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Leuprolide Mesylate

Leuprolide Mesylate

Synopsis, Chemistry

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Also known as: Leuprorelin mesilate, Leuprorelin mesylate, Camcevi, 8e3c3c493w, Pglu-his-trp-ser-tyr-d-leu-leu-arg-pro-nhc2h5 mesylate, Pglu-his-trp-ser-tyr-d-leu-leu-arg-pro-nhc2h5 methanesulfonate

Molecular Formula

C₆₀H₈₈N₁₆O₁₅S

Molecular Weight

1305.5 g/mol

InChI Key

MBIDSOMXPLCOHS-XNHQSDQCSA-N

FDA UNII

8E3C3C493W

1 2D Structure

Leuprolide Mesylate

2 Identification

2.1 Computed Descriptors

2.1.1 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;methanesulfonic acid

2.1.2 InChI

InChI=1S/C59H84N16O12.CH4O3S/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;1-5(2,3)4/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);1H3,(H,2,3,4)/t40-,41-,42-,43+,44-,45-,46-,47-,48-;/m0./s1

2.1.3 InChI Key

MBIDSOMXPLCOHS-XNHQSDQCSA-N

2.1.4 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.CS(=O)(=O)O

2.1.5 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.CS(=O)(=O)O

2.2 Other Identifiers

2.2.1 UNII

8E3C3C493W

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Leuprorelin Mesilate

2. Leuprorelin Mesylate

3. Camcevi

4. 8e3c3c493w

5. Pglu-his-trp-ser-tyr-d-leu-leu-arg-pro-nhc2h5 Mesylate

6. Pglu-his-trp-ser-tyr-d-leu-leu-arg-pro-nhc2h5 Methanesulfonate

7. 1-9-luteinizing Hormone-releasing Factor (swine), 6-d-leucine-9-(n-ethyl-l-prolinamide)-, Methanesulfonate (1:1)

8. 944347-41-5

9. Unii-8e3c3c493w

10. Schembl4075500

11. Chembl4802223

12. Leuprorelin Mesilate [who-dd]

13. Leuprolide Mesylate [orange Book]

14. Q27270242

2.4 Create Date

2014-05-03

3 Chemical and Physical Properties

Molecular Formula	C₆₀H₈₈N₁₆O₁₅S
Molecular Weight	1305.5 g/mol
Hydrogen Bond Donor Count	16
Hydrogen Bond Acceptor Count	17
Rotatable Bond Count	32
Exact Mass	1304.63357734 g/mol
Monoisotopic Mass	1304.63357734 g/mol
Topological Polar Surface Area	494 Å²
Heavy Atom Count	92
Formal Charge	0
Complexity	2480
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Indication

Camcevi is indicated for the treatment of hormone dependent advanced prostate cancer and for the treatment of high-risk localised and locally advanced hormone dependent prostate cancer in combination with radiotherapy.