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Ozarelix

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Chemical compound Pharmaceutical 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-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-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
3D model (JSmol)	Interactive image
SMILES CCCC(C(=O)N(CCCN=C(N)N)C(=O)N1CCC1C(=O)N(C)C(=O)N)NC(=O)(CCCCNC(=O)N)NC(=O)(CC2=CC=C(C=C2)O)N(C)C(=O)(CO)NC(=O)(CC3=CN=CC=C3)NC(=O)(CC4=CC=C(C=C4)Cl)NC(=O)(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. It has also been investigated for the treatment of endometriosis, but no development has been reported. 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. As of June 2015, it was in phase II clinical trials for prostate cancer. It seems to no longer be under development.

See also

Gonadotropin-releasing hormone receptor § Antagonists

References

^ "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

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GnRHTooltip Gonadotropin-releasing hormone and gonadotropins

GnRH modulators
(incl. analogues)

Non-peptide: Elagolix
Linzagolix
Relugolix (+estradiol/norethisterone acetate)

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

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

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GnRHTooltip Gonadotropin-releasing hormone receptor and gonadotropin receptor modulators

GnRHTooltip Gonadotropin-releasing hormone receptor

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

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

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