Chemistry:Ozarelix

Ozarelix
Clinical data
Other names	D-63153; SPI-153
Routes of; administration	Injection
Drug class	GnRH modulator; GnRH antagonist; Antigonadotropin
Identifiers
	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]-methylamino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-(carbamoylamino)hexanoyl]amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]-N-[(2R)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide;
CAS Number	295350-45-7 ; 896710-46-6 (acetate);
PubChem CID	25080293;
DrugBank	DB12581;
ChemSpider	17291594;
UNII	Q1IF8M2YL3;
Chemical and physical data
Formula	C72H96ClN17O14
Molar mass	1459.12 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCC[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(=O)N)NC(=O)[C@@H](CCCCNC(=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;
	InChI InChI=1S/C72H96ClN17O14/c1-5-6-17-52(63(96)85-54(19-12-33-79-71(75)76)70(103)90-34-13-20-59(90)67(100)81-42(2)61(74)94)83-62(95)53(18-9-10-32-80-72(77)104)84-68(101)60(39-45-24-29-51(93)30-25-45)89(4)69(102)58(41-91)88-66(99)57(38-47-14-11-31-78-40-47)87-65(98)56(36-44-22-27-50(73)28-23-44)86-64(97)55(82-43(3)92)37-46-21-26-48-15-7-8-16-49(48)35-46/h7-8,11,14-16,21-31,35,40,42,52-60,91,93H,5-6,9-10,12-13,17-20,32-34,36-39,41H2,1-4H3,(H2,74,94)(H,81,100)(H,82,92)(H,83,95)(H,84,101)(H,85,96)(H,86,97)(H,87,98)(H,88,99)(H4,75,76,79)(H3,77,80,104)/t42-,52+,53-,54+,55-,56-,57-,58+,59+,60+/m1/s1; Key:KATZUZNTRINHDT-HALMFYTRSA-N;

Short description: Chemical compound

Ozarelix (developmental code names D-63153, SPI-153) is a peptide gonadotropin-releasing hormone antagonist (GnRH antagonist) which is or was under development by AEterna Zentaris Inc. and Spectrum Pharmaceuticals as a long-acting injection formulation for the treatment of prostate cancer.^[1]^[2] It has also been investigated for the treatment of endometriosis, but no development has been reported.^[1] The drug was previously under investigation for the treatment of benign prostatic hyperplasia and Alzheimer's disease as well, but development for these indications was discontinued.^[1] As of June 2015, it was in phase II clinical trials for prostate cancer.^[1] It seems to no longer be under development.^[1]

References

↑ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 "Ozarelix - AdisInsight". http://adisinsight.springer.com/drugs/800013299.
↑ "Ozarelix, a fourth generation GnRH antagonist, induces apoptosis in hormone refractory androgen receptor negative prostate cancer cells modulating expression and activity of death receptors". Prostate 70 (12): 1340–9. 2010. doi:10.1002/pros.21169. PMID 20623634.

External links

Ozarelix - AdisInsight

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Original source: https://en.wikipedia.org/wiki/Ozarelix. Read more

[AdisInsight-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 "Ozarelix - AdisInsight". http://adisinsight.springer.com/drugs/800013299.

[pmid20623634-2] "Ozarelix, a fourth generation GnRH antagonist, induces apoptosis in hormone refractory androgen receptor negative prostate cancer cells modulating expression and activity of death receptors". Prostate 70 (12): 1340–9. 2010. doi:10.1002/pros.21169. PMID 20623634.

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Clinical data

Other names	D-63153; SPI-153
Routes of administration	Injection
Drug class	GnRH modulator; GnRH antagonist; Antigonadotropin
Identifiers
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]-methylamino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-(carbamoylamino)hexanoyl]amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]-N-[(2R)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide
CAS Number	295350-45-7 896710-46-6 (acetate)
PubChem CID	25080293
DrugBank	DB12581
ChemSpider	17291594
UNII	Q1IF8M2YL3
Chemical and physical data
Formula	C₇₂H₉₆ClN₁₇O₁₄
Molar mass	1459.12 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCC[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(=O)N)NC(=O)[C@@H](CCCCNC(=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
InChI InChI=1S/C72H96ClN17O14/c1-5-6-17-52(63(96)85-54(19-12-33-79-71(75)76)70(103)90-34-13-20-59(90)67(100)81-42(2)61(74)94)83-62(95)53(18-9-10-32-80-72(77)104)84-68(101)60(39-45-24-29-51(93)30-25-45)89(4)69(102)58(41-91)88-66(99)57(38-47-14-11-31-78-40-47)87-65(98)56(36-44-22-27-50(73)28-23-44)86-64(97)55(82-43(3)92)37-46-21-26-48-15-7-8-16-49(48)35-46/h7-8,11,14-16,21-31,35,40,42,52-60,91,93H,5-6,9-10,12-13,17-20,32-34,36-39,41H2,1-4H3,(H2,74,94)(H,81,100)(H,82,92)(H,83,95)(H,84,101)(H,85,96)(H,86,97)(H,87,98)(H,88,99)(H4,75,76,79)(H3,77,80,104)/t42-,52+,53-,54+,55-,56-,57-,58+,59+,60+/m1/s1 Key:KATZUZNTRINHDT-HALMFYTRSA-N

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