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Chemistry

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Also known as: 129311-55-3, Ganirelix acetate [usan], Ganirelix acetate injection, Antagon, 56u7906fqw, Orgalutran
Molecular Formula
C84H121ClN18O17
Molecular Weight
1690.4  g/mol
InChI Key
OVBICQMTCPFEBS-SATRDZAXSA-N
FDA UNII
56U7906FQW

Ganirelix
Ganirelix Acetate is the acetate salt form of ganirelix, a synthetic decapeptide with high antagonistic activity against naturally occurring gonadotropin-releasing hormone (GnRH). Ganirelix directly competes with the GnRH for receptor binding in the anterior pituitary gland, thus induces a rapid and reversible suppression of the release of follicle stimulating hormone (FSH) and luteinizing hormone (LH). This agent is used for the inhibition of premature LH surges in women undergoing controlled ovarian hyperstimulation, and in combination with other hormones for retrieval of the mature follicles for in-vitro fertilization.
1 2D Structure

Ganirelix

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-1-[(2S)-2-[[(2S)-2-[[(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]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-[bis(ethylamino)methylideneamino]hexanoyl]amino]-4-methylpentanoyl]amino]-6-[bis(ethylamino)methylideneamino]hexanoyl]-N-[(2R)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide;acetic acid
2.1.2 InChI
InChI=1S/C80H113ClN18O13.2C2H4O2/c1-9-84-79(85-10-2)88-38-17-15-24-60(70(104)94-62(41-49(5)6)71(105)93-61(25-16-18-39-89-80(86-11-3)87-12-4)78(112)99-40-20-26-68(99)77(111)90-50(7)69(82)103)92-73(107)64(44-53-30-35-59(102)36-31-53)97-76(110)67(48-100)98-75(109)66(46-55-21-19-37-83-47-55)96-74(108)65(43-52-28-33-58(81)34-29-52)95-72(106)63(91-51(8)101)45-54-27-32-56-22-13-14-23-57(56)42-54;2*1-2(3)4/h13-14,19,21-23,27-37,42,47,49-50,60-68,100,102H,9-12,15-18,20,24-26,38-41,43-46,48H2,1-8H3,(H2,82,103)(H,90,111)(H,91,101)(H,92,107)(H,93,105)(H,94,104)(H,95,106)(H,96,108)(H,97,110)(H,98,109)(H2,84,85,88)(H2,86,87,89);2*1H3,(H,3,4)/t50-,60-,61+,62+,63-,64+,65-,66-,67+,68+;;/m1../s1
2.1.3 InChI Key
OVBICQMTCPFEBS-SATRDZAXSA-N
2.1.4 Canonical SMILES
CCNC(=NCCCCC(C(=O)NC(CC(C)C)C(=O)NC(CCCCN=C(NCC)NCC)C(=O)N1CCCC1C(=O)NC(C)C(=O)N)NC(=O)C(CC2=CC=C(C=C2)O)NC(=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)NCC.CC(=O)O.CC(=O)O
2.1.5 Isomeric SMILES
CCNC(=NCCCC[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN=C(NCC)NCC)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(=O)N)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=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)NCC.CC(=O)O.CC(=O)O
2.2 Other Identifiers
2.2.1 UNII
56U7906FQW
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Antagon

2. Ganirelix

3. Ganirelix Diacetate

4. Gnrh, N-ac-2-nal(1)-4-cl-phe(2)-3-pal(3)-et2-harg(6,8)-alanh2(10)-

5. Lhrh, N-acetyl-2-naphthylalanyl(1)-(4-chlorophenylalanyl)(2)-3-pyrdinylalanyl(3)-diethylhomoarginyl(6,8)-alaninamide(10)-

6. Lhrh,n-ac-2-nal(1)-4-cl-phe(2)-3-pal(3)-et2-harg(6,8)-alanh2(10)-

7. N-ac-(2-naphthyl)ala-2-(4-cl-phe)-3-(3-pyridinyl-ala)-6,8-et2-harg-10-alanh2-lhrh

8. N-acetyl-3-(2-naphthyl)-d-alanyl-p-chloro-d-phenylalanyl-3-(3-pyridyl)-d-alanyl-l-seryl-l-tyrosyl-n(sup 6)-(n,n'-diethylamidino)-d-lysyl-l-leucyl-n(sup 6)-(n,n'-diethylamidino)-l-lysyl-l-prolyl-d-alaninamide Diacetate (salt)

9. Orgalutran

10. Rs 26306

11. Rs-26306

12. Rs-26306-298

2.3.2 Depositor-Supplied Synonyms

1. 129311-55-3

2. Ganirelix Acetate [usan]

3. Ganirelix Acetate Injection

4. Antagon

5. 56u7906fqw

6. Orgalutran

7. Rs-26306

8. Ganirelix (acetate)

9. Ganirest

10. D-alaninamide,n-acetyl-3-(2-naphthalenyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridinyl)-d-alanyl-l-seryl-l-tyrosyl-n6-[bis(ethylamino)methylene]-d-lysyl-l-leucyl-n6-[bis(ethylamino)methylene]-l-lysyl-l-prolyl-, Diacetate (salt)

11. N-acetyl-3-(2-naphthyl)-d-alanyl-p-chloro-d-phenylalanyl-3-(3-pyridyl)-d-alanyl-l-seryl-l-tyrosyl-n(sup 6)-(n,n'-diethylamidino)-d-lysyl-l-leucyl-n(sup 6)-(n,n'-diethylamidino)-l-lysyl-l-prolyl-d-alaninamide Diacetate (salt)

12. Rs-26306-298

13. Unii-56u7906fqw

14. Ganirest (tn)

15. Orgalutran Tfa Salt

16. Ganirelix Acetate [mi]

17. Ganirelix Acetate (jan/usan)

18. Ganirelix Acetate [jan]

19. Org-37462

20. Ganirelix Acetate [vandf]

21. Ganirelix Acetate Injection (tn)

22. Ganirelix Acetate [mart.]

23. Ganirelix Acetate [who-dd]

24. Akos025394292

25. Ganirelix Acetate [orange Book]

26. Hy-109532

27. D04302

28. 311g553

29. J-005666

30. Q27261435

31. D-alaninamide, N-acetyl-3-(2-naphthalenyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridinyl)-d-alanyl-l-seryl-l-tyrosyl-n(sup 6)-((ethylamino)(ethylimino)methyl)-d-lysyl-l-leucyl-n(sup 6)-((ethylamino)(ethylimino)methyl)-l-lysyl-l-prolyl-, Diacetate (salt)

2.4 Create Date
2008-02-08
3 Chemical and Physical Properties
Molecular Weight 1690.4 g/mol
Molecular Formula C84H121ClN18O17
Hydrogen Bond Donor Count18
Hydrogen Bond Acceptor Count20
Rotatable Bond Count48
Exact Mass1688.8845622 g/mol
Monoisotopic Mass1688.8845622 g/mol
Topological Polar Surface Area526 Ų
Heavy Atom Count120
Formal Charge0
Complexity3060
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameGanirelix acetate
Drug LabelGanirelix Acetate Injection is a synthetic decapeptide with high antagonistic activity against naturally occurring gonadotropin-releasing hormone (GnRH). Ganirelix Acetate is derived from native GnRH with substitutions of amino acids at positions 1,...
Active IngredientGanirelix acetate
Dosage FormInjectable
RouteInjection
Strengtheq 250mcg base/0.5ml
Market StatusPrescription
CompanyOrganon Usa

2 of 2  
Drug NameGanirelix acetate
Drug LabelGanirelix Acetate Injection is a synthetic decapeptide with high antagonistic activity against naturally occurring gonadotropin-releasing hormone (GnRH). Ganirelix Acetate is derived from native GnRH with substitutions of amino acids at positions 1,...
Active IngredientGanirelix acetate
Dosage FormInjectable
RouteInjection
Strengtheq 250mcg base/0.5ml
Market StatusPrescription
CompanyOrganon Usa

4.2 Drug Indication

The prevention of premature luteinising-hormone surges in women undergoing controlled ovarian hyperstimulation for assisted reproduction techniques.

In clinical studies, Orgalutran was used with recombinant human follicle-stimulating hormone or corifollitropin alfa, the sustained follicle stimulant.


Prevention of premature luteinising hormone (LH) surges in women undergoing controlled ovarian hyperstimulation (COH) for assisted reproduction techniques (ART).


5 Pharmacology and Biochemistry
5.1 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.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Gonadotropin Releasing Hormone Receptor Antagonist [EPC]; Gonadotropin Releasing Hormone Receptor Antagonists [MoA]; Decreased GnRH Secretion [PE]
5.3 ATC Code

H01CC01


H01CC01


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14-Oct-2021
25-Sep-2024
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