Pepleomycin sulfate
Basic information
- CAS
70384-29-1- Standard SMILES
Cc1c(N)nc(C(CC(N)=O)NCC(N)C(N)=O)nc1C(=O)NC(C(=O)NC(C)C(O)C(C)C(=O)NC(C(=O)NCCc1nc(-c2nc(C(=O)NCCCNC(C)c3ccccc3)cs2)cs1)C(C)O)C(OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(OC(N)=O)C1O)c1cnc[nH]1.O=S(=O)(O)O- InChIKey
ZHHIHQFAUZZMTG-UHFFFAOYSA-N- Molecular formula
- C61H90N18O25S3
- Average molar mass
- 1,571.7 g/mol
- Monoisotopic mass
- 1,570.5486639
Names & identifiers
- Preferred name
- Pepleomycin sulfate
- IUPAC
- [2-[2-[2-[[6-amino-2-[3-amino-1-[(2,3-diamino-3-oxopropyl)amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[[3-hydroxy-5-[[3-hydroxy-1-oxo-1-[2-[4-[4-[3-(1-phenylethylamino)propylcarbamoyl]-1,3-thiazol-2-yl]-1,3-thiazol-2-yl]ethylamino]butan-2-yl]amino]-4-methyl-5-oxopentan-2-yl]amino]-1-(1H-imidazol-5-yl)-3-oxopropoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] carbamate;sulfuric acid
- English name
- PEPLOMYCIN SULFATE
- Molecular formula
- C61H90N18O25S3
- Molecular weight
- 1571.67
Names & synonyms
Pepleomycin sulfateBLM-PEP(-CU)SCHEMBL1650390CHEMBL1994483BLEOMYCIN PEP -CU (FORMERLY)(S)-N'-[3-[(1-Phenylethyl)amino]propyl]bleomycinamide sulfate (1:1) (salt)PepleoNK 631Nsc276382PEPLOMYCIN SULFATEN1-[3-[[(1S)-1-phenylethyl]aMino]propyl]bleoMycinaMideN1-[3-[[(1S)-1-phenylethyl]amino]propyl]bleomycinamide Sulfate
Show more names
Bleomycinamide, N1-[3-[(1-phenylethyl)amino]propyl]-, (S)-, sulfate (1:1) (salt)
Database identifiers
- CAS
70384-29-1- PubChem CID
- 122804
- ChEMBL
CHEMBL1994483
Properties
Computed structural properties
- Topological polar surface area
- 779 Ų
- Hydrogen bond donors
- 23
- Hydrogen bond acceptors
- 36
- Rotatable bonds
- 38
- Heavy atoms
- 107
- Formal charge
- 0
- Complexity
- 2,820
Physicochemical properties
- Melting point
- 196 · 196-198°C
- alpha
- 25436 · 25436 -2.0° (c = 1 in water)
- solubility
- DMSO, DMF, Methanol, Water
- form
- Powder
- pka
- 2.9 · 2.9, 4.8, 7.4, 9.0(at 25℃)
- color
- Pale Yellow Amorphous
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 6 A668951HW · 6A668951HW
- Toxicity
- 50 in · LD50 in male rats, mice (mg/kg): 234, 88 s.c.; 208, 85 i.p.; 245, 51 i.v. (Ito)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Toxicity
- LD50 in male rats, mice (mg/kg): 234, 88 s.c.; 208, 85 i.p.; 245, 51 i.v. (Ito)
Chemistry & industry
Applications
DescriptionPeplomycin was derived biosynthetically from Streptomyces verticillus, the bleomycinproducing organism, in the course of efforts to obtain bleomycin derivatives with high activity and low toxicity. This antibiotic was found by Nippon Kayaku Co. and the Institute of Microbial Chemistry, Japan, in 1974. Its anticancer effects appear earlier than those of bleomycin; consequently, the period of therapy is shortened. Peplomycin is also active against metastatic cancer of the lymph nodes and shows less pneumotoxicity than bleomycin.
UsesA derivative of Bleomycin with cytostatic activity and less pulmonary toxicity than the natural Bleomycin mixture.
Upstream & downstream products
Upstream raw materials
Related reactions
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Compound notes
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