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Synopsis

ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: 57773-65-6, Somagard, D-trp lhrh-pea, D-trp-lhrh-pea, Bachem 9022, Tkg3i66tve

Molecular Formula

C₆₄H₈₃N₁₇O₁₂

Molecular Weight

1282.4 g/mol

InChI Key

GJKXGJCSJWBJEZ-XRSSZCMZSA-N

FDA UNII

TKG3I66TVE

Deslorelin is a synthetic nonapeptide analogue of the natural gonadotrophin releasing hormone (GnRH) with potential antineoplastic activity. Deslorelin binds to and activates pituitary gonadotropin releasing hormone (GnRH) receptors. Continuous, prolonged administration of goserelin in males results in pituitary GnRH receptor desensitization and inhibition of pituitary secretion of follicle stimulating hormone (FSH) and luteinizing hormone (LH), leading to a significant decline in testosterone production; in females, prolonged administration results in a decrease in estradiol production. (NCI04)

1 2D Structure

Deslorelin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(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]-3-(1H-indol-3-yl)-1-oxopropan-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/C64H83N17O12/c1-4-68-62(92)53-16-10-24-81(53)63(93)46(15-9-23-69-64(65)66)74-56(86)47(25-35(2)3)75-58(88)49(27-37-30-70-43-13-7-5-11-41(37)43)77-57(87)48(26-36-17-19-40(83)20-18-36)76-61(91)52(33-82)80-59(89)50(28-38-31-71-44-14-8-6-12-42(38)44)78-60(90)51(29-39-32-67-34-72-39)79-55(85)45-21-22-54(84)73-45/h5-8,11-14,17-20,30-32,34-35,45-53,70-71,82-83H,4,9-10,15-16,21-29,33H2,1-3H3,(H,67,72)(H,68,92)(H,73,84)(H,74,86)(H,75,88)(H,76,91)(H,77,87)(H,78,90)(H,79,85)(H,80,89)(H4,65,66,69)/t45-,46-,47-,48-,49+,50-,51-,52-,53-/m0/s1

2.1.3 InChI Key

GJKXGJCSJWBJEZ-XRSSZCMZSA-N

2.1.4 Canonical SMILES

CCNC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(CC2=CNC3=CC=CC=C32)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(CO)NC(=O)C(CC5=CNC6=CC=CC=C65)NC(=O)C(CC7=CN=CN7)NC(=O)C8CCC(=O)N8

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](CC2=CNC3=CC=CC=C32)NC(=O)[C@H](CC4=CC=C(C=C4)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC5=CNC6=CC=CC=C65)NC(=O)[C@H](CC7=CN=CN7)NC(=O)[C@@H]8CCC(=O)N8

2.2 Other Identifiers

2.2.1 UNII

TKG3I66TVE

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 6-trp-10-n-et-glynh2-lhrh

2. D-trp(6)-n-et-d-glynh2(10)-lhrh

3. Deslorelin Acetate

4. Gnrh, Trp(6)-n-et-glynh2(10)-

5. Lhrh, Trp(6)-n-et-glynh2(10)-

6. Lhrh, Tryptophyl(6)-n-ethylglycinamide(10)-

7. Ovuplant

8. Somagard

2.3.2 Depositor-Supplied Synonyms

1. 57773-65-6

2. Somagard

3. D-trp Lhrh-pea

4. D-trp-lhrh-pea

5. Bachem 9022

6. Tkg3i66tve

7. 1-9-luteinizing Hormone-releasing Factor (swine),6-d-tryptophan-9-(n-ethyl-l-prolinamide)-

8. 5-oxo-l-prolyl-l-histidyl-l-tryptophyl-l-seryl-l-tyrosyl-d-tryptophyl-l-leucyl-l-arginyl-n-ethyl-l-prolinamide

9. Deslorelina

10. Desloreline

11. Deslorelinum

12. Ncgc00167516-01

13. Unii-tkg3i66tve

14. Desloreline [inn-french]

15. Deslorelinum [inn-latin]

16. Deslorelina [inn-spanish]

17. Gnrh (d-trp6,pro9-net)

18. Deslorelin [usan:inn:ban]

19. (d-trp6,pro9-nhet)lh-rh

20. (d-trp6,des-gly10)-lh-rh Ethylamide

21. (de-gly10,d-trp6,pro-nhet)-lh-rh

22. (des-gly10(d-tro6)-lh-rh Ethylamide

23. Lhrh-t

24. (d-trp(sub 6)-pro(sup 9)-net)-gnrh

25. Deslorelin [mi]

26. Deslorelin [inn]

27. Deslorelin (usan/inn)

28. Deslorelin [usan]

29. (d-trp6,des-gly-nh210)-lh-rh Ethylamide

30. D-trp(sup 6)-pro(sup 9)-n-ethylamide-lhrh

31. (d-trp(sup 6)-pro(sup 9))-lhrh Ethylamide

32. H 4065

33. Deslorelin [mart.]

34. Deslorelin [who-dd]

35. Schembl59413

36. Gtpl9343

37. Chembl2365665

38. Dtxsid2048323

39. Schembl19409316

40. Bdbm84726

41. Chebi:177570

42. (d-trp(sub 6)-pro(sup 9)-net)-gonadotropin Releasing Hormone

43. Gonadotropin Releasing Hormone, (d-trp(sup 6)-pro(sup 9)-net)-

44. Des-gly-10-trp-6-ethylamide-lhrh

45. (d-trp(sup 6)-pro(sup 9))-luteinizing Hormone-releasing Hormone Ethylamide

46. Akos015994649

47. Cs-5746

48. Db11510

49. Hs-2009

50. 6-d-tryptophan-9-(n-ethyl-l-prolinamide)-1-9-luteinizing Hormone-releasing Factor (swine)

51. Gnrh, Trp(6)-n-et-pronh2(9)-

52. Lhrh, Trp(6)-n-et-pronh2(9)-

53. Ncgc00167516-02

54. Ncgc00167516-03

55. Gnrh, Des-gly(10)-trp(6)-ethylamide-

56. Hy-12556

57. Lhrh, Des-gly(10)-trp(6)-ethylamide-

58. 6-trp-9-n-et-pro-10-des-glynh2-lhrh

59. 6-d-phenylalanine-9-(n-ethyl-l-prolinamide)-

60. D03694

61. 773d656

62. Des-gly10,(d-trp6)luteinizing Hormone*releasing H

63. Lhrh, Des-glycyl(10)-tryptophyl(6)-ethylamide-

64. Q5264591

65. (d-trp6-pro9-net)luteinizing Hormone-releasing Factor

66. (d-trp(sup 6),des-gly(sup 10))-lh-rh Ethylamide

67. [des-gly10, D-trp6]-lh-rh Ethylamide, >=97% (hplc)

68. Lhrh, Tryptophyl(6)-n-ethylprolinamide(9)-des-glycinamide(10)-

69. 1-9-luteinizing Hormone-releaasing Factor (swine), 6-d-tryptophan-9-(n-ethyl-l-prolinamide)-

70. Luteinizing Hormone-releasing Factor (pig), 6-d-tryptophan-9-(n-ethyl-l-prolinamide)-10-deglycinamide-

71. Luteinizing Hormone-releasing Factor, 6-d-tryptophan-9-(n-ethyl-l-prolinamide)-10-deglycinamide-

2.4 Create Date

2008-12-10

3 Chemical and Physical Properties

Molecular Formula	C₆₄H₈₃N₁₇O₁₂
Molecular Weight	1282.4 g/mol
XLogP3	1.1
Hydrogen Bond Donor Count	16
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	32
Exact Mass	1281.64071115 g/mol
Monoisotopic Mass	1281.64071115 g/mol
Topological Polar Surface Area	447 Å²
Heavy Atom Count	93
Formal Charge	0
Complexity	2610
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	1

4 Pharmacology and Biochemistry

4.1 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.)

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