Lanreotide Acetate

Synopsis, Chemistry

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SOLUTION;SUBCUTANEOUS - EQ 120MG BASE/0.5ML (EQ 120MG BASE/0.5ML), SOLUTION;SUBCUTANEOUS - EQ 60MG BASE/0.2ML (EQ 60MG BASE/0.2ML), SOLUTION;SUBCUTANEOUS - EQ 90MG BASE/0.3ML (EQ 90MG BASE/0.3ML), SOLUTION;SUBCUTANEOUS - EQ 120MG BASE/0.5ML (EQ 120MG BASE/0.5ML), SOLUTION;SUBCUTANEOUS - EQ 60MG BASE/0.2ML (EQ 60MG BASE/0.2ML), SOLUTION;SUBCUTANEOUS - EQ 90MG BASE/0.3ML (EQ 90MG BASE/0.3ML)

SOLUTION;SUBCUTANEOUS - EQ 120MG BASE/0.5ML (EQ 120MG BASE/0.5ML)
SOLUTION;SUBCUTANEOUS - EQ 60MG BASE/0.2ML (EQ 60MG BASE/0.2ML)
SOLUTION;SUBCUTANEOUS - EQ 90MG BASE/0.3ML (EQ 90MG BASE/0.3ML)
SOLUTION;SUBCUTANEOUS - EQ 120MG BASE/0.5ML (EQ 120MG BASE/0.5ML)
SOLUTION;SUBCUTANEOUS - EQ 60MG BASE/0.2ML (EQ 60MG BASE/0.2ML)
SOLUTION;SUBCUTANEOUS - EQ 90MG BASE/0.3ML (EQ 90MG BASE/0.3ML)

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Also known as: Somatuline lp, Lanreotide (acetate), Bim-23014c, Ipstyl, Somatuline, Somatuline autogel

Molecular Formula

C₅₆H₇₃N₁₁O₁₂S₂

Molecular Weight

1156.4 g/mol

InChI Key

DEXPIBGCLCPUHE-UISHROKMSA-N

1 2D Structure

Lanreotide Acetate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

acetic acid;(4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-N-[(2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl]-19-[[(2R)-2-amino-3-naphthalen-2-ylpropanoyl]amino]-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-7-propan-2-yl-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxamide

2.1.2 InChI

InChI=1S/C54H69N11O10S2.C2H4O2/c1-29(2)45-54(75)63-44(53(74)65-46(30(3)66)47(57)68)28-77-76-27-43(62-48(69)38(56)23-32-15-18-33-10-4-5-11-34(33)22-32)52(73)60-41(24-31-16-19-36(67)20-17-31)50(71)61-42(25-35-26-58-39-13-7-6-12-37(35)39)51(72)59-40(49(70)64-45)14-8-9-21-55;1-2(3)4/h4-7,10-13,15-20,22,26,29-30,38,40-46,58,66-67H,8-9,14,21,23-25,27-28,55-56H2,1-3H3,(H2,57,68)(H,59,72)(H,60,73)(H,61,71)(H,62,69)(H,63,75)(H,64,70)(H,65,74);1H3,(H,3,4)/t30-,38-,40+,41+,42-,43+,44+,45+,46+;/m1./s1

2.1.3 InChI Key

DEXPIBGCLCPUHE-UISHROKMSA-N

2.1.4 Canonical SMILES

CC(C)C1C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=C(C=C4)O)NC(=O)C(CC5=CC6=CC=CC=C6C=C5)N)C(=O)NC(C(C)O)C(=O)N.CC(=O)O

2.1.5 Isomeric SMILES

C[C@H]([C@@H](C(=O)N)NC(=O)[C@@H]1CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)C(C)C)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=C(C=C4)O)NC(=O)[C@@H](CC5=CC6=CC=CC=C6C=C5)N)O.CC(=O)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. 188re-lanreotide

2. 2-naphthylalanyl-cyclo(cysteinyl-tyrosyl-tryptophyl-lysyl-valyl-cysteinyl)-threoninamide

3. 3-(2-naphthyl)-d-ala-cys-tyr-d-trp-lys-val-cys-thr-nh2

4. 3-(2-naphthyl)alanyl-cystinyl-tyrosyl-tryptophyl-lysyl-valyl-cystinyl-threonine Amide

5. Angiopeptin

6. Bim 23014

7. Bim 23014 C

8. Bim 23014c

9. Bim-23014

10. Bim-23014 C

11. D-nal-cys-tyr-trp-lys-val-cys-thr-nh2

12. Dc 13-116

13. Dc-13-116

14. Dc13-116

15. L-threoninamide, 3-(2-naphthalenyl)-d-alanyl-l-cysteinyl-l-tyrosyl-d-tryptophyl-l-lysyl-l-valyl-l-cysteinyl-, Cyclic (2-7)-disulfide

16. Lanreotide

17. Lanreotide Acetate

18. Lanreotide-sr

19. Nal-cyclo(cys-tyr-trp-lys-val-cys)-thr-nh2

20. Nal-cyclo(cys-tyr-trp-lys-val-cys)thr-nh2

21. Naphthalenyl-cyclo(cysteinyl-tyrosyl-tryptophyl-lysyl-valyl-cysteinyl)threoninamide

22. Naphthyl-cyclo(cys-tyr-trp-lys-val-cys)thr-nh2

23. Somatulin

24. Somatulina

25. Somatuline

2.2.2 Depositor-Supplied Synonyms

1. Somatuline Lp

2. Lanreotide (acetate)

3. Bim-23014c

4. Ipstyl

5. Somatuline

6. Somatuline Autogel

7. 2378114-72-6

8. Angiopeptin Acetate

9. Somatulina

10. Somatuline La

11. Acetic Acid;(4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-n-[(2s,3r)-1-amino-3-hydroxy-1-oxobutan-2-yl]-19-[[(2r)-2-amino-3-naphthalen-2-ylpropanoyl]amino]-16-[(4-hydroxyphenyl)methyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-7-propan-2-yl-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxamide

12. Chembl1201184

13. Hy-p1959a

14. Itm-014

15. Mfcd00873576

16. Bn-52030

17. Dc13-116

18. Cs-0113779

19. P1088

2.3 Create Date

2006-07-28

3 Chemical and Physical Properties

Molecular Formula	C₅₆H₇₃N₁₁O₁₂S₂
Molecular Weight	1156.4 g/mol
Hydrogen Bond Donor Count	14
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	17
Exact Mass	1155.48815915 g/mol
Monoisotopic Mass	1155.48815915 g/mol
Topological Polar Surface Area	443 Å²
Heavy Atom Count	81
Formal Charge	0
Complexity	2030
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 Information

1 of 2
Drug Name	Somatuline depot
PubMed Health	Lanreotide (Subcutaneous)
Drug Classes	Endocrine-Metabolic Agent
Drug Label	Somatuline Depot (lanreotide) Injection 60, 90 and 120 mg is a prolonged-release formulation for deep subcutaneous injection containing the drug substance lanreotide acetate, a synthetic octapeptide with a biological activity similar to naturally occ...
Active Ingredient	Lanreotide acetate
Dosage Form	Injectable
Route	Subcutaneous
Strength	eq 90mg base; eq 120mg base; eq 60mg base
Market Status	Prescription
Company	Ipsen Pharma

2 of 2
Drug Name	Somatuline depot
PubMed Health	Lanreotide (Subcutaneous)
Drug Classes	Endocrine-Metabolic Agent
Drug Label	Somatuline Depot (lanreotide) Injection 60, 90 and 120 mg is a prolonged-release formulation for deep subcutaneous injection containing the drug substance lanreotide acetate, a synthetic octapeptide with a biological activity similar to naturally occ...
Active Ingredient	Lanreotide acetate
Dosage Form	Injectable
Route	Subcutaneous
Strength	eq 90mg base; eq 120mg base; eq 60mg base
Market Status	Prescription
Company	Ipsen Pharma