Teverelix

DRACPC ID  DRACPC0075

Active Ingredients   Teverelix

Description  A synthetic decapeptide and antagonist of the naturally occurring gonadotropin-releasing hormone (GnRH), with potential hormone production inhibitory and antineoplastic activities. Upon administration, teverelix directly competes with GnRH for receptor binding in the anterior pituitary gland, thereby inhibiting GnRH receptor signaling. This inhibits the secretion and release of luteinizing hormone (LH) and follicle stimulating hormone (FSH). In males, the inhibition of LH secretion prevents the release of testosterone. Since testosterone is required to sustain prostate growth, reducing testosterone levels may inhibit hormone-dependent prostate cancer cell proliferation. In females, this prevents the production of estrogen by the ovaries and may relieve symptoms from sex-hormone dependent diseases.

Synonyms  ANB019; EP 24332; Ac-D-Nal-D-cpa-D-pal-ser-tyr-D-hci-leu-lys(ipr)-pro-D-ala-NH2; D-Alaninamide, N-acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N6-(aminocarbonyl)-D-lysyl-L-leucyl-N6-(1-methylethyl)-L-lysyl-L-prolyl-; Teverelix

Type  Small Molecule

Disease  Prostate cancer, Prostatic hyperplasia, Endometriosis

Classification

  

GnRH antagonist Peptide and derivative

Structure Information


Molecular Formula  C74H100ClN15O14

Molecular Weight  1459.1

Active Sequence  xxxSYxLXPa

Sequence Length  10

Modification  x(1)=D-2Nal, x(2)=D-Phe(4-Cl), x(3)=D-3Pal, x(6)=D-hCit, X(8)=Lys(iPr), C-terminal Ac, N-terminal NH2

Structure

 

Show IUPAC/InChI/SMILES

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-(carbamoylamino)hexanoyl]amino]-4-methylpentanoyl]amino]-6-(propan-2-ylamino)hexanoyl]-N-[(2R)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide

InChI  InChI=1S/C74H100ClN15O14/c1-43(2)35-57(66(96)84-56(19-10-11-32-79-44(3)4)73(103)90-34-14-20-63(90)72(102)81-45(5)64(76)94)85-65(95)55(18-9-12-33-80-74(77)104)83-68(98)59(38-48-24-29-54(93)30-25-48)88-71(101)62(42-91)89-70(100)61(40-50-15-13-31-78-41-50)87-69(99)60(37-47-22-27-53(75)28-23-47)86-67(97)58(82-46(6)92)39-49-21-26-51-16-7-8-17-52(51)36-49/h7-8,13,15-17,21-31,36,41,43-45,55-63,79,91,93H,9-12,14,18-20,32-35,37-40,42H2,1-6H3,(H2,76,94)(H,81,102)(H,82,92)(H,83,98)(H,84,96)(H,85,95)(H,86,97)(H,87,99)(H,88,101)(H,89,100)(H3,77,80,104)/t45-,55-,56+,57+,58-,59+,60-,61-,62?,63+/m1/s1

InChI_Key NOENHWMKHNSHGX-DGWYIYCFSA-N

SMILES  OC(C=C1)=CC=C1C[C@H](NC(C(NC([C@H](NC([C@H](NC([C@H](NC(C)=O)CC2=CC3=C(C=C2)C=CC=C3)=O)CC4=CC=C(Cl)C=C4)=O)CC5=CC=CN=C5)=O)CO)=O)C(N[C@H](CCCCNC(N)=O)C(N[C@H](C(N[C@@H](CCCCNC(C)C)C(N6[C@@H](CCC6)C(N[C@H](C)C(N)=O)=O)=O)=O)CC(C)C)=O)=O

External Codes


PubChem CID  16135076

DrugBank Accession Number  DB05624

NCI Thesaurus Code  C132277  

UNII  D19V7048JK   GSRS

CAS  151272-78-5



Drug approval


Drug indication
    Investigated for use/treatment in benign prostatic hyperplasia, endometriosis, and prostate cancer.

    The drug is not approved.

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT04693507 An Adaptive Phase 2, Open-Label, Multicentre Study Investigating the Pharmacokinetics, Pharmacodynamics, Efficacy and Safety of Teverelix Trifluoroacetate, a GnRH Antagonist, in Participants With Advanced Prostate Cancer Prostatic Adenoma Phase 2 Treatment
NCT03781947 A Phase I, Open-label, Single Centre Study Investigating the PK, Safety and PD of a Single Dose of Teverelix TFA, a GnRH Antagonist, Via s.c. or i.m. Route of Administration in Healthy Male Volunteers Healthy Phase 1 Basic Science

    More clinical information is obtained from ClinicalTrials.gov.





DRACP is developed by Dr.Zheng's team.