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CHEMISTRY
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DEVELOPMENTS

1 Drugs in Development

1 Drugs in Development

Synopsis

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Also known as: Mmc lipid-based prodrug (mlp), Jnj-27548547, 3i8jkl1chb, Mitomycin c lipid-based prodrug (mlp), 303983-00-8, Azirino(2',3':3,4)pyrrolo(1,2-a)indole-1(2h)-carboxylic acid, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1a,4,7,8,8a,8b-hexahydro-8a-methoxy-5-methyl-4,7-dioxo-, (4-((2,3-bis((1-oxooctadecyl)oxy)propyl)dithio)phenyl)methyl ester, (1as,8s,8ar,8bs)-

Molecular Formula

C₆₂H₉₈N₄O₁₁S₂

Molecular Weight

1139.6 g/mol

InChI Key

LIHIIWJRSSLKKX-YCTALCSSSA-N

FDA UNII

3I8JKL1CHB

Pegylated Liposomal Mitomycin C Lipid-based Prodrug is a pegylated liposomal formulation comprised of a lipophilic prodrug of the antineoplastic antibiotic mitomycin C containing a cleavable disulfide bond (PL-MLP), with potential antineoplastic activity. Upon administration of the pegylated liposomal mitomycin C lipid-based prodrug, the MLP moiety becomes activated upon thiolysis at the tumor site, thereby releasing mitomycin C. Bioreduced mitomycin C generates oxygen radicals, alkylates DNA, and produces interstrand DNA cross-links, thereby inhibiting DNA synthesis. The thiolytic environment and upregulated expression of thioredoxins at the tumor site allow for the activation and release of mitomycin C. This prodrug formulation allows for greater circulation time, less systemic toxicity and increased accumulation of mitomycin C at the tumor site.

1 2D Structure

Promitil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[4-[2,3-di(octadecanoyloxy)propyldisulfanyl]phenyl]methyl (4S,6S,7R,8S)-11-amino-8-(carbamoyloxymethyl)-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-diene-5-carboxylate

2.1.2 InChI

InChI=1S/C62H98N4O11S2/c1-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-52(67)74-43-48(77-53(68)36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-2)45-78-79-49-39-37-47(38-40-49)42-76-61(72)66-51-41-65-56-54(58(70)55(63)46(3)57(56)69)50(44-75-60(64)71)62(65,73-4)59(51)66/h37-40,48,50-51,59H,5-36,41-45,63H2,1-4H3,(H2,64,71)/t48?,50-,51+,59+,62-,66?/m1/s1

2.1.3 InChI Key

LIHIIWJRSSLKKX-YCTALCSSSA-N

2.1.4 Canonical SMILES

CCCCCCCCCCCCCCCCCC(=O)OCC(CSSC1=CC=C(C=C1)COC(=O)N2C3C2C4(C(C5=C(N4C3)C(=O)C(=C(C5=O)N)C)COC(=O)N)OC)OC(=O)CCCCCCCCCCCCCCCCC

2.1.5 Isomeric SMILES

CCCCCCCCCCCCCCCCCC(=O)OCC(CSSC1=CC=C(C=C1)COC(=O)N2[C@@H]3[C@H]2[C@@]4([C@@H](C5=C(N4C3)C(=O)C(=C(C5=O)N)C)COC(=O)N)OC)OC(=O)CCCCCCCCCCCCCCCCC

2.2 Other Identifiers

2.2.1 UNII

3I8JKL1CHB

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Mmc Lipid-based Prodrug (mlp)

2. Jnj-27548547

3. 3i8jkl1chb

4. Mitomycin C Lipid-based Prodrug (mlp)

5. 303983-00-8

6. Azirino(2',3':3,4)pyrrolo(1,2-a)indole-1(2h)-carboxylic Acid, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1a,4,7,8,8a,8b-hexahydro-8a-methoxy-5-methyl-4,7-dioxo-, (4-((2,3-bis((1-oxooctadecyl)oxy)propyl)dithio)phenyl)methyl Ester, (1as,8s,8ar,8bs)-

7. Unii-3i8jkl1chb

8. Chembl4297496

9. Db15372

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₆₂H₉₈N₄O₁₁S₂
Molecular Weight	1139.6 g/mol
XLogP3	18.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	48
Exact Mass	1138.66735230 g/mol
Monoisotopic Mass	1138.66735230 g/mol
Topological Polar Surface Area	258 Å²
Heavy Atom Count	79
Formal Charge	0
Complexity	1960
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1