5-Oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide

Basic Information

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CAS Number

53714-56-0

Molecular Formula

C59H84N16O12

Molecular Weight

1209.42 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Amines

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

Water Solubility

Soluble in water at 1mg/ml

Specific Rotation

D25 -31.7° (c = 1 in 1% acetic acid)

SMILES

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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

InChI

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

InChIKey

GFIJNRVAKGFPGQ-LIJARHBVSA-N

LogP

-1.2284300000000077

Topological Polar Surface Area

429.03999999999985 Å²

Hydrogen Bond Donor/Acceptor

17 / 28

Complexity

2390

Safety Information

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GHS Hazard Pictograms

H360

Hazard Statement

H360 May damage fertility or the unborn child
Reproductive toxicity

Hazard Class

Class 6.1 Class 6.1

Synonyms & References

English

LEUPRORELIN [MART.]
Leuprorelin [INN:BAN]
Leuproreline
Leuprorelina
TAP-144 FREE BASE
DTXCID00820063
AKOS037515838
LEUPRORELIN [WHO-DD]
CS-4947
NCGC00485984-01
Leuprolide acetate, United States Pharmacopeia (USP) Reference Standard
EN300-7481165
GFIJNRVAKGFPGQ-LIJARHBVSA-N
CKD-841
(2S)-1-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2S)-2-[(2S)-3-(1H-imidazol-4-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-(1H-indol-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]-4-methylpentanamido]-4-methylpentanamido]pentanoyl]-N-ethylpyrrolidine-2-carboxamide
Leuprorelina [INN-Spanish]
Leuprorelina (INN-Spanish)
HY-12553
LEUPROLIDE [VANDF]
Leuprolide acetate salt
LEUPRORELIN [EP MONOGRAPH]
DTXSID50872411
HS-2016
leuprolide
SCHEMBL4585
6-D-Leucine-9-(N-ethyl-L-prolinamide)-10-deglycinamide Luteinizing Hormone-Releasing Factor (Pig)
LEUPROLIDE [HSDB]
53714-56-0
Leuprorelin slow release
pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHC2H5
Leuprorelin acetate (JAN)

MDL Number

MFCD00167544

FAQ

What are the physical and chemical properties of 5-Oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide (CAS: 53714-56-0)?

5-Oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide (CAS: 53714-56-0) is a cyclic heptapeptide. It crystallizes in the form of a white solid. The molecular weight is approximately 1698.4 g/mol. This compound is poorly soluble in water but soluble in organic solvents such as methanol and ethanol. It exhibits moderate reactivity, particularly towards nucleophiles and reducing agents.

How is 5-Oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide (CAS: 53714-56-0) typically synthesized?

5-Oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide (CAS: 53714-56-0) is synthesized through solid-phase peptide synthesis (SPPS). Common methods include using Rink amide or Fmoc (fluorenylmethyloxycarbonyl) resin. This peptide is synthesized using standard coupling reagents such as HBTU (1-hydroxybenzotriazole, 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide), with high selectivity and yield. The final product is typically deprotected and cleaved from the resin using strong acid, followed by purification.

What industries use 5-Oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide (CAS: 53714-56-0)?

5-Oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide (CAS: 53714-56-0) is primarily used in the pharmaceutical industry for drug discovery and development. It also finds applications in biotechnology, where it is used in the development of biosensors and in polymer-based materials for specific industrial applications. Additionally, this compound can be utilized in the semiconductor industry for specific functionalization purposes.

What precautions should be taken when handling 5-Oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide (CAS: 53714-56-0)?

When handling 5-Oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide (CAS: 53714-56-0), it is essential to wear appropriate personal protective equipment (PPE) including gloves, safety goggles, and a lab coat. Handle this compound in a well-ventilated area or fume hood to avoid inhalation. In case of a spill, immediately clean it up using appropriate absorbent materials and wash the area thoroughly. Always refer to the Safety Data Sheet (SDS) for detailed handling and disposal instructions.