AVORELIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C65H85N17O12
Molecular Weight	1296.4771
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC2=C(C)NC3=C2C=CC=C3)NC(=O)[C@H](CC4=CC=C(O)C=C4)NC(=O)[C@H](CO)NC(=O)[C@H](CC5=CNC6=C5C=CC=C6)NC(=O)[C@H](CC7=CN=CN7)NC(=O)[C@@H]8CCC(=O)N8

InChI

InChIKey=HJNZCKLMRAOTMA-BRBGIFQRSA-N

InChI=1S/C65H85N17O12/c1-5-69-63(93)54-17-11-25-82(54)64(94)47(16-10-24-70-65(66)67)75-57(87)48(26-35(2)3)76-61(91)52(30-43-36(4)73-45-15-9-7-13-42(43)45)80-58(88)49(27-37-18-20-40(84)21-19-37)77-62(92)53(33-83)81-59(89)50(28-38-31-71-44-14-8-6-12-41(38)44)78-60(90)51(29-39-32-68-34-72-39)79-56(86)46-22-23-55(85)74-46/h6-9,12-15,18-21,31-32,34-35,46-54,71,73,83-84H,5,10-11,16-17,22-30,33H2,1-4H3,(H,68,72)(H,69,93)(H,74,85)(H,75,87)(H,76,91)(H,77,92)(H,78,90)(H,79,86)(H,80,88)(H,81,89)(H4,66,67,70)/t46-,47-,48-,49-,50-,51-,52+,53-,54-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C65H85N17O12
Molecular Weight	1296.4771
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	3
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10569560
Curator's Comment: description was created based on several sources, including: DOI: 10.1023/A:1008898216113 | https://www.ncbi.nlm.nih.gov/pubmed/16939388

Avorelin is a superagonist of natural luteinizing-hormone-releasing-hormone. Avorelin has been formulated in high molecular weight polylactic glycolic acid to afford protracted and continuous release of the peptide from subcutaneous implants. Avorelin has been in phase II clinical trials by Mediolanum for the treatment of prostate cancer, breast cancer and endometriosis. However, this research has been discontinued. Adverse events mainly related to androgen suppression (hot flushes, decreased libido and impotence) or the nature of the disease (skeletal pain).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Gonadotropin-releasing hormone receptor 41 Target ID: CHEMBL1855 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16939388 \| DOI: 10.1023/A:1008898216113	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10569560 DOI: 10.1023/A:1008898216113	Primary	Phase II 1132	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.pharmacodia.com/yaodu/html/v1/chemicals/b9978645dcddd6ff72f77cf90e6f4bd5.html	Primary	Phase II 1132	Unknown Approved Use Unknown
Endometriosis 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16939388 https://www.pharmacodia.com/yaodu/html/v1/chemicals/b9978645dcddd6ff72f77cf90e6f4bd5.html	Primary	Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Manipulation of postnatal testosterone levels affects phallic and clitoral development in infant rhesus monkeys.	1999 Apr	10194644
Investigation of the role of postnatal testosterone in the expression of sex differences in behavior in infant rhesus macaques (Macaca mulatta).	1999 Apr	10202126
Pharmacodynamics of a long acting depot preparation of avorelin in patients with prostate cancer. Avorelin Study Group.	1999 Dec	10569560

Patents

Sample Use Guides

In Vivo Use Guide

10 or 15 mg implants

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:48:30 GMT 2023` Edited by `admin` on `Fri Dec 15 18:48:30 GMT 2023`
Record UNII	FSB5837STQ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

AVORELIN

Official Name

English

EP-23904

Code

English

METERELIN

Common Name

English

1-9-LUTEINIZING HORMONE-RELEASING FACTOR (SWINE), 6-(2-METHYL-D-TRYPTOPHAN)-9-(N-ETHYL-L-PROLINAMIDE)-

Common Name

English

avorelin [INN]

Common Name

English

5-OXO-L-PROLYL-L-HISTIDYL-L-TRYPTOPHYL-L-SERYL-L-TYROSYL-2-METHYL-D-TRYPTOPHYL-L-LEUCYL-L-ARGINYL-N-ETHYL-L-PROLINAMIDE

Common Name

English

MF-6001

Code

English

Avorelin [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1910