Teverelix

Identification

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Name
Teverelix
Accession Number
DB05624
Type
Small Molecule
Groups
Investigational
Description

A synthetic decapeptide, water-soluble Gonadotropin-releasing hormone antagonist. It has reached phase II clinical trials.

Structure
Thumb
Synonyms
  • Antarelix
External IDs
D-23234 / EP 24332 / EP-24332 / TZTX 001 / TZTX-001
International/Other Brands
Teverelix LA
Categories
UNII
D19V7048JK
CAS number
151272-78-5
Weight
Average: 1459.16
Monoisotopic: 1457.7262707
Chemical Formula
C74H100ClN15O14
InChI Key
NOENHWMKHNSHGX-IAOPALDYSA-N
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
IUPAC Name
(2R)-6-(carbamoylamino)-N-[(1S)-1-{[(2S)-1-[(2S)-2-{[(1R)-1-carbamoylethyl]carbamoyl}pyrrolidin-1-yl]-1-oxo-6-[(propan-2-yl)amino]hexan-2-yl]carbamoyl}-3-methylbutyl]-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2R)-3-(4-chlorophenyl)-2-[(2R)-2-acetamido-3-(naphthalen-2-yl)propanamido]propanamido]-3-(pyridin-3-yl)propanamido]-3-hydroxypropanamido]-3-(4-hydroxyphenyl)propanamido]hexanamide
SMILES
CC(C)C[C@H](NC(=O)[C@@H](CCCCNC(N)=O)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(=O)[C@@H](CC1=CC=CN=C1)NC(=O)[C@@H](CC1=CC=C(Cl)C=C1)NC(=O)[C@@H](CC1=CC2=C(C=CC=C2)C=C1)NC(C)=O)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(N)=O

Pharmacology

Indication

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

Pharmacodynamics
Not Available
Mechanism of action

Teverelix is a GnRH (Gonadotropin releasing hormone) antagonist.

TargetActionsOrganism
AGonadotropin-releasing hormone receptor
antagonist
Humans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
ChemSpider
16742548

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00393 mg/mLALOGPS
logP2.7ALOGPS
logP0.12ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)9.47ChemAxon
pKa (Strongest Basic)10.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area445.8 Å2ChemAxon
Rotatable Bond Count41ChemAxon
Refractivity386.59 m3·mol-1ChemAxon
Polarizability154.3 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Peptide binding
Specific Function
Receptor for gonadotropin releasing hormone (GnRH) that mediates the action of GnRH to stimulate the secretion of the gonadotropic hormones luteinizing hormone (LH) and follicle-stimulating hormone...
Gene Name
GNRHR
Uniprot ID
P30968
Uniprot Name
Gonadotropin-releasing hormone receptor
Molecular Weight
37730.355 Da
References
  1. Deghenghi R, Boutignon F, Wuthrich P, Lenaerts V: Antarelix (EP 24332) a novel water soluble LHRH antagonist. Biomed Pharmacother. 1993;47(2-3):107-10. [PubMed:7693007]

Drug created on November 18, 2007 11:26 / Updated on June 04, 2019 06:18