U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C56H78N16O12
Molecular Weight 1167.3185
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALARELIN

SMILES

CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)[C@H](CO)NC(=O)[C@H](CC3=CNC4=CC=CC=C34)NC(=O)[C@H](CC5=CN=CN5)NC(=O)[C@@H]6CCC(=O)N6

InChI

InChIKey=QLGKMLRGKPKGKI-QWQCQAQZSA-N
InChI=1S/C56H78N16O12/c1-5-60-54(83)45-13-9-21-72(45)55(84)39(12-8-20-61-56(57)58)66-50(79)40(22-30(2)3)67-47(76)31(4)64-49(78)41(23-32-14-16-35(74)17-15-32)68-53(82)44(28-73)71-51(80)42(24-33-26-62-37-11-7-6-10-36(33)37)69-52(81)43(25-34-27-59-29-63-34)70-48(77)38-18-19-46(75)65-38/h6-7,10-11,14-17,26-27,29-31,38-45,62,73-74H,5,8-9,12-13,18-25,28H2,1-4H3,(H,59,63)(H,60,83)(H,64,78)(H,65,75)(H,66,79)(H,67,76)(H,68,82)(H,69,81)(H,70,77)(H,71,80)(H4,57,58,61)/t31-,38+,39+,40+,41+,42+,43+,44+,45+/m1/s1

HIDE SMILES / InChI
Alarelin (Gonadotrophin-releasing hormone) is a synthetic LH-RH agonist, which is used to treat endmometriosis. Alarelin Acetate is the acetate form of a hypothalamic peptide that stimulates the release of FSH and LH from the pituitary gland.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P01148
Gene ID: 2796.0
Gene Symbol: GNRH1
Target Organism: Homo sapiens (Human)
Conditions
PubMed

PubMed

TitleDatePubMed
Expression of gonadotropin-releasing hormone receptor and effect of gonadotropin-releasing hormone analogue on proliferation of cultured gastric smooth muscle cells of rats.
2004 Jun 15
[Comparison of Alarelin and Triptorelin in the long-protocol ovulation induction in in vitro fertilization and embryo transfer].
2010 Jul
Electromembrane extraction of gonadotropin-releasing hormone agonists from plasma and wastewater samples.
2016 Mar
Patents

Patents

Sample Use Guides

ewes: Forty-two pre-pubertal ewes were assigned to experimental groups 1 to 5 (EG-I to EG-V) and control group (CG). Ewes in EG-I, EG-II and EG-III were subcutaneously injected with 200, 300 or 400 μg alarelin antigens twice (on days 0 and 14), respectively. Ewes in EG-IV and EG-V were subcutaneously injected with 200 μg and 300 μg alarelin antigen four times (on days 0, 7, 14 and 21). Ewes in CG were subcutaneously injected with a solvent twice (on days 0 and 14). Alarelin immunization stimulated GnRH antibody production, suppressed expression of GnRHR protein, enhanced expressions of FSHR and LHR proteins in ovaries, promoted FSH secretion and thereby accelerated the development of ovaries and follicles in ewes.
Route of Administration: Other
The cultured gastric smooth muscle cells (GSMC) of rats showed immunoreactivity for GnRH receptor; positive staining was located in cytoplasm. GnRH receptor mRNA hybridized signals were also detected in cytoplasm. When alarelin (10(-9), 10(-7), 10(-5) mol/L) was administered into the medium and incubated for 24 h, OD value of MTT, (3)H-TdR incorporation and average fluorescent values of PCNA all decreased significantly as compared with the control group (P<0.05). The maximum inhibitory effect on cell proliferation was achieved a concentration of 10(-5) mol/L and it acted in a dose-dependent manner. Flow cytometric DNA analysis revealed that alarelin could significantly enhance ratio of G(1) phase and decrease ratio of S phase of GSMC of rats (P<0.05).
Name Type Language
ALARELIN
Common Name English
SURFAGON
Common Name English
L-4513
Code English
Alarelin [WHO-DD]
Common Name English
TAP-127
Code English
WY-18481
Code English
LHRH-A2
Common Name English
1-9-LUTEINIZING HORMONE-RELEASING FACTOR (SWINE), 6-D-ALANINE-9-(N-ETHYL-L-PROLINAMIDE)-
Common Name English
AY-25205
Code English
DALARELIN
Common Name English
Code System Code Type Description
FDA UNII
NJS328SUA7
Created by admin on Sat Dec 16 08:37:24 GMT 2023 , Edited by admin on Sat Dec 16 08:37:24 GMT 2023
PRIMARY
CAS
52435-06-0
Created by admin on Sat Dec 16 08:37:24 GMT 2023 , Edited by admin on Sat Dec 16 08:37:24 GMT 2023
PRIMARY
PUBCHEM
5484741
Created by admin on Sat Dec 16 08:37:24 GMT 2023 , Edited by admin on Sat Dec 16 08:37:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID40873497
Created by admin on Sat Dec 16 08:37:24 GMT 2023 , Edited by admin on Sat Dec 16 08:37:24 GMT 2023
PRIMARY