Ozarelix

Chemical compound

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
CompTox Dashboard (EPA)	DTXSID60183722
ECHA InfoCard	100.232.650
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

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

^ ^a ^b ^c ^d ^e "Ozarelix - AdisInsight".
^ Festuccia C, Dondi D, Piccolella M, Locatelli A, Gravina GL, Tombolini V, Motta M (2010). "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. doi:10.1002/pros.21169. PMID 20623634. S2CID 2788093.

External links

Ozarelix - AdisInsight

GnRHTooltip Gonadotropin-releasing hormone and gonadotropins

GnRH modulators
(incl. analogues)

Agonists	Peptide: Azagly-nafarelin Buserelin Deslorelin Fertirelin Gonadorelin Goserelin Histrelin Lecirelin Leuprorelin (leuprolide) Nafarelin Peforelin Triptorelin
Antagonists	Peptide: Abarelix Cetrorelix Degarelix Ganirelix Non-peptide: Elagolix Linzagolix^† Relugolix (+estradiol/norethisterone acetate)

Gonadotropins

Preparations	Follicle-stimulating hormone Human chorionic gonadotropin Luteinizing hormone Menotropin Urofollitropin

Others
(indirect)

Progonadotropins	Sex steroid antagonists (via disinhibition of the HPG axis): Antiandrogens (e.g., flutamide, bicalutamide, enzalutamide) Antiestrogens/SERMsTooltip Selective estrogen receptor modulators (e.g., tamoxifen, clomifene, enclomifene) Aromatase inhibitors (e.g., anastrozole) GnRH agonists (e.g., GnRHTooltip gonadotropin-releasing hormone)
Antigonadotropins	Sex steroid agonists (via negative feedback on the HPG axis): Androgens/anabolic steroids (e.g., testosterone, nandrolone esters, oxandrolone) D₂ receptor antagonists (prolactin releasers) (incl., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride) Estrogens (incl., bifluranol, estradiol, estradiol esters, ethinylestradiol, diethylstilbestrol, paroxypropione) Progestogens (incl. progestins, e.g., chlormadinone acetate, cyproterone acetate, hydroxyprogesterone caproate, gestonorone caproate, medroxyprogesterone acetate, megestrol acetate) Others (mixed or unknown mechanism of action): Danazol Gestrinone Metallibure

Progonadotropins

Sex steroid antagonists (via disinhibition of the HPG axis): Antiandrogens (e.g., flutamide, bicalutamide, enzalutamide)
Antiestrogens/SERMsTooltip Selective estrogen receptor modulators (e.g., tamoxifen, clomifene, enclomifene)
Aromatase inhibitors (e.g., anastrozole)
GnRH agonists (e.g., GnRHTooltip gonadotropin-releasing hormone)

Antigonadotropins

Sex steroid agonists (via negative feedback on the HPG axis): Androgens/anabolic steroids (e.g., testosterone, nandrolone esters, oxandrolone)
D₂ receptor antagonists (prolactin releasers) (incl., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride)
Estrogens (incl., bifluranol, estradiol, estradiol esters, ethinylestradiol, diethylstilbestrol, paroxypropione)
Progestogens (incl. progestins, e.g., chlormadinone acetate, cyproterone acetate, hydroxyprogesterone caproate, gestonorone caproate, medroxyprogesterone acetate, megestrol acetate)

Others (mixed or unknown mechanism of action): Danazol
Gestrinone
Metallibure

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

See also: GnRH and gonadotropin receptor modulators; Androgens and antiandrogens; Estrogens and antiestrogens; Progestogens and antiprogestogens

GnRHTooltip Gonadotropin-releasing hormone receptor and gonadotropin receptor modulators

GnRHTooltip Gonadotropin-releasing hormone receptor

Agonists: Peptides: Alarelin
Avorelin
Azagly-nafarelin
Buserelin
Deslorelin
Fertirelin
GnRH
Gonadorelin
Goserelin
Histrelin
Leuprorelin (leuprolide)
Lutrelin
Nafarelin
Peforelin
Salmon GnRH
Triptorelin
Zoptarelin
Zoptarelin doxorubicin

Antagonists: Peptides: Abarelix
Acyline
Azaline B
Cetrorelix
Degarelix
Detirelix
Ganirelix
Iturelix (antide)
LXT-101
Ornirelix (ornitide)
Ozarelix
Prazarelix
Ramorelix
Teverelix (antarelix); Non-peptides: Elagolix
Linzagolix
Opigolix
Relugolix
Sufugolix

Gonadotropin

LH/hCGTooltip Luteinizing hormone/choriogonadotropin receptor	Agonists: Peptides: Choriogonadotropin alfa Human chorionic gonadotropin Luteinizing hormone Lutropin alfa Menotropin (human menopausal gonadotropin)
FSHTooltip Follicle-stimulating hormone receptor	Agonists: Peptides: Corifollitropin alfa Follicle-stimulating hormone Follitropin alfa Follitropin beta Follitropin epsilon Menotropin (human menopausal gonadotropin) Urofollitropin Varfollitropin alfa NAMs: Non-peptides: ADX-61623