12.C2H4O2/c1-6-63-57(86)48-14-10-22-75(48)58(87)41(13-9-21-64-59(60)61)68-51(80)42(23-32(2)3)69-52(81)43(24-33(4)5)70-53(82)44(25-34-15-17-37(77)18-16-34)71-56(85)47(30-76)74-54(83)45(26-35-28-65-39-12-8-7-11-38(35)39)72-55(84)46(27-36-29-62-31-66-36)73-50(79)40-19-20-49(78)67-40;1-2(3)4/h7-8,11-12,15-18,28-29,31-33,40-48,65,76-77H,6,9-10,13-14,19-27,30H2,1-5H3,(H,62,66)(H,63,86)(H,67,78)(H,68,80)(H,69,81)(H,70,82)(H,71,85)(H,72,84)(H,73,79)(H,74,83)(H4,60,61,64);1H3,(H,3,4)/t40-,41-,42-,43+,44-,45-,46-,47-,48-;/m0./s1

2.1.3 InChI Key

RGLRXNKKBLIBQS-XNHQSDQCSA-N

2.1.4 Canonical SMILES

CCNC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(CO)NC(=O)C(CC3=CNC4=CC=CC=C43)NC(=O)C(CC5=CN=CN5)NC(=O)C6CCC(=O)N6.CC(=O)O

2.1.5 Isomeric SMILES

CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC3=CNC4=CC=CC=C43)NC(=O)[C@H](CC5=CN=CN5)NC(=O)[C@@H]6CCC(=O)N6.CC(=O)O

2.2 Other Identifiers

2.2.1 UNII

37JNS02E7V

2.3 Synonyms

2.3.1 MeSH Synonyms

1. A 43818

2. A-43818

3. A43818

4. Acetate, Leuprolide

5. Enantone

6. Leuprolide

7. Leuprolide Monoacetate

8. Leuprolide, (dl-leu)-isomer

9. Leuprolide, (l-leu)-isomer

10. Leuprorelin

11. Lupron

12. Monoacetate, Leuprolide

13. Tap 144

14. Tap-144

15. Tap144

2.3.2 Depositor-Supplied Synonyms

1. Leuprorelin Acetate

2. Lupron

3. 74381-53-6

4. Carcinil

5. Enantone

6. Lucrin

7. Eligard

8. Leuplin

9. Viadur

10. Lupron Depot

11. Tap-144

12. Abbott-43818

13. Prostap

14. Leuprolide Monoacetate

15. Trenantone

16. Fensolvi

17. Lupaneta

18. Tap-144-sr

19. Lupron Depot-ped

20. Lutrate Depot

21. Leuporelin Acetate

22. A-43818

23. Leuprolide (acetate)

24. Chebi:63597

25. 53714-56-0

26. 37jns02e7v

27. Leuprolide Acetate [usan]

28. Leuprin

29. Procrin

30. Leuplin Depot

31. Procren Depot

32. Uno-enantone

33. Depo-lupron

34. Lupron Ped

35. Leuprorelin Acetate [jan]

36. Leuprolide Acetate Depot

37. Abbott 43818

38. Lupron Depot-3

39. Lupron Depot-4

40. Unii-37jns02e7v

41. Enanton

42. Lutrate

43. Onectyl

44. Mfcd00072080

45. Leuprolide Acetate [usan:usp]

46. Lupron Depot Ped

47. Leuprolide Acetate Salt

48. Des-gly10-[d-leu6]-lh-rh Ethylamide

49. Ncgc00183364-01

50. Schembl3174

51. Dsstox_cid_28935

52. Dsstox_rid_83201

53. Dsstox_gsid_49009

54. Mls000028695

55. Chembl1200775

56. Dtxsid7049009

57. Leuprolide Acetate [vandf]

58. Leuprolide Monoacetate [mi]

59. Leuprolide Acetate [usp-rs]

60. Leuprorelin Acetate [mart.]

61. Tox21_113507

62. Bdbm50247891

63. Leuprorelin Acetate [who-dd]

64. S3718

65. Akos015895632

66. Akos030485977

67. Ccg-270666

68. Cs-1434

69. Leuprolide Acetate [orange Book]

70. 5-oxo-l-prolyl-l-histidyl-l-tryptophyl-l-seryl-l-tryosyl-d-leucyl-l-leucyl-l-arginyl-n-ethyl-l-prolinamide Monoacetate (salt)

71. Ac-28731

72. Hy-13665

73. Leuprolide Acetate [usp Monograph]

74. Smr000058945

75. Cas-74381-53-6

76. L0249

77. (des-gly10,d-leu6,pro-nhet9)-lhrh Acetate

78. Leuprolide Acetate (53714-56-0 Free Base)

79. 381l536

80. 743l536

81. A829746

82. A838107

83. Pyr-his-trp-ser-tyr-d-leu-leu-arg-pro-nhet.hoac

84. Q27104908

85. Pglu-his-trp-ser-tyr-d-leu-leu-arg-pro-nhc2h5 Acetate Salt

86. 1-9-leutenizing Hormone-releasing Factor (swine), 6-d-leucine-9-(n-ethyl-l-prolinamide)-, Monoacetate (salt)

87. 5-oxo-l-prolyl-l-histidyl-l-tryptophyl-l-seryl-l-tryosyl-d-leucyl-l-leucyl-l-arginyl-n-ethyl-l-prolinamide Acetate (salt)

88. 5-oxo-l-prolyl-l-histidyl-l-tryptophyl-l-seryl-l-tryosyl-d-leucyl-l-leucyl-l-arginyl-n-ethyl-l-prolinamide Monoacetate

89. 5-oxo-l-prolyl-l-histidyl-l-tryptophyl-l-seryl-l-tyrosyl-d-leucyl-l-leucyl-l-arginyl-n-ethyl-l-prolinamide--acetic Acid (1/1)

90. 88793-81-1

91. Acetic Acid; N-[2-[[2-[[2-[[2-[[1-[[1-[[1-[2-(ethylcarbamoyl)pyrrolidine-1-carbonyl]-4-guanidino-butyl]carbamoyl]-2-methyl-propyl]carbamoyl]-2-methyl-propyl]amino]-1-[(4-hydroxyphenyl)methyl]-2-oxo-ethyl]amino]-1-(hydroxymethyl)-2-oxo-ethyl]amino]-1-(1h-i

92. Acetic Acid; N-[2-[[2-[[2-[[2-[[1-[[1-[[1-[2-(ethylcarbamoyl)pyrrolidine-1-carbonyl]-4-guanidino-butyl]carbamoyl]-3-methyl-butyl]carbamoyl]-3-methyl-butyl]amino]-1-[(4-hydroxyphenyl)methyl]-2-oxo-ethyl]amino]-1-(hydroxymethyl)-2-oxo-ethyl]amino]-1-(1h-ind;leuprolide Acetate

93. L-prolinamide, 5-oxo-l-prolyl-l-histidyl-l-tryptophyl-l-seryl-l-tyrosyl-d-leucyl-l-leucyl-l-arginyl-n-ethyl-, Acetate (1:1)

94. Luteinizing Hormone-releasing Factor (pig), 6-d-leucine-9-(n-ethyl-l-prolinamide)-10-deglycinamide-, Monoacetate (salt)

95. Luteinizing Hormone-releasing Factor, 6-d-leucine-9-(n-ethyl-l-prolinamide)-10-deglycinamide Acetate (salt)

2.4 Create Date

2005-06-29

3 Chemical and Physical Properties

Molecular Formula	C₆₁H₈₈N₁₆O₁₄
Molecular Weight	1269.4 g/mol
Hydrogen Bond Donor Count	16
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	32
Exact Mass	1268.66659154 g/mol
Monoisotopic Mass	1268.66659154 g/mol
Topological Polar Surface Area	469 Å²
Heavy Atom Count	91
Formal Charge	0
Complexity	2420
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 5
Drug Name	ELIGARD
Active Ingredient	LEUPROLIDE ACETATE
Company	TOLMAR THERAP (Application Number: N021343. Patents: 6565874, 6626870, 6773714, 9254307); TOLMAR THERAP (Application Number: N021379. Patents: 6565874, 6626870, 6773714, 8470359, 8486455, 8840916, 9283282, 9539333); TOLMAR THERAP (Application Number: N021488. Patents: 6565874, 6626870, 6773714, 8470359, 8486455, 8840916, 9283282, 9539333); TOLMAR THERAP (Application Number: N021731. Patents: 6565874, 6626870, 6773714, 8470359, 8486455, 8840916, 9283282, 9539333)

2 of 5
Drug Name	LEUPROLIDE ACETATE
Active Ingredient	LEUPROLIDE ACETATE
Company	SANDOZ (Application Number: A074728); SUN PHARMA GLOBAL (Application Number: A078885); TEVA PHARMS USA (Application Number: A075471)

3 of 5
Drug Name	LUPRON DEPOT-PED
Active Ingredient	LEUPROLIDE ACETATE
Company	ABBVIE ENDOCRINE INC (Application Number: N020263)

4 of 5
Drug Name	LUPRON DEPOT
Active Ingredient	LEUPROLIDE ACETATE
Company	ABBVIE ENDOCRINE INC (Application Number: N019732); ABBVIE ENDOCRINE INC (Application Number: N020011); ABBVIE ENDOCRINE INC (Application Number: N020517. Patents: 7429559, 8815801, 8921326); ABBVIE ENDOCRINE INC (Application Number: N020708)

5 of 5
Drug Name	LUPANETA PACK
Active Ingredient	LEUPROLIDE ACETATE; NORETHINDRONE ACETATE
Company	ABBVIE ENDOCRINE (Application Number: N203696)

4.2 Therapeutic Uses

Antineoplastic Agents, Hormonal; Fertility Agents, Female

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

Leuprolide is indicated for the palliative treatment of advanced prostatic cancer, especially as an alternative to orchiectomy or estrogen administration. /Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 1708

Leuprolide is indicated for management of endometriosis, including pain relief and reduction of endometriotic lesions. /Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 1708

Leuprolide is about 30 times more active than natural gonadotropin-releasing hormone ... and 100 times more active than gonadorelin.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1354

For more Therapeutic Uses (Complete) data for LEUPROLIDE (15 total), please visit the HSDB record page.

4.3 Drug Warning

Patients sensitive to other synthetic gonadotropin-releasing hormone analogs may also be sensitive to leuprolide.

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 1708

In males: Suppression of testosterone secretion results in impairment of fertility. Although it is not known whether fertility is restored after leuprolide is withdrawn, reversal of fertility suppression does occur after withdrawal of similar analogs.

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 1708

Leuprolide is not recommended during pregnancy. Because the effects on fetal mortality would logically result from the hormonal effects of leuprolide, it can be concluded that there is a risk of spontaneous abortion if leuprolide is administered during pregnancy.

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 1708

It is not known whether leuprolide passes into breast milk. However, because of potential adverse effects in the infant, breast-feeding is usually not recommended during treatment with leuprolide.

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 1708

For more Drug Warnings (Complete) data for LEUPROLIDE (14 total), please visit the HSDB record page.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antineoplastic Agents, Hormonal

Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal.)

Fertility Agents, Female

Compounds which increase the capacity to conceive in females. (See all compounds classified as Fertility Agents, Female.)

5.2 Absorption, Distribution and Excretion

Bioavailablity after intramuscular injection of the depot formulation is estimated to be about 90%.

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 1708

The pharmacological effects of leuprolide acetate depot microspheres were studied in rats and dogs following subcutaneous and intramuscular injection. After injection the microspheres provided similar linear drug release and sustained serum drug levels for 3 months. Persistent suppression of serum luteinizing hormone, follicle stimulating hormone in rats, and testosterone in rats and dogs for over 16 wk was achieved with microspheres at a dose of 100 ug/kg/day in rats and 25.6 ug/kg/day in dogs. Responses upon periodic challenge tests revealed that a single injection of microspheres dramatically suppressed the function of the pituitary-gonadal system for 15 wks in rats. The growth of genital organs was also suppressed dose-dependently for over 3 months. It was concluded that persistent pharmacological effects are obtained with an injection of leuprolide 3-month depot microspheres.

PMID:7971724 Okada H et al; Pharm Res 11 (Aug): 1199-1203 (1994)

The effect of formulation adjuvants on the absorption of leuprolide acetate after intraduodenal injection and oral administration to male castrate rats is reported. Absorption was low, approximately 0.01% and 0.08% by oral and intraduodenal administration, respectively, compared with intravenous controls. An aqueous formulation and a water-in-oil emulsion of a lipophilic salt, a decane sulfonic acid derivative of leuprolide gave intraduodenal bioavailabilities of approximately 0.2% and 1% respectively. Evaluation of formulation effects on the oral absorption of the drug showed that lipophilicity, surfactant, and vehicle properties significantly affected intraduodenal absorption of leuprolide. Absolute bioavailability of the drug in typical emulsion systems ranged from approximately 3-10% and represented an improvement of about 100-fold in gastrointestinal bioavailability of this peptide. The implications of these findings relative to the effect of formulation adjuvants on oral absorption of leuprolide and other peptides following intraduodenal administration are discussed.

Adjel A et al; L Drug Target 1 (3): 251-8 (1993)

The bioavailability of leuprolide acetate was studied in rats and in healthy males (ages 19-39 yr) after inhalation and intranasal administration, compared with intravenous and subcutaneous injection. Intranasal bioavailability in rats was significantly increased by alpha-cyclodextrin, eidetic acid, and solution volume. Intra-animal variability was 30-60% and absorption ranged from 8 to 46% compared with intravenous controls. In humans, the subcutaneous injection was 94% bioavailable compared with intravenous. Intranasal bioavailability averaged 2.4%, with significant intersubject variability. Plasma peak concentrations for one and 3 mg dosages were 0.24-1.6 and 0.1-11 ng/ml, respectively. Mean plasma peak concentrations of one mg aerosol and 2 mg suspension aerosols, respectively. Bioavailability of suspension aerosols was fourfold greater than that of the solution aerosol. /Leuprolide acetate/

PMID:1553349 Adjel A et al; Pharm Res 9 (Feb): 244-9 (1992)

5.3 Mechanism of Action

Like naturally occurring luteinizing hormone-releasing hormone, initial or intermittent administration of leuprolide stimulates release of luteinizing hormone and follicle-stimulating hormone from the anterior pituitary.

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 1708

Luteinizing hormone and follicle-stimulating hormone release from the anterior pituitary transiently increases testosterone concentration in males. However, continuous administration of leuprolide in the treatment of prostatic carcinoma suppresses secretion of gonadotropin-releasing hormone, with a resultant fall in testosterone concentrations and a "medical castration".

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 1708

Initial stimulation of gonadotropins form the anterior pituitary is followed by prolonged suppression. Gonadotropin release from the anterior pituitary transiently increases estrone and estradiol concentrations in females. However, continuous administration of leuprolide in the treatment of endometriosis produces a fall in estrogens to postmenopausal levels. As a consequence of suppression of ovarian function, both normal and ectopic endometrial tissues become inactive and atrophic. As a result, amenorrhea occurs.

USP Convention. USPDI - Drug Information for the Health Care Professional. 15 th ed. Volume 1. Rockville, MD: United States Pharmacopeial Convention, Inc., 1995. (Plus updates.), p. 1708

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