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Abarelix

Abarelix

Synopsis, Chemistry

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1 Dossiers, 1 FDA Orange Book

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Also known as: Plenaxis, 183552-38-7, Ppi-149, Ppi 149, R 3827, R3827

Molecular Formula

C₇₂H₉₅ClN₁₄O₁₄

Molecular Weight

1416.1 g/mol

InChI Key

AIWRTTMUVOZGPW-HSPKUQOVSA-N

Abarelix is a synthetic decapeptide and antagonist of naturally occurring gonadotropin-releasing hormone (GnRH). Abarelix directly and competitively binds to and blocks the gonadotropin releasing hormone receptor in the anterior pituitary gland, thereby inhibiting the secretion and release of luteinizing hormone (LH) and follicle stimulating hormone (FSH). In males, the inhibition of LH secretion prevents the release of testosterone. As a result, this may relieve symptoms associated with prostate hypertrophy or prostate cancer, since testosterone is required to sustain prostate growth.

1 2D Structure

Abarelix

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]-methylamino]-3-(4-hydroxyphenyl)propanoyl]amino]-N-[(2S)-1-[[(2S)-1-[(2S)-2-[[(2R)-1-amino-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxo-6-(propan-2-ylamino)hexan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]butanediamide

2.1.2 InChI

InChI=1S/C72H95ClN14O14/c1-41(2)32-54(64(93)80-53(17-10-11-30-77-42(3)4)72(101)87-31-13-18-60(87)69(98)78-43(5)63(75)92)81-68(97)58(38-62(74)91)84-70(99)61(37-46-22-27-52(90)28-23-46)86(7)71(100)59(40-88)85-67(96)57(36-48-14-12-29-76-39-48)83-66(95)56(34-45-20-25-51(73)26-21-45)82-65(94)55(79-44(6)89)35-47-19-24-49-15-8-9-16-50(49)33-47/h8-9,12,14-16,19-29,33,39,41-43,53-61,77,88,90H,10-11,13,17-18,30-32,34-38,40H2,1-7H3,(H2,74,91)(H2,75,92)(H,78,98)(H,79,89)(H,80,93)(H,81,97)(H,82,94)(H,83,95)(H,84,99)(H,85,96)/t43-,53+,54+,55-,56-,57-,58-,59+,60+,61+/m1/s1

2.1.3 InChI Key

AIWRTTMUVOZGPW-HSPKUQOVSA-N

2.1.4 Canonical SMILES

CC(C)CC(C(=O)NC(CCCCNC(C)C)C(=O)N1CCCC1C(=O)NC(C)C(=O)N)NC(=O)C(CC(=O)N)NC(=O)C(CC2=CC=C(C=C2)O)N(C)C(=O)C(CO)NC(=O)C(CC3=CN=CC=C3)NC(=O)C(CC4=CC=C(C=C4)Cl)NC(=O)C(CC5=CC6=CC=CC=C6C=C5)NC(=O)C

2.1.5 Isomeric SMILES

C[C@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCNC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(=O)N)NC(=O)[C@H](CC2=CC=C(C=C2)O)N(C)C(=O)[C@H](CO)NC(=O)[C@@H](CC3=CN=CC=C3)NC(=O)[C@@H](CC4=CC=C(C=C4)Cl)NC(=O)[C@@H](CC5=CC6=CC=CC=C6C=C5)NC(=O)C

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Plenaxis

2. Ppi-149

2.2.2 Depositor-Supplied Synonyms

1. Plenaxis

2. 183552-38-7

3. Ppi-149

4. Ppi 149

5. R 3827

6. R3827

7. R-3827

8. Chembl1252

9. Plenaxis Depot

10. Chebi:337298

11. D-alaninamide, N-acetyl-3-(2-naphthalenyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridinyl)-d-alanyl-l-seryl-n-methyl-l-tyrosyl-d-asparaginyl-l-leucyl-n6-(1-methylethyl)-l-lysyl-l-prolyl-

12. Abarelix-depot-m

13. Plenaxis (tn)

14. Abarelix (usan/inn)

15. Abarelix [usan:inn]

16. Unii-w486sj5824

17. N-acetyl-3-(2-naphthyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridyl)-d-alanyl-l-seryl-n-methyl-l-tyrosyl-d-asparginyl-l-leucyl-n6-isopropyl-l-lysyl-l-prolyl-d-alaninamide

18. Schembl9533

19. Gtpl1188

20. Ppi149

21. Schembl19712245

22. Dtxsid20171443

23. Bdbm50102442

24. Ppi 149r3827

25. R3827;ppi 149

26. Cs-5873

27. Db00106

28. D-alaninamide, N-acetyl-3-(2-naphthalenyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridinyl)-d-alanyl-l-seryl-n-methyl-l-tyrosyl-d-asparaginyl-l-leucyl-n6-(1-methylethyl)-l-lysyl-l-prolyl- 10

29. Hy-13534

30. N-acetyl-3-(2-naphthyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(pyridin-3-yl)-d-alanyl-l-seryl-n-methyl-l-tyrosyl-d-asparginyl-l-leucyl-n(6)-isopropyl-l-lysyl-l-prolyl-d-alaninamide

31. A12613

32. D02738

33. 552a387

34. Q305555

35. Ac-d-nal-[d-(pcl)phe]-d-pal-ser-[nalpha-me-tyr]-d-asn-leu-ilys-pro-dala-nh2

36. N-acetyl-3-(2-naphthyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridyl)-d-alanyl-l-seryl-n-methyl-l-tyrosyl-d-asparagyl-l-leucyl-n6-isopropyl-l-lysyl-l-prolyl-d-alaninamide

2.3 Create Date

2007-07-03

3 Chemical and Physical Properties

Molecular Formula	C₇₂H₉₅ClN₁₄O₁₄
Molecular Weight	1416.1 g/mol
XLogP3	3.7
Hydrogen Bond Donor Count	13
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	38
Exact Mass	1414.6840715 g/mol
Monoisotopic Mass	1414.6840715 g/mol
Topological Polar Surface Area	425 Å²
Heavy Atom Count	101
Formal Charge	0
Complexity	2770
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
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

For palliative treatment of advanced prostate cancer.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Used in the palliative treatment of advanced prostate cancer. Abarelix is a luteinizing hormone agonist that results in suppression of testicular or follicular steroidogenesis.

5.2 MeSH Pharmacological Classification

Hormone Antagonists

Chemical substances which inhibit the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites. (See all compounds classified as Hormone Antagonists.)

5.3 ATC Code

L - Antineoplastic and immunomodulating agents

L02 - Endocrine therapy

L02B - Hormone antagonists and related agents

L02BX - Other hormone antagonists and related agents

L02BX01 - Abarelix

5.4 Absorption, Distribution and Excretion

Absorption

Following IM administration of 100 mg, abarelix is absorbed slowly with a mean peak concentration of 43.4 ng/mL observed approximately 3 days after the injection.

5.5 Metabolism/Metabolites

In vitro hepatocyte (rat, monkey, human) studies and in vivo studies in rats and monkeys showed that the major metabolites of abarelix were formed via hydrolysis of peptide bonds. No significant oxidative or conjugated metabolites of abarelix were found either in vitro or in vivo. There is no evidence of cytochrome P-450 involvement in the metabolism of abarelix.

5.6 Biological Half-Life

13.2 ± 3.2 days

5.7 Mechanism of Action

Abarelix binds to the gonadotropin releasing hormone receptor and acts as a potent inhibitor of gonadotropin secretion.