Histrelin

Identification

Summary

Histrelin is a GnRH agonist found in subcutaneous implants used for the treatment of pediatric patients with central precocious puberty and the palliative treatment of advanced prostate cancer.

Brand Names

Supprelin

Generic Name

Histrelin

DrugBank Accession Number

DB06788

Background

Histrelin is a gonadotropin-releasing hormone (GnRH) agonist that acts as a potent inhibitor of gonadotropin when administered as an implant delivering continuous therapeutic doses. This drug is a synthetic analog of naturally occurring GnRH with a higher potency. Histrelin implants are non-biodegradable, diffusion-controlled, hydrogel polymer reservoirs containing histrelin acetate that need to be replaced every 52 weeks.^5,7,8

Initially, histrelin implants were developed to reduce testosterone to castration levels in patients with advanced prostate cancer.⁷ The Vantas product was approved by the FDA in October 2004 for the palliative treatment of this condition.⁷ Vantas was later discontinued by Endo Pharmaceuticals Inc. on September 21, 2021.⁶

GnRH agonists are the first line of treatment for children with central precocious puberty (CPP) due to their capacity to reduce LH levels and the concentration of sex steroids. As the product Supprelin LA, histrelin is indicated for the treatment of CPP in children (approved by the FDA in May 2007).⁵

Type

Small Molecule

Groups

Approved, Withdrawn

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Histrelin (DB06788)

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Weight

Average: 1443.632
Monoisotopic: 1442.709519019

Chemical Formula

C₇₀H₉₄N₁₈O₁₆

Synonyms

• [(im-Bzl)-D-His6,Pro9-NEt]-gonadotropin releasing hormone
• 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-1-benzyl-D-histidyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide
• 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-Nτ-benzyl-D-histidyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide
• Histrelin
• histrelina
• histreline
• histrelinum
• L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-Nim-benzyl-histidyl-L-leucyl-L-arginyl-L-proline ethylamide

External IDs

• ORF 17070
• ORF-17070
• ORF17070
• RWJ 17070
• RWJ-17070
• RWJ17070

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Pharmacology

Indication

As the product Supprelin LA (FDA), histrelin is indicated for the treatment of children with central precocious puberty (CPP).⁵ As the product Vantas (FDA), histrelin is indicated for the palliative treatment of advanced prostate cancer.⁷

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Symptomatic treatment of	Advanced prostate cancer		••••••••••••			•••••••
Management of	Central precocious puberty		••••••••••••	••••••••		•••••••

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Pharmacodynamics

Histrelin inhibits gonadotropin secretion through the reversible down-regulation of gonadotropin-releasing hormone (GnRH) receptors in the pituitary gland and desensitization of the pituitary gonadotropes.^5,7 In pediatric patients with central precocious puberty (CPP), long-term treatment with histrelin acetate suppresses the luteinizing hormone (LH) response to GnRH, causing LH levels to decrease to prepubertal levels within one month of treatment.⁵ This reduces ovarian and testicular steroidogenesis and slows down linear growth velocity, improving the chance of attaining predicted adult height.⁵ When given orally, histrelin acetate is not active.⁷

Both histrelin products (Vantas and Supprelin LA from Endo Pharmaceuticals) cause a transient increase in serum concentrations of estradiol in females and testosterone in both sexes during the first week of treatment.^5,7 Laboratory tests are also recommended in order to monitor hormone levels. For pediatric patients with central precocious puberty (CPP) using histrelin (Supprelin LA, Endo Pharmaceuticals), LH, follicle-stimulating hormone and estradiol or testosterone should be monitored.⁵ In patients with advanced prostate cancer using histrelin (Vantas, Endo Pharmaceuticals), testosterone and prostate-specific antigen should be measured periodically.⁷ Issues such as breakage during insertion and difficulty locating and removing implants have been reported.^5,7

The Supprelin LA (Endo Pharmaceuticals) product label alerts users about psychiatric events, convulsions and cases of pseudotumor cerebri (idiopathic intracranial hypertension) that have been reported in patients receiving GnRH agonists.⁵ The Vantas (Endo Pharmaceuticals) product label alerts users about cases of spinal cord compression and urinary tract obstruction, and an increased risk of hyperglycemia/diabetes and cardiovascular disease in men receiving GnRH agonists.⁷

Mechanism of action

Histrelin is a gonadotropin-releasing hormone (GnRH) agonist that acts as a potent inhibitor of gonadotropin.^5,7 GnRH binds to the GnRH receptor located on the pituitary gonadotrophs, and this leads to the production of luteinizing hormone (LH) and follicle-stimulating hormone (FSH), as well as the regulation of sexual maturation and reproductive function.⁴

When administered as an implant, histrelin is delivered in continuous therapeutic doses.^5,7 As a GnRH agonist, this drug binds and, at first, activates the GnRH receptor. This increases the circulating levels of LH and FSH, leading to a transient increase in the concentration of gonadal steroids (testosterone and dihydrotestosterone in males and estrone and estradiol in premenopausal females).^5,7 However, the continuous administration of histrelin induces the reversible down-regulation of the GnRH receptor and the desensitization of pituitary gonadotropes, which reduce LH and FSH levels.^5,7

Pediatric patients with central precocious puberty (CPP) have a lower height potential. When treated with histrelin, LH levels in CPP are lowered, reducing the concentration of sex steroids.^1,5 In adult males with advanced prostate cancer, histrelin reduces testosterone production to castration levels, hindering the growth of prostate cancer cells.^2,3,7

Target	Actions	Organism
AGonadotropin-releasing hormone receptor	agonist	Humans

Absorption

Advanced prostate cancer patients (n = 17) that received a subcutaneous histrelin implant (Vantas, Endo Pharmaceuticals) had peak serum concentrations of 1.10 ± 0.375 ng/mL (mean ± SD) at 12 hours.⁷ The continuous subcutaneous release of the histrelin implant was confirmed, as serum levels were sustained throughout the 52-week dosing period. At the end of the 52-week period, the mean serum histrelin concentration was 0.13 ± 0.065 ng/mL.⁷ In patients that received a second implant at the end of the 52-week period, the serum histrelin concentration in the first eight weeks was similar to the one detected with the first implant. On average, the residual drug content of 41 histrelin implants (Vantas, Endo Pharmaceuticals) was 56.7 ± 7.71 mcg/day over 52 weeks.⁷ Compared to healthy male volunteers that received a subcutaneous bolus dose, the relative bioavailability of histrelin in patients with prostate cancer and normal renal and hepatic function was 92%.⁷

In children with central precocious puberty (CPP, n=47) that received a subcutaneous histrelin implant (Supprelin LA, Endo Pharmaceuticals), the median maximum serum histrelin concentration over the study period was 0.43 ng/mL, which is expected to maintain gonadotropins at prepubertal levels.⁵ There were no pharmacokinetic differences between patients previously treated with luteinizing hormone-releasing hormone (LHRH) agonists and those that had not.⁵ Food-drug interaction studies have not been performed for histrelin products.^7,5 Serum histrelin concentrations are 50% higher in prostate cancer patients with mild to severe renal impairment compared to those with no renal or hepatic impairment; however, this difference is not considered clinically relevant.⁷

Volume of distribution

The apparent volume of distribution of histrelin following a subcutaneous bolus dose of histrelin (Vantas, Endo Pharmaceuticals, 500 mcg) in healthy volunteers was 58.4 ± 7.86 L.⁷

Protein binding

In an in vitro measurement, the fraction of histrelin (Vantas, Endo Pharmaceuticals) unbound in plasma was 29.5% ± 8.9% (mean ± SD).⁷

Metabolism

As a synthetic peptide, histrelin is expected to be metabolized by proteases throughout the body. This will likely result in several peptide fragments produced by hydrolysis.⁷ In an in vitro drug metabolism study using human hepatocytes, a single histrelin metabolite resulting from C-terminal dealkylation was identified.⁷

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• Histrelin
  • Histrelin metabolite

Route of elimination

Drug excretion studies have not been performed for histrelin ⁷.

Half-life

In healthy volunteers administered a subcutaneous bolus dose of histrelin, the terminal half-life was 3.92 ± 1.01 hr (mean ± SD).⁷

Clearance

In prostate cancer patients (n=17) administered a histrelin implant (Vantas, Endo Pharmaceuticals) the apparent clearance was 174 ± 56.5 mL/min (mean ± SD).⁷

Adverse Effects

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Toxicity

There were no signs of systemic toxicity in animals injected with up to 200 mcg/kg (rats, rabbits), or 2000 mcg/kg (mice) of histrelin acetate. These concentrations represent 20 to 200 times the maximal recommended human dose of 10 mcg/kg/day.⁷ Patients receiving one, two or four histrelin implants (Vantas, Endo Pharmaceuticals) had similar adverse event profiles.⁷

No overdose cases were reported in the clinical trials of the histrelin product Supprelin LA (Vantas, Endo Pharmaceuticals). The administration of high doses of histrelin in animal studies was associated with the expected pharmacological effects.⁵ Since both products of histrelin are administered using implants that deliver a constant dose, accidental or intentional overdose is unlikely.

Pathways

Not Available

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Not Available

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Acarbose	The therapeutic efficacy of Acarbose can be decreased when used in combination with Histrelin.
Acetohexamide	The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Histrelin.
Acrivastine	The risk or severity of QTc prolongation can be increased when Histrelin is combined with Acrivastine.
Adenosine	The risk or severity of QTc prolongation can be increased when Histrelin is combined with Adenosine.
Ajmaline	The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Histrelin.

Food Interactions

No interactions found.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Histrelin acetate	Not Available	Not Available	Not applicable

International/Other Brands

Supprelin / Supprelin LA / Vantas

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Supprelin LA	Implant	50 mg/1	Subcutaneous	Endo Pharmaceuticals Inc.	2007-05-31	Not applicable
Vantas	Implant; Kit	50 mg	Subcutaneous	Paladin Labs Inc	2006-07-14	2017-04-07
Vantas	Implant	50 mg/1	Subcutaneous	Valera Pharmaceuticals, Inc	2007-03-09	2007-04-11
Vantas	Implant	50 mg/1	Subcutaneous	Endo Pharmaceuticals Inc.	2004-11-01	2022-03-31

Categories

ATC Codes

L02AE05 — Histrelin

• L02AE — Gonadotropin releasing hormone analogues
• L02A — HORMONES AND RELATED AGENTS
• L02 — ENDOCRINE THERAPY
• L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Drug Categories

• Adrenal Cortex Hormones
• Amino Acids, Peptides, and Proteins
• Antineoplastic and Immunomodulating Agents
• Endocrine Therapy
• Gonadotropin Releasing Hormone Receptor Agonist
• Gonadotropin Releasing Hormone Receptor Agonists
• Gonadotropin-releasing hormone agonist
• Hormones
• Hormones and Related Agents
• Hormones, Hormone Substitutes, and Hormone Antagonists
• Hyperglycemia-Associated Agents
• Hypothalamic Hormones
• Nerve Tissue Proteins
• Neuropeptides
• Oligopeptides
• Peptide Hormones
• Peptides
• Potential QTc-Prolonging Agents
• Proteins
• QTc Prolonging Agents

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Tyrosine and derivatives / Phenylalanine and derivatives / Histidine and derivatives / Leucine and derivatives / N-acyl-alpha amino acids and derivatives / Proline and derivatives / Tryptamines and derivatives / Serine and derivatives / Alpha amino acid amides / Amphetamines and derivatives / 3-alkylindoles / N-acylpyrrolidines / Pyrrolidinecarboxamides / 1-hydroxy-2-unsubstituted benzenoids / N-acyl amines / N-substituted imidazoles / Substituted pyrroles / Pyrrolidine-2-ones / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Guanidines / Lactams / Propargyl-type 1,3-dipolar organic compounds / Carboxylic acids / Carboximidamides / Azacyclic compounds / Monocarboxylic acids and derivatives / Organic oxides / Carbonyl compounds / Organopnictogen compounds / Hydrocarbon derivatives / Primary alcohols

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Substituents

1-hydroxy-2-unsubstituted benzenoid / 2-pyrrolidone / 3-alkylindole / Alcohol / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amphetamine or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Carbonyl group / Carboxamide group / Carboximidamide / Carboxylic acid / Fatty acyl / Fatty amide / Guanidine / Heteroaromatic compound / Histidine or derivatives / Hydrocarbon derivative / Imidazole / Indole / Indole or derivatives / Lactam / Leucine or derivatives / Monocarboxylic acid or derivatives / Monocyclic benzene moiety / N-acyl-alpha amino acid or derivatives / N-acyl-amine / N-acylpyrrolidine / N-substituted imidazole / N-substituted-alpha-amino acid / Organic 1,3-dipolar compound / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Phenol / Phenylalanine or derivatives / Primary alcohol / Proline or derivatives / Propargyl-type 1,3-dipolar organic compound / Pyrrole / Pyrrolidine / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine-2-carboxamide / Pyrrolidone / Secondary carboxylic acid amide / Serine or derivatives / Substituted pyrrole / Tertiary carboxylic acid amide / Triptan / Tyrosine or derivatives

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Molecular Framework

Not Available

External Descriptors

acetate salt (CHEBI:63530)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

H50H3S3W74

CAS number

76712-82-8

InChI Key

BKEMVGVBBDMHKL-VYFXDUNUSA-N

InChI

InChI=1S/C66H86N18O12.2C2H4O2/c1-4-70-64(95)55-17-11-25-84(55)65(96)48(16-10-24-71-66(67)68)76-58(89)49(26-38(2)3)77-62(93)53(30-43-34-83(37-74-43)33-40-12-6-5-7-13-40)81-59(90)50(27-39-18-20-44(86)21-19-39)78-63(94)54(35-85)82-60(91)51(28-41-31-72-46-15-9-8-14-45(41)46)79-61(92)52(29-42-32-69-36-73-42)80-57(88)47-22-23-56(87)75-47;2*1-2(3)4/h5-9,12-15,18-21,31-32,34,36-38,47-55,72,85-86H,4,10-11,16-17,22-30,33,35H2,1-3H3,(H,69,73)(H,70,95)(H,75,87)(H,76,89)(H,77,93)(H,78,94)(H,79,92)(H,80,88)(H,81,90)(H,82,91)(H4,67,68,71);2*1H3,(H,3,4)/t47-,48-,49-,50-,51-,52-,53+,54-,55-;;/m0../s1

IUPAC Name

(2S)-1-[(2S)-2-[(2S)-2-[(2R)-3-(1-benzyl-1H-imidazol-4-yl)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2S)-2-[(2S)-3-(1H-imidazol-4-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-(1H-indol-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]propanamido]-4-methylpentanamido]-5-carbamimidamidopentanoyl]-N-ethylpyrrolidine-2-carboxamide; bis(acetic acid)

SMILES

CC(O)=O.CC(O)=O.CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC1=CN(CC2=CC=CC=C2)C=N1)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CNC2=C1C=CC=C2)NC(=O)[C@H](CC1=CNC=N1)NC(=O)[C@@H]1CCC(=O)N1

References

General References

1. Lewis KA, Eugster EA: Experience with the once-yearly histrelin (GnRHa) subcutaneous implant in the treatment of central precocious puberty. Drug Des Devel Ther. 2009 Sep 21;3:1-5. [Article]
2. Shore N, Cookson MS, Gittelman MC: Long-term efficacy and tolerability of once-yearly histrelin acetate subcutaneous implant in patients with advanced prostate cancer. BJU Int. 2012 Jan;109(2):226-32. doi: 10.1111/j.1464-410X.2011.10370.x. Epub 2011 Aug 18. [Article]
3. Djavan B, Schlegel P, Salomon G, Eckersberger E, Sadri H, Graefen M: Analysis of testosterone suppression in men receiving histrelin, a novel GnRH agonist for the treatment of prostate cancer. Can J Urol. 2010 Aug;17(4):5265-71. [Article]
4. Ortmann O, Weiss JM, Diedrich K: Gonadotrophin-releasing hormone (GnRH) and GnRH agonists: mechanisms of action. Reprod Biomed Online. 2002;5 Suppl 1:1-7. doi: 10.1016/s1472-6483(11)60210-1. [Article]
5. FDA Approved Drug Products: Supprelin LA (histrelin acetate) subcutaneous implant [Link]
6. FDA Drug Shortages: Vantas 50 mg Implantation Kit [Link]
7. FDA Approved Drug Products: Vantas (histrelin acetate) subcutaneous implant [Link]
8. Health Canada Approved Drug Products: Vantas (histrelin acetate) subdermal implant [Link]

External Links

KEGG Drug

D02369

PubChem Compound

56927879

PubChem Substance

347827797

ChemSpider

26606349

RxNav

50975

ChEBI

63530

ChEMBL

CHEMBL1201255

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Histrelin

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
3	Completed	Treatment	Adenocarcinoma of Prostate / Prostate Cancer	2
3	Completed	Treatment	Central Precocious Puberty (CPP)	1
3	Recruiting	Treatment	Adenocarcinoma of Prostate	1
3	Recruiting	Treatment	Adenocarcinoma of Prostate / Metastatic Malignant Neoplasm in the Bone / Stage III Prostate Cancer AJCC v8 / Stage IIIA Prostate Cancer AJCC v8 / Stage IIIB Prostate Cancer AJCC v8 / Stage IIIC Prostate Cancer AJCC v8 / Stage IVA Prostate Cancer AJCC v8	1
3	Recruiting	Treatment	Castration Levels of Testosterone / Metastatic Prostate Adenocarcinoma / Stage IV Prostate Cancer AJCC v8 / Stage IVA Prostate Cancer AJCC v8 / Stage IVB Prostate Cancer AJCC v8	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Implant	Subcutaneous
Implant	Subcutaneous	50 mg/1
Implant; kit	Subcutaneous	50 mg

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US8062652	No	2011-11-22	2026-06-16

Properties

State

Solid

Experimental Properties

Property	Value	Source
water solubility	10 mg/mL	Health Canada Label
pKa	5.3 (His-base)	Health Canada Label

Predicted Properties

Property	Value	Source
logP	-2.1	Chemaxon
pKa (Strongest Acidic)	9.49	Chemaxon
pKa (Strongest Basic)	11.59	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	17	Chemaxon
Hydrogen Donor Count	16	Chemaxon
Polar Surface Area	446.86 Å2	Chemaxon
Rotatable Bond Count	34	Chemaxon
Refractivity	360.07 m3·mol-1	Chemaxon
Polarizability	138.34 Å3	Chemaxon
Number of Rings	8	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Not Available

Chromatographic Properties

Collision Cross Sections (CCS)

Not Available

Targets

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Details1. Gonadotropin-releasing hormone receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Agonist

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. FDA Approved Drug Products: Supprelin LA (histrelin acetate) subcutaneous implant [Link]
2. FDA Approved Drug Products: Vantas (histrelin acetate) subcutaneous implant [Link]

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Drug created at September 14, 2010 16:21 / Updated at December 02, 2023 07:02