General Information of Drug (ID: DMAQ469)

Drug Name
Gonadorelin
Synonyms
Dirigestran; Factrel; Fertagyl; Gonadorelina; Gonadorelinum; Hypocrine; Kryptocur; LFRH; LHFSHRH; Luforan; Luliberin; Lutal; Lutamin; Lutrefact; Relefact; Relisorm; Dirigestran Spofa; Gonadoliberin I; Gonadotropin releasing hormone; LHFSH Releasing Hormone; LUTEINIZING HORMONE; Lutrepulse KIT; MammalianGnRH; Relisorm l; Synthetic LRF; Synthetic gonadoliberin; HOE 471; AY-24031; FSH-Releasing Hormone; Fertagyl (TN); GnRH-I; Gonadorelin (INN); Gonadorelin [INN:BAN]; Gonadorelina [INN-Spanish]; Gonadorelinum [INN-Latin]; Gonadotropin-releasing factor; Gonadotropin-releasing hormone; Gonadotropin-releasing hormone I; Human LH-RH; LH-FSH Releasing Hormone; LH-Releasing hormone; Luteinizing hormone-releasing hormone; Mammalian LH-RH; Mammalian gonadotropin-releasing hormone; Ovine LH-RH; Ovine gonadotropin-releasing hormone; Porchine LH-RH; Porcine LH-releasing factor; Synthetic Gn-RH; Synthetic LH-FSH releasing hormone; Synthetic LH-RF; Synthetic LH-RH; Synthetic LH-releasing factor; Synthetic LH-releasing hormone; Synthetic gonadotropic hormone-releasing hormone; Synthetic gonadotropin-releasing hormone; LH-RH (swine); LH-Releasing factor (pig); LH-Releasing hormone (porcine); Luteinizing hormone-releasing factor (human); Luteinizing hormone-releasing factor (pig); Luteinizing hormone-releasing factor (rat); Luteinizing hormone-releasing factor (sheep); Luteinizing hormone-releasing factor (swine); Luteinizing hormone-releasing hormone (swin); Synthetic LH-FSH-RH; Synthetic decapeptide FSH/LH-RH; Follicle-stimulating hormone-releasing factor (pig); Gonadotropin, luteinizing hormone-releasing hormone, synthetic; Synthetic LH-RH/FSH-RH; Synthetic LH-releasing hormone/FSH-releasing hormone; PyroGlu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2
Indication
Disease Entry ICD 11 Status REF
Amenorrhea GA20.0 Approved [1]
Hypothalamic hypogonadism 5A61.2 Approved [2]
Therapeutic Class
Fertility Agents
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 5 Molecular Weight (mw) 1182.3
Logarithm of the Partition Coefficient (xlogp) -2.4
Rotatable Bond Count (rotbonds) 31
Hydrogen Bond Donor Count (hbonddonor) 16
Hydrogen Bond Acceptor Count (hbondacc) 15
ADMET Property
Absorption
The drug is rapidly absorbed when injected []
Half-life
The concentration or amount of drug in body reduced by one-half in 2 - 10 minutes [3]
Metabolism
The drug is metabolized via the hydrolyzed to inactive peptide components []
Chemical Identifiers
Formula
C55H75N17O13
IUPAC Name
(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-[(2S)-2-[(2-amino-2-oxoethyl)carbamoyl]pyrrolidin-1-yl]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
Canonical SMILES
CC(C)C[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N)NC(=O)CNC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC3=CNC4=CC=CC=C43)NC(=O)[C@H](CC5=CN=CN5)NC(=O)[C@@H]6CCC(=O)N6
InChI
InChI=1S/C55H75N17O13/c1-29(2)19-38(49(80)67-37(9-5-17-60-55(57)58)54(85)72-18-6-10-43(72)53(84)62-25-44(56)75)66-46(77)26-63-47(78)39(20-30-11-13-33(74)14-12-30)68-52(83)42(27-73)71-50(81)40(21-31-23-61-35-8-4-3-7-34(31)35)69-51(82)41(22-32-24-59-28-64-32)70-48(79)36-15-16-45(76)65-36/h3-4,7-8,11-14,23-24,28-29,36-43,61,73-74H,5-6,9-10,15-22,25-27H2,1-2H3,(H2,56,75)(H,59,64)(H,62,84)(H,63,78)(H,65,76)(H,66,77)(H,67,80)(H,68,83)(H,69,82)(H,70,79)(H,71,81)(H4,57,58,60)/t36-,37-,38-,39-,40-,41-,42-,43-/m0/s1
InChIKey
XLXSAKCOAKORKW-AQJXLSMYSA-N
Cross-matching ID
PubChem CID
638793
ChEBI ID
CHEBI:5520
CAS Number
9034-40-6
DrugBank ID
DB00644
TTD ID
D04ODH
INTEDE ID
DR1929
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Gonadotropin-releasing hormone receptor (GNRHR) TT8R70G GNRHR_HUMAN Agonist [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Metallo-endopeptidase-like 1 (MMEL1) DEYCUQ2 MMEL1_HUMAN Substrate [5]
Prolyl endopeptidase (PREP) DEVSCNZ PPCE_HUMAN Substrate [6]
Thimet oligopeptidase (THOP1) DE95LJC THOP1_HUMAN Substrate [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Gonadorelin FDA Label
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4391).
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Use of cognitive behavior therapy for functional hypothalamic amenorrhea. Ann N Y Acad Sci. 2006 Dec;1092:114-29.
5 Cell-specific activity of neprilysin 2 isoforms and enzymic specificity compared with neprilysin. Biochem J. 2002 May 1;363(Pt 3):697-705.
6 Ion-exchange chromatography: basic principles and application to the partial purification of soluble mammalian prolyl oligopeptidase. Methods Mol Biol. 2011;681:215-28.
7 Sleep deprivation changes thimet oligopeptidase (THOP1) expression and activity in rat brain. Heliyon. 2019 Nov 26;5(11):e02896.