Leuprorelin - 10mM in Water , CAS No.53714-56-0

CAS: 53714-56-0 Cat. No.: L424593 Molecular Weight: 1209.40 EC Number: 633-395-9

GRADE & PURITY 10mM in Water

Synonyms

Leuprolide acetate salt, >=98% (HPLC) | pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHC2H5 | 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide | Leuproreline | NCGC00485984-01 | (D-Leu(sup 6),des-gly-NH2

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Information

Leuprolide is an agonist at pituitary GnRH receptors.GnRH receptor Leuprorelin is a gonadotrophin-releasing hormone (GnRH) analogue used to treat a wide range of sex hormone-related disorders including advanced prostatic cancer, endometriosis and precocious puberty. Leuprorelin acts primarily on the anterior pituitary, inducing a transient early rise in gonadotrophin release. With continued use, Leuprorelin causes pituitary desensitisation and/or down-regulation, leading to suppressed circulating levels of gonadotrophins and sex hormones.By interrupting the normal pulsatile stimulation of, and thus desensitizing, the GnRH receptors, it indirectly downregulates the secretion of gonadotropins luteinizing hormone (LH) and follicle-stimulating hormone (FSH), leading to hypogonadism and thus a dramatic reduction in estradiol and testosterone levels in both sexes.

Specifications

Synonyms

Leuprolide acetate salt, >=98% (HPLC) | pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHC2H5 | 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide | Leuproreline | NCGC00485984-01 | (D-Leu(sup 6), des-gly-NH2

Specifications & Purity

10mM in Water

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: CCNC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(CO)NC(=O)C(CC3=CNC4=CC=CC=C43)NC(=O)C(CC5=CN=CN5)NC(=O)C6CCC(=O)N6
• IUPAC Name: (2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(2S)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]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
• InChIKey: GFIJNRVAKGFPGQ-LIJARHBVSA-N
• INCHI: 1S/C59H84N16O12/c1-6-63-57(86)48-14-10-22-75(48)58(87)41(13-9-21-64-59(60)61)68-51(80)42(23-32(2)3)69-52(81)43(24-33(4)5)70-53(82)44(25-34-15-17-37(77)18-16-34)71-56(85)47(30-76)74-54(83)45(26-35-28-65-39-12-8-7-11-38(35)39)72-55(84)46(27-36-29-62-31-66-36)73-50(79)40-19-20-49(78)67-40/h7-8,11-12,15-18,28-29,31-33,40-48,65,76-77H,6,9-10,13-14,19-27,30H2,1-5H3,(H,62,66)(H,63,86)(H,67,78)(H,68,80)(H,69,81)(H,70,82)(H,71,85)(H,72,84)(H,73,79)(H,74,83)(H4,60,61,64)/t40-,41-,42-,43+,44-,45-,46-,47-,48-/m0/s1
• Isomeric SMILES: CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=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
• Molecular Weight: 1209.40
• Reaxy-Rn: 25294586
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25294586&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Peptides
          • Level6 Oligopeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides
• 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 Substituted pyrroles N-acyl amines Pyrrolidine-2-ones Tertiary carboxylic acid amides Imidazoles Heteroaromatic compounds Secondary carboxylic acid amides Guanidines Lactams Propargyl-type 1,3-dipolar organic compounds Carboximidamides Azacyclic compounds Carbonyl compounds Organopnictogen compounds Organic oxides Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Alpha-oligopeptide - Tyrosine or derivatives - Phenylalanine or derivatives - Histidine or derivatives - Leucine or derivatives - N-acyl-alpha amino acid or derivatives - Proline or derivatives - Alpha-amino acid amide - Triptan - Serine or derivatives - 3-alkylindole - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Amphetamine or derivatives - Indole or derivatives - Indole - N-acylpyrrolidine - Pyrrolidine-2-carboxamide - Pyrrolidine carboxylic acid or derivatives - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Monocyclic benzene moiety - Fatty amide - N-acyl-amine - Fatty acyl - Pyrrolidone - 2-pyrrolidone - Substituted pyrrole - Benzenoid - Pyrrole - Tertiary carboxylic acid amide - Azole - Pyrrolidine - Heteroaromatic compound - Imidazole - Secondary carboxylic acid amide - Lactam - Carboxamide group - Guanidine - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Carboximidamide - Organoheterocyclic compound - Azacycle - Primary alcohol - Organic nitrogen compound - Hydrocarbon derivative - Carbonyl group - Organic oxygen compound - Organic oxide - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Alcohol - Aromatic heteropolycyclic compound
• 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.
• External Descriptors: oligopeptide

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

GNRHR Tclin Gonadotropin-releasing hormone receptor (4 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

F2 Tclin Thrombin (11687 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHE Tclin Acetylcholinesterase (18204 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOB Tclin Monoamine oxidase B (8835 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GNRHR Tclin Gonadotropin-releasing hormone receptor (3398 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A4 Tclin Serotonin transporter (12625 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRM1 Tclin Mu opioid receptor (19785 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A3 Tclin Dopamine transporter (10535 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KCNH2 Tclin HERG (29587 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH3 Tclin Histamine H3 receptor (10389 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

Discover Target: CYP2C9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HEK293 (82097 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Liver microsomes (16955 Activities)

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Pneumocystis carinii (749 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Leishmania infantum (5912 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trypanosoma brucei (78846 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trypanosoma brucei brucei (13300 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Entamoeba histolytica (2676 Activities)

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Cryptosporidium parvum (1150 Activities)

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Plasmodium falciparum (966862 Activities)

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Leishmania amazonensis (3813 Activities)

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Leishmania donovani (89745 Activities)

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Leishmania major (2877 Activities)

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Leishmania mexicana (936 Activities)

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Trypanosoma cruzi (99888 Activities)

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Trichomonas vaginalis (2376 Activities)

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Toxoplasma gondii (4585 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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Trypanosoma brucei rhodesiense (7991 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 1209.400 g/mol
• XLogP3: 0.700
• Hydrogen Bond Donor Count: 15
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 32
• Exact Mass: 1208.65 Da
• Monoisotopic Mass: 1208.65 Da
• Topological Polar Surface Area: 432.000 Ų
• Heavy Atom Count: 87
• Formal Charge: 0
• Complexity: 2390.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1