N-(1-{2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl}-5-[(diaminomethylidene)amino]-1-oxopentan-2-yl)-2-{2-[2-(3-hydroxy-2-{2-[3-(1H-imidazol-5-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]-3-(1H-indol-3-yl)propanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]acetamido}-4-methylpentanamide

• ChemBase ID: 526
• Molecular Formular: C55H75N17O13
• Molecular Mass: 1182.2901
• Monoisotopic Mass: 1181.57302555
• SMILES: O=C(N1C(CCC1)C(=O)NCC(=O)N)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C1NC(=O)CC1)Cc1[nH]cnc1)Cc1c2c([nH]c1)cccc2)CO)Cc1ccc(O)cc1)CC(C)C)CCCN=C(N)N
• Canonical SMILES: OCC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)NCC(=O)N)CCCN=C(N)N)CC(C)C)Cc1ccc(cc1)O)NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(NC(=O)C1CCC(=O)N1)Cc1[nH]cnc1
• 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)
• InChIKey: XLXSAKCOAKORKW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(1-{2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl}-5-[(diaminomethylidene)amino]-1-oxopentan-2-yl)-2-{2-[2-(3-hydroxy-2-{2-[3-(1H-imidazol-5-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]-3-(1H-indol-3-yl)propanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]acetamido}-4-methylpentanamide
• IUPAC Traditional name: gonadorelin
• Brand Name: Dirigestran; Dirigestran Spofa; Factrel; Fertagyl; Gonadorelina [INN-Spanish]; Gonadorelinum [INN-Latin]; Gonadotropin releasing hormone; Gonadotropin-releasing factor; Gonadotropin-releasing hormone; Human LH-RH; Hypocrine; Luforan; Lutal; Lutamin; Lutrefact; Lutrepulse; Lutrepulse KIT; Mammalian GnRH; Mammalian LH-RH; Ovine LH-RH; Porchine LH-RH; Porcine LH-releasing factor; Relefact; Relisorm; Relisorm L; Synthetic Gn-RH; Synthetic LH-FSH releasing hormone; Synthetic LH-RF; Synthetic LH-RH; Synthetic LH-releasing factor; Synthetic LH-releasing hormone; Synthetic LRF; Synthetic decapeptide FSH/LH-RH; Synthetic gonadoliberin
• Synonyms: Gonadorelin

Database IDs

• CAS Number: 6918-09-8
• PubChem SID: 160963989; 46506144
• PubChem CID: 36523

CALCULATED PROPERTIES

JChem

• Lipinski's Rule of Five: false
• Acid pKa: 9.470687
• H Acceptors: 17
• H Donor: 16
• LogD (pH = 5.5): -8.74699
• LogD (pH = 7.4): -7.980599
• Log P: -6.3192887
• Molar Refractivity: 302.5053 cm^3
• Polarizability: 117.86165 Å^3
• Polar Surface Area: 474.63 Å^2
• Rotatable Bonds: 31

ALOGPS 2.1

• Solubility (Water): 5.88e-02 g/l
• Log P: -0.09
• LOG S: -4.3

PROPERTIES

Physical Property

• Solubility: 1 mg/mL
• Hydrophobicity(logP): -3.6

DETAILS

DrugBank - DB00644

• Drug Groups: approved
• Description: Gonadorelin is another name for gonadotropin-releasing hormone (GnRH). It is a synthetic decapeptide prepared using solid phase peptide synthesis. GnRH is responsible for the release of follicle stimulating hormone and leutinizing hormone from the anterior pitutitary.
• Indication: For evaluating the functional capacity and response of the gonadotropes of the anterior pituitary also for evaluating residual gonadotropic function of the pituitary following removal of a pituitary tumor by surgery and/or irradiation.
• Pharmacology: Gonadorelin is responsible for the release of follicle stimulating hormone and leutinizing hormone from the anterior pitutitary. In the pituitary GnRH stimulates synthesis and release of FSH and LH, a process that is controlled by the frequency and amplitude of GnRH pulses, as well as the feedback of androgens and estrogens. The pulsatility of GnRH secretion has been seen in all vertebrates, and it is necessary to ensure a correct reproductive function. Thus a single hormone, GnRH, controls a complex process of follicular growth, ovulation, and corpus luteum maintenance in the female, and spermatogenesis in the male. Its short half life requires infusion pumps for its clinical use
• Toxicity: LD₅₀>3000 mg/kg (rat, oral)
• Affected Organisms: Humans and other mammals
• Biotransformation: Rapidly hydrolyzed to inactive peptide components
• Absorption: Rapidly absorbed when injected
• Half Life: Very short, initial, 2 to 10 minutes; terminal, 10 to 40 minutes
• References: Dungan HM, Clifton DK, Steiner RA: Minireview: kisspeptin neurons as central processors in the regulation of gonadotropin-releasing hormone secretion. Endocrinology. 2006 Mar;147(3):1154-8. Epub 2005 Dec 22. [Pubmed] ; Franceschini I, Lomet D, Cateau M, Delsol G, Tillet Y, Caraty A: Kisspeptin immunoreactive cells of the ovine preoptic area and arcuate nucleus co-express estrogen receptor alpha. Neurosci Lett. 2006 Jul 3;401(3):225-30. Epub 2006 Apr 18. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Dungan HM, Clifton DK, Steiner RA: Minireview: kisspeptin neurons as central processors in the regulation of gonadotropin-releasing hormone secretion. Endocrinology. 2006 Mar;147(3):1154-8. Epub 2005 Dec 22. Pubmed
• Franceschini I, Lomet D, Cateau M, Delsol G, Tillet Y, Caraty A: Kisspeptin immunoreactive cells of the ovine preoptic area and arcuate nucleus co-express estrogen receptor alpha. Neurosci Lett. 2006 Jul 3;401(3):225-30. Epub 2006 Apr 18. Pubmed