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Chemistry

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Also known as: 934016-19-0, Gonax, Firmagon, Ext215f4zu, Degarelix (as acetate), Degarelix acetate hydrate

Molecular Formula

C₈₄H₁₀₇ClN₁₈O₁₈

Molecular Weight

1692.3 g/mol

InChI Key

AUTFSFUMNFDPLH-KYMMNHPFSA-N

FDA UNII

EXT215F4ZU

Degarelix Acetate is the acetate form of a long-acting, synthetic peptide with gonadotrophin-releasing hormone (GnRH) antagonistic properties. Degarelix targets and blocks GnRH receptors located on the surfaces of gonadotroph cells in the anterior pituitary, thereby reducing secretion of luteinizing hormone (LH) by pituitary gonadotroph cells and so decreasing testosterone production by interstitial (Leydig) cells in the testes.

1 2D Structure

Degarelix Acetate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4S)-N-[4-[(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]amino]-3-[[(2R)-1-[[(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]amino]-3-[4-(carbamoylamino)phenyl]-1-oxopropan-2-yl]amino]-3-oxopropyl]phenyl]-2,6-dioxo-1,3-diazinane-4-carboxamide;acetic acid

2.1.2 InChI

InChI=1S/C82H103ClN18O16.C2H4O2/c1-45(2)35-60(72(107)92-59(16-9-10-33-87-46(3)4)80(115)101-34-12-17-68(101)79(114)88-47(5)70(84)105)93-74(109)63(38-51-23-30-58(31-24-51)91-81(85)116)95-76(111)64(39-50-21-28-57(29-22-50)90-71(106)66-42-69(104)100-82(117)99-66)97-78(113)67(44-102)98-77(112)65(41-53-13-11-32-86-43-53)96-75(110)62(37-49-19-26-56(83)27-20-49)94-73(108)61(89-48(6)103)40-52-18-25-54-14-7-8-15-55(54)36-52;1-2(3)4/h7-8,11,13-15,18-32,36,43,45-47,59-68,87,102H,9-10,12,16-17,33-35,37-42,44H2,1-6H3,(H2,84,105)(H,88,114)(H,89,103)(H,90,106)(H,92,107)(H,93,109)(H,94,108)(H,95,111)(H,96,110)(H,97,113)(H,98,112)(H3,85,91,116)(H2,99,100,104,117);1H3,(H,3,4)/t47-,59+,60+,61-,62-,63-,64+,65-,66+,67+,68+;/m1./s1

2.1.3 InChI Key

AUTFSFUMNFDPLH-KYMMNHPFSA-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(CC2=CC=C(C=C2)NC(=O)N)NC(=O)C(CC3=CC=C(C=C3)NC(=O)C4CC(=O)NC(=O)N4)NC(=O)C(CO)NC(=O)C(CC5=CN=CC=C5)NC(=O)C(CC6=CC=C(C=C6)Cl)NC(=O)C(CC7=CC8=CC=CC=C8C=C7)NC(=O)C.CC(=O)O

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](CC2=CC=C(C=C2)NC(=O)N)NC(=O)[C@H](CC3=CC=C(C=C3)NC(=O)[C@@H]4CC(=O)NC(=O)N4)NC(=O)[C@H](CO)NC(=O)[C@@H](CC5=CN=CC=C5)NC(=O)[C@@H](CC6=CC=C(C=C6)Cl)NC(=O)[C@@H](CC7=CC8=CC=CC=C8C=C7)NC(=O)C.CC(=O)O

2.2 Other Identifiers

2.2.1 UNII

EXT215F4ZU

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ac-2nal-4cpa-3pal-ser-4aph(hydroorotyl)-4aph(carbamoyl)-leu-ilys-pro-ala-nh2

2. Acetyl-2-naphthylalanyl-3-chlorophenylalanyl-1-oxohexadecyl-seryl-4-aminophenylalanyl(hydroorotyl)-4-aminophenylalanyl(carbamoyl)-leucyl-ilys-prolyl-alaninamide

3. Degarelix

4. Fe 200486

5. Fe-200486

6. Fe200486

7. Firmagon

8. Gonax

9. Uglypeptide1

2.3.2 Depositor-Supplied Synonyms

1. 934016-19-0

2. Gonax

3. Firmagon

4. Ext215f4zu

5. Degarelix (as Acetate)

6. Degarelix Acetate Hydrate

7. Fe-200486

8. Degarelix Acetate (jan)

9. N-acetyl-3-(2-naphthalenyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridinyl)-d-alanyl-l-seryl-4-[[[(4s)-hexahydro-2,6-dioxo-4-pyrimidinyl]carbonyl]amino]-l-phenylalanyl-4-[(aminocarbonyl)amino]-d-phenylalanyl-l-leucyl-n6-(1-methylethyl)-l-lysyl-l-prolyl-d-alaninamide,monoacetate

10. Asp3550

11. Fe200486

12. Unii-ext215f4zu

13. Fe200486 (free Base)

14. Firmagon (tn)

15. Degarelix Monoacetate

16. Chembl2028987

17. Degarelix Acetate Anhydrous

18. Dtxsid201027699

19. Asp-3550

20. Mfcd16879085

21. Degarelix Monoacetate Anhydrous

22. Degarelix (acetate) Pound>>fe 200486

23. Degarelix Acetate(214766-78-6 Free Base)

24. D09400

25. Q27277419

26. D-alaninamide, N-acetyl-3-(naphtalen-2-yl)-d-alanyl-4-chloro-d-phenylalanyl-3-(pyridin-3-yl)-d-alanyl-l-seryl-4-((((4s)-2,6-dioxohexahydropyrimidin-4-yl)carbonyl)amino)-l-phenylalanyl-4-(carbamoylamino)-d-phenylalanyl-l-leucyl-n6-(1-methylethyl)-l-lysyl-l-prolyl-, Acetate (1:1)

2.4 Create Date

2007-07-04

3 Chemical and Physical Properties

Molecular Formula	C₈₄H₁₀₇ClN₁₈O₁₈
Molecular Weight	1692.3 g/mol
Hydrogen Bond Donor Count	18
Hydrogen Bond Acceptor Count	20
Rotatable Bond Count	41
Exact Mass	1690.7699263 g/mol
Monoisotopic Mass	1690.7699263 g/mol
Topological Polar Surface Area	550 Å²
Heavy Atom Count	121
Formal Charge	0
Complexity	3420
Isotope Atom Count	0
Defined Atom Stereocenter Count	11
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 Indication

FIRMAGON is a gonadotrophin releasing hormone (GnRH) antagonist indicated:

- for treatment of adult male patients with advanced hormone-dependent prostate cancer .

- for treatment of high-risk localised and locally advanced hormone dependent prostate cancer in combination with radiotherapy.

- as neo-adjuvant treatment prior to radiotherapy in patients with high-risk localised or locally advanced hormone dependent prostate cancer .

5 Pharmacology and Biochemistry

5.1 ATC Code

L02BX02

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