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Chemistry

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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

Promitil
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 Weight 1139.6 g/mol
Molecular Formula C62H98N4O11S2
XLogP318.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count15
Rotatable Bond Count48
Exact Mass1138.66735230 g/mol
Monoisotopic Mass1138.66735230 g/mol
Topological Polar Surface Area258 Ų
Heavy Atom Count79
Formal Charge0
Complexity1960
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

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