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Buserelin Acetate

Buserelin Acetate

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Also known as: 57982-77-1, Pxw8u3yxdv, Ici 123215, Hoe 766, Etilamide, (des-gly10,d-ser(tbu)6,pro-nhet9)-lhrh

Molecular Formula

C₆₀H₈₆N₁₆O₁₃

Molecular Weight

1239.4 g/mol

InChI Key

CUWODFFVMXJOKD-UVLQAERKSA-N

FDA UNII

PXW8U3YXDV

A potent synthetic analog of GONADOTROPIN-RELEASING HORMONE with D-serine substitution at residue 6, glycine10 deletion, and other modifications.

1 2D Structure

Buserelin Acetate

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-[(2-methylpropan-2-yl)oxy]-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/C60H86N16O13/c1-7-64-57(87)48-15-11-23-76(48)58(88)41(14-10-22-65-59(61)62)69-51(81)42(24-33(2)3)70-56(86)47(31-89-60(4,5)6)75-52(82)43(25-34-16-18-37(78)19-17-34)71-55(85)46(30-77)74-53(83)44(26-35-28-66-39-13-9-8-12-38(35)39)72-54(84)45(27-36-29-63-32-67-36)73-50(80)40-20-21-49(79)68-40/h8-9,12-13,16-19,28-29,32-33,40-48,66,77-78H,7,10-11,14-15,20-27,30-31H2,1-6H3,(H,63,67)(H,64,87)(H,68,79)(H,69,81)(H,70,86)(H,71,85)(H,72,84)(H,73,80)(H,74,83)(H,75,82)(H4,61,62,65)/t40-,41-,42-,43-,44-,45-,46-,47+,48-/m0/s1

2.1.3 InChI Key

CUWODFFVMXJOKD-UVLQAERKSA-N

2.1.4 Canonical SMILES

CCNC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(COC(C)(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

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](COC(C)(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

2.2 Other Identifiers

2.2.1 UNII

PXW8U3YXDV

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acetate, Buserelin

2. Bigonist

3. Buserelin Acetate

4. Hoe 766

5. Hoe-766

6. Hoe766

7. Profact

8. Receptal

9. Suprecur

10. Suprefact

11. Tiloryth

2.3.2 Depositor-Supplied Synonyms

1. 57982-77-1

2. Pxw8u3yxdv

3. Ici 123215

4. Hoe 766

5. Etilamide

6. (des-gly10,d-ser(tbu)6,pro-nhet9)-lhrh

7. Buserelin (inn)

8. Buserelin [inn]

9. 68630-75-1

10. Buserelina

11. Busereline

12. Buserelinum

13. Luteinizing Hormone-releasing Factor (pig), 6-(o-(1,1-dimethylethyl)-d-serine)-9-(n-ethyl-l-prolinamide)-10-deglycinamide-

14. Buserelin [inn:ban]

15. Unii-pxw8u3yxdv

16. Busereline [inn-french]

17. Buserelinum [inn-latin]

18. Buserelina [inn-spanish]

19. Metrelef

20. Ccris 2657

21. Hoe 766a

22. Tiloryth (tn)

23. Einecs 261-061-9

24. D-ser-(tbu)(sup 6)-lhrh-ethylamide

25. Buserelin [mi]

26. (d-ser(tbu)(sup 6)-ea(sup 10))-lhrh

27. Buserelin [mart.]

28. Buserelin [who-dd]

29. Schembl13354

30. S 746766

31. Gtpl3860

32. Buserelin [ep Monograph]

33. Buserelin For Nmr Identification

34. Chembl2110824

35. D-ser(tbu(sup 6))-lh-rh-(1-9)-nonapeptide Ethylamide

36. Schembl19409318

37. Schembl19459955

38. Buserelin For Peak Identification

39. Chebi:135907

40. Dtxsid301024155

41. (d-ser(bu(sup T)(sup 6)))-lh-rh(1-9)nonapeptide-ethylamide

42. (d-ser(tbu)(sup 6)-ea(sup 10))-luteinizing Hormone-releasing Hormone

43. Akos015994645

44. Akos030213242

45. Luteinizing Hormone-releasing Hormone, (d-ser(tbu)(sup 6)-ea(sup 10))-

46. Hs-2005

47. Ncgc00181295-01

48. D07259

49. 982b771

50. A831694

51. Q414745

52. W-105422

53. (2s)-n-[(2s)-1-[[(2s)-1-[[(2s)-1-[[(2s)-1-[[(2r)-1-[[(2s)-1-[[(2s)-5-(diaminomethylideneamino)-1-[(2s)-2-(ethylcarbamoyl)-1-pyrrolidinyl]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]amino]-3-(4-hy

54. (2s)-n-[(2s)-1-[[(2s)-1-[[(2s)-1-[[(2s)-1-[[(2r)-1-[[(2s)-1-[[(2s)-5-[bis(azanyl)methylideneamino]-1-[(2s)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxidanylidene-pentan-2-yl]amino]-4-methyl-1-oxidanylidene-pentan-2-yl]amino]-3-[(2-methylpropan-2-yl)oxy]-1-oxi

55. 5-oxo-l-prolyl-l-histidyl-l-tryptophyl-l-seryl-l-tyrosyl-o-tert-butyl-d-seryl-l-leucyl-l-arginyl-n-ethyl-l-prolinamide

56. Luteinizing Hormone-releasing Hormone (pig), 6-(o-(1,1-dimethylethyl)-d-serine)-9-(n-ethyl-l-prolinamide)-10-deglycinamide-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₆₀H₈₆N₁₆O₁₃
Molecular Weight	1239.4 g/mol
XLogP3	-0.1
Hydrogen Bond Donor Count	15
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	33
Exact Mass	1238.65602686 g/mol
Monoisotopic Mass	1238.65602686 g/mol
Topological Polar Surface Area	441 Å²
Heavy Atom Count	89
Formal Charge	0
Complexity	2450
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 Drug and Medication Information

4.1 Drug Indication

Buserelin may be used in the treatment of hormone-responsive cancers such as prostate cancer or breast cancer, estrogen-dependent conditions (such as endometriosis or uterine fibroids), and in assisted reproduction.

5 Pharmacology and Biochemistry

5.1 Pharmacology

The substitution of glycine in position 6 by D-serine, and that of glycinamide in position 10 by ethylamide, leads to a nonapeptide with a greatly enhanced LHRH effect. The effects of buserelin on FSH and LH release are 20 to 170 times greater than those of LHRH. Buserelin also has a longer duration of action than natural LHRH. Investigations in healthy adult males and females have demonstrated that the increase in plasma LH and FSH levels persist for at least 7 hours and that a return to basal values requires about 24 hours. Clinical inhibition of gonadotropin release, and subsequent reduction of serum testosterone or estradiol to castration level, was found when large pharmacologic doses (50-500 mcg SC/day or 300-1200 mcg IN/day) were administered for periods greater than 1 to 3 months. Chronic administration of such doses of buserelin results in sustained inhibition of gonadotropin production, suppression of ovarian and testicular steroidogenesis and, ultimately, reduced circulating levels of gonadotropin and gonadal steroids. These effects form the basis for buserelin use in patients with hormone-dependent metastatic carcinoma of the prostate gland as well as in patients with endometriosis.

5.2 MeSH Pharmacological Classification

Fertility Agents, Female

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

5.3 ATC Code

L - Antineoplastic and immunomodulating agents

L02 - Endocrine therapy

L02A - Hormones and related agents

L02AE - Gonadotropin releasing hormone analogues

L02AE01 - Buserelin

5.4 Absorption, Distribution and Excretion

Absorption

Buserelin is water soluble and readily absorbed after subcutaneous injection (70% bioavailable). However, bioavailability after oral absorption. When administered correctly via the nasal route, it may be absorbed in the nasal mucosa to achieve sufficient plasma levels.

Route of Elimination

Buserelin and its inactive metabolites are excreted via the renal and biliary routes. In man it is excreted in urine at 50% in its intact form.

Volume of Distribution

Buserelin circulates in serum predominantly in intact active form. Preferred accumulation is preferentially in the liver and kidneys as well as in the anterior pituitary lobe, the biological target organ.

5.5 Metabolism/Metabolites

It is metabolized and subsequently inactivated by peptidase (pyroglutamyl peptidase and chymotrypsin-like endopeptidase) in the liver and kidneys as well as in the gastrointestinal tract. In the pituitary gland, it is inactivated by membrane-located enzymes.

5.6 Biological Half-Life

The elimination half-life is approximately 50 to 80 minutes following intravenous administration, 80 minutes after subcutaneous administration and approximately 1 to 2 hours after intranasal administration.

5.7 Mechanism of Action

Buserelin stimulates the pituitary gland's gonadotrophin-releasing hormone receptor (GnRHR). Buserelin desensitizes the GnRH receptor, reducing the amount of gonadotropin. In males, this results in a reduction in the synthesis and release of testosterone. In females, estrogen secretion is inhibited. While initially, there is a rise in FSH and LH levels, chronic administration of Buserelin results in a sustained suppression of these hormones.