Dicetrorelix pamoate

• CAT Number: I026067
• CAS Number: 165186-69-6
• Molecular Formula: C163H200Cl2N34O34
• Molecular Weight: 3250.49
• Purity: 98%
• Synonyms: Dicetrorelix pamoate; Cetrorelix embonate; Dicetrorelix embonate
• Solubility: To be determined
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: D-Alaninamide, N-acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N5-(aminocarbonyl)-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-, 4,4'-methylenebis(3-hydroxy-2-naphthalenecarboxylate) (2:1) (salt)
• InChI: InChI=1S/2C70H92ClN17O14.C23H16O6/c2*1-39(2)31-52(61(94)82-51(15-9-28-77-69(73)74)68(101)88-30-10-16-58(88)67(100)79-40(3)59(72)92)83-60(93)50(14-8-29-78-70(75)102)81-63(96)54(34-43-20-25-49(91)26-21-43)86-66(99)57(38-89)87-65(98)56(36-45-11-7-27-76-37-45)85-64(97)55(33-42-18-23-48(71)24-19-42)84-62(95)53(80-41(4)90)35-44-17-22-46-12-5-6-13-47(46)32-44;24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29/h2*5-7,11-13,17-27,32,37,39-40,50-58,89,91H,8-10,14-16,28-31,33-36,38H2,1-4H3,(H2,72,92)(H,79,100)(H,80,90)(H,81,96)(H,82,94)(H,83,93)(H,84,95)(H,85,97)(H,86,99)(H,87,98)(H4,73,74,77)(H3,75,78,102);1-10,24-25H,11H2,(H,26,27)(H,28,29)/t2*40-,50-,51+,52+,53-,54+,55-,56-,57+,58+;/m11./s1
• InChIKey: UCANQOXFIYWYIX-IDEADWEOSA-N
• SMILES: C[C@H](C(N)=O)NC([C@H]1N(C([C@H](CCCNC(N)=N)NC([C@H](CC(C)C)NC([C@@H](CCCNC(N)=O)NC([C@H](CC2=CC=C(O)C=C2)NC([C@H](CO)NC([C@@H](CC3=CC=CN=C3)NC([C@@H](CC4=CC=C(Cl)C=C4)NC([C@@H](CC5=CC=C6C=CC=CC6=C5)NC(C)=O)=O)=O)=O)=O)=O)=O)=O)=O)CCC1)=O.C[C@H](C(N)=O)NC([C@H]7N(C([C@H](CCCNC(N)=N)NC([C@H](CC(C)C)NC([C@@H](CCCNC(N)=O)NC([C@H](CC8=CC=C(O)C=C8)NC([C@H](CO)NC([C@@H](CC9=CC=CN=C9)NC([C@@H](CC%10=CC=C(Cl)C=C%10)NC([C@@H](CC%11=CC=C%12C=CC=CC%12=C%11)NC(C)=O)=O)=O)=O)=O)=O)=O)=O)=O)CCC7)=O.O=C(C%13=C(O)C(CC%14=C%15C=CC=CC%15=CC(C(O)=O)=C%14O)=C%16C=CC=CC%16=C%13)O

Dicetrorelix pamoate is a synthetic decapeptide with gonadotropin-releasing hormone (GnRH) antagonistic activity. GnRH induces the production and release of luteinizing hormone (LH) and follicle stimulating hormone (FSH) from the gonadotrophic cells of the anterior pituitary. Due to a positive estradiol (E2) feedback at midcycle, GnRH liberation is enhanced resulting in an LH-surge. This LH-surge induces the ovulation of the dominant follicle, resumption of oocyte meiosis and subsequently luteinization as indicated by rising progesterone levels. Cetrorelix competes with natural GnRH for binding to membrane receptors on pituitary cells and thus controls the release of LH and FSH in a dose-dependent manner. Cetrorelix binds to the gonadotropin releasing hormone receptor and acts as a potent inhibitor of gonadotropin secretion. It competes with natural GnRH for binding to membrane receptors on pituitary cells and thus controls the release of LH and FSH in a dose-dependent manner. Cetrorelix is marketed primarily under the brand name Cetrotide. Cetrotide (cetrorelix acetate for injection) is indicated for the inhibition of premature LH surges in women undergoing controlled ovarian stimulation.

Reference

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